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美睾酮的微生物转化及转化产物的抗癌活性

Microbial transformation of mestanolone by and and anticancer activities of the transformed products.

作者信息

Farooq Rabia, Hussain Nusrat, Yousuf Sammer, Ahmad Malik Shoaib, Choudhary M Iqbal

机构信息

H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi Karachi-75270 Pakistan

Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi Karachi-75270 Pakistan

出版信息

RSC Adv. 2018 Jun 14;8(39):21985-21992. doi: 10.1039/c8ra01309h. eCollection 2018 Jun 13.

DOI:10.1039/c8ra01309h
PMID:35541749
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9081080/
Abstract

The microbial transformation of anabolic androgenic steroid mestanolone (1) with and 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 (IC = 27.6 ± 1.1 μM), and its metabolites 2 (IC = 19.2 ± 2.9 μM) and 6 (IC = 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.

摘要

合成代谢雄激素美睾酮（1）在[具体微生物或条件1]和[具体微生物或条件2]作用下发生微生物转化，产生了七种代谢产物。这些代谢产物的结构经鉴定分别为17β-羟基-17α-甲基-5α-雄甾-1-烯-3,11-二酮（2）、14α,17β-二羟基-17α-甲基-5α-雄甾烷-3,11-二酮（3）、17β-羟基-17α-甲基-5α-雄甾-1,14-二烯-3,11-二酮（4）、17β-羟基-17α-甲基-5α-雄甾烷-3,11-二酮（5）、11β,17β-二羟基-17α-甲基-5α-雄甾-1-烯-3-酮（6）、9α,11β,17β-三羟基-17α-甲基-5α-雄甾烷-3-酮（7）和1β,11α,17β-三羟基-17α-甲基-5α-雄甾烷-3-酮（8）。除5和6外，所有代谢产物均被鉴定为新化合物。底物1（IC₅₀ = 27.6 ± 1.1 μM）及其代谢产物2（IC₅₀ = 19.2 ± 2.9 μM）和6（IC₅₀ = 12.8 ± 0.6 μM）对HeLa癌细胞系（人宫颈癌）表现出中等细胞毒性。所有代谢产物对3T3（小鼠成纤维细胞）和H460（人肺癌）细胞系均无细胞毒性。还对这些代谢产物的免疫调节活性进行了评估，发现它们均无活性。

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