SDRP Journal of Computational Chemistry & Molecular Modelling

Synthesis and in silico evaluation of 16?-azido pregnenolone analogue as a clickable substrate for steroid-converting enzymes

Co-Authors

Jan U. Panada, Yaroslav V. Faletrov, Vladimir M. Shkumatov

Citation

Vladimir M. Shkumatov, Synthesis and in silico evaluation of 16?-azido pregnenolone analogue as a clickable substrate for steroid-converting enzymes(2016)SDRP Journal of Computational Chemistry & Molecular Modelling 1(2)

Abstract

Synthesis and characterization of 16?-azidopregn-5-en-3?,17?-diol-21-one are reported. The azido steroid was studied by docking simulations as a substrate for a range of steroid-converting enzymes, including bacterial cholesterol oxidase and mammalian cytochromes P450 17-hydroxylase/17,20-lyase (CYP17A1) and 21-hydroxylase (CYP21A2). The derivative was calculated to localize similarly to natural substrates with binding energy values ranging from -7.2 to -11.9 kcal•mol-1. A fluorescent triazole derivative of 16?-azidopregn-5 en-3?,17?-diol-21-one has been obtained using click chemistry approach. The azido steroid is proposed as a suitable molecular tool for studies of steroid biotransformations.

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