Inhibitors of rabbit plasma prostaglandin A isomerase

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Abstract
1. The potent inhibitory activities of three groups of prostaglandin analogues on the prostaglandin A isomerase of rabbit plasma were demonstrated. 2. Six of the compounds were prepared by NaBH4 reduction of the C-9 oxo groups of prostaglandin A2 and prostaglandin C2 and their C-15 epimers. The remaining four were racemates and were synthesized in another laboratory. Unknown configurations at C-9 and at C-15 were assigned. 3. All the compounds were found to be competitive inhibitors of the isomerase in vitro. Km/Ki ratios were determined and it was found that both the 15(S) and 15(R) epimers have potent inhibitory activity. 4. One of the inhibitors was used to study the reversibility of the isomerase. 5. It is suggested that these compounds may be useful for determining the biological significance of prostaglandin A isomerase. In view of its weak biological activity and possibly extended half-life in vivo, the reduction product of 15-epiprostaglandin C2 may be the most suitable agent for this purpose.