Reassignment of the structure for the antitumor agent RR-150.
7-Cysteaminomitosane (RR-150) has been reported to be superior to mitomycin C against P388 leukemia and B-16 melanoma in mice and is less leukopenic. Studies reported here indicated the absence of a free thiol group in RR-150 and therefore the structure was incorrectly assigned. Reaction of mitomycin A with either 2-aminoethanethiol or cystamine gave the same disulfide, 7-N,7'-N'-dithiodiethylenedimitomycin C, which is the newly proposed structure for RR-150. Attempts to produce 7-cysteaminomitosane by reduction of the disulfide have not succeeded because of its apparent instability.
Senter
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PD
Antitumor Chemistry Department, Bristol-Myers Company, Wallingford, CT 06492.
Langley
D R
DR
Manger
W E
WE
Vyas
D M
DM
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D008937:Mitomycins / Q000138:chemical synthesis*
D000903:Antibiotics, Antineoplastic; D008937:Mitomycins; C043641:7-cysteaminomitosane