Optical probe for the cytochrome P-450 cholesterol side chain cl

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

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544 35, 544 37, 544347, 546102, 546104, 549223, 549 16, C07D26538

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active

052083322

ABSTRACT:
An optical probe enables the study of enzyme activity by absorbance spectroscopy or by sensitive fluorescence methods. In particular, the probe provides the ability to monitor the activity of cytochrome P-450.sub.scc enzyme, the rate limiting enzyme for steroid biosynthesis. Located on the inner mitochondrial membrane, P-450.sub.scc catalyzes the conversion of cholesterol to pregnenolone and isocapraldehyde by sequential oxidations of the cholesterol side chain. The fluorogenic probe includes a cholesterol-like steroid linked to a chromophore through a linking group. The chromophore is selected to have little optical response when linked to the steroid substrate and an enhanced optical response when cleaved from the substrate and linking group. Thus, a fluorescent anion that can be optically detected is generated by the side-chain cleavage reaction during steroidogenesis.

REFERENCES:
patent: 5110725 (1992-01-01), Marrone et al.
Simpson, Daniel, et al., J. Org. Chem., 56(18), pp. 5391-5396, 1991.
Marrone, Babetta, et al., Endocrinology, 128(5), pp. 2654-2656, 1991.

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