Microbial transformation of danazol with Cunninghamella blakesleeana and anti-cancer activity of danazol and its transformed products

Elias Baydoun, Atia‐tul Wahab, Hina Mehmood, Malik Shoaib Ahmad, Rizwana Malik, C.A. Smith, M. Iqbal Choudhary
In: Steroids · 2015 · vol. 105 , pp. 121–127 · doi:10.1016/j.steroids.2015.11.010 · PMID:26666360 · W2243447040
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Cunninghamella blakesleeana transformed danazol into new metabolites, some of which exhibited anti-cancer activity.

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Abstract

Biotransformation of danazol (1) (17β-hydroxy-17α-pregna-2,4-dien-20-yno-[2,3-d]-isoxazole) with Cunninghamella blakesleeana yielded three new metabolites 2-4 and a known metabolite 5. These metabolites were identified as 14β,17β-dihydroxy-2-(hydroxymethyl)-17α-pregn-4-en-20-yn-3-one (2), 1α,17β-dihydroxy-17α-pregna-2,4-dien-20-yno-[2,3-d]-isoxazole (3), 6β,17β-dihydroxy-17α-pregna-2,4-dien-20-yno-[2,3-d]-isoxazole (4), and 17β-hydroxy-2-(hydroxymethyl)-17α-pregn-1,4-dien-20-yn-3-one (5). Danazol (1) and its derivatives were evaluated against cervical cancer cell line (HeLa). Compound 1 showed a potent cytotoxicity with IC50=0.283±0.013 μM, as compared to doxorubicin (IC50=0.506±0.015 μM), where compound 3 was also found to be significantly active with IC50=13.427±0.819 μM.

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