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Titolo:
Formation of 2-chloroinosine from guanosine by treatment of HNO2 in the presence of NaCl
Autore:
Suzuki, T; Ide, H; Yamada, M; Morii, T; Makino, K;
Indirizzi:
Kyoto Univ, Inst Adv Energy, Kyoto 6110011, Japan Kyoto Univ Kyoto Japan6110011 iv, Inst Adv Energy, Kyoto 6110011, Japan Hiroshima Univ, Grad Sch Sci, Dept Math & Life Sci, Higashihiroshima 7398526, Japan Hiroshima Univ Higashihiroshima Japan 7398526 hihiroshima 7398526, Japan
Titolo Testata:
BIOORGANIC & MEDICINAL CHEMISTRY
fascicolo: 11, volume: 9, anno: 2001,
pagine: 2937 - 2941
SICI:
0968-0896(200111)9:11<2937:FO2FGB>2.0.ZU;2-0
Fonte:
ISI
Lingua:
ENG
Soggetto:
GASTRIC-CANCER; SODIUM-NITRITE; STOMACH-CANCER; DIETARY SALT; NITROUS-ACID; HUMAN SALIVA; 2'-DEOXYOXANOSINE; NITRATE; 2'-DEOXYGUANOSINE; OLIGODEOXYNUCLEOTIDE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
30
Recensione:
Indirizzi per estratti:
Indirizzo: Makino, K Kyoto Univ, Inst Adv Energy, Kyoto 6110011, Japan Kyoto Univ Kyoto Japan 6110011 dv Energy, Kyoto 6110011, Japan
Citazione:
T. Suzuki et al., "Formation of 2-chloroinosine from guanosine by treatment of HNO2 in the presence of NaCl", BIO MED CH, 9(11), 2001, pp. 2937-2941

Abstract

We investigated the reaction of Guo with nitrous acid in the presence of NaCl. When 1 mM Guo was incubated with 100 mM NaNO2 and 2 M NaCl in sodium acetate buffer at pH 3.2 and 37 degreesC, 2-chloroinosine (2-Cl-Ino) was produced in addition to oxanosine (Oxo) and xanthosine (Xao). The yield of 2-Cl-Ino was 0.033 mM at an incubation time of 2 h. Under the same reaction conditions, GMP and dGuo gave rise to the corresponding 2-chloro derivatives with comparable yields. All the 2-chloro derivatives were fairly stable (t(1/2) > 360 h) at physiological pH and temperature. To elucidate the reaction mechanism of the chlorination, the diazoate derivative of Guo, a reactionintermediate of the Guo-HNO2 system, was employed as a starting compound. When the diazoate was incubated with 2M NaCl in a neutral solution, 2-Cl-Ino was produced in addition to Oxo and Xao. These results suggest that the 2-chloro derivatives can be produced from foodstuffs in the human stomach and may have potential importance as a carcinogen causing gastric cancer. (C)2001 Elsevier Science Ltd. All rights reserved.

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Documento generato il 22/01/20 alle ore 21:43:17