Abstract
Certain thiol-containing compounds catalyze, in a chemical reaction, the isomerization of 9-cis-retinoic acid to a mixture of all-trans-retinoic acid, 9-cis-retinoic acid, 13-cis-retinoic acid, and 9,13-dicis-retinoic acid. In the presence of such catalysts, all-trans-retinoic acid gives rise to the same mixture. Reactions approaching equilibrium contain more all-trans-retinoic acid than either of the other isomers. Small molecules effective as catalysts are mercaptoethanol,l-cysteine methyl ester, glutathione, andN-acetyl-l-cysteine. Apoferritin (a thiol-containing protein), native microsomes, and, to a lesser extent, boiled microsomes catalyze the reaction. In intact cells, these interconversions also occur in a process inhibited by a sulfhydryl-specific reagent. The thiol-catalyzed isomerization of 9-cis-retinoic acid may be relevant in the biological activity of this compound.
Footnotes
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Send reprint requests to: Dr. Donald L. Hill, Southern Research Institute, P.O. Box 55305, Birmingham, AL 35255-5305.
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This study was supported by Grant PO1 CA34968 from the National Cancer Institute, National Institutes of Health, Department of Health and Human Services.
- Abbreviations used are::
- RA
- retinoic acid
- RAR
- nuclear RA receptor
- RXR
- nuclear retinoid X receptor
- GSH
- (reduced) glutathione
- PHMB
- p-hydroxymercuribenzoate
- Received November 6, 1995.
- Accepted September 26, 1996.
- The American Society for Pharmacology and Experimental Therapeutics
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