Add time:08/14/2019         Source:sciencedirect.com

The title compound (22-Thiol) was prepared from the 22-hydroxy derivative via the isothiouronium salt. Using purified enzyme components from bovine adrenocortical mitochondria, 22-Thiol was found to be a potent, competitive inhibitor (Ki = 0.7 μM) of cholesterol side chain cleavage. Spectral studies showed that binding of 22-Thiol to cytochrome P450scc produces changes characteristic of sulfur coordination to the heme-iron, suggesting that its high affinity arises from a dual interaction with the cholesterol binding site and the heme. Together with previous results obtained with 22-amino and 22-hydroxy analogues, these findings provide support for the proximity of C-22 and the heme-iron of cytochrome P450scc in the enzyme-substrate complex.

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