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In silico molecular docking and in vitro antidiabetic studies of dihydropyrimido[4,5-a]acridin-2-amines.

ABSTRACT: An in vitro antidiabetic activity on ? -amylase and ? -glucosidase activity of novel 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amines (3a-3f) were evaluated. Structures of the synthesized molecules were studied by FT-IR, (1)H NMR, (13)C NMR, EI-MS, and single crystal X-ray structural analysis data. An in silico molecular docking was performed on synthesized molecules (3a-3f). Overall studies indicate that compound 3e is a promising compound leading to the development of selective inhibition of ? -amylase and ? -glucosidase.

SUBMITTER: Bharathi A

PROVIDER: S-EPMC4060768 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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In silico molecular docking and in vitro antidiabetic studies of dihydropyrimido[4,5-a]acridin-2-amines.

Bharathi A A Roopan Selvaraj Mohana SM Vasavi C S CS Munusami Punnagai P Gayathri G A GA Gayathri M M

BioMed research international 20140602

An in vitro antidiabetic activity on α -amylase and α -glucosidase activity of novel 10-chloro-4-(2-chlorophenyl)-12-phenyl-5,6-dihydropyrimido[4,5-a]acridin-2-amines (3a-3f) were evaluated. Structures of the synthesized molecules were studied by FT-IR, (1)H NMR, (13)C NMR, EI-MS, and single crystal X-ray structural analysis data. An in silico molecular docking was performed on synthesized molecules (3a-3f). Overall studies indicate that compound 3e is a promising compound leading to the develop ...[more]

PMID: 24991576

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Project description:BackgroundOxidative stress and diabetes are medical conditions that have a growing prevalence worldwide, significantly impacting our bodies. Thus, it is essential to develop new natural antioxidant and antidiabetic agents. Dypsis pembana (H.E.Moore) Beentje & J.Dransf (DP) is an ornamental palm of the family Arecaceae. This study aimed to broaden the understanding of this plant's biological properties by evaluating its in vitro antioxidant and antidiabetic activities.MethodsThe in vitro antioxidant activities of the crude extract, fractions, and selected isolates were evaluated by DPPH method. While the in vitro antidiabetic activities of these samples were evaluated by assessing the degree of inhibition of α-glucosidase. Additionally, molecular docking analysis was performed to investigate the interactions of tested compounds with two potential targets, the cytochrome c peroxidase and alpha glucosidase.ResultsThe crude extract displayed the highest antioxidant activity (IC50 of 11.56 µg/ml), whereas among the fractions, the EtOAc fraction was the most potent (IC50 of 14.20 µg/ml). Among tested compounds, isoquercetrin (10) demonstrated the highest potency, with an IC50 value of 3.30 µg/ml, followed by rutin (8) (IC50 of 3.61 µg/ml). Regarding antidiabetic activity, the EtOAc (IC50 of 60.4 µg/ml) and CH2Cl2 fractions (IC50 of 214.9 µg/ml) showed activity, while the other fractions did not demonstrate significant antidiabetic effects. Among tested compounds, kaempferol-3-O-neohesperidoside (9) showed the highest antidiabetic activity, with an IC50 value of 18.38 µg/ml, followed by kaempferol (4) (IC50 of 37.19 µg/ml). These experimental findings were further supported by molecular docking analysis, which revealed that isoquercetrin and kaempferol-3-O-neohesperidoside exhibited strong enzyme-binding affinities to the studied enzyme targets. This analysis provided insights into the structure-activity relationships among the investigated flavonol-O-glycosides.ConclusionThe biological and computational findings revealed that isoquercetrin and kaempferol-3-O-neohesperidoside have potential as lead compounds for inhibiting cytochrome c peroxidase and alpha glucosidase enzymes, respectively.

Project description:In this paper, we present the synthesis and characterization of two known sulfonyl hydrazides (1 and 2) and their new sulfonyl hydrazone derivatives (9-20), as well as in vitro and in silico investigations of their cytotoxic properties against human lung (A549) and human breast (MCF-7) cancer cell lines. The target compounds (9-20) obtained in high yields were synthesized for the first time by a multi-step reaction, and their structures were confirmed by elemental analysis and various spectral techniques, including FT-IR, 1H-, and 13C-NMR. The antiproliferative profiles of these compounds (1, 2, and 9-20) in this study were determined at concentrations of 200, 100, 50, and 25 µM against selected cancer cell lines for 72 h using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method. Except for compounds 1 and 2, other compounds (9-20) demonstrated cytotoxic activity at concentrations lower than 200 µM. The newly synthesized compounds (9-20) demonstrated antiproliferative activities at a micromolar level, with IC50 values in the range of 29.59-176.70 μM for the A549 cell line and 27.70-170.30 μM for the MCF-7 cell line. Among these compounds, compound 15 (IC50 = 29.59 μM against A549 cell line and IC50 = 27.70 μM against MCF-7 cell line) showed the highest cytotoxic activity against these two cancer cell lines compared to the reference drug cisplatin (IC50 = 22.42 μM against A549 cell line and IC50 = 18.01 μM against MCF-7 cell line). From docking simulations, to establish a plausible binding mode of compounds, we noticed that compound 15 demonstrated the highest affinity (-6.8508 kcal/mol) for estrogen receptor-beta (ERbeta) compared to others, suggesting promising ERbeta binding potential. Most compounds followed Lipinski's rule of five, with acceptable logP values. Additionally, all had mixed gastrointestinal absorption and limited blood-brain barrier permeability. Overall, our study proposed new sulfonyl hydrazones as a potential class of anticancer agents.

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In silico molecular docking and in vitro antidiabetic studies of dihydropyrimido[4,5-a]acridin-2-amines.

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In silico molecular docking and in vitro antidiabetic studies of dihydropyrimido[4,5-a]acridin-2-amines.

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