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Zahid Hussain Atia-tul-Wahab Nusrat Hussain Shabbir Hussain Atta-ur-Rahman M. Iqbal Choudhary 《RSC advances》2019,10(1):451
The present study reports the biotransformation of an anabolic-androgenic steroid (AAS) drostanolone heptanoate (1) by using two microbial cultures, Beauveria bassiana, and Macrophomina phaseolina. Fermentation of 1 with B. bassiana yielded five new transformed products 2–6, while with M. phaseolina it afforded two new 7–8, and two known 9–10 metabolites. The main sites of hydroxylation in the steroidal skeleton of 1 were at C-5, C-7, C-11, C-14, C-15, and C-20, hydrolysis of the ester moiety at C-17, and reduction of the carbonyl group at C-3. The structures of the transformed products were determined by using mass, NMR, and other spectroscopic techniques.Incubation of drostanolone heptanoate (1) with B. bassiana and M. phaseolina afforded seven new and two known metabolites.The main sites of hydroxylation include C-5, C-7, C-11, C-14, C-15, and C-20, hydrolysis at C-17, and reduction at C-3 of 1. 相似文献
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Muhammad Saleem Aamer Saeed Atia-tul-Wahab Ajmal Khan Sanaullah Abbasi Waqasuddin Khan Sher Bahadar Khan M. Iqbal Choudhary 《Medicinal chemistry research》2016,25(3):438-448
Benzamide sulfonamide and its derivatives were identified as potent inhibitors of carbonic anhydrase-II (bovine carbonic anhydrase-II (bCA-II) and human recombinant carbonic anhydrase-II (hCA-II)) with IC50 values 0.06–0.28 μM and 0.09–0.58 μM, respectively. Different kinetics parameter, such as V max, K m , and K i , were determined. Molecular docking simulation studies on the lead compounds were carried out by AutoDock Vina docking software. The compounds were also evaluated for their cytotoxicity against 3T3 (Normal Cell Lines Mouse Fibroblast) cell line. All the compounds have shown non-cytotoxic effect toward 3T3 cell lines. This study has identified novel scaffolds for further hit-to-lead optimization for the discovery of effective drugs against carbonic anhydrase-II-associated disorder, such as glaucoma, leukemia, cystic fibrosis, and epilepsy. 相似文献
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Muhammad Aamer Mahwish Siddiqui Almas Jabeen Rimsha Irshad Farooq-Ahmad Khan Atia-tul-Wahab M. Iqbal Choudhary Yan Wang 《RSC advances》2022,12(15):9494
An anabolic-androgenic synthetic steroidal drug, methasterone (1) was transformed by two fungi, Cunninghamella blakesleeana and Macrophimina phaseclina. A total of six transformed products, 6β,7β,17β-trihydroxy-2α,17α-dimethyl-5α-androstane-3-one (2), 6β,7α,17β-trihydroxy-2α,17α-dimethyl-5α-androstane-3-one (3), 6α,17β-dihydroxy-2α,17α-dimethyl-5α-androstane-3,7-dione (4), 3β,6β,17β-trihydroxy-2α,17α-dimethyl-5α-androstane-7-one (5), 7α,17β-dihydroxy-2α,17α-dimethyl-5α-androstane-3-one (6), and 6β,9α,17β-trihydroxy-2α,17α-dimethyl-5α-androstane-3-one (7) were synthesized. Among those, compounds 2–5, and 7 were identified as new transformed products. MS, NMR, and other spectroscopic techniques were performed for the characterization of all compounds. Substrate 1 (IC50 = 23.9 ± 0.2 μg mL−1) showed a remarkable anti-inflammatory activity against nitric oxide (NO) production, in comparison to standard LNMMA (IC50 = 24.2 ± 0.8 μg mL−1). Whereas, its metabolites 2, and 7 showed moderate inhibition with IC50 values of 38.1 ± 0.5 μg mL−1, and 40.2 ± 3.3 μg mL−1, respectively. Moreover, substrate 1 was found to be cytotoxic for the human normal cell line (BJ) with an IC50 of 8.01 ± 0.52 μg mL−1, while metabolites 2–7 were identified as non-cytotoxic. Compounds 1–7 showed no cytotoxicity against MCF-7 (breast cancer), NCI-H460 (lung cancer), and HeLa (cervical cancer) cell lines.Fungal transformation of methasterone resulted in six products (2–7). 2–5, and 7 were identified as new. Substrate 1 showed remarkable anti-inflammatory activity but was cytotoxic. Products 2 and 7 showed moderate activity but were non-cytotoxic. 相似文献
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Rabia Farooq Nusrat Hussain Sammer Yousuf Atia-tul-Wahab Malik Shoaib Ahmad Atta-ur-Rahman M. Iqbal Choudhary 《RSC advances》2018,8(39):21985
The microbial transformation of anabolic androgenic steroid mestanolone (1) with Macrophomina phaseolina and Cunninghamella blakesleeana has afforded seven metabolites. The structures of these metabolites were characterized as 17β-hydroxy-17α-methyl-5α-androsta-1-ene-3,11-dione (2), 14α,17β-dihydroxy-17α-methyl-5α-androstan-3,11-dione (3), 17β-hydroxy-17α-methyl-5α-androstan-1,14-diene-3,11-dione (4), 17β-hydroxy-17α-methyl-5α-androstan-3,11-dione (5), 11β,17β-dihydroxy-17α-methyl-5α-androstan-1-ene-3-one (6), 9α,11β,17β-trihydroxy-17α-methyl-5α-androstan-3-one (7), and 1β,11α,17β-trihydroxy-17α-methyl-5α-androstan-3-one (8). All the metabolites, except 5 and 6, were identified as new compounds. Substrate 1 (IC50 = 27.6 ± 1.1 μM), and its metabolites 2 (IC50 = 19.2 ± 2.9 μM) and 6 (IC50 = 12.8 ± 0.6 μM) exhibited moderate cytotoxicity against the HeLa cancer cell line (human cervical carcinoma). All metabolites were noncytotoxic to 3T3 (mouse fibroblast) and H460 (human lung carcinoma) cell lines. The metabolites were also evaluated for immunomodulatory activity, and all were found to be inactive.The microbial transformation of anabolic androgenic steroid mestanolone (1) with Macrophomina phaseolina and Cunninghamella blakesleeana has afforded seven metabolites. Some of them have exhibited moderate cytotoxicity against HeLa cancer cell line. 相似文献
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