A mechanism-based fluorogenic probe for the cytochrome P-450 cholesterol side chain cleavage enzyme

DJ Simpson, CJ Unkefer, TW Whaley…

Index: Simpson, Daniel J.; Unkefer, Clifford J.; Whaley, Thomas W.; Marrone, Babetta L. Journal of Organic Chemistry, 1991 , vol. 56, # 18 p. 5391 - 5396

Full Text: HTML

Citation Number: 27

Abstract

The rate-limiting step of steroid biosynthesis is the enzymatic conversion of cholesterol to pregnenolone by cytochrome P-450,(side chain cleavage) located in the inner mitochondrial membrane of all steroid producing cells. We report here the synthesis and application of a fluorogenic probe which is a cholene-based steroid with a fluorogenic moiety (resorufin) strategically located at the site of side chain cleavage. Synthesis of the probe required four ...