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Volume 22
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Molecules, Volume 22, Issue 5 (May 2017) – 174 articles

Cover Story (view full-size image): The fluorescent chemical probe PDI-1 was designed for strong binding and quantification of glycosaminoglycans, a class of complex polysaccharides, by a simple mix-and-read assay. The interaction between probe and analyte leads to the formation of fluorescence-quenched aggregates. Performance of the probe in a competitive blood plasma matrix is exemplified by the detection of dermatan sulfate, a component of antithrombotic drugs. View the paper
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3105 KiB  
Article
Development of Optimized Inhibitor RNAs Allowing Multisite-Targeting of the HCV Genome
by Cristina Romero-López, Thomas Lahlali, Beatriz Berzal-Herranz and Alfredo Berzal-Herranz
Molecules 2017, 22(5), 861; https://doi.org/10.3390/molecules22050861 - 22 May 2017
Cited by 10 | Viewed by 4881
Abstract
Engineered multivalent drugs are promising candidates for fighting infection by highly variable viruses, such as HCV. The combination into a single molecule of more than one inhibitory domain, each with its own target specificity and even a different mechanism of action, results in [...] Read more.
Engineered multivalent drugs are promising candidates for fighting infection by highly variable viruses, such as HCV. The combination into a single molecule of more than one inhibitory domain, each with its own target specificity and even a different mechanism of action, results in drugs with potentially enhanced therapeutic properties. In the present work, the anti-HCV chimeric inhibitor RNA HH363-10, which has a hammerhead catalytic domain and an aptamer RNA domain, was subjected to an in vitro selection strategy to isolate ten different optimised chimeric inhibitor RNAs. The catalytic domain was preserved while the aptamer RNA domain was evolved to contain two binding sites, one mapping to the highly conserved IIIf domain of the HCV genome’s internal ribosome entry site (IRES), and the other either to IRES domain IV (which contains the translation start codon) or the essential linker region between domains I and II. These chimeric molecules efficiently and specifically interfered with HCV IRES-dependent translation in vitro (with IC50 values in the low µM range). They also inhibited both viral translation and replication in cell culture. These findings highlight the feasibility of using in vitro selection strategies for obtaining improved RNA molecules with potential clinical applications. Full article
(This article belongs to the Special Issue Synthesis and Applications of Oligonucleotide Conjugates)
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3882 KiB  
Article
CTAB-Assisted Fabrication of Bi2WO6 Thin Nanoplates with High Adsorption and Enhanced Visible Light-Driven Photocatalytic Performance
by Yuxue Zhou, Pengfei Lv, Xiangdong Meng, Yanping Tang, Pingping Huang, Xiaobing Chen, Xiaoshuang Shen and Xianghua Zeng
Molecules 2017, 22(5), 859; https://doi.org/10.3390/molecules22050859 - 22 May 2017
Cited by 19 | Viewed by 5916
Abstract
Two-dimensional thin Bi2WO6 nanoplates have been fabricated using a cetyltrimethylammonium bromide (CTAB)-assisted hydrothermal method. We investigated the proposed formation mechanism based on the crystalline structures of the thin Bi2WO6 nanoplates. The high adsorption ability and excellent visible-light [...] Read more.
Two-dimensional thin Bi2WO6 nanoplates have been fabricated using a cetyltrimethylammonium bromide (CTAB)-assisted hydrothermal method. We investigated the proposed formation mechanism based on the crystalline structures of the thin Bi2WO6 nanoplates. The high adsorption ability and excellent visible-light driven photocatalytic activities of the Bi2WO6 nanoplates were illustrated, in view of exposed (001) facets of nanoplates possessing faster separation of photo-generated charge carriers and increased catalytically active sites. Such a cost-effective way to obtain Bi2WO6 nanoplates offers new possibilities for the design of adsorptive semiconductor photocatalysts with strengthened photocatalytic activities. Full article
(This article belongs to the Special Issue Nanocrystals: Synthesis, Characterization and Applications)
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3619 KiB  
Review
Applications of Gold Nanoparticles in Nanomedicine: Recent Advances in Vaccines
by Sónia Alexandra Correia Carabineiro
Molecules 2017, 22(5), 857; https://doi.org/10.3390/molecules22050857 - 22 May 2017
Cited by 105 | Viewed by 12711
Abstract
Nowadays, gold is used in (nano-)medicine, usually in the form of nanoparticles, due to the solid proofs given of its therapeutic effects on several diseases. Gold also plays an important role in the vaccine field as an adjuvant and a carrier, reducing toxicity, [...] Read more.
Nowadays, gold is used in (nano-)medicine, usually in the form of nanoparticles, due to the solid proofs given of its therapeutic effects on several diseases. Gold also plays an important role in the vaccine field as an adjuvant and a carrier, reducing toxicity, enhancing immunogenic activity, and providing stability in storage. An even brighter golden future is expected for gold applications in this area. Full article
(This article belongs to the Special Issue Women in Organic Chemistry)
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1071 KiB  
Article
Synthesis and Characterization of Constrained Geometry Oxygen and Sulphur Functionalized Cyclopentadienylchromium Complexes and Their Use in Catalysis for Olefin Polymerization
by Ruiguo Zhao, Jun Ma, Hao Zhang and Jiling Huang
Molecules 2017, 22(5), 856; https://doi.org/10.3390/molecules22050856 - 22 May 2017
Cited by 7 | Viewed by 5281
Abstract
A series of constrained geometry O-functionalized cyclopentadienylchromium complexes (1–6) and a S-functionalized cyclopentadienylchromium complex (7) were first synthesized, characterized, and tested as catalyst precursors for the olefin polymerization. In the presence of MAO, the complexes exhibited high [...] Read more.
A series of constrained geometry O-functionalized cyclopentadienylchromium complexes (1–6) and a S-functionalized cyclopentadienylchromium complex (7) were first synthesized, characterized, and tested as catalyst precursors for the olefin polymerization. In the presence of MAO, the complexes exhibited high catalytic activity for the polymerization of ethylene. It is shown that ligand variations can have a substantial effect on catalyst activity and stability. The effect of Al/Cr ratio on catalytic activity was also studied. Full article
(This article belongs to the Special Issue Organometallic Catalysis for Olefin Polymerization/Oligomerization)
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4683 KiB  
Article
A 4-Phenoxyphenol Derivative Exerts Inhibitory Effects on Human Hepatocellular Carcinoma Cells through Regulating Autophagy and Apoptosis Accompanied by Downregulating α-Tubulin Expression
by Wen-Tsan Chang, Wangta Liu, Yi-Han Chiu, Bing-Hung Chen, Shih-Chang Chuang, Yen-Chun Chen, Yun-Tzh Hsu, Mei-Jei Lu, Shean-Jaw Chiou, Chon-Kit Chou and Chien-Chih Chiu
Molecules 2017, 22(5), 854; https://doi.org/10.3390/molecules22050854 - 21 May 2017
Cited by 18 | Viewed by 6442
Abstract
Hepatocellular carcinoma (HCC) is a leading cancer worldwide. Advanced HCCs are usually resistant to anticancer drugs, causing unsatisfactory chemotherapy outcomes. In this study, we showed that a 4-phenoxyphenol derivative, 4-[4-(4-hydroxyphenoxy)phenoxy]phenol (4-HPPP), exerts an inhibitory activity against two HCC cell lines, Huh7 and Ha22T. [...] Read more.
Hepatocellular carcinoma (HCC) is a leading cancer worldwide. Advanced HCCs are usually resistant to anticancer drugs, causing unsatisfactory chemotherapy outcomes. In this study, we showed that a 4-phenoxyphenol derivative, 4-[4-(4-hydroxyphenoxy)phenoxy]phenol (4-HPPP), exerts an inhibitory activity against two HCC cell lines, Huh7 and Ha22T. We further investigated the anti-HCC activities of 4-HPPP, including anti-proliferation and induction of apoptosis. Our results showed that higher dosage of 4-HPPP downregulates the expression of α-tubulin and causes nuclear enlargement in both the Huh-7 and Ha22T cell lines. Interestingly, the colony formation results showed a discrepancy in the inhibitory effect of 4-HPPP on HCC and rat liver epithelial Clone 9 cells, suggesting the selective cytotoxicity of 4-HPPP toward HCC cells. Furthermore, the cell proliferation and apoptosis assay results illustrated the differences between the two HCC cell lines. The results of cellular proliferation assays, including trypan blue exclusion and colony formation, revealed that 4-HPPP inhibits the growth of Huh7 cells, but exerts less cytotoxicity in Ha22T cells. Furthermore, the annexin V assay performed for detecting the apoptosis showed similar results. Western blotting results showed 4-HPPP caused the increase of pro-apoptotic factors including cleaved caspase-3, Bid and Bax in HCC cells, especially in Huh-7. Furthermore, an increase of autophagy-associated protein microtubule-associated protein-1 light chain-3B (LC3B)-II and the decrease of Beclin-1 and p62/SQSTM1 were observed following 4-HPPP treatment. Additionally, the level of γH2A histone family, member X (γH2AX), an endogenous DNA damage biomarker, was dramatically increased in Huh7 cells after 4-HPPP treatment, suggesting the involvement of DNA damage pathway in 4-HPPP-induced apoptosis. On the contrary, the western blotting results showed that treatment up-regulates pro-survival proteins, including the phosphorylation of protein kinase B (Akt) and the level of survivin on Ha22T cells, which may confer a resistance toward 4-HPPP. Notably, the blockade of extracellular signal-regulated kinases (ERK), but not Akt, enhanced the cytotoxicity of 4-HPPP against Ha22T cells, indicating the pro-survival role of ERK in 4-HPPP-induced anti-HCC effect. Our present work suggests that selective anti-HCC activity of 4-HPPP acts through induction of DNA damage. Accordingly, the combination of ERK inhibitor may significantly enhance the anti-cancer effect of 4-HPPP for those HCC cells which overexpress ERK in the future. Full article
(This article belongs to the Special Issue Tubulin Inhibitors)
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973 KiB  
Article
Phytochemical Composition and Antioxidant Capacity of Seven Saskatoon Berry (Amelanchier alnifolia Nutt.) Genotypes Grown in Poland
by Sabina Lachowicz, Jan Oszmiański, Łukasz Seliga and Stanisław Pluta
Molecules 2017, 22(5), 853; https://doi.org/10.3390/molecules22050853 - 21 May 2017
Cited by 48 | Viewed by 6178
Abstract
The basic chemical composition, bioactive compounds, and antioxidant capacity of fruits of three new Polish breeding clones (No. 5/6, type S, and type N) and four Canadian cultivars (cvs.) (“Martin”, “Smoky”, “Pembina”, and “Honeywood”) grown in Poland in 2016 were investigated. Fruits were [...] Read more.
The basic chemical composition, bioactive compounds, and antioxidant capacity of fruits of three new Polish breeding clones (No. 5/6, type S, and type N) and four Canadian cultivars (cvs.) (“Martin”, “Smoky”, “Pembina”, and “Honeywood”) grown in Poland in 2016 were investigated. Fruits were analyzed for their contents of triterpenoids, carotenoids, chlorophylls, and polyphenolics with the ultra-performance liquid chromatography photodiode detector-quadrupole/time-of-flight mass spectrometry (UPLC-PDA-Q/TOF-MS) method, sugar with the high-performance liquid chromatography–evaporative light scattering detector (HPLC-ELSD) method, and antioxidant capacity with the ability to reduce free radical (ABTS) and ferric reducing ability of plasma (FRAP) method. Thirty-eight bioactive compounds, including twenty-eight polyphenolic compounds (four anthocyanins, nine phenolic acids, nine flavonols, and seven flavan-3-ols), four carotenoids, two chlorophylls, and three triterpenoids were identified in the fruits. The fruits of the tested Saskatoon berry genotypes were found to be rich in phenolic compounds (3773.94–6390.36 mg/100 g·dm), triterpenoids (66.55–91.31 mg/kg·dm), and carotenoids (478.62–561.57 mg/kg·dm), with high ABTS and FRAP capacity (10.38–34.49 and 9.66–25.34 mmol·Trolox/100 g·dm, respectively). Additionally, the berries of these genotypes seemed to be a good source of sugar (9.02–19.69 g/100 g), pectins (0.67%–1.33%), and ash (0.59%–0.67%). Some genotypes of Saskatoon berry, especially the clones type S, type N, and cvs. “Honeywood” and “Smoky”, may be selected for their potential applications in commercial cultivation to produce fruits with valuable health-promoting nutritional effects on human health. Additionally, three new genotypes that may offer new functional materials can be recommended for fruit growers. Full article
(This article belongs to the Section Natural Products Chemistry)
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907 KiB  
Article
Synthesis and Excellent Duplex Stability of Oligonucleotides Containing 2′-Amino-LNA Functionalized with Galactose Units
by Rajesh Kumar, Annika Ries and Jesper Wengel
Molecules 2017, 22(5), 852; https://doi.org/10.3390/molecules22050852 - 21 May 2017
Cited by 8 | Viewed by 7206
Abstract
A convenient method for the preparation of oligonucleotides containing internally-attached galactose and triantennary galactose units has been developed based on click chemistry between 2′-N-alkyne 2′-amino-LNA nucleosides and azido-functionalized galactosyl building blocks. The synthesized oligonucleotides show excellent binding affinity and selectivity towards [...] Read more.
A convenient method for the preparation of oligonucleotides containing internally-attached galactose and triantennary galactose units has been developed based on click chemistry between 2′-N-alkyne 2′-amino-LNA nucleosides and azido-functionalized galactosyl building blocks. The synthesized oligonucleotides show excellent binding affinity and selectivity towards complementary DNA/RNA strands with an increase in the melting temperature of up to +23.5 °C for triply-modified variants. Full article
(This article belongs to the Special Issue Synthesis and Applications of Oligonucleotide Conjugates)
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6174 KiB  
Article
Rapid and Cost-Effective Quantification of Glucosinolates and Total Phenolic Content in Rocket Leaves by Visible/Near-Infrared Spectroscopy
by Eva María Toledo-Martín, Rafael Font, Sara Obregón-Cano, Antonio De Haro-Bailón, Myriam Villatoro-Pulido and Mercedes Del Río-Celestino
Molecules 2017, 22(5), 851; https://doi.org/10.3390/molecules22050851 - 20 May 2017
Cited by 22 | Viewed by 5607
Abstract
The potential of visible-near infrared spectroscopy to predict glucosinolates and total phenolic content in rocket (Eruca vesicaria) leaves has been evaluated. Accessions of the E. vesicaria species were scanned by NIRS as ground leaf, and their reference values regressed against different [...] Read more.
The potential of visible-near infrared spectroscopy to predict glucosinolates and total phenolic content in rocket (Eruca vesicaria) leaves has been evaluated. Accessions of the E. vesicaria species were scanned by NIRS as ground leaf, and their reference values regressed against different spectral transformations by modified partial least squares (MPLS) regression. The coefficients of determination in the external validation (R2VAL) for the different quality components analyzed in rocket ranged from 0.59 to 0.84, which characterize those equations as having from good to excellent quantitative information. These results show that the total glucosinolates, glucosativin and glucoerucin equations obtained, can be used to identify those samples with low and high contents. The glucoraphanin equation obtained can be used for rough predictions of samples and in case of total phenolic content, the equation showed good correlation. The standard deviation (SD) to standard error of prediction ratio (RPD) and SD to range (RER) were variable for the different quality compounds and showed values that were characteristic of equations suitable for screening purposes or to perform accurate analyses. From the study of the MPLS loadings of the first three terms of the different equations, it can be concluded that some major cell components such as protein and cellulose, highly participated in modelling the equations for glucosinolates. Full article
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1027 KiB  
Article
Photoreactions of Endohedral Metallofullerene with Siliranes: Electronic Properties of Carbosilylated Lu3N@Ih-C80
by Masahiro Kako, Kazuya Minami, Taiki Kuroiwa, Shinpei Fukazawa, Yuki Arikawa, Michio Yamada, Yutaka Maeda, Qiao-Zhi Li, Shigeru Nagase and Takeshi Akasaka
Molecules 2017, 22(5), 850; https://doi.org/10.3390/molecules22050850 - 20 May 2017
Cited by 3 | Viewed by 4230
Abstract
Photochemical carbosilylation of Lu3N@Ih-C80 was performed using siliranes (silacyclopropanes) to afford the corresponding [5,6]- and [6,6]-adducts. Electrochemical studies indicated that the redox potentials of the carbosilylated derivatives were shifted cathodically in comparison with those of the [5,6]-pyrrolidino [...] Read more.
Photochemical carbosilylation of Lu3N@Ih-C80 was performed using siliranes (silacyclopropanes) to afford the corresponding [5,6]- and [6,6]-adducts. Electrochemical studies indicated that the redox potentials of the carbosilylated derivatives were shifted cathodically in comparison with those of the [5,6]-pyrrolidino adducts. The electronic effect of the silirane addends on Lu3N@Ih-C80 was verified on the basis of density functional theory calculations. Full article
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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254 KiB  
Review
Antidiabetic Effects of Tea
by Qiu-Yue Fu, Qing-Sheng Li, Xiao-Ming Lin, Ru-Ying Qiao, Rui Yang, Xu-Min Li, Zhan-Bo Dong, Li-Ping Xiang, Xin-Qiang Zheng, Jian-Liang Lu, Cong-Bo Yuan, Jian-Hui Ye and Yue-Rong Liang
Molecules 2017, 22(5), 849; https://doi.org/10.3390/molecules22050849 - 20 May 2017
Cited by 94 | Viewed by 13748
Abstract
Diabetes mellitus (DM) is a chronic endocrine disease resulted from insulin secretory defect or insulin resistance and it is a leading cause of death around the world. The care of DM patients consumes a huge budget due to the high frequency of consultations [...] Read more.
Diabetes mellitus (DM) is a chronic endocrine disease resulted from insulin secretory defect or insulin resistance and it is a leading cause of death around the world. The care of DM patients consumes a huge budget due to the high frequency of consultations and long hospitalizations, making DM a serious threat to both human health and global economies. Tea contains abundant polyphenols and caffeine which showed antidiabetic activity, so the development of antidiabetic medications from tea and its extracts is increasingly receiving attention. However, the results claiming an association between tea consumption and reduced DM risk are inconsistent. The advances in the epidemiologic evidence and the underlying antidiabetic mechanisms of tea are reviewed in this paper. The inconsistent results and the possible causes behind them are also discussed. Full article
(This article belongs to the Special Issue Plant Polyphenols as Potential Therapeutic Agents for Diabetes and Obesity)
1657 KiB  
Article
Functional Mitochondria Are Important for the Effect of Resveratrol
by Anne L. Widlund, Kaushal Baral, Louise T. Dalgaard and Ole Vang
Molecules 2017, 22(5), 847; https://doi.org/10.3390/molecules22050847 - 20 May 2017
Cited by 9 | Viewed by 7344
Abstract
Resveratrol (Resv) is a polyphenol reported to modulate mitochondrial activity. The aim was to use HeLa and 143B cells to characterize the action of Resv on mitochondrial activity, cell size and proliferation using wild type (WT) and Rho 0 cells deficient in mitochondrial [...] Read more.
Resveratrol (Resv) is a polyphenol reported to modulate mitochondrial activity. The aim was to use HeLa and 143B cells to characterize the action of Resv on mitochondrial activity, cell size and proliferation using wild type (WT) and Rho 0 cells deficient in mitochondrial DNA. In both HeLa WT and Rho 0 cells, the oxygen consumption rate (OCR) was increased at 20 µM Resv after 24 h, whereas only a non-significant increase of OCR was observed in 143B WT cells. Resv decreased cell number concentration-dependently in both WT and Rho 0 cell types. An increased cell diameter was observed in HeLa WT, but not in Rho 0 when treated with Resv. Overall, the findings presented indicate that functional mitochondria are a prerequisite for cell enlargement by Resv. Full article
(This article belongs to the Special Issue Improvements for Resveratrol Efficacy)
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413 KiB  
Article
Synthesis of 1,2,3-Triazolo[4,5-h]quinolone Derivatives with Novel Anti-Microbial Properties against Metronidazole Resistant Helicobacter pylori
by Mohammad Abu-Sini, Amal Mayyas, Nehaya Al-Karablieh, Rula Darwish, Yusuf Al-Hiari, Talal Aburjai, Shereen Arabiyat and Luay Abu-Qatouseh
Molecules 2017, 22(5), 841; https://doi.org/10.3390/molecules22050841 - 20 May 2017
Cited by 16 | Viewed by 5618
Abstract
Helicobacter pylori infection can lead to gastritis, peptic ulcer, and the development of mucosa associated lymphoid tissue (MALT) lymphoma. Treatment and eradication of H. pylori infection can prevent relapse and accelerate the healing of gastric and duodenal ulcers as well as regression of [...] Read more.
Helicobacter pylori infection can lead to gastritis, peptic ulcer, and the development of mucosa associated lymphoid tissue (MALT) lymphoma. Treatment and eradication of H. pylori infection can prevent relapse and accelerate the healing of gastric and duodenal ulcers as well as regression of malignancy. Due to the increasing emergence of antibiotic resistance among clinical isolates of H. pylori, alternative approaches using newly discovered antimicrobial agents in combination with the standard antibiotic regimens for the treatment of H. pylori are of major importance. The purpose of the present study was to investigate the effect of newly synthesized 8-amino 7-substituted fluoroquinolone and their correspondent cyclized triazolo derivatives when either alone or combined with metronidazole against metronidazole-resistant H. pylori. Based on standard antimicrobial susceptibility testing methods and checkerboard titration assay, all of the tested compounds showed interesting antimicrobial activity against 12 clinical strains of H. pylori, with best in vitro effect for compounds 4b and 4c. Fractional inhibitory concentration (FIC) mean values showed synergistic pattern in all compounds of Group 5. In addition, additive activities of some of the tested compounds of Group 4 were observed when combined with metronidazole. In contrast, the tested compounds showed no significant urease inhibition activity. These results support the potential of new fluoroquinolone derivatives to be useful in combination with anti-H. pylori drugs in the management of H. pylori-associated diseases. Full article
(This article belongs to the Collection Antibiotics & Superbugs: New Strategies to Combat Antimicrobial Resistance)
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4294 KiB  
Review
The Impact of Halloysite on the Thermo-Mechanical Properties of Polymer Composites
by Tayser Sumer Gaaz, Abu Bakar Sulong, Abdul Amir H. Kadhum, Ahmed A. Al-Amiery, Mohamed H. Nassir and Ahed Hameed Jaaz
Molecules 2017, 22(5), 838; https://doi.org/10.3390/molecules22050838 - 20 May 2017
Cited by 97 | Viewed by 9411
Abstract
Nanotubular clay minerals, composed of aluminosilicate naturally structured in layers known as halloysite nanotubes (HNTs), have a significant reinforcing impact on polymer matrixes. HNTs have broad applications in biomedical applications, the medicine sector, implant alloys with corrosion protection and manipulated transportation of medicines. [...] Read more.
Nanotubular clay minerals, composed of aluminosilicate naturally structured in layers known as halloysite nanotubes (HNTs), have a significant reinforcing impact on polymer matrixes. HNTs have broad applications in biomedical applications, the medicine sector, implant alloys with corrosion protection and manipulated transportation of medicines. In polymer engineering, different research studies utilize HNTs that exhibit a beneficial enhancement in the properties of polymer-based nanocomposites. The dispersion of HNTs is improved as a result of pre-treating HNTs with acids. The HNTs’ percentage additive up to 7% shows the highest improvement of tensile strength. The degradation of the polymer can be also significantly improved by doping a low percentage of HNTs. Both the mechanical and thermal properties of polymers were remarkably improved when mixed with HNTs. The effects of HNTs on the mechanical and thermal properties of polymers, such as ultimate strength, elastic modulus, impact strength and thermal stability, are emphasized in this study. Full article
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2350 KiB  
Article
Microwave-Assisted Synthesis of Imidazo[4,5-f][1,10]phenanthroline Derivatives as Apoptosis Inducers in Chemotherapy by Stabilizing Bcl-2 G-quadruplex DNA
by Li Li, Jie-Qiong Cao, Hui-Min Liu, Qiong Wu, Qiu-Hui Pan, Zhi-Ping Zeng, Yu-Tao Lan, Yu-Mei Li, Wen-Jie Mei, Xi-Cheng Wang and Wen-Jie Zheng
Molecules 2017, 22(5), 829; https://doi.org/10.3390/molecules22050829 - 20 May 2017
Cited by 9 | Viewed by 5777
Abstract
Herein, a series of imidazo[4,5-f][1,10] phenanthroline derivatives RPIP (PIP = imidazo [4,5-f][1,10] phenanthroline, R = NO2, 1; CF3, 2; Cl, 3; OH, 4) have been synthesized in yields of 82.3–94.7% at [...] Read more.
Herein, a series of imidazo[4,5-f][1,10] phenanthroline derivatives RPIP (PIP = imidazo [4,5-f][1,10] phenanthroline, R = NO2, 1; CF3, 2; Cl, 3; OH, 4) have been synthesized in yields of 82.3–94.7% at 100 °C under the irradiation of microwave. MTT assay has been utilized to evaluate the inhibitory activity (IC50) of these compounds against the growth of various tumor cells, and the results revealed that these compounds, especially 1, exhibited excellent inhibitory activity against the growth of A549 cells with IC50 of 15.03 μM. Moreover, it’s also confirmed that 1 can penetrate into the membrane of tumor cells and distribute in mitochondria when observed under microscopy, resulting apoptosis of tumor cells. The further studies showed that 1 can bind to bcl-2 G-quadruplex DNA, which demonstrated by the increase of melting point of bcl-2 G4 DNA in the presence of 1, as well as electronic titration and emission spectra. In a word, this kind of compound may develop as a potential apoptosis inducer in cancer chemotherapy via binding and stabilizing to the bcl-2 G-quadruplex DNA. Full article
(This article belongs to the Special Issue ECSOC-20)
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4430 KiB  
Article
Study on the Alkylation Reactions of N(7)-Unsubstituted 1,3-Diazaoxindoles
by Eszter Kókai, Judit Halász, András Dancsó, József Nagy, Gyula Simig and Balázs Volk
Molecules 2017, 22(5), 846; https://doi.org/10.3390/molecules22050846 - 19 May 2017
Cited by 2 | Viewed by 6441
Abstract
The chemistry of the 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (1,3-diazaoxindole) compound family, possessing a drug-like scaffold, is unexplored. In this study, the alkylation reactions of N(7)-unsubstituted 5-isopropyl-1,3-diazaoxindoles bearing various substituents at the C(2) position have been investigated. The starting compounds were [...] Read more.
The chemistry of the 5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (1,3-diazaoxindole) compound family, possessing a drug-like scaffold, is unexplored. In this study, the alkylation reactions of N(7)-unsubstituted 5-isopropyl-1,3-diazaoxindoles bearing various substituents at the C(2) position have been investigated. The starting compounds were synthesized from the C(5)-unsubstituted parent compounds by condensation with acetone and subsequent catalytic reduction of the 5-isopropylidene moiety. Alkylation of the thus obtained 5-isopropyl derivatives with methyl iodide or benzyl bromide in the presence of a large excess of sodium hydroxide led to 5,7-disubstituted derivatives. Use of butyllithium as the base rendered alkylation in the C(5) position possible with reasonable selectivity, without affecting the N(7) atom. During the study on the alkylation reactions, some interesting by-products were also isolated and characterized. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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5547 KiB  
Article
Preparation and In Vitro Photodynamic Activity of Glucosylated Zinc(II) Phthalocyanines as Underlying Targeting Photosensitizers
by Jian-Yong Liu, Chen Wang, Chun-Hui Zhu, Zhi-Hong Zhang and Jin-Ping Xue
Molecules 2017, 22(5), 845; https://doi.org/10.3390/molecules22050845 - 19 May 2017
Cited by 15 | Viewed by 5411
Abstract
Two novel glucosylated zinc(ІІ) phthalocyanines 7a–7b, as well as the acetyl-protected counterparts 6a–6b, have been synthesized by the Cu(I)-catalyzed 1,3-dipolar cycloaddition between the propargylated phthalocyanine and azide-substituted glucoses. All of these phthalocyanines were characterized with various spectroscopic methods and studied for their photo-physical, [...] Read more.
Two novel glucosylated zinc(ІІ) phthalocyanines 7a–7b, as well as the acetyl-protected counterparts 6a–6b, have been synthesized by the Cu(I)-catalyzed 1,3-dipolar cycloaddition between the propargylated phthalocyanine and azide-substituted glucoses. All of these phthalocyanines were characterized with various spectroscopic methods and studied for their photo-physical, photo-chemical, and photo-biological properties. With glucose as the targeting unit, phthalocyanines 7a–7b exhibit a specific affinity to MCF-7 breast cancer cells over human embryonic lung fibroblast (HELF) cells, showing higher cellular uptake. Upon illumination, both photosensitizers show high cytotoxicity with IC50 as low as 0.032 µM toward MCF-7 cells, which are attributed to their high cellular uptake and low aggregation tendency in the biological media, promoting the generation of intracellular reactive oxygen species (ROS). Confocal laser fluorescence microscopic studies have also revealed that they have high and selective affinities to the lysosomes, but not the mitochondria, of MCF-7 cells. The results show that these two glucosylated zinc(II) phthalocyanines are potential anticancer agents for targeting photodynamic therapy. Full article
(This article belongs to the Special Issue Porphyrins and Phthalocyanines: Synthesis, Properties and Applications)
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2176 KiB  
Article
Enhanced Production of Gypenoside LXXV Using a Novel Ginsenoside-Transforming β-Glucosidase from Ginseng-Cultivating Soil Bacteria and Its Anti-Cancer Property
by Chang-Hao Cui, Da Jung Kim, Suk-Chae Jung, Sun-Chang Kim and Wan-Taek Im
Molecules 2017, 22(5), 844; https://doi.org/10.3390/molecules22050844 - 19 May 2017
Cited by 38 | Viewed by 6589
Abstract
Minor ginsenosides, such as compound K, Rg3(S), which can be produced by deglycosylation of ginsenosides Rb1, showed strong anti-cancer effects. However, the anticancer effects of gypenoside LXXV, which is one of the deglycosylated shapes of ginsenoside Rb [...] Read more.
Minor ginsenosides, such as compound K, Rg3(S), which can be produced by deglycosylation of ginsenosides Rb1, showed strong anti-cancer effects. However, the anticancer effects of gypenoside LXXV, which is one of the deglycosylated shapes of ginsenoside Rb1, is still unknown due to the rarity of its content in plants. Here, we cloned and characterized a novel ginsenoside-transforming β-glucosidase (BglG167b) derived from Microbacterium sp. Gsoil 167 which can efficiently hydrolyze gypenoside XVII into gypenoside LXXV, and applied it to the production of gypenoside LXXV at the gram-scale with high specificity. In addition, the anti-cancer activity of gypenoside LXXV was investigated against three cancer cell lines (HeLa, B16, and MDA-MB231) in vitro. Gypenoside LXXV significantly reduced cell viability, displaying an enhanced anti-cancer effect compared to gypenoside XVII and Rb1. Taken together, this enzymatic method would be useful in the preparation of gypenoside LXXV for the functional food and pharmaceutical industries. Full article
(This article belongs to the Special Issue Synthesis and Modification of Natural Product)
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1046 KiB  
Communication
Rapidly Simultaneous Determination of Six Effective Components in Cistanche tubulosa by Near Infrared Spectroscopy
by Xinhong Wang, Xiaoguang Wang and Yuhai Guo
Molecules 2017, 22(5), 843; https://doi.org/10.3390/molecules22050843 - 19 May 2017
Cited by 25 | Viewed by 4998
Abstract
Quantitative determination of multiple effective components in a given plant usually requires a very large amount of authentic natural products. In this study, we proposed a rapid and non-destructive method for the simultaneous determination of echinacoside, verbascoside, mannitol, sucrose, glucose and fructose in [...] Read more.
Quantitative determination of multiple effective components in a given plant usually requires a very large amount of authentic natural products. In this study, we proposed a rapid and non-destructive method for the simultaneous determination of echinacoside, verbascoside, mannitol, sucrose, glucose and fructose in Cistanche tubulosa by near infrared spectroscopy (NIRS). Near infrared diffuse reflectance spectroscopy (DRS) and high performance liquid chromatography (HPLC) were conducted on 116 batches of C. tubulosa samples. The DRS data were processed using standard normal variety (SNV) and multiplicative scatter correction (MSC) methods. Partial least squares regression (PLSR) was utilized to build calibration models for components-of-interest in C. tubulosa. All models were then assessed by calculating the root mean square error of calibration (RMSEC), correlation coefficient of calibration (r). The r values of all six calibration models were determined to be greater than 0.94, suggesting each model is reliable. Therefore, the quantitative NIR models reported in this study can be qualified to accurately quantify the contents of six medicinal components in C. tubulosa. Full article
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889 KiB  
Article
Three New Abietane-Type Diterpenoids from Callicarpa macrophylla Vahl.
by Zhen-Hui Wang, Chao Niu, De-Jun Zhou, Ji-Chuan Kong and Wen-Kui Zhang
Molecules 2017, 22(5), 842; https://doi.org/10.3390/molecules22050842 - 19 May 2017
Cited by 13 | Viewed by 5343
Abstract
Three new abietane-type diterpenoids, named callicapoic acid M3 (1), callicapoic acid M4 (2) and callicapoic acid M5 (3), were isolated from the Callicarpa macrophylla Vahl. Their structures were established by spectroscopic techniques (IR, UV, MS, 1D and [...] Read more.
Three new abietane-type diterpenoids, named callicapoic acid M3 (1), callicapoic acid M4 (2) and callicapoic acid M5 (3), were isolated from the Callicarpa macrophylla Vahl. Their structures were established by spectroscopic techniques (IR, UV, MS, 1D and 2D NMR). All the isolated three compounds were evaluated for inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells by using MTT assays. Compounds 1, 2 and 3 showed potent inhibitory activity, with inhibition rates of 34.47–40.13%. Full article
(This article belongs to the Section Natural Products Chemistry)
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2453 KiB  
Article
Exploring the Pivotal Role of the CK2 Hinge Region Sub-Pocket in Binding with Tricyclic Quinolone Analogues by Computational Analysis
by Yue Zhou, Na Zhang, Shan Tang, Xiaoqian Qi, Lijiao Zhao, Rugang Zhong and Yongzhen Peng
Molecules 2017, 22(5), 840; https://doi.org/10.3390/molecules22050840 - 19 May 2017
Cited by 5 | Viewed by 4801
Abstract
Protein kinase CK2 has been considered as an attractive therapeutic target of cancer therapy. The tricyclic quinoline compound CX-4945 is the first representative of CK2 inhibitors used in human clinical trials. The binding of non-2,6-naphtyridine substituted compounds 27e (IC50 > 500 nM) [...] Read more.
Protein kinase CK2 has been considered as an attractive therapeutic target of cancer therapy. The tricyclic quinoline compound CX-4945 is the first representative of CK2 inhibitors used in human clinical trials. The binding of non-2,6-naphtyridine substituted compounds 27e (IC50 > 500 nM) and 27h (IC50 > 1000 nM) to CK2 is abolished. However, the unbinding mechanisms due to the key pharmacophore group replacement of compounds 27e and 27h are unveiled. In the present work, combined computational analysis was performed to investigate the underlying structural basis of the low-affinity of two systems. As indicated in the results, the loss of hydrogen bonds between the non-2,6-naphtyridine and the hinge region destroyed the proper recognition of the two complexes. Besides, the allosteric mechanisms between the deviated ligands and the changed regions (G-loop, C-loop and β4/β5 loop) are proposed. Furthermore, energetic analysis was evaluated by detailed energy calculation and residue-based energy decomposition. More importantly, the summary of known polar pharmacophore groups elucidates the pivotal roles of hinge region sub-pocket in the binding of CK2 inhibitors. These results provide rational clues to the fragment-based design of more potent CK2 inhibitors. Full article
(This article belongs to the Special Issue Frontiers in Computational Chemistry for Drug Discovery)
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963 KiB  
Article
Methodical Challenges and a Possible Resolution in the Assessment of Receptor Reserve for Adenosine, an Agonist with Short Half-Life
by Judit Zsuga, Tamas Erdei, Katalin Szabó, Nora Lampe, Csaba Papp, Akos Pinter, Andras Jozsef Szentmiklosi, Bela Juhasz, Zoltán Szilvássy and Rudolf Gesztelyi
Molecules 2017, 22(5), 839; https://doi.org/10.3390/molecules22050839 - 19 May 2017
Cited by 14 | Viewed by 5464
Abstract
The term receptor reserve, first introduced and used in the traditional receptor theory, is an integrative measure of response-inducing ability of the interaction between an agonist and a receptor system (consisting of a receptor and its downstream signaling). The underlying phenomenon, i.e., stimulation [...] Read more.
The term receptor reserve, first introduced and used in the traditional receptor theory, is an integrative measure of response-inducing ability of the interaction between an agonist and a receptor system (consisting of a receptor and its downstream signaling). The underlying phenomenon, i.e., stimulation of a submaximal fraction of receptors can apparently elicit the maximal effect (in certain cases), provides an opportunity to assess the receptor reserve. However, determining receptor reserve is challenging for agonists with short half-lives, such as adenosine. Although adenosine metabolism can be inhibited several ways (in order to prevent the rapid elimination of adenosine administered to construct concentration–effect (E/c) curves for the determination), the consequent accumulation of endogenous adenosine biases the results. To address this problem, we previously proposed a method, by means of which this bias can be mathematically corrected (utilizing a traditional receptor theory-independent approach). In the present investigation, we have offered in silico validation of this method by simulating E/c curves with the use of the operational model of agonism and then by evaluating them using our method. We have found that our method is suitable to reliably assess the receptor reserve for adenosine in our recently published experimental setting, suggesting that it may be capable for a qualitative determination of receptor reserve for rapidly eliminating agonists in general. In addition, we have disclosed a possible interference between FSCPX (8-cyclopentyl-N3-[3-(4-(fluorosulfonyl)benzoyloxy)propyl]-N1-propylxanthine), an irreversible A1 adenosine receptor antagonist, and NBTI (S-(2-hydroxy-5-nitrobenzyl)-6-thioinosine), a nucleoside transport inhibitor, i.e., FSCPX may blunt the effect of NBTI. Full article
(This article belongs to the Special Issue Adenosine Receptors)
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381 KiB  
Article
Emulsion-Based Intradermal Delivery of Melittin in Rats
by Sang Mi Han, Se Gun Kim and Sok Cheon Pak
Molecules 2017, 22(5), 836; https://doi.org/10.3390/molecules22050836 - 19 May 2017
Cited by 5 | Viewed by 4744
Abstract
Bee venom (BV) has long been used as a traditional medicine. The aim of the present study was to formulate a BV emulsion with good rheological properties for dermal application and investigate the effect of formulation on the permeation of melittin through dermatomed [...] Read more.
Bee venom (BV) has long been used as a traditional medicine. The aim of the present study was to formulate a BV emulsion with good rheological properties for dermal application and investigate the effect of formulation on the permeation of melittin through dermatomed rat skin. A formulated emulsion containing 1% (w/v) BV was prepared. The emulsion was compared with distilled water (DW) and 25% (w/v) N-methyl-2-pyrrolidone (NMP) in DW. Permeation of melittin from aqueous solution through the dermatomed murine skin was evaluated using the Franz diffusion cells. Samples of receptor cells withdrawn at pre-determined time intervals were measured for melittin amount. After the permeation study, the same skin was used for melittin extraction. In addition, a known amount of melittin (5 μg/mL) was added to stratum corneum, epidermis, and dermis of the rat skin, and the amount of melittin was measured at pre-determined time points. The measurement of melittin from all samples was done with HPLC-MS/MS. No melittin was detected in the receptor phase at all time points in emulsion, DW, or NMP groups. When the amount of melittin was further analyzed in stratum corneum, epidermis, and dermis from the permeation study, melittin was still not detected. In an additional experiment, the amount of melittin added to all skin matrices was corrected against the amount of melittin recovered. While the total amount of melittin was retained in the stratum corneum, less than 10% of melittin remained in epidermis and dermis within 15 and 30 min, respectively. Skin microporation with BV emulsion facilitates the penetration of melittin across the stratum corneum into epidermis and dermis, where emulsified melittin could have been metabolized by locally-occurring enzymes. Full article
(This article belongs to the Special Issue Bioactive Natural Peptides As A Pipeline For Therapeutics)
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2787 KiB  
Review
Electrophilic Selenium Catalysis with Electrophilic N-F Reagents as the Oxidants
by Ruizhi Guo, Lihao Liao and Xiaodan Zhao
Molecules 2017, 22(5), 835; https://doi.org/10.3390/molecules22050835 - 19 May 2017
Cited by 76 | Viewed by 8741
Abstract
A suitable oxidative system is crucial to electrophilic selenium catalysis (ESC). This short review offers the overview of recent development in ESC with electrophilic N-F reagents as the oxidants. Several highly selective transformations of alkenes such as allylic or vinylic imidation, pyridination, syn [...] Read more.
A suitable oxidative system is crucial to electrophilic selenium catalysis (ESC). This short review offers the overview of recent development in ESC with electrophilic N-F reagents as the oxidants. Several highly selective transformations of alkenes such as allylic or vinylic imidation, pyridination, syn-dichlorination, oxidative cyclization and asymmetric cyclization have been described. Full article
(This article belongs to the Special Issue Celebrating Two Centuries of Research in Selenium Chemistry: State of the Art and New Prospectives)
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569 KiB  
Review
Combining Pharmacological Countermeasures to Attenuate the Acute Radiation Syndrome—A Concise Review
by Michal Hofer, Zuzana Hoferová, Daniel Depeš and Martin Falk
Molecules 2017, 22(5), 834; https://doi.org/10.3390/molecules22050834 - 19 May 2017
Cited by 14 | Viewed by 5091
Abstract
The goal of combined pharmacological approaches in the treatment of the acute radiation syndrome (ARS) is to obtain an effective therapy producing a minimum of undesirable side effects. This review summarizes important data from studies evaluating the efficacy of combining radioprotective agents developed [...] Read more.
The goal of combined pharmacological approaches in the treatment of the acute radiation syndrome (ARS) is to obtain an effective therapy producing a minimum of undesirable side effects. This review summarizes important data from studies evaluating the efficacy of combining radioprotective agents developed for administration prior to irradiation and therapeutic agents administered in a post-irradiation treatment regimen. Many of the evaluated results show additivity, or even synergism, of the combined treatments in comparison with the effects of the individual component administrations. It can be deduced from these findings that the research in which combined treatments with radioprotectors/radiomitigators are explored, tested, and evaluated is well-founded. The requirement for studies highly emphasizing the need to minimize undesirable side effects of the radioprotective/radiomitigating therapies is stressed. Full article
(This article belongs to the Section Medicinal Chemistry)
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1497 KiB  
Article
Electrophilic Trifluoromethylselenolation of Boronic Acids
by Clément Ghiazza, Anis Tlili and Thierry Billard
Molecules 2017, 22(5), 833; https://doi.org/10.3390/molecules22050833 - 19 May 2017
Cited by 27 | Viewed by 7579
Abstract
Trifluoromethylselenylated compounds are emergent compounds with interesting physicochemical properties that still suffer from a lack of efficient synthetic methods. We recently developed an efficient one-pot strategy to generate in situ CF3SeCl and use it in various reactions. Herein, we continue our [...] Read more.
Trifluoromethylselenylated compounds are emergent compounds with interesting physicochemical properties that still suffer from a lack of efficient synthetic methods. We recently developed an efficient one-pot strategy to generate in situ CF3SeCl and use it in various reactions. Herein, we continue our study of the reactivity scope of this preformed reagent. Cross-coupling reactions with aromatic and heteroaromatic boronic acids have been investigated. The expected products have been obtained, using a stoichiometric amount of copper, with moderate yields. Full article
(This article belongs to the Special Issue Tri- and Di-Fluoromethylation and Tri- and Di-Fluoromethylchalcogenation Reactions)
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0 pages, 15378 KiB  
Article
In Vitro Assessment of Early Bacterial Activity on Micro/Nanostructured Ti6Al4V Surfaces
by Benjamin Valdez-Salas, Ernesto Beltrán-Partida, Sandra Castillo-Uribe, Mario Curiel-Álvarez, Roumen Zlatev, Margarita Stoytcheva, Gisela Montero-Alpírez and Lidia Vargas-Osuna
Molecules 2017, 22(5), 832; https://doi.org/10.3390/molecules22050832 - 18 May 2017
Cited by 16 | Viewed by 5563
Abstract
It is imperative to understand and systematically compare the initial interactions between bacteria genre and surface properties. Thus, we fabricated a flat, anodized with 80 nm TiO2 nanotubes (NTs), and a rough Ti6Al4V surface. The materials were characterized using field-emission scanning electron [...] Read more.
It is imperative to understand and systematically compare the initial interactions between bacteria genre and surface properties. Thus, we fabricated a flat, anodized with 80 nm TiO2 nanotubes (NTs), and a rough Ti6Al4V surface. The materials were characterized using field-emission scanning electron microscopy (FE-SEM), energy dispersive X-ray spectroscopy (EDX) and atomic force microscopy (AFM). We cultured in vitro Staphylococcus epidermidis (S. epidermidis) and Pseudomonas aeruginosa (P. aeruginosa) to evaluate the bacterial-surface behavior by FE-SEM and viability calculation. In addition, the initial effects of human osteoblasts were tested on the materials. Gram-negative bacteria showed promoted adherence and viability over the flat and rough surface, while NTs displayed opposite activity with altered morphology. Gram-positive bacteria illustrated similar cellular architecture over the surfaces but with promoted surface adhesion bonds on the flat alloy. Rough surfaces supported S. epidermidis viability, whilst NTs exhibited lower vitality. NTs advocated promoted better osteoblast organization with enhanced vitality. Gram-positive bacteria suggested preferred adhesion capability over flat and carbon-rich surfaces. Gram-negative bacteria were strongly disturbed by NTs but largely stimulated by flat and rough materials. Our work proposed that the chemical profile of the material surface and the bacterial cell wall characteristics might play an important role in the bacteria-surface interactions. Full article
(This article belongs to the Special Issue Antibacterial Materials and Coatings)
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3571 KiB  
Article
Protective Effects of Tormentic Acid, a Major Component of Suspension Cultures of Eriobotrya japonica Cells, on Acetaminophen-Induced Hepatotoxicity in Mice
by Wen-Ping Jiang, Shyh-Shyun Huang, Yoshikazu Matsuda, Hiroshi Saito, Naoto Uramaru, Hui-Ya Ho, Jin-Bin Wu and Guan-Jhong Huang
Molecules 2017, 22(5), 830; https://doi.org/10.3390/molecules22050830 - 18 May 2017
Cited by 37 | Viewed by 7088
Abstract
An acetaminophen (APAP) overdose can cause hepatotoxicity and lead to fatal liver damage. The hepatoprotective effects of tormentic acid (TA) on acetaminophen (APAP)-induced liver damage were investigated in mice. TA was intraperitoneally (i.p.) administered for six days prior to APAP administration. Pretreatment with [...] Read more.
An acetaminophen (APAP) overdose can cause hepatotoxicity and lead to fatal liver damage. The hepatoprotective effects of tormentic acid (TA) on acetaminophen (APAP)-induced liver damage were investigated in mice. TA was intraperitoneally (i.p.) administered for six days prior to APAP administration. Pretreatment with TA prevented the elevation of serum aspartate aminotransferase (AST), alanine aminotransferase (ALT), total bilirubin (T-Bil), total cholesterol (TC), triacylglycerol (TG), and liver lipid peroxide levels in APAP-treated mice and markedly reduced APAP-induced histological alterations in liver tissues. Additionally, TA attenuated the APAP-induced production of nitric oxide (NO), reactive oxygen species (ROS), tumor necrosis factor-alpha (TNF-α), interleukin-1beta (IL-1β), and IL-6. Furthermore, the Western blot analysis showed that TA blocked the protein expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2), as well as the inhibition of nuclear factor-kappa B (NF-κB) and mitogen-activated protein kinases (MAPKs) activation in APAP-injured liver tissues. TA also retained the superoxidase dismutase (SOD), glutathione peroxidase (GPx), and catalase (CAT) in the liver. These results suggest that the hepatoprotective effects of TA may be related to its anti-inflammatory effect by decreasing thiobarbituric acid reactive substances (TBARS), iNOS, COX-2, TNF-α, IL-1β, and IL-6, and inhibiting NF-κB and MAPK activation. Antioxidative properties were also observed, as shown by heme oxygenase-1 (HO-1) induction in the liver, and decreases in lipid peroxides and ROS. Therefore, TA may be a potential therapeutic candidate for the prevention of APAP-induced liver injury by inhibiting oxidative stress and inflammation. Full article
(This article belongs to the Section Natural Products Chemistry)
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2627 KiB  
Article
Highly Stereoselective Synthesis of a Compound Collection Based on the Bicyclic Scaffolds of Natural Products
by Murali Annamalai, Stanimira Hristeva, Martyna Bielska, Raquel Ortega and Kamal Kumar
Molecules 2017, 22(5), 827; https://doi.org/10.3390/molecules22050827 - 18 May 2017
Cited by 11 | Viewed by 8041
Abstract
Despite the great contribution of natural products in the history of successful drug discovery, there are significant limitations that persuade the pharmaceutical industry to evade natural products in drug discovery research. The extreme scarcity as well as structural complexity of natural products renders [...] Read more.
Despite the great contribution of natural products in the history of successful drug discovery, there are significant limitations that persuade the pharmaceutical industry to evade natural products in drug discovery research. The extreme scarcity as well as structural complexity of natural products renders their practical synthetic access and further modifications extremely challenging. Although other alternative technologies, particularly combinatorial chemistry, were embraced by the pharmaceutical industry to get quick access to a large number of small molecules with simple frameworks that often lack three-dimensional complexity, hardly any success was achieved in the discovery of lead molecules. To acquire chemotypes beholding structural features of natural products, for instance high sp3 character, the synthesis of compound collections based on core-scaffolds of natural products presents a promising strategy. Here, we report a natural product inspired synthesis of six different chemotypes and their derivatives for drug discovery research. These bicyclic hetero- and carbocyclic scaffolds are highly novel, rich in sp3 features and with ideal physicochemical properties to display drug likeness. The functional groups on the scaffolds were exploited further to generate corresponding compound collections. Synthesis of two of these collections exemplified with ca. 350 compounds are each also presented. The whole compound library is being exposed to various biological screenings within the European Lead Factory consortium. Full article
(This article belongs to the Special Issue Natural Product Inspired Scaffolds Designs)
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2074 KiB  
Article
Cs2CO3-Initiated Trifluoro-Methylation of Chalcones and Ketones for Practical Synthesis of Trifluoromethylated Tertiary Silyl Ethers
by Cheng Dong, Xing-Feng Bai, Ji-Yuan Lv, Yu-Ming Cui, Jian Cao, Zhan-Jiang Zheng and Li-Wen Xu
Molecules 2017, 22(5), 769; https://doi.org/10.3390/molecules22050769 - 18 May 2017
Cited by 6 | Viewed by 8100
Abstract
It was found that 1,2-trifluoromethylation reactions of ketones, enones, and aldehydes were easily accomplished using the Prakash reagent in the presence of catalytic amounts of cesium carbonate, which represents an experimentally convenient, atom-economic process for this anionic trifluoromethylation of non-enolisable aldehydes and ketones. [...] Read more.
It was found that 1,2-trifluoromethylation reactions of ketones, enones, and aldehydes were easily accomplished using the Prakash reagent in the presence of catalytic amounts of cesium carbonate, which represents an experimentally convenient, atom-economic process for this anionic trifluoromethylation of non-enolisable aldehydes and ketones. Full article
(This article belongs to the Special Issue Progress in Silicon and Organosilicon Chemistry)
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621 KiB  
Article
New Glycosides from the Fruits of Nicandra physaloides
by Yan Liu, Hai-Bing Jiang, Zhen-Peng Xu, Yan-Gang Cheng, Shao-Wa Lv, Bing-You Yang, Hong-Wei Guo and Hai-Xue Kuang
Molecules 2017, 22(5), 828; https://doi.org/10.3390/molecules22050828 - 17 May 2017
Cited by 15 | Viewed by 5626
Abstract
Three new glycosides (1–3) and 15 known ones (4–18) were isolated and identified from the fruits of Nicandra physaloides. The structures of these compounds were established by 1D and 2D NMR spectra and HR-ESI-MS. [...] Read more.
Three new glycosides (1–3) and 15 known ones (4–18) were isolated and identified from the fruits of Nicandra physaloides. The structures of these compounds were established by 1D and 2D NMR spectra and HR-ESI-MS. The compounds (4–18) were the first time isolated from the Nicandra genus and they (except 8, 10, 14) exhibited inhibitions on the NO release of LPS-induced RAW 264.7 cells with IC50 values from 26.9 to 47.5 μM. Full article
(This article belongs to the Collection Bioactive Compounds)
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