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Titolo:
SYNTHESIS AND CHARACTERIZATION OF COVALENT ADDUCTS DERIVED FROM THE BINDING OF BENZO[A]PYRENE DIOL EPOXIDE TO A -GGG- SEQUENCE IN A DEOXYOLIGONUCLEOTIDE
Autore:
MAO B; XU J; LI B; MARGULIS LA; SMIRNOV S; YA NQ; COURTNEY SH; GEACINTOV NE;
Indirizzi:
NYU,DEPT CHEM NEW YORK NY 10003 NYU,DEPT CHEM NEW YORK NY 10003 NYU,RADIAT & SOLID STATE LAB NEW YORK NY 10003
Titolo Testata:
Carcinogenesis
fascicolo: 2, volume: 16, anno: 1995,
pagine: 357 - 365
SICI:
0143-3334(1995)16:2<357:SACOCA>2.0.ZU;2-B
Fonte:
ISI
Lingua:
ENG
Soggetto:
GUANINE PHOSPHORIBOSYLTRANSFERASE GENE; POLYCYCLIC AROMATIC-HYDROCARBONS; DOSE-DEPENDENT DIFFERENCES; ESCHERICHIA-COLI PLASMID; DNA ADDUCTS; MODIFIED OLIGODEOXYNUCLEOTIDES; ACTIVATED BENZO)A>PYRENE; OLIGONUCLEOTIDE ADDUCTS; SOLUTION CONFORMATION; CODING REGION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
57
Recensione:
Indirizzi per estratti:
Citazione:
B. Mao et al., "SYNTHESIS AND CHARACTERIZATION OF COVALENT ADDUCTS DERIVED FROM THE BINDING OF BENZO[A]PYRENE DIOL EPOXIDE TO A -GGG- SEQUENCE IN A DEOXYOLIGONUCLEOTIDE", Carcinogenesis, 16(2), 1995, pp. 357-365

Abstract

Direct synthesis and purification procedures are described for the preparation of adducts derived from the covalent binding of xy-9S,10R-epoxy-7,8,9,10-tetrahydro-benzo[a]pyrene [(+)-anti-BPDE or (+)-BPDE 2] to each of the three guanine residues (trans-N-2-dG lesions) in the oligodeoxyribonucleotide d(CTATG(1)G(2)G(3)TATC). The positions of the modified Gs are defined by Maxam - Gilbert sequencing techniques. Six different oligonucleotides with one or two precisely positioned (+)-anti-BPDE residues are identified. The absorbance, circular dichroism and fluorescence characteristics are changed upon formation of duplexes with the complementary strands d(GATACCCATAG). In the doubly-modified oligonucleotides, a broad, excimer-like long wavelength fluorescence emission band is observed with a maximum near 455 nm only if the two (+)-anti-BPDE-modified Gs are adjacent to one another. The covalently attached (+)-anti-BPDE residues decrease the thermodynamic stabilities of the duplexes; their melting points are markedly dependent on the position of the lesions, being highest with the (+)-anti-BPDE residue at G(1) (T-m = 40 degrees C, only 2 degrees C lower than in the case of theunmodified oligonucleotide) and lowest when it is situated at G(3) (T-m = 29 degrees C). The implications of these and other physical characteristics are discussed. The facile synthesis of these or similar site-specific and stereochemically defined (+)-trans-anti-BPDE-N-2-dG lesions in runs of contiguous guanines in oligodeoxyribonucleotides of specified base sequence should be useful for the design of site-directedmutagenesis studies in vitro and in vivo.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 12:21:49