Biological N-oxidation of adenine and 9-alkyl derivatives.
In vitro metabolism of adenine, 9-methyladenine, and 9-benzyladenine using hepatic microsomes of hamster, mouse and rat was investigated. The results indicated that adenine was apparently not susceptible to microsomal N-oxidation. N-oxidation of 9-methyladenine was also not detected, whereas N-demethylation was observed with hepatic microsomes derived from hamster and rat but not from mouse. With 9-benzyladenine, both 1-N-oxide formation and N-debenzylation occurred with microsomes of all species in various amounts. N-Hydroxylation of the 6-amino group was not observed with any substrate in any species. Metabolic results are discussed in relation to chemical structure, electronic, lipophilic and steric factors.
Lam
S P
SP
Chelsea Department of Pharmacy, King's College London, University of London, UK.
Devinsky
F
F
Gorrod
J W
JW
D000225:Adenine / Q000031:analogs & derivatives* / Q000032:analysis / Q000378:metabolism*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D006224:Cricetinae; D003497:Cyclic N-Oxides / Q000032:analysis / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008647:Mesocricetus; D051379:Mice; D008815:Mice, Inbred Strains; D008862:Microsomes, Liver / Q000201:enzymology / Q000378:metabolism; D010084:Oxidation-Reduction; D051381:Rats; D011919:Rats, Inbred Strains
D003497:Cyclic N-Oxides; C055872:9-benzyladenine; C013115:9-methyladenine; D000225:Adenine