Reaction of reductively activated mitomycin C with aqueous bicarbonate: Isolation and characterization of an oxazolidinone derivative of cis-1-hydroxy-2,7-diaminomitosene.
The reductive activation of mitomycin C in aqueous bicarbonate buffer resulted in the formation of a previously unknown compound, characterized as an oxazolidinone derivative of cis-1-hydroxy-2,7-diaminomitosene. This compound is the result of a cyclization reaction of bicarbonate with the aziridine ring of aziridinomitosene, and was observed at bicarbonate concentrations close to those present in physiological plasma.
Paz
Manuel M
MM
Departamento de Química Orgánica, Facultade de Ciencias, Universidade de Santiago de Compostela, Campus de Lugo, 27002 Lugo, Spain. manuel.paz@usc.es
D000903:Antibiotics, Antineoplastic / Q000737:chemistry* / Q000378:metabolism; D001388:Aziridines / Q000737:chemistry; D001639:Bicarbonates / Q000737:chemistry*; D003500:Cyclization; D007536:Isomerism; D016685:Mitomycin / Q000737:chemistry* / Q000378:metabolism; D008937:Mitomycins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D023303:Oxazolidinones / Q000737:chemistry*; D010084:Oxidation-Reduction
D000903:Antibiotics, Antineoplastic; D001388:Aziridines; D001639:Bicarbonates; D008937:Mitomycins; D023303:Oxazolidinones; D016685:Mitomycin; C033132:aziridine; C049686:1-hydroxy-2,7-diaminomitosene