Mechanism of action of the marine natural product stypoldione: evidence for reaction with sulfhydryl groups.
Stypoldione, a marine natural product that possesses an o-quinone functional group, has been shown to inhibit a variety of biological processes including cell division. We found that stypoldione binds covalently to sulfhydryl groups of thiol-containing compounds via addition of sulfur to the C-4' position of the quinone ring. We examined the ability of stypoldione to add to sulfhydryl groups of a number of thiol-containing substances, including glutathione, thiophenol, beta-mercaptoethanol, and the protein tubulin. We suggest that the biological actions of stypoldione may be caused by the addition of this compound to thiol groups of biological molecules.
D002455:Cell Division / Q000187:drug effects; D003078:Colchicine / Q000378:metabolism; D008387:Marine Toxins / Q000494:pharmacology*; D008870:Microtubules / Q000187:drug effects; D011809:Quinones / Q000378:metabolism / Q000494:pharmacology*; D013438:Sulfhydryl Compounds / Q000378:metabolism*; D014404:Tubulin / Q000378:metabolism
D008387:Marine Toxins; D011809:Quinones; D013438:Sulfhydryl Compounds; D014404:Tubulin; C039754:stypoldione; D003078:Colchicine