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Titolo:
Alternative heterocycles for DNA recognition: An N-methylpyrazole/N-methylpyrrole pair specifies for A center dot T/T center dot A biase pairs
Autore:
Nguyen, DH; Szewczyk, JW; Baird, EE; Dervan, PB;
Indirizzi:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH Pasadena CAUSA 91125 iv Chem & Chem Engn, Pasadena, CA 91125 USA
Titolo Testata:
BIOORGANIC & MEDICINAL CHEMISTRY
fascicolo: 1, volume: 9, anno: 2001,
pagine: 7 - 17
SICI:
0968-0896(200101)9:1<7:AHFDRA>2.0.ZU;2-6
Fonte:
ISI
Lingua:
ENG
Soggetto:
MINOR-GROOVE; FOOTPRINT TITRATION; BINDING LIGANDS; BASE-PAIRS; SEQUENCE; POLYAMIDES; INHIBITION; IMIDAZOLE; ACIDS; DISTAMYCIN;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
36
Recensione:
Indirizzi per estratti:
Indirizzo: Dervan, PB CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA CALTECH Pasadena CA USA 91125 hem Engn, Pasadena, CA 91125 USA
Citazione:
D.H. Nguyen et al., "Alternative heterocycles for DNA recognition: An N-methylpyrazole/N-methylpyrrole pair specifies for A center dot T/T center dot A biase pairs", BIO MED CH, 9(1), 2001, pp. 7-17

Abstract

Side-by-side pairs of three five-membered rings, N-methylpyrrole (Py), N-methylimidazole (Im), and N-methylhy-droxypyrrole (Hp), have been demonstrated to distinguish each of the four Watson-Crick base pairs in the minor groove of DNA. However, not all DNA sequences targeted by these pairing rules achieve affinities and specificities comparable to DNA binding proteins. Wehave initiated a search for new heterocycles which can expand the sequencerepetoire currently available. Two het erocyclic aromatic amino acids, N-methylpyrazole (Pz) and 4-methylthiazole (Th), were incorporated into a single position of an eight-ring polyamide of sequence ImImXPy-gamma -ImPyPyPy-beta -Dp to examine the modulation of affinity and specificity for DNA binding by a Pz/Py pair and/or a Th/Py pair. The X/Py pairings Pz/Py and Th/Py were evaluated by quantitative DNase I footprint titrations on a DNA fragment with the four sites 5'-TGGNCA-3' (N=T, A, G, C). The Pz/Py pair binds T.A and A.T with similar affinity to a Py/Py pair but with improved specificity, disfavoring both G.C and C.G by about 100-fold. The Th/Py pair binds poorly to all four Watson-Crick base pairs. These results demonstrate that insome instances new heterocyclic aromatic amino acid pairs can be incorporated into imidazole-pyrrole polyamides to mimic the DNA specificity of Py/Pypairs which may be relevant as biological criteria in animal studies become important. (C) 2000 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/09/20 alle ore 23:05:42