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Anticancer Drug Discovery and Development II

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (31 July 2024) | Viewed by 22343

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Prof. Dr. Dorota Bartusik-Aebisher

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Department of Biochemistry and General Chemistry, Medical College, University of Rzeszów, 35-310 Rzeszów, Poland
Interests: MRI; MRS; cancer; biochemistry; drug delivery systems
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. David Aebisher

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Department of Photomedicine and Physical Chemistry, Medical College, University of Rzeszów, 35-310 Rzeszów, Poland
Interests: photochemistry; photobiology; medical chemistry
Special Issues, Collections and Topics in MDPI journals

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Dear Colleagues,

Photodynamic therapy, which uses a photosensitizer, light and oxygen to kill cancer cells, is an adjuvant therapy that can be applied following the removal of a tumor to kill residual cancer cells on the resection border. Despite the use of traditional treatment, which may include adjuvant photodynamic therapy, there is still a poor prognosis for cancer patients, since cancer cells have been detected at a distance up to 4 cm beyond the identifiable borders of the tumor and recurrent cancer usually develops adjacent to the resection borders. As there is evidence to suggest that is necessary to develop third-generation photosensitizers for precision photodynamic therapy, which can bind to targeted areas of difficult-to-reach microinvasion for cancer eradication, while preserving sensitive healthy tissues and improving patient outcomes. This Special Issue will be devoted to various aspects of photodynamic therapy; however, each of these aspects will oscillate around anticancer drug discovery and development. We welcome papers pertaining to the synthesis and applications of photosensitizers for photodynamic therapy, clinical trials with the use of photosensitizers, papers regarding the interactions of photosensitizers with drugs and vitamins, reviews and metanalyses, and original research. Precision photodynamic therapy, with the use of novel photosensitizers, represents a type of point source targeting. Ensuring precision in this therapy is important for killing cancer cells, and may help provide insights into treatment and diagnostics.

Prof. Dr. Dorota Bartusik-Aebisher
Prof. Dr. David Aebisher
Guest Editors

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Keywords

cancer
drug delivery
magnetic resonance imaging
diagnostics
treatment
photodynamic therapy
diagnostics
photosensitizers
photomedicine

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Published Papers (12 papers)

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25 pages, 6055 KiB

Open AccessArticle

Thiazolidinedione-Conjugated Lupeol Derivatives as Potent Anticancer Agents Through a Mitochondria-Mediated Apoptotic Pathway

by Siqi Deng, Yinxu Zhao, Xiaoshan Guo, Xian Hong, Gang Li, Yuchun Wang, Qingyi Li, Ming Bu and Ming Wang

Molecules 2024, 29(20), 4957; https://doi.org/10.3390/molecules29204957 - 20 Oct 2024

Viewed by 806

Abstract

To improve the potential of lupeol against cancer cells, a privileged structure, thiazolidinedione, was introduced into its C-3 hydroxy group with ester, piperazine-carbamate, or ethylenediamine as a linker, and three series of thiazolidinedione-conjugated compounds (6a–i, 9a–i, and 12a–i) were prepared. The target compounds were evaluated for their cytotoxic activities against human lung cancer A549, human breast cancer MCF-7, human hepatocarcinoma HepG2, and human hepatic LO2 cell lines, and the results revealed that most of the compounds displayed improved potency over lupeol. Compound 12i exhibited significant activity against the HepG2 cell line, with an IC₅₀ value of 4.40 μM, which is 9.9-fold more potent than lupeol (IC₅₀ = 43.62 μM). Mechanistic studies suggested that 12i could induce HepG2 cell apoptosis, as evidenced by AO/EB staining and annexin V-FITC/propidium iodide dual staining assays. Western blot analysis suggested that compound 12i can upregulate Bax expression, downregulate Bcl-2 expression, and activate the mitochondria-mediated apoptotic pathway. Collectively, compound 12i is worthy of further investigation to support the discovery of effective agents against cancer. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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16 pages, 7453 KiB

Open AccessArticle

Preparation and Tumor Inhibitory Activity of Tricin from Carex Meyeriana Kunth

by Baiji Cui, Jie Sun, Sheng Chang, Hongmei Zhang, Yawei Li, Xianmin Feng and Zengjun Guo

Molecules 2024, 29(19), 4530; https://doi.org/10.3390/molecules29194530 - 24 Sep 2024

Viewed by 425

Abstract

This study describes the purification and preparation of tricin (5, 7, 4-trihydroxy-3, 5-dimethoxyflavone) from Carex Meyeriana Kunth via adsorption and desorption using macroporous resins and high-performance liquid chromatography. Six resins were tested to evaluate the static adsorption and desorption capacities. The HPD-300 resin was selected as the adsorption material to enrich tricin because of its suitable adsorption and desorption capacities. Adsorption thermodynamics and kinetics were studied on HPD-300 resin, and the results agreed with the Langmuir model and quasi-second-order kinetics model, respectively. The parameters of the dynamic adsorption and desorption tests were then optimized. The purity of tricin increased from 2.6 mg/g to 45.1 mg/g with a recovery yield of 76.4% after purification using HPD-300 resin. Then, Prep-HPLC was used to further purify tricin. The purity of tricin reached 99.4%, with a recovery yield of 78.0% thereafter. Tricin exerts an inhibitory effect on the proliferation of various tumor cells, including gastric cancer SGC-7901 cells. It significantly suppresses cell colony formation while also altering cell cycle progression metabolism by decreasing the proportion of cells in the G₀/G₁ phase and increasing the proportion in the S and G₂/M phases. Additionally, tricin affects the efficiency of SGC-7901 cell lactate production, ATP content, and glucose uptake. These findings suggest that tricin may impede tumor cell proliferation through its impact on cell cycle progression and energy metabolism. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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25 pages, 9813 KiB

Open AccessArticle

The Importance of Biotinylation for the Suitability of Cationic and Neutral Fourth-Generation Polyamidoamine Dendrimers as Targeted Drug Carriers in the Therapy of Glioma and Liver Cancer

by Łukasz Uram, Magdalena Twardowska, Żaneta Szymaszek, Maria Misiorek, Andrzej Łyskowski, Zuzanna Setkowicz, Zuzanna Rauk and Stanisław Wołowiec

Molecules 2024, 29(18), 4293; https://doi.org/10.3390/molecules29184293 - 10 Sep 2024

Viewed by 1122

Abstract

In this study, we hypothesized that biotinylated and/or glycidol-flanked fourth-generation polyamidoamine (PAMAM G4) dendrimers could be a tool for efficient drug transport into glioma and liver cancer cells. For this purpose, native PAMAM (G4) dendrimers, biotinylated (G4B), glycidylated (G4gl), and biotinylated and glycidylated (G4Bgl), were synthesized, and their cytotoxicity, uptake, and accumulation in vitro and in vivo were studied in relation to the transport mediated by the sodium-dependent multivitamin transporter (SMVT). The studies showed that the human temozolomide-resistant glioma cell line (U-118 MG) and hepatocellular carcinoma cell line (HepG2) indicated a higher amount of SMVT than human HaCaT keratinocytes (HaCaTs) used as a model of normal cells. The G4gl and G4Bgl dendrimers were highly biocompatible in vitro (they did not affect proliferation and mitochondrial activity) against HaCaT and U-118 MG glioma cells and in vivo (against Caenorhabditis elegans and Wistar rats). The studied compounds penetrated efficiently into all studied cell lines, but inconsistently with the uptake pattern observed for biotin and disproportionately for the level of SMVT. G4Bgl was taken up and accumulated after 48 h to the highest degree in glioma U-118 MG cells, where it was distributed in the whole cell area, including the nuclei. It did not induce resistance symptoms in glioma cells, unlike HepG2 cells. Based on studies on Wistar rats, there are indications that it can also penetrate the blood–brain barrier and act in the central nervous system area. Therefore, it might be a promising candidate for a carrier of therapeutic agents in glioma therapy. In turn, visualization with a confocal microscope showed that biotinylated G4B penetrated efficiently into the body of C. elegans, and it may be a useful vehicle for drugs used in anthelmintic therapy. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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23 pages, 42125 KiB

Open AccessArticle

Integration of Transcriptomics and Metabolomics Reveals the Antitumor Mechanism of Protopanaxadiol Triphenylphosphate Derivative in Non-Small-Cell Lung Cancer

by Liu Han, Xingbo Bian, Xiangyu Ma, Ting Ren, Yawei Li, Lijing Huang, Zebo Tang, Liancong Gao, Sheng Chang and Xin Sun

Molecules 2024, 29(17), 4275; https://doi.org/10.3390/molecules29174275 - 9 Sep 2024

Viewed by 857

Abstract

The objective of this study was to enhance the membrane permeability and anticancer effectiveness of (20S)-protopanaxadiol (PPD) by introducing triphenylphosphonium into the OH group at the C-3 site. This study shows that the anti-proliferation activity of CTPPPPD, with an IC50 value of 1.65 ± 0.10 μmol/L, was 33-times better than that of PPD (with an IC50 value of 54.56 ± 4.56 μmol/L) and superior to that of cisplatin (with an IC50 value of 1.82 ± 0.25 μmol/L) against A549 cells. Biological examinations suggested that CTPPPPD treatment reduced the growth rate of A549 cells, increased the permeability of cell membranes, and changed the structure of chromosomal DNA in a concentration-dependent manner. Annexin V/PI assay and flow cytometry were employed to detect the effect of CTPPPPD on the apoptosis of A549 cells. The results showed that CTPPPPD could induce the apoptosis of A549 cells, and the apoptosis rate of A549 cells treated with 0, 1.0, 2.0, and 4.0 μM of CTPPPPD for 24 h was 0%, 4.9%, 12.7%, and 31.0%, respectively. The integration of transcriptomics and metabolomics provided a systematic and detailed perspective on the induced antitumor mechanisms. A combined analysis of DEGs and DAMs suggested that they were primarily involved in the central carbon metabolism pathway in cancer, as well as the metabolism of aminoacyl-tRNA biosynthesis, alanine, aspartate, and glutamate. Central carbon metabolism in cancer-related genes, i.e., SLC16A3, FGFR3, LDHA, PGAM1, and SLC2A1, significantly reduced after treatment with CTPPPPD. In particular, the dominant mechanism responsible for total antitumor activity may be attributed to perturbations in the PI3K-AKT, MAPK, and P53 pathways. The findings derived from transcriptomics and metabolomics were empirically confirmed through q-PCR and molecular docking. Further analyses revealed that CTPPPPD could be a promising lead for the development of protopanaxadiol for non-small-cell lung cancer (NSCLC) drugs. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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16 pages, 10592 KiB

Open AccessArticle

Novel 9-Methylanthracene Derivatives as p53 Activators for the Treatment of Glioblastoma Multiforme

by Yuxin Feng, Yingjie Wang, Xiaoxue Li, Ziqiang Sun, Sihan Qiang, Hongbo Wang and Yi Liu

Molecules 2024, 29(10), 2396; https://doi.org/10.3390/molecules29102396 - 19 May 2024

Viewed by 1140

Abstract

Glioblastoma multiforme, a highly aggressive and lethal brain tumor, is a substantial clinical challenge and a focus of increasing concern globally. Hematological toxicity and drug resistance of first-line drugs underscore the necessity for new anti-glioma drug development. Here, 43 anthracenyl skeleton compounds as p53 activator XI-011 analogs were designed, synthesized, and evaluated for their cytotoxic effects. Five compounds (13d, 13e, 14a, 14b, and 14n) exhibited good anti-glioma activity against U87 cells, with IC₅₀ values lower than 2 μM. Notably, 13e showed the best anti-glioma activity, with an IC₅₀ value up to 0.53 μM, providing a promising lead compound for new anti-glioma drug development. Mechanistic analyses showed that 13e suppressed the MDM4 protein expression, upregulated the p53 protein level, and induced cell cycle arrest at G2/M phase and apoptosis based on Western blot and flow cytometry assays. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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11 pages, 1374 KiB

Open AccessArticle

Design and Evaluation of NSAID Derivatives as AKR1C3 Inhibitors for Breast Cancer Treatment through Computer-Aided Drug Design and In Vitro Analysis

by Victoria Fonseca-Benítez, Paola Acosta-Guzmán, Juan Esteban Sánchez, Zaira Alarcón, Ronald Andrés Jiménez and James Guevara-Pulido

Molecules 2024, 29(8), 1802; https://doi.org/10.3390/molecules29081802 - 16 Apr 2024

Viewed by 1371

Abstract

Breast cancer is a major global health issue, causing high incidence and mortality rates as well as psychological stress for patients. Chemotherapy resistance is a common challenge, and the Aldo-keto reductase family one-member C3 enzyme is associated with resistance to anthracyclines like doxorubicin. Recent studies have identified celecoxib as a potential treatment for breast cancer. Virtual screening was conducted using a quantitative structure–activity relationship model to develop similar drugs; this involved backpropagation of artificial neural networks and structure-based virtual screening. The screening revealed that the C-6 molecule had a higher affinity for the enzyme (−11.4 kcal/mol), a lower half-maximal inhibitory concentration value (1.7 µM), and a safer toxicological profile than celecoxib. The compound C-6 was synthesized with an 82% yield, and its biological activity was evaluated. The results showed that C-6 had a more substantial cytotoxic effect on MCF-7 cells (62%) compared to DOX (63%) and celecoxib (79.5%). Additionally, C-6 had a less harmful impact on healthy L929 cells than DOX and celecoxib. These findings suggest that C-6 has promising potential as a breast cancer treatment. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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13 pages, 3201 KiB

Open AccessArticle

Carbon Dots Derived from Tea Polyphenols as Photosensitizers for Photodynamic Therapy

by Yuxiang Yang, Haizhen Ding, Zijian Li, Antonio Claudio Tedesco and Hong Bi

Molecules 2022, 27(23), 8627; https://doi.org/10.3390/molecules27238627 - 6 Dec 2022

Cited by 23 | Viewed by 2941

Abstract

Photodynamic therapy (PDT) has become an emerging cancer treatment method. Choosing the photosensitizer (PS) compounds is one of the essential factors that can influence the PDT effect and action. Carbon dots (CDs) have shown great potential as photosensitizers in PDT of cancers due to their excellent biocompatibility and high generation of reactive oxygen species (ROS). Here, we used tea polyphenol as raw material for synthesized tea polyphenol carbon dots (T−CDs) that show dual emission bands of red and blue fluorescence and can efficiently generate hydroxyl radicals (OH) under mildly visible irradiation with a LED light (400–500 nm, 15 mW cm⁻²). The extremely low cytotoxicity and excellent biocompatibility of T−CDs without light irradiation were tested using MTT and hemolytic assay. Further, T−CDs have been shown by in vivo experiments, using a mouse breast cancer cell line (4T1) subcutaneously injected in the back of the mouse buttock as a model, to effectively inhibit the tumor cell proliferation in solid tumors and show an excellent PDT effect. In addition, pathological sections of the mice tissues after further treatment showed that the T−CDs had no apparent impact on the major organs of the mice and did not produce any side effect lesions. This work demonstrates that the as−synthesized T−CDs has the potential to be used as a PS in cancer treatment. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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18 pages, 3366 KiB

Open AccessFeature PaperArticle

The Lebanese Red Algae Jania rubens: Promising Biomolecules against Colon Cancer Cells

by Mariam Rifi, Zeina Radwan, Reem AlMonla, Ziad Fajloun, Jean Marc Sabatier, Achraf Kouzayha, Marwan El-Sabban, Hiba Mawlawi and Zeina Dassouki

Molecules 2022, 27(19), 6617; https://doi.org/10.3390/molecules27196617 - 5 Oct 2022

Cited by 3 | Viewed by 3127

Abstract

Colorectal cancer (CRC) is ranked the second most lethal type of tumor globally. Thus, developing novel anti-cancer therapeutics that are less aggressive and more potent is needed. Recently, natural bioactive molecules are gaining interest as complementary and supportive antineoplastic treatments due to their safety, effectiveness, and low cost. Jania rubens (J. rubens) is a red coral seaweed abundant in the Mediterranean and bears a significant pharmacological essence. Despite its therapeutic potential, the natural biomolecules extracted from this alga are poorly identified. In this study, the proximal analysis revealed high levels of total ash content (66%), 11.3% proteins, 14.5% carbohydrates, and only 4.5% lipids. The elemental identification showed magnesium and calcium were high among its macro minerals, (24 ± 0.5 mg/g) and (33 ± 0.5 mg/g), respectively. The Chlorophyll of J. rubens was dominated by other pigments with (0.82 ± 0.02 mg/g). A 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay identified effective antioxidant activity in various J. rubens extracts. More importantly, a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) tetrazolium reduction and wound healing assays indicate that organic extracts from J. rubens significantly counteract the proliferation of colon cancer cell lines (HCT-116 and HT-29) and inhibit their migratory and metastatic properties in a dose and time-dependent manner. Overall, this study provides insight into the physicochemical properties of red seaweed, J. rubens, and identifies its significant antioxidant, cytotoxic, and anti-migratory potential on two colorectal cell lines, HCT-116 and HT-29. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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20 pages, 3786 KiB

Open AccessArticle

Photon Upconversion in Small Molecules

by Dorota Bartusik-Aebisher, Mateusz Mielnik, Grzegorz Cieślar, Ewa Chodurek, Aleksandra Kawczyk-Krupka and David Aebisher

Molecules 2022, 27(18), 5874; https://doi.org/10.3390/molecules27185874 - 10 Sep 2022

Cited by 3 | Viewed by 2918

Abstract

Upconversion (UC) is a process that describes the emission of shorter-wavelength light compared to that of the excitation source. Thus, UC is also referred to as anti-Stokes emission because the excitation wavelength is longer than the emission wavelength. UC materials are used in many fields, from electronics to medicine. The objective of using UC in medical research is to synthesize upconversion nanoparticles (UCNPs) composed of a lanthanide core with a coating of adsorbed dye that will generate fluorescence after excitation with near-infrared light to illuminate deep tissue. Emission occurs in the visible and UV range, and excitation mainly in the near-infrared spectrum. UC is observed for lanthanide ions due to the arrangement of their energy levels resulting from f-f electronic transitions. Organic compounds and transition metal ions are also able to form the UC process. Biocompatible UCNPs are designed to absorb infrared light and emit visible light in the UC process. Fluorescent dyes are adsorbed to UCNPs and employed in PDT to achieve deeper tissue effects upon irradiation with infrared light. Fluorescent UCNPs afford selectivity as they may be activated only by illumination of an area of diseased tissue, such as a tumor, with infrared light and are by themselves atoxic in the absence of infrared light. UCNP constructs can be monitored as to their location in the body and uptake by cancer cells, aiding in evaluation of exact doses required to treat the targeted cancer. In this paper, we review current research in UC studies and UCNP development. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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Review

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16 pages, 1324 KiB

Open AccessReview

Anti-Cancer Strategy Based on Changes in the Role of Autophagy Depending on the Survival Environment and Tumorigenesis Stages

by Michael Lee and Hye-Gyo Kim

Molecules 2024, 29(21), 5134; https://doi.org/10.3390/molecules29215134 - 30 Oct 2024

Viewed by 182

Abstract

Autophagy is a crucial mechanism for recycling intracellular materials, and under normal metabolic conditions, it is maintained at low levels in cells. However, when nutrients are deficient or under hypoxic conditions, the level of autophagy significantly increases. Particularly in cancer cells, which grow more rapidly than normal cells and tend to grow in a three-dimensional manner, cells inside the cell mass often face limited oxygen supply, leading to inherently higher levels of autophagy. Therefore, the initial development of anticancer drugs targeting autophagy was based on a strategy to suppress these high levels of autophagy. However, anticancer drugs that inhibit autophagy have not shown promising results in clinical trials, as it has been revealed that autophagy does not always play a role that favors cancer cell survival. Hence, this review aims to suggest anticancer strategies based on the changes in the role of autophagy according to survival conditions and tumorigenesis stage. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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16 pages, 1341 KiB

Open AccessReview

The Use of Photodynamic Therapy in the Treatment of Brain Tumors—A Review of the Literature

by Dorota Bartusik-Aebisher, Aleksandra Żołyniak, Edyta Barnaś, Agnieszka Machorowska-Pieniążek, Piotr Oleś, Aleksandra Kawczyk-Krupka and David Aebisher

Molecules 2022, 27(20), 6847; https://doi.org/10.3390/molecules27206847 - 13 Oct 2022

Cited by 25 | Viewed by 3623

Abstract

The treatment of neoplastic disease of the brain is still a challenge for modern medicine. Therefore, advanced methodologies are needed that can rationally and successfully contribute to the early diagnosis of primary and metastatic tumors growing within the brain. Photodynamic therapy (PDT) seems to be a valuable method of treatment for precancerous and cancerous lesions including brain tumors. The main advantage of PDT is its high efficiency, minimal invasiveness and no serious side effects, compared with chemotherapy and radiotherapy. This review was conducted through a comprehensive search of articles, scientific information databases and the websites of organizations dealing with cancer treatment. Key points from clinical trials conducted by other researchers are also discussed. The common databases such as PubMed, Google Scholar, EBSCO, Scopus, and Elsevier were used. Articles in the English language of reliable credibility were mainly analyzed. The type of publications considered included clinical and preclinical studies, systematic reviews, and case reports. Based on these collected materials, we see that scientists have already demonstrated the potential of PDT application in the field of brain tumors. Therefore, in this review, the treatment of neoplasm of the Central Nervous System (CNS) and the most common tumor, glioblastoma multiforme (GBM), have been explored. In addition, an overview of the general principles of PDT, as well as the mechanism of action of the therapy as a therapeutic platform for brain tumors, is described. The research was carried out in June 2022. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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25 pages, 2165 KiB

Open AccessReview

Multinuclear MRI in Drug Discovery

by Dorota Bartusik-Aebisher, Zuzanna Bober, Jolanta Zalejska-Fiolka, Aleksandra Kawczyk-Krupka and David Aebisher

Molecules 2022, 27(19), 6493; https://doi.org/10.3390/molecules27196493 - 1 Oct 2022

Cited by 7 | Viewed by 2680

Abstract

The continuous development of magnetic resonance imaging broadens the range of applications to newer areas. Using MRI, we can not only visualize, but also track pharmaceutical substances and labeled cells in both in vivo and in vitro tests. ¹H is widely used in the MRI method, which is determined by its high content in the human body. The potential of the MRI method makes it an excellent tool for imaging the morphology of the examined objects, and also enables registration of changes at the level of metabolism. There are several reports in the scientific publications on the use of clinical MRI for in vitro tracking. The use of multinuclear MRI has great potential for scientific research and clinical studies. Tuning MRI scanners to the Larmor frequency of a given nucleus, allows imaging without tissue background. Heavy nuclei are components of both drugs and contrast agents and molecular complexes. The implementation of hyperpolarization techniques allows for better MRI sensitivity. The aim of this review is to present the use of multinuclear MRI for investigations in drug delivery. Full article

(This article belongs to the Special Issue Anticancer Drug Discovery and Development II)

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