Benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxide adducts in native and denatured DNA

被引：13

作者：

Agarwal, R

Yagi, H

Jerina, DM

Dipple, A

机构：

[1] NCI, FREDERICK CANC RES & DEV CTR, ABL BASIC RES PROGRAM, CHEM CARCINOGENESIS LAB, FREDERICK, MD 21702 USA

[2] NIDDKD, BIOORGAN CHEM LAB, BETHESDA, MD 20892 USA

来源：

CARCINOGENESIS | 1996年 / 17卷 / 08期

关键词：

D O I：

10.1093/carcin/17.8.1773

中图分类号：

R73 [肿瘤学];

学科分类号：

100214 ;

摘要：

High performance liquid chromatography/UV-absorption and P-32-postlabeling were used to quantitate adducts generated by reaction of the four configurationally isomeric benzo[c]phenanthrene 3,4-dihydrodiol 1,2-epoxides with native or denatured DNA in vitro. For both the 4R,3S-dihydrodiol 2S,1R-epoxide and the 4S,3R-dihydrodiol 2S,1R-epoxide, the amount of product resulting from trans-opening of the epoxide ring by the exocyclic amino group of deoxyadenosine in denatured DNA was much less than the level found in native DNA, indicating that the native DNA structure probably intercalates the hydrocarbon residue in a fashion that promotes adenine reaction for 2S,1R-epoxides.

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页码：1773 / 1776

页数：4

相关论文

共 25 条

[1] CHEMICAL CHARACTERIZATION OF DNA ADDUCTS DERIVED FROM THE CONFIGURATIONALLY ISOMERIC BENZO[C]PHENANTHRENE-3,4-DIOL 1,2-EPOXIDES [J].

AGARWAL, SK ;

SAYER, JM ;

YEH, HJC ;

PANNELL, LK ;

HILTON, BD ;

PIGOTT, MA ;

DIPPLE, A ;

YAGI, H ;

JERINA, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2497-2504

[2] TUMOR-INITIATING ACTIVITY ON MOUSE SKIN OF BAY-REGION DIOL-EPOXIDES OF 5,6-DIMETHYLCHRYSENE AND BENZO[C]PHENANTHRENE [J].

AMIN, S ;

DESAI, D ;

HECHT, SS .

CARCINOGENESIS, 1993, 14 (10) :2033-2037

[3]

[Anonymous], [No title captured], DOI DOI 10.1074/JBC.M409155200

[4] IDENTIFICATION OF INDIVIDUAL BENZO[C]PHENANTHRENE DIHYDRODIOL EPOXIDE-DNA ADDUCTS BY THE P-32 POSTLABELING ASSAY [J].

CANELLA, KA ;

PELTONEN, K ;

YAGI, H ;

JERINA, DM ;

DIPPLE, A .

CHEMICAL RESEARCH IN TOXICOLOGY, 1992, 5 (05) :685-690

[5] STEREOSELECTIVE RELEASE OF POLYCYCLIC AROMATIC HYDROCARBON DEOXYADENOSINE ADDUCTS FROM DNA BY THE P-32 POSTLABELING AND DEOXYRIBONUCLEASE-I SNAKE-VENOM PHOSPHODIESTERASE DIGESTION METHODS [J].

CHEH, AM ;

YAGI, H ;

JERINA, DM .

CHEMICAL RESEARCH IN TOXICOLOGY, 1990, 3 (06) :545-550

[6] EFFECT OF DNA-BASE SEQUENCE ON THE CONFIGURATION OF DEOXYADENOSINE ADDUCTS FORMED BY THE FJORD REGION DIOL EPOXIDE, (+)-(1R,2S,3R,4S)-3,4-DIHYDROXY-1,2-EPOXY-1,2,3,4-TETRAHYDROBENZO[C]PHENANTHRENE [J].

CHEH, AM ;

YAGI, H ;

JERINA, DM .

BIOCHEMISTRY, 1994, 33 (43) :12911-12919

[7] SOLUTION CONFORMATION OF THE (+)-TRANS-ANTI-[BPH]DA ADDUCT OPPOSITE DT IN A DNA DUPLEX - INTERCALATION OF THE COVALENTLY ATTACHED BENZO[C]PHENANTHRENE TO THE 5'-SIDE OF THE ADDUCT SITE WITHOUT DISRUPTION OF THE MODIFIED BASE-PAIR [J].

COSMAN, M ;

FIALA, R ;

HINGERTY, BE ;

LARYEA, A ;

LEE, HM ;

HARVEY, RG ;

AMIN, S ;

GEACINTOV, NE ;

BROYDE, S ;

PATEL, D .

BIOCHEMISTRY, 1993, 32 (46) :12488-12497

[8] SOLUTION CONFORMATION OF THE (-)-TRANS-ANTI-BENZO[C]PHENANTHRENE-DA ([BPH]DA) ADDUCT OPPOSITE DT IN A DNA DUPLEX - INTERCALATION OF THE COVALENTLY ATTACHED BENZO[C]PHENANTHRENYL RING TO THE 3'-SIDE OF THE ADDUCT SITE AND COMPARISON WITH THE (+)-TRANS-ANTI-[BPH]DA OPPOSITE DT STEREOISOMER [J].

COSMAN, M ;

LARYEA, A ;

FIALA, R ;

HINGERTY, BE ;

AMIN, S ;

GEACINTOV, NE ;

BROYDE, S ;

PATEL, DJ .

BIOCHEMISTRY, 1995, 34 (04) :1295-1307

[9] OPTICALLY-ACTIVE BENZO[C]PHENANTHRENE DIOL EPOXIDES BIND EXTENSIVELY TO ADENINE IN DNA [J].

DIPPLE, A ;

PIGOTT, MA ;

AGARWAL, SK ;

YAGI, H ;

SAYER, JM ;

JERINA, DM .

NATURE, 1987, 327 (6122) :535-536

[10] RESISTANCE OF 7,12-DIMETHYLBENZ[A]ANTHRACENE DEOXYADENOSINE ADDUCTS IN DNA TO HYDROLYSIS BY SNAKE-VENOM PHOSPHODIESTERASE [J].

DIPPLE, AJ ;

PIGOTT, MA .

CARCINOGENESIS, 1987, 8 (03) :491-493