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Molecules, Volume 17, Issue 5 (May 2012), Pages 4770-6178

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Open AccessCommunication Chiral Bis(Imidazolidine)Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates
Molecules 2012, 17(5), 6170-6178; https://doi.org/10.3390/molecules17056170
Received: 27 April 2012 / Revised: 18 May 2012 / Accepted: 21 May 2012 / Published: 24 May 2012
Cited by 41 | PDF Full-text (284 KB)
Abstract
[3+2] Cycloaddition of azomethine imines with electron-deficient terminal alkynes was smoothly catalyzed by a chiral bis(imidazolidine)pyridine-CuOAc complex to give bicyclic pyrazolo[1,2-a]pyrazolone derivatives with up to 74% ee. Full article
(This article belongs to the Special Issue Asymmetric Catalysis)
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Open AccessArticle Chemical Constituents of the Ethyl Acetate Extract of Belamcanda chinensis (L.) DC Roots and Their Antitumor Activities
Molecules 2012, 17(5), 6156-6169; https://doi.org/10.3390/molecules17056156
Received: 19 April 2012 / Revised: 8 May 2012 / Accepted: 14 May 2012 / Published: 24 May 2012
Cited by 37 | PDF Full-text (539 KB)
Abstract
An activity-directed fractionation and purification process was used to isolate antitumor compounds from the roots of Belamcanda chinensis (L.) DC. The ethyl acetate extract showed greater antitumor activities than the other extracts, consequently leading to the isolation of 18 compounds identified as b-
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An activity-directed fractionation and purification process was used to isolate antitumor compounds from the roots of Belamcanda chinensis (L.) DC. The ethyl acetate extract showed greater antitumor activities than the other extracts, consequently leading to the isolation of 18 compounds identified as b-sitosterol (1), dausterol (2), quercetin (3), kampferol (4), shikimic acid (5), gallic acid (6), ursolic acid (7), betulin (8), betulonic acid (9), betulone (10), tectoridin (11), irisflorentin (12), 4′,5,6-trihydroxy-7-methoxyisoflavone (13), tectorigenin (14), irilins A (15), iridin (16), irigenin (17), and iristectongenin A (18). Compounds 310, 13, and 15 were isolated from B. chinensis for the first time. Compounds 4 and 710 showed potent cytotoxic activities against PC3, MGC-803, Bcap-37, and MCF-7 cell lines. The mechanism of the antitumor action of compound 7 was preliminarily investigated through acridine orange/ethidium bromide (AO/EB) staining, Hoechst 33258 staining, and terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) assay, which indicated the growth inhibition of MGC-803 cells via the induction of tumor cell apoptosis. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Ipomoea aquatica Extract Shows Protective Action Against Thioacetamide-Induced Hepatotoxicity
Molecules 2012, 17(5), 6146-6155; https://doi.org/10.3390/molecules17056146
Received: 1 April 2012 / Revised: 20 April 2012 / Accepted: 23 April 2012 / Published: 22 May 2012
Cited by 16 | PDF Full-text (513 KB)
Abstract
In the Indian system of traditional medicine (Ayurveda) it is recommended to consume Ipomoea aquatica to mitigate disorders like jaundice. In this study, the protective effects of ethanol extract of I. aquatica against liver damage were evaluated in thioacetamide (TAA)-induced chronic hepatotoxicity in
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In the Indian system of traditional medicine (Ayurveda) it is recommended to consume Ipomoea aquatica to mitigate disorders like jaundice. In this study, the protective effects of ethanol extract of I. aquatica against liver damage were evaluated in thioacetamide (TAA)-induced chronic hepatotoxicity in rats. There was no sign of toxicity in the acute toxicity study, in which Sprague-Dawley (SD) rats were orally fed with I. aquatica (250 and 500 mg/kg) for two months along with administration of TAA (i.p injection 200 mg/kg three times a week for two months). The results showed that the treatment of I. aquatica significantly lowered the TAA-induced serum levels of hepatic enzyme markers (ALP, ALT, AST, protein, albumin, bilirubin and prothrombin time). The hepatic content of activities and expressions SOD and CAT that were reduced by TAA were brought back to control levels by the plant extract supplement. Meanwhile, the rise in MDA level in the TAA receiving groups also were significantly reduced by I. aquatica treatment. Histopathology of hepatic tissues by H&E and Masson trichrome stains displayed that I. aquatica has reduced the incidence of liver lesions, including hepatic cells cloudy swelling, infiltration, hepatic necrosis, and fibrous connective tissue proliferation induced by TAA in rats. Therefore, the results of this study show that the protective effect of I. aquatica in TAA-induced liver damage might be contributed to its modulation on detoxification enzymes and its antioxidant and free radical scavenger effects. Moreover, it confirms a scientific basis for the traditional use of I. aquatica for the treatment of liver disorders. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle A QSAR Study of Environmental Estrogens Based on a Novel Variable Selection Method
Molecules 2012, 17(5), 6126-6145; https://doi.org/10.3390/molecules17056126
Received: 10 March 2012 / Revised: 19 April 2012 / Accepted: 26 April 2012 / Published: 21 May 2012
Cited by 10 | PDF Full-text (718 KB) | Supplementary Files
Abstract
A large number of descriptors were employed to characterize the molecular structure of 53 natural, synthetic, and environmental chemicals which are suspected of disrupting endocrine functions by mimicking or antagonizing natural hormones and may thus pose a serious threat to the health of
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A large number of descriptors were employed to characterize the molecular structure of 53 natural, synthetic, and environmental chemicals which are suspected of disrupting endocrine functions by mimicking or antagonizing natural hormones and may thus pose a serious threat to the health of humans and wildlife. In this work, a robust quantitative structure-activity relationship (QSAR) model with a novel variable selection method has been proposed for the effective estrogens. The variable selection method is based on variable interaction (VSMVI) with leave-multiple-out cross validation (LMOCV) to select the best subset. During variable selection, model construction and assessment, the Organization for Economic Co-operation and Development (OECD) principles for regulation of QSAR acceptability were fully considered, such as using an unambiguous multiple-linear regression (MLR) algorithm to build the model, using several validation methods to assessment the performance of the model, giving the define of applicability domain and analyzing the outliers with the results of molecular docking. The performance of the QSAR model indicates that the VSMVI is an effective, feasible and practical tool for rapid screening of the best subset from large molecular descriptors. Full article
(This article belongs to the Special Issue QSAR and Its Applications)
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Open AccessArticle Preussianone, a New Flavanone-Chromone Biflavonoid from Garcinia preussii Engl.
Molecules 2012, 17(5), 6114-6125; https://doi.org/10.3390/molecules17056114
Received: 20 March 2012 / Revised: 26 April 2012 / Accepted: 14 May 2012 / Published: 21 May 2012
Cited by 20 | PDF Full-text (273 KB)
Abstract
A new flavanone-chromone biflavonoid, preussianone (1), has been isolated from the leaves of Garcinia preussii, along with four known biflavonoids. The absolute stereostructures were elucidated by chemical, spectroscopic, and chiroptical methods. The biological properties of the new biflavonoid against several
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A new flavanone-chromone biflavonoid, preussianone (1), has been isolated from the leaves of Garcinia preussii, along with four known biflavonoids. The absolute stereostructures were elucidated by chemical, spectroscopic, and chiroptical methods. The biological properties of the new biflavonoid against several bacterial strains were evaluated. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents
Molecules 2012, 17(5), 6100-6113; https://doi.org/10.3390/molecules17056100
Received: 5 April 2012 / Revised: 5 May 2012 / Accepted: 7 May 2012 / Published: 21 May 2012
Cited by 16 | PDF Full-text (273 KB) | Supplementary Files
Abstract
In the present work, we report the synthesis and in vitro anticancer and antimicrobial activity evaluation of a new series of 1-substituted-β-carboline derivatives bearing a 4-benzylidene-4H-oxazol-5-one unity at C-3. The compound 2-[1-(4-methoxyphenyl)-9H-β-carbolin-3-yl]-4-(benzylidene)-4H-oxazol-5-one (11) was the
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In the present work, we report the synthesis and in vitro anticancer and antimicrobial activity evaluation of a new series of 1-substituted-β-carboline derivatives bearing a 4-benzylidene-4H-oxazol-5-one unity at C-3. The compound 2-[1-(4-methoxyphenyl)-9H-β-carbolin-3-yl]-4-(benzylidene)-4H-oxazol-5-one (11) was the most active derivative, exhibiting a potent cytotoxic activity against glioma (U251), prostate (PC-3) and ovarian (OVCAR-03) cancer cell lines with IC50 values of 0.48, 1.50 and 1.07 µM, respectively. An in silico study of the ADME properties of the novel synthesized β-carboline derivatives was also performed. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessReview Synthesis and Bioactivity of Secondary Metabolites from Marine Sponges Containing Dibrominated Indolic Systems
Molecules 2012, 17(5), 6083-6099; https://doi.org/10.3390/molecules17056083
Received: 20 April 2012 / Revised: 14 May 2012 / Accepted: 15 May 2012 / Published: 21 May 2012
Cited by 37 | PDF Full-text (293 KB)
Abstract
Marine sponges. (e.g., Hyrtios sp., Dragmacidin sp., Aglophenia pleuma, Aplidium cyaneum, Aplidium meridianum.) produce bioactive secondary metabolites involved in their defence mechanisms. Recently it was demonstrated that several of those compounds show a large variety of biological activities against different
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Marine sponges. (e.g., Hyrtios sp., Dragmacidin sp., Aglophenia pleuma, Aplidium cyaneum, Aplidium meridianum.) produce bioactive secondary metabolites involved in their defence mechanisms. Recently it was demonstrated that several of those compounds show a large variety of biological activities against different human diseases with possible applications in medicinal chemistry and in pharmaceutical fields, especially related to the new drug development process. Researchers have focused their attention principally on secondary metabolites with anti-cancer and cytotoxic activities. A common target for these molecules is the cytoskeleton, which has a central role in cellular proliferation, motility, and profusion involved in the metastatic process associate with tumors. In particular, many substances containing brominated indolic rings such as 5,6-dibromotryptamine, 5,6-dibromo-N-methyltryptamine, 5,6-dibromo-N-methyltryptophan (dibromoabrine), 5,6-dibromo-N,N-dimethyltryptamine and 5,6-dibromo-L-hypaphorine isolated from different marine sources, have shown anti-cancer activity, as well as antibiotic and anti-inflammatory properties. Considering the structural correlation between endogenous monoamine serotonin with marine indolic alkaloids 5,6-dibromoabrine and 5,6-dibromotryptamine, a potential use of some dibrominated indolic metabolites in the treatment of depression-related pathologies has also been hypothesized. Due to the potential applications in the treatment of various diseases and the increasing demand of these compounds for biological assays and the difficult of their isolation from marine sources, we report in this review a series of recent syntheses of marine dibrominated indole-containing products. Full article
(This article belongs to the collection Bioactive Compounds)
Open AccessArticle Antioxidant, Antimicrobial and Tyrosinase Inhibitory Activities of Xanthones Isolated from Artocarpus obtusus F.M. Jarrett
Molecules 2012, 17(5), 6071-6082; https://doi.org/10.3390/molecules17056071
Received: 5 March 2012 / Revised: 17 April 2012 / Accepted: 20 April 2012 / Published: 21 May 2012
Cited by 24 | PDF Full-text (250 KB)
Abstract
One of the most promising plants in biological screening test results of thirteen Artocarpus species was Artocarpus obtusus FM Jarrett and detailed phytochemical investigation of powdered dried bark of the plant has led to the isolation and identification of three xanthones; pyranocycloartobiloxanthone A
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One of the most promising plants in biological screening test results of thirteen Artocarpus species was Artocarpus obtusus FM Jarrett and detailed phytochemical investigation of powdered dried bark of the plant has led to the isolation and identification of three xanthones; pyranocycloartobiloxanthone A (1), dihydroartoindonesianin C (2) and pyranocycloartobiloxanthone B (3). These compounds were screened for antioxidant, antimicrobial and tyrosinase inhibitory activities. Pyranocycloartobiloxanthone A (1) exhibited a strong free radical scavenger towards DPPH free radicals with IC50 value of 2 µg/mL with prominent discoloration observed in comparison with standard ascorbic acid, α-tocopherol and quercetin, The compound also exhibited antibacterial activity against methicillin resistant Staphylococcus aureus (ATCC3359) and Bacillus subtilis (clinically isolated) with inhibition zone of 20 and 12 mm, respectively. However the other two xanthones were found to be inactive. For the tyrosinase inhibitory activity, again compound (1) displayed strong activity comparable with the standard kojic acid. Full article
(This article belongs to the Section Medicinal Chemistry)
Open AccessArticle Physicochemical Characterization and Cytotoxic Activity Evaluation of Hydroxymethylferrocene:β-Cyclodextrin Inclusion Complex
Molecules 2012, 17(5), 6056-6070; https://doi.org/10.3390/molecules17056056
Received: 24 April 2012 / Revised: 14 May 2012 / Accepted: 15 May 2012 / Published: 21 May 2012
Cited by 16 | PDF Full-text (662 KB)
Abstract
An inclusion complex of hydroxymethylferrocene (FeMeOH) with β-cyclodextrin (β-CD) was prepared in the solid state by different techniques such as physical mixture, coprecipitation, kneading and freeze-drying. The formation of the inclusion complex was confirmed by X-ray Powder Diffractometry and Fourier Transform-Infrared spectroscopy. In
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An inclusion complex of hydroxymethylferrocene (FeMeOH) with β-cyclodextrin (β-CD) was prepared in the solid state by different techniques such as physical mixture, coprecipitation, kneading and freeze-drying. The formation of the inclusion complex was confirmed by X-ray Powder Diffractometry and Fourier Transform-Infrared spectroscopy. In aqueous solution, the 1:1 stoichiometry was established by a Job plot. The inclusion complex formation was also investigated by NMR and the stability constant (Kb) of the complex was determined to be 478 M−1, which is in agreement with that obtained with UV-Vis tritation (Kb = 541.3 M−1). The phase solubility study showed a diagram classified as BS type and that the solubility of FeMeOH was slightly increased in the presence of β-CD. Furthermore, utilizing phase solubility diagram data, the Kb was estimated to be equal to 528.0 M−1. The cytotoxic activity of FeMeOH and its complexation product with β-CD was determined using the MTT-assay on MDA-MB-231 cell line, showing that the inclusion complex has a higher capability of inhibiting cell growth compared to that of pure FeMeOH. Full article
Open AccessArticle Effect of Soluble Sulfide on the Activity of Luminescent Bacteria
Molecules 2012, 17(5), 6046-6055; https://doi.org/10.3390/molecules17056046
Received: 23 February 2012 / Revised: 11 May 2012 / Accepted: 14 May 2012 / Published: 21 May 2012
Cited by 5 | PDF Full-text (476 KB)
Abstract
Sulfide is an important water pollutant widely found in industrial waste water that has attracted much attention. S2−, as a weak acidic anion, is easy hydrolyzed to HS and H2S in aqueous solution. In this study, biological tests
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Sulfide is an important water pollutant widely found in industrial waste water that has attracted much attention. S2−, as a weak acidic anion, is easy hydrolyzed to HS and H2S in aqueous solution. In this study, biological tests were performed to establish the toxicity of sulfide solutions on luminescent bacteria. Considering the sulfide solution was contained three substances—S2−, HS and H2S—the toxicity test was performed at different pH values to investigate which form of sulfide increased light emission and which reduced light emission. It was shown that the EC50 values were close at pH 7.4, 8.0 and 9.0 which were higher than pH 5 and 10. The light emission and sulfide concentrations displayed an inverse exponential dose-response relationship within a certain concentration range at pH 5, 6.5 and 10. The same phenomenon occurred for the high concentration of sulfide at pH 7.4, 8 and 9, in which the concentration of sulfide was HS >> H2S > S2−. An opposite hormesis-effect appeared at the low concentrations of sulfide. Full article
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Open AccessArticle Protective Effect of T. violacea Rhizome Extract Against Hypercholesterolemia-Induced Oxidative Stress in Wistar Rats
Molecules 2012, 17(5), 6033-6045; https://doi.org/10.3390/molecules17056033
Received: 29 March 2012 / Revised: 27 April 2012 / Accepted: 28 April 2012 / Published: 21 May 2012
Cited by 19 | PDF Full-text (368 KB)
Abstract
The present study examines the effect of methanolic extract of T. violacea rhizomes on high cholesterol (2%) diet fed rats (HCD). At the end of 4 weeks, serum total protein, albumin, reduced glutathione (GSH), and markers of oxidative stress viz., catalase (CAT), superoxide
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The present study examines the effect of methanolic extract of T. violacea rhizomes on high cholesterol (2%) diet fed rats (HCD). At the end of 4 weeks, serum total protein, albumin, reduced glutathione (GSH), and markers of oxidative stress viz., catalase (CAT), superoxide dismutase (SOD), thiobarbituric acid reactive substances (TBARS—a marker of lipid peroxidation), glutathione-S-transferase (GST) and glutathione peroxidase (GPx) in the serum, aorta, liver and heart of HCD and normal rats were assessed and compared. A significant (p < 0.05) elevation in TBARS, and a reduction (p < 0.05) in serum total protein, albumin, GSH and antioxidant enzyme activities was observed in tissues of HCD fed rats compared with the normal group. Co-administration of crude extracts of T. violacea rhizomes protected the liver, heart, serum and aorta against HCD-induced lipid peroxidation in a dose dependant manner. The activities of the extract (500 mg/kg) compared favorably with gemfibrozil. The extracts also protected against HCD-induced reduction in serum total protein, GSH and restored the activities of antioxidant tissues (liver, heart and aorta) enzymes to near normal values. This result suggested that consumption of T. violacea rhizome may help to protect against hypercholesterolemia- induced oxidative stress diseases in the heart and liver. Full article
Open AccessArticle Chemical Composition of Artemisia annua L. Leaves and Antioxidant Potential of Extracts as a Function of Extraction Solvents
Molecules 2012, 17(5), 6020-6032; https://doi.org/10.3390/molecules17056020
Received: 12 April 2012 / Revised: 9 May 2012 / Accepted: 11 May 2012 / Published: 21 May 2012
Cited by 21 | PDF Full-text (237 KB)
Abstract
This study was conducted to investigate the chemical and nutritional composition of Artemisia annua leaves in addition to determination of antioxidant potential of their extracts prepared in different solvents. Chemical composition was determined by quantifying fat, protein, carbohydrate, fiber, tocopherol, phytate, and tannin
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This study was conducted to investigate the chemical and nutritional composition of Artemisia annua leaves in addition to determination of antioxidant potential of their extracts prepared in different solvents. Chemical composition was determined by quantifying fat, protein, carbohydrate, fiber, tocopherol, phytate, and tannin contents. Extraction of A. annua leaves, for antioxidant potential evaluation, was carried out using five solvents of different polarities, i.e., hexane, chloroform, ethyl acetate, methanol and water. Antioxidant potential was evaluated by estimating total phenolic (TPC), flavonoid (TFC) contents, ferric reducing antioxidant power (FRAP), Trolox equivalent antioxidant capacity (TEAC), DPPH radical scavenging activity and lipid peroxidation. Efficiency of different solvents was compared for the yield of antioxidant extracts from leaf samples and a clear variation was observed. The highest TPC, TFC, TEAC, DPPH radical scavenging and lowest lipid peroxidation were observed in MeOH extracts, whereas aqueous extract exhibited high ferric reducing antioxidant power; suggesting MeOH to be the most favorable extractant. Full article
(This article belongs to the Section Natural Products Chemistry)
Open AccessArticle Green and Highly Efficient Synthesis of 2-Arylbenzothiazoles Using Glycerol without Catalyst at Ambient Temperature
Molecules 2012, 17(5), 6011-6019; https://doi.org/10.3390/molecules17056011
Received: 27 March 2012 / Revised: 9 May 2012 / Accepted: 10 May 2012 / Published: 18 May 2012
Cited by 22 | PDF Full-text (175 KB)
Abstract
A one-pot and clean synthesis of 2-arylbenzothiazoles via the ambient temperature reaction of 2-aminothiophenols and aromatic aldehydes without catalyst in glycerol as a green solvent has been reported. Full article
(This article belongs to the Section Organic Chemistry)
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Open AccessArticle Metathesis Transformations of Natural Products: Cross-Metathesis of Natural Rubber and Mandarin Oil by Ru-Alkylidene Catalysts
Molecules 2012, 17(5), 6001-6010; https://doi.org/10.3390/molecules17056001
Received: 16 March 2012 / Revised: 30 April 2012 / Accepted: 3 May 2012 / Published: 18 May 2012
Cited by 15 | PDF Full-text (245 KB)
Abstract
This study reports on the degradation of natural rubber (NR) via cross-metathesis with mandarin oil and d-limonene, an abundant compound in essential oils; that were used as chain transfer agents (CTAs) and green solvents. Reactions were performed in the presence of the
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This study reports on the degradation of natural rubber (NR) via cross-metathesis with mandarin oil and d-limonene, an abundant compound in essential oils; that were used as chain transfer agents (CTAs) and green solvents. Reactions were performed in the presence of the ruthenium-alkylidene catalysts (PCy3)2(Cl)2Ru=CHPh (I) and (1,3-dimesityl-4,5-dihydroimidazol-2-ylidene) (PCy3)Cl2Ru=CHPh (II), respectively. Catalyst II bears an N-heterocyclic carbene ligand (NHC) bounded to the ruthenium atom, which has a strong basic character; therefore it is more active toward trisubstituted olefins in comparison with catalyst I. In both cases, isolated monoterpene-terminated isoprene oligomers were obtained as products of the cross-metathesis degradation of NR. In the presence of catalyst II molecular weight values around Mn × 102 and yields of 80% were obtained; whereas with catalyst I, the molecular weights of products were about Mn × 104 with yields ranging 70 to 74%. The composition and yield of NR degradation products were determined by GC/MS (EI) analysis and it was found that the oligomers obtained have primarily one vinyl group and one terpene-monocyclic group at the chain end, with isoprene units Am = 2, 3 y 4. Full article
(This article belongs to the Special Issue Olefin Metathesis and Its Application)
Open AccessArticle A Sandwich HIV p24 Amperometric Immunosensor Based on a Direct Gold Electroplating-Modified Electrode
Molecules 2012, 17(5), 5988-6000; https://doi.org/10.3390/molecules17055988
Received: 8 March 2012 / Revised: 25 April 2012 / Accepted: 9 May 2012 / Published: 18 May 2012
Cited by 31 | PDF Full-text (590 KB)
Abstract
Acquired immune deficiency syndrome (AIDS) is a severe communicable immune deficiency disease caused by the human immune deficiency virus (HIV). The analysis laboratory diagnosis of HIV infection is a crucial aspect of controlling AIDS. The p24 antigen, the HIV-1 capsid protein, is of
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Acquired immune deficiency syndrome (AIDS) is a severe communicable immune deficiency disease caused by the human immune deficiency virus (HIV). The analysis laboratory diagnosis of HIV infection is a crucial aspect of controlling AIDS. The p24 antigen, the HIV-1 capsid protein, is of considerable diagnostic interest because it is detectable several days earlier than host-generated HIV antibodies following HIV exposure. We present herein a new sandwich HIV p24 immunosensor based on directly electroplating an electrode surface with gold nanoparticles using chronoamperometry, which greatly increased the conductivity and reversibility of the electrode. Under optimum conditions, the electrochemical signal showed a linear relationship with the concentration of p24, ranging from 0.01 ng/mL to 100 ng/mL (R > 0.99), and the detection limit was 0.008 ng/mL. Compared with ELISA, this method increased the sensitivity by more than two orders of magnitude (the sensitivity of ELISA for p24 is about 1 ng/mL). This immunosensor may be broadly applied to clinical samples, being distinguished by its ease of use, mild reaction conditions, guaranteed reproducibility, and good anti-interference ability. Full article
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