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Titolo:
DIRECT SYNTHESIS AND CHARACTERIZATION OF SITE-SPECIFIC ADENOSYL ADDUCTS DERIVED FROM THE BINDING OF A 3,4-DIHYDROXY-1,2-EPOXYBENZO[C]PHENANTHRENE STEREOISOMER TO AN 11-MER OLIGODEOXYRIBONUCLEOTIDE
Autore:
LARYEA A; COSMAN M; LIN JM; LIU TM; AGARWAL R; SMIRNOV S; AMIN S; HARVEY RG; DIPPLE A; GEACINTOV NE;
Indirizzi:
NYU,DEPT CHEM,31 WASHINGTON PL NEW YORK NY 10003 NYU,DEPT CHEM NEW YORK NY 10003 MEM SLOAN KETTERING CANC CTR,CELLULAR BIOCHEM & BIOPHYS PROGRAM NEW YORK NY 10021 AMER HLTH FDN VALHALLA NY 10595 UNIV CHICAGO,BEN MAY INST CHICAGO IL 60637 NCI,FREDERICK CANC RES & DEV CTR,CHEM CARCINOGENESIS LAB FREDERICK MD21702
Titolo Testata:
Chemical research in toxicology
fascicolo: 3, volume: 8, anno: 1995,
pagine: 444 - 454
SICI:
0893-228X(1995)8:3<444:DSACOS>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
BENZO)A>PYRENE DIOL EPOXIDE; BENZO)C>PHENANTHRENE DIHYDRODIOL EPOXIDES; POLYCYCLIC AROMATIC-HYDROCARBONS; SNAKE-VENOM PHOSPHODIESTERASE; DNA-ADDUCTS; DEOXYADENOSINE ADDUCTS; SOLUTION CONFORMATION; MODIFIED OLIGODEOXYNUCLEOTIDES; ABSOLUTE-CONFIGURATION; LIVER MICROSOMES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Science Citation Index Expanded
Citazioni:
58
Recensione:
Indirizzi per estratti:
Citazione:
A. Laryea et al., "DIRECT SYNTHESIS AND CHARACTERIZATION OF SITE-SPECIFIC ADENOSYL ADDUCTS DERIVED FROM THE BINDING OF A 3,4-DIHYDROXY-1,2-EPOXYBENZO[C]PHENANTHRENE STEREOISOMER TO AN 11-MER OLIGODEOXYRIBONUCLEOTIDE", Chemical research in toxicology, 8(3), 1995, pp. 444-454

Abstract

Site-specifically modified oligonucleotides were obtained in milligram quantities by reacting racemic -1,2t-epoxy-1,2,3,4-tetrahydrobenzo[c]phenanthrene (B[c]PhDE-2, or anti-B[c]PhDE) with the single deoxyadenosine (dA) residue in the oligodeoxynucleotide d(CTCTCACTTCC). Enzyme digestion of the covalently modified oligonucleotides with the exonuclease spleen phosphodiesterase yielded covalently linked B[c]PhDE-N-6-deoxyadenosyl monophosphate (dAMP) adducts. Comparisons of the reverse phase HPLC retention times and CD spectra of these B[c]PhDE-3'-dAMP mononucleotide adducts, with those of standards derived from the reaction of the enantiomers (+)- and (-)-anti-B[c]PhDE with 3'-dAMP, show that two major oligonucleotide adducts (I and II) were obtained upon reacting racemic anti-B[c]PhDE with d(CTCTCACTTCC). In oligonucleotide adduct I, the lesion is a (+)-trans-anti-B [c]PhDE-N-6-dA residue, and inoligonucleotide adduct II it is a (-)-trans-anti-B[c]PhDE-N-6-dA residue. These assignments were further confirmed using a standard P-32 postlabeling assay of B[c]PhDE-3'-dAMP mononucleotide adducts obtained from the digestion of oligonucleotides I and II by spleen phosphodiesterase. The melting points (T-m) of duplexes of modified oligonucleotides I and II and their natural complementary strands are not affected significantly by the presence of the covalently bound benzo[c]phenanthrenyl residues. Opposite stereoselective resistance to enzyme digestion by the exonucleases snake venom phosphodiesterase and spleen phosphodiesterase is exhibited by the stereoisomeric (+)-trans- and (-)-trans-anti-B[c]PhDE-modified oligonucleotide adducts I and II; these results are consistent with the intercalative insertion of the benzo[c]phenanthrenyl residues on the 5'-side of the modified dA residue in adduct I,and its insertion on the 3'-side of the dA residue in adduct II, as observed in the duplexes by high resolution NMR techniques [Cosman et al. (1993) Biochemistry 32, 12488-12497, and Cosman et al., Biochemistry, in press].

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 12:59:18