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Reductive fragmentation of 2-nitroimidazoles: amines and aldehydes

Journal Article · · Int. J. Radiat. Oncol., Biol. Phys.; (United States)
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Glyoxal has been identified as a product in the fragmentation of reduced 2-nitroimidazole radiosensitizers. Quantitative analysis of glyoxal as its bis (2,4-dinitrophenylhydrazone) derivative shows that it is formed in good yield (9-23%) in a variety of 2-nitroimidazoles. In addition to glyoxal a second as-yet-unidentified carbonyl compound, and a series of amines are formed when reduced 2-nitroimidazoles fragment in the presence of water. One of the amines derived from misonidazole is identified as 1-amino-3-methoxypropan-2-ol, the product of extensive ring cleavage. Radiation chemical reduction of the 2-nitroimidazoles proceeds with the consumption of 3 electrons for each molecule reduced. This could imply that a radical disproportionation or dimerization step is involved in the reductive degradation of 2-nitroimidazoles.

Research Organization:
Cross Cancer Inst., Edmonton, Alberta
OSTI ID:
6507254
Journal Information:
Int. J. Radiat. Oncol., Biol. Phys.; (United States), Journal Name: Int. J. Radiat. Oncol., Biol. Phys.; (United States) Vol. 10:8; ISSN IOBPD
Country of Publication:
United States
Language:
English

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Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400600* -- Radiation Chemistry
ALDEHYDES
AMINES
AZOLES
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
CHEMICAL RADIATION EFFECTS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMISTRY
COBALT 60
COBALT ISOTOPES
DRUGS
ELECTROMAGNETIC RADIATION
GAMMA RADIATION
GLYOXAL
HETEROCYCLIC COMPOUNDS
IMIDAZOLES
INTERMEDIATE MASS NUCLEI
INTERNAL CONVERSION RADIOISOTOPES
IONIZING RADIATIONS
ISOMERIC TRANSITION ISOTOPES
ISOTOPES
MINUTES LIVING RADIOISOTOPES
NITRO COMPOUNDS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
RADIATION CHEMISTRY
RADIATION EFFECTS
RADIATIONS
RADIOINDUCTION
RADIOISOTOPES
RADIOSENSITIZERS
REDUCTION
YEARS LIVING RADIOISOTOPES
YIELDS