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Japanese Journal of Cancer Research : Gann logoLink to Japanese Journal of Cancer Research : Gann
. 1992 Oct;83(10):1025–1029. doi: 10.1111/j.1349-7006.1992.tb02716.x

Adduct 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

Hiroaki Nagaoka 1, Keiji Wakabayashi 1, Seon‐Bong Kim 1,†, In‐Soo Kim 1, Yoshino Tanaka 1, Masako Ochiai 1, Akihiro Tada 2, Haruo Nukaya 2, Takashi Sugimura 1, Minako Nagao 1
PMCID: PMC5918676  PMID: 1452454

Abstract

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. 32P‐Postlabeling analysis demonstrated that the levels of adducts with 2′‐deoxyguanosine 3′‐moiiophosphate were much higher than those with the other three nucleotides. 1H‐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.

Keywords: PhIP, N‐OH‐PhIP, Deoxyguanosine, dG‐C8‐PhIP

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