Urinary metabolite of 1-(2,4,6-trichlorophenyl)-3,3-dimethyltriazene with an intact diazoamino structure.
The tumour-inhibiting substance 1-(2,4,6-trichlorophenyl)-3,3-dimethyltriazene is metabolised in rats to the corresponding substituted 1-O-(triazenyl-methyl) glucuronic acid. The urinary metabolite was purified by ion exchange chromatography and gel filtration, and isolated from the enriched fractions by freeze-drying. Cold acid cleavage into the 2,4,6-trichlorobenzene-diazonium cation and hydrolysis to glucuronic acid and formaldehyde indicated the presence of an O-glycosidic bond through an enzymically-introduced hydroxymethyl oxygen. This novel type of glucuronoside structure was established by chemical evidence, and confirmed by NMR and field-desorption mass spectrometry. It is conceivable that this metabolite represents a stabilised carrier form of the biologically-active triazene that transports the methylating agent from its site of formation to its ultimate target.
D000818:Animals; D000970:Antineoplastic Agents / Q000378:metabolism / Q000494:pharmacology; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D005965:Glucuronates / Q000652:urine; D008297:Male; D051381:Rats; D014226:Triazenes / Q000652:urine*
D000970:Antineoplastic Agents; D005965:Glucuronates; D014226:Triazenes; C020945:1-(2,4,6-trichlorophenyl)-3,3-dimethyltriazene