Adduct Formation at C-8 of Guanine on in Vitro Reaction of the Ultimate Form of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine with 2'-deoxyguanosine and Its Phosphate Esters

Overview

Journal Jpn J Cancer Res

Specialty Oncology

Date 1992 Oct 1

PMID 1452454

Citations 14

Authors

H Nagaoka

K Wakabayashi

S B Kim

I S Kim

Y Tanaka

M Ochiai

A Tada

H Nukaya

T Sugimura

M Nagao

Affiliations

Soon will be listed here.

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'-monophosphate 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-acetyoxy-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.

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References

Buonarati M, Turteltaub K, Shen N, FELTON J . Role of sulfation and acetylation in the activation of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine to intermediates which bind DNA. Mutat Res. 1990; 245(3):185-90. DOI: 10.1016/0165-7992(90)90048-o. View

Sugimura T . New environmental carcinogens in daily life. Trends Pharmacol Sci. 1988; 9(6):205-9. DOI: 10.1016/0165-6147(88)90086-7. View

Hashimoto Y, Shudo K, Okamoto T . Activation of a mutagen, 3-amino-1-methyl-5H-pyrido[4,3-b]indole. Identification of 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole and its reacion with DNA. Biochem Biophys Res Commun. 1980; 96(1):355-62. DOI: 10.1016/0006-291x(80)91222-x. View

Esumi H, Ohgaki H, Kohzen E, Takayama S, Sugimura T . Induction of lymphoma in CDF1 mice by the food mutagen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Jpn J Cancer Res. 1989; 80(12):1176-8. PMC: 5917934. DOI: 10.1111/j.1349-7006.1989.tb01651.x. View

Sugimura T . Studies on environmental chemical carcinogenesis in Japan. Science. 1986; 233(4761):312-8. DOI: 10.1126/science.3088728. View

FELTON J, Knize M, Shen N, Lewis P, Andresen B, Happe J . The isolation and identification of a new mutagen from fried ground beef: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Carcinogenesis. 1986; 7(7):1081-6. DOI: 10.1093/carcin/7.7.1081. View

Snyderwine E, Roller P, Adamson R, Sato S, Thorgeirsson S . Reaction of N-hydroxylamine and N-acetoxy derivatives of 2-amino-3-methylimidazolo[4,5-f]quinoline with DNA. Synthesis and identification of N-(deoxyguanosin-8-yl)-IQ. Carcinogenesis. 1988; 9(6):1061-5. DOI: 10.1093/carcin/9.6.1061. View

Takayama K, Yamashita K, Wakabayashi K, Sugimura T, Nagao M . DNA modification by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in rats. Jpn J Cancer Res. 1989; 80(12):1145-8. PMC: 5917929. DOI: 10.1111/j.1349-7006.1989.tb01644.x. View

Ito N, Hasegawa R, Sano M, Tamano S, Esumi H, Takayama S . A new colon and mammary carcinogen in cooked food, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Carcinogenesis. 1991; 12(8):1503-6. DOI: 10.1093/carcin/12.8.1503. View

10.

Wallin H, Mikalsen A, Guengerich F, Ingelman-Sundberg M, Solberg K, Rossland O . Differential rates of metabolic activation and detoxication of the food mutagen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by different cytochrome P450 enzymes. Carcinogenesis. 1990; 11(3):489-92. DOI: 10.1093/carcin/11.3.489. View

11.

Ochiai M, Ogawa K, Wakabayashi K, Sugimura T, Nagase S, Esumi H . Induction of intestinal adenocarcinomas by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Nagase analbuminemic rats. Jpn J Cancer Res. 1991; 82(4):363-6. PMC: 5918438. DOI: 10.1111/j.1349-7006.1991.tb01855.x. View

12.

Wakabayashi K, Nagao M, Esumi H, Sugimura T . Food-derived mutagens and carcinogens. Cancer Res. 1992; 52(7 Suppl):2092s-2098s. View

13.

Frandsen H, Grivas S, Andersson R, Dragsted L, Larsen J . Reaction of the N2-acetoxy derivative of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) with 2'-deoxyguanosine and DNA. Synthesis and identification of N2-(2'-deoxyguanosin-8-yl)-PhIP. Carcinogenesis. 1992; 13(4):629-35. DOI: 10.1093/carcin/13.4.629. View