TY - JOUR
T1 - Chemical oxidation and metabolism of N-methyl-N-formylhydrazine. Evidence for diazenium and radical intermediates
AU - Gannett, P. M.
AU - Garrett, C.
AU - Lawson, T.
AU - Toth, B.
N1 - Funding Information:
ForgioneP . S., SpragueG . S. and Troffkin H. J. (1966) ProughR . A., FreemanP. C. and HinesR . N. (1981)T he Stereospecifoicx idationo f a l,l-disubstitutehdyd razine oxidationo f hydrazined erivativesc atalyzedb y the via metail on coordinationA. newa pproachto isomeric purifiedl iverm icrosomaFlA D-containinmg onooxygen-azo compoundsJ.o urnal of the American Chemical ase.J ournal of BiologicalC hemistry2 56,4 178-4184. Society8 8, 1079-1080. RoganE . G., CavalieriE . L., TibbelsS . R., CremonesPi. , George M. V. and BalachandraKn. S. (1975)N ickel WarneCr . D., NagelD . L., TomerK . B., CernyR . L. and peroxide oxidationo f organicc ompoundsC. hemical GrossM . L. (1988S) ynthesisa ndi dentificatioonf bcn-Reviews7 5, 491-519. zo\[a\]pyrene--guannuincele osidaed ductfso rmedb y elec- Acknowledgements--Twhoisr kw asf undedb y NIH Grants ROI-CA44075a nd RR01968,N CI laboratorcyo regrant PO1-CA36727a nda minorityh ighs chools tudenatp pren-ticeshipg rantS 03RR03408to C. GarrettW. e alsow isht o thankM s Carol Kolar for her technicaals sistancwe iththe microsomainl cubations.
PY - 1991
Y1 - 1991
N2 - N-Methyl N-formylhydrazine (1), a component of the mushroom Gyromitra esculenta, is a carcinogen. Its mode of action, however, is poorly understood. To determine the intermediates that may form during the metabolism of 1, we examined its oxidative chemistry, identified the products and inferred the intermediates on the basis of these products. The incubation of 1 with rat liver microsomes was also studied and the metabolites determined and quantified. Both the chemical and the microsome-mediated oxidation of 1 yielded formaldehyde and acetaldehyde. The formation of acetaldehyde requires (i) the oxidation of 1 to a diazenium ion (I) or diazene (II) and (ii) fragmentation of I/II to formyl and methyl radicals. It is suggested that these radical intermediates may be important in understanding and elucidating carcinogenesis by 1.
AB - N-Methyl N-formylhydrazine (1), a component of the mushroom Gyromitra esculenta, is a carcinogen. Its mode of action, however, is poorly understood. To determine the intermediates that may form during the metabolism of 1, we examined its oxidative chemistry, identified the products and inferred the intermediates on the basis of these products. The incubation of 1 with rat liver microsomes was also studied and the metabolites determined and quantified. Both the chemical and the microsome-mediated oxidation of 1 yielded formaldehyde and acetaldehyde. The formation of acetaldehyde requires (i) the oxidation of 1 to a diazenium ion (I) or diazene (II) and (ii) fragmentation of I/II to formyl and methyl radicals. It is suggested that these radical intermediates may be important in understanding and elucidating carcinogenesis by 1.
UR - http://www.scopus.com/inward/record.url?scp=0025980546&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0025980546&partnerID=8YFLogxK
U2 - 10.1016/0278-6915(91)90062-C
DO - 10.1016/0278-6915(91)90062-C
M3 - Article
C2 - 1999305
AN - SCOPUS:0025980546
SN - 0278-6915
VL - 29
SP - 49
EP - 56
JO - Food and Chemical Toxicology
JF - Food and Chemical Toxicology
IS - 1
ER -