Open AccessAdduct Formation at C‐8 of Guanine on in vitro Reaction f the Ultimate Form of 2‐Amino‐l‐methyl‐6‐phenylimidazo[4,5‐ b ]pyridine with 2′‐Deoxyguanosine and Its Phosphate Esters
Author(s) -
Nagaoka Hiroaki,
Wakabayashi Keiji,
Kim SeonBong,
Kim InSoo,
Tanaka Yoshino,
Ochiai Masako,
Tada Akihiro,
Nukaya Haruo,
Sugimura Takashi,
Nagao Minako
Publication year - 1992
Publication title -
japanese journal of cancer research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.035
H-Index - 141
eISSN - 1349-7006
pISSN - 0910-5050
DOI - 10.1111/j.1349-7006.1992.tb02716.x
Subject(s) - guanine , deoxyguanosine , adduct , chemistry , in vitro , pyridine , stereochemistry , medicinal chemistry , biochemistry , organic chemistry , nucleotide , gene
We examined the reactivity of the N ‐hydroxyamino derivative of a carcinogenic heterocyclic amine, 2‐amino‐1‐methyl‐6‐phenylimidazo[4,5‐ b ]pyridine (PhIP), after its O ‐acetylation with four 2′‐deoxyribonucleoside 3′‐monophosphates. 32 P‐Postlabeling analysis demonstrated that the levels of adducts with 2′‐deoxyguanosine 3′‐moiiophosphate were much higher than those with the other three nucleotides. 1 H‐NMR, mass spectral and UV absorption spectral analyses of the major adducts formed by N ‐acetoxy‐PhIP with 2′‐deoxyguanosine and with its phosphate esters indicated that PhIP bound at the C‐8 position of guanine, as previously demonstrated with other heterocyclic amines.