Adriamycin analogs. Periodate oxidation of adriamycin.
Adriamycin is selectively cleaved in high yield at the C13-C14 bond by 1 equiv of sodium metaperiodate to yield carboxylic acid 3. The corresponding methyl ester 4 is obtained by Fischer esterification. Spectral studies indicate that 3 and 4 bind to calf thymus DNA in a manner similar to adriamycin and daunomycin but Tm measurements suggest that less stable complexes are formed. Ester 4 inhibits DNA and RNA synthesis in cultured L1210 cells at levels comparable to adriamycin but acid 3 is much less effective. Both new compounds are moderately effective as antitumor agents against P388 lymphocytic leukemia in the mouse.
D000818:Animals; D004273:DNA, Neoplasm / Q000096:biosynthesis; D003864:Depression, Chemical; D004317:Doxorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D007942:Leukemia, Experimental / Q000188:drug therapy; D051379:Mice; D010084:Oxidation-Reduction; D010504:Periodic Acid; D012334:RNA, Neoplasm / Q000096:biosynthesis; D013056:Spectrophotometry, Ultraviolet
D004273:DNA, Neoplasm; D012334:RNA, Neoplasm; D010504:Periodic Acid; D004317:Doxorubicin