Synthesis and biological activity of potential antimetabolites of L-fucose.
6-Substituted 6-deoxy-L-galactose (L-fucose) derivatives were synthesized as potential antimetabolites of L-fucose. The cytotoxic effects of these compounds were evaluated on P388 leukemia cells in culture. The L-fucose analogues which showed the most potent growth inhibition were the sulfonyl ester, bromo, and iodo derivatives; since these compounds were all capable of alkylation, it is conceivable that their cytotoxic action is a consequence of this property. In agreement with this interpretation, none of the agents synthesized showed specific inhibition of the incorporation of L-[3H]fucose into glycoprotein.
D000818:Animals; D000963:Antimetabolites / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D005643:Fucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006023:Glycoproteins / Q000138:chemical synthesis; D007941:Leukemia P388 / Q000188:drug therapy
D000963:Antimetabolites; D006023:Glycoproteins; D005643:Fucose