INTERACTION AND REACTIVITY OF CARCINOGENIC N-ACETYL-N-(ACYLOXY)-2-AMINOFLUORENE WITH DEOXYGUANOSINE - AN INTRAMOLECULAR APPROACH

被引：8

作者：

DEFRANCQ, E ^{[1
]}

PELLOUX, N ^{[1
]}

LETERME, A ^{[1
]}

LHOMME, MF ^{[1
]}

LHOMME, J ^{[1
]}

机构：

[1] UNIV GRENOBLE 1,LEDSS,CNRS,WRA 332,BP 53X,F-38041 GRENOBLE,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 16期

关键词：

D O I：

10.1021/jo00016a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Solvolysis of 3 in water-acetone mixtures yields the ''adduct'' 4 (65% in water) with product and rate data consistent with the hypothesis that hydrophobic guanine-fluorene stacking, similar to that which occurs when the carcinogenic aminofluorene metabolite is intercalated in DNA, is responsible for selective binding of the carcinogen at the C-8 guanine center.

引用

页码：4817 / 4819

页数：3

共 31 条

[1] THE SN2-SN1 SPECTRUM .4. THE SN2 (INTERMEDIATE) MECHANISM FOR SOLVOLYSES OF TERT-BUTYL CHLORIDE - A REVISED Y-SCALE OF SOLVENT IONIZING POWER BASED ON SOLVOLYSES OF 1-ADAMANTYL CHLORIDE
BENTLEY, TW
CARTER, GE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (21) : 5741 - 5747
[2] SOLVENT IONIZING POWER - COMPARISONS OF SOLVOLYSES OF 1-ADAMANTYL CHLORIDES, BROMIDES, IODIDES, AND TOSYLATES IN PROTIC SOLVENTS
BENTLEY, TW
CARTER, GE
ROBERTS, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) : 5183 - 5189
[3] BENTLEY TW, 1977, ADV PHYS ORG CHEM, V14, P1
[4] HETERODIMERIC MOLECULES INCLUDING NUCLEIC-ACID BASES AND 9-AMINOACRIDINE - SPECTROSCOPIC STUDIES, CONFORMATIONS, AND INTERACTIONS WITH DNA
CONSTANT, JF
LAUGAA, P
ROQUES, BP
LHOMME, J
[J]. BIOCHEMISTRY, 1988, 27 (11) : 3997 - 4003
[5] ADENINE-THYMINE PAIRING IN WATER INDUCED BY AN INTERCALATING AGENT
CONSTANT, JF
FAHY, J
LHOMME, J
ANDERSON, JE
[J]. TETRAHEDRON LETTERS, 1987, 28 (16) : 1777 - 1780
[6] DECOUT JL, 1988, PHOTOCHEM PHOTOBIOL, V48, P583, DOI 10.1111/j.1751-1097.1988.tb02868.x
[7] CONCERNING THE MODE OF REACTION OF THE PROPOSED ULTIMATE METABOLITE OF THE CARCINOGEN 4-NITROQUINOLINE 1-OXIDE - EVIDENCE FOR INTERMEDIACY OF NITRENIUM IONS
DEMEUNYNCK, M
TOHME, N
LHOMME, MF
MELLOR, JM
LHOMME, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) : 3539 - 3541
[8] CONCERNING MODEL METABOLITES OF THE CARCINOGEN 4-NITROQUINOLINE 1-OXIDE - REACTIVITY AND SOLVOLYTIC BEHAVIOR OF 1-HYDROXY-4-(ACETOXYIMINO)-1,4-DIHYDROQUINOLINE
DEMEUNYNCK, M
LHOMME, MF
MELLOR, JM
LHOMME, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) : 399 - 405
[9] CONCERNING MODEL METABOLITES OF THE CARCINOGEN 4-NITROQUINOLINE 1-OXIDE - REACTIVITY OF 1-ACETOXY-4-(HYDROXYIMINO)-1,4-DIHYDROQUINOLINE
DEMEUNYNCK, M
TOHME, N
LHOMME, MF
MELLOR, JM
LHOMME, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) : 405 - 410
[10] SYNTHESIS OF O-ACETYL-N-(4-BIPHENYLYL)HYDROXYLAMINE (N-ACETOXY-4-AMINOBIPHENYL), AN ULTIMATE METABOLITE OF CARCINOGENIC 4-AMINOBIPHENYL, AND ITS REACTION WITH DEOXYGUANOSINE
FAMULOK, M
BOSOLD, F
BOCHE, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (03): : 337 - 338

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