Introduction of a nitroxide group on position 2 of 9-phenoxyacridine: Easy access to spin labelled DNA-binding conjugates

被引：18

作者：

Belmont, P ^{[1
]}

Chapelle, C ^{[1
]}

Demeunynck, M ^{[1
]}

Michon, J ^{[1
]}

Michon, P ^{[1
]}

Lhomme, J ^{[1
]}

机构：

[1] Univ Grenoble 1, CNRS, LEDSS, F-38041 Grenoble 09, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 06期

关键词：

D O I：

10.1016/S0960-894X(98)00089-4

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In the search for spin labelled intercalators of general use to construct DNA-binding conjugates, 6-chloro-2-[(1-oxyl-2,2,5,5-tetramethyl-pyrrolin-3-yl)methyloxy]-9-phenoxy-acridine 5, has been prepared. This key-intermediate reacts with amines to give the corresponding labelled 9-amino substituted acridines. Comparative EPR and fluorescence measurements show that the label causes only little modification of the binding properties of acridine. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：669 / 674

页数：6

共 23 条

[1] SUBCELLULAR-DISTRIBUTION OF A NITROXIDE SPIN-LABELED NETROPSIN-ACRIDINE HYBRID IN LIVING KB CELLS - ELECTRON-SPIN-RESONANCE STUDY [J].

BAILLY, C ;

HENICHART, JP .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 167 (02) :798-806

[2] THE HYDROXYETHYL ANALOG OF QUINACRINE [J].

CARLSON, WW ;

CRETCHER, LH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (02) :597-599

[3] SPIN-LABELED OXAZOLOPYRIDOCARBAZOLE AS A PROBE FOR STUDYING NONINTERCALATING DNA GROOVE BINDING LIGANDS [J].

CARRIER, A ;

LEBER, P ;

AUCLAIR, C .

BIOCHEMISTRY, 1990, 29 (25) :6002-6009

[4] NMR and molecular modeling studies of the interaction of artificial AP lyases with a DNA duplex containing an apurinic abasic site model [J].

Coppel, Y ;

Constant, JF ;

Coulombeau, C ;

Demeunynck, M ;

Garcia, J ;

Lhomme, J .

BIOCHEMISTRY, 1997, 36 (16) :4831-4843

[5] A NEW CLASS OF ARTIFICIAL NUCLEASES THAT RECOGNIZE AND CLEAVE APURINIC SITES IN DNA WITH GREAT SELECTIVITY AND EFFICIENCY [J].

FKYERAT, A ;

DEMEUNYNCK, M ;

CONSTANT, JF ;

MICHON, P ;

LHOMME, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :9952-9959

[6]

HANKOVSZKY HO, 1980, SYNTHESIS-STUTTGART, P914

[7]

HIDEG K, 1980, SYNTHESIS-STUTTGART, P911

[8]

HONG SJ, 1976, CANCER RES, V36, P1159

[9] TORSIONAL MOTION AND ELASTICITY OF THE DEOXYRIBONUCLEIC-ACID DOUBLE HELIX AND ITS NUCLEOSOMAL COMPLEXES [J].

HURLEY, I ;

OSEIGYIMAH, P ;

ARCHER, S ;

SCHOLES, CP ;

LERMAN, LS .

BIOCHEMISTRY, 1982, 21 (20) :4999-5009

[10] THEORY OF ESR LINEWIDTHS OF FREE RADICALS [J].

KIVELSON, D .

JOURNAL OF CHEMICAL PHYSICS, 1960, 33 (04) :1094-1106

← 1 2 3 →