Exploring the differential recognition of DNA G-quadruplex targets by small molecules using dynamic combinatorial chemistry

被引：85

作者：

Bugaut, Anthony ^{[1
]}

Jantos, Katja ^{[1
]}

Wietor, Jean-Luc ^{[1
]}

Rodriguez, Raphael ^{[1
]}

Sanders, Jeremy K. M. ^{[1
]}

Balasubramanian, Shankar ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 14期

基金：

英国生物技术与生命科学研究理事会;

关键词：

carbohydrates; combinatorial chemistry; DNA; molecular recognition; quadruplexes;

D O I：

10.1002/anie.200705589

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tuning affinities: Dynamic combinatorial chemistry has been employed to explore the effect of chemical modifications on the DNA G-quadruplex binding properties of anoxazole-based peptide macrocycle. Two dynamic libraries of molecules, containing cationic and carbohydrate motifs, respectively, were screened by using structurally diverse nucleic acid targets (see scheme; each colored shape represents a cation or carbohydrate). (Chemical Equation Presented). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2677 / 2680

页数：4

共 33 条

[1] Solution structure of the biologically relevant g-quadruplex element in the human c-MYC promoter. implications for g-quadruplex stabilization [J].

Ambrus, A ;

Chen, D ;

Dai, JX ;

Jones, RA ;

Yang, DZ .

BIOCHEMISTRY, 2005, 44 (06) :2048-2058

[2] Trisubstituted isoalloxazines as a new class of G-quadruplex binding ligands: Small molecule regulation of c-kit oncogene expression [J].

Bejugam, Mallesham ;

Sewitz, Sven ;

Shirude, Pravin S. ;

Rodriguez, Raphael ;

Shahid, Ramla ;

Balasubramanian, Shankar .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (43) :12926-+

[3] Target-induced selection of ligands from a dynamic combinatorial library of mono- and bi-conjugated oligonucleotides [J].

Bugaut, A ;

Bathany, K ;

Schmitter, JM ;

Rayner, B .

TETRAHEDRON LETTERS, 2005, 46 (04) :687-690

[4] Use of dynamic combinatorial chemistry for the identification of covalently appended residues that stabilize oligonucleotide complexes [J].

Bugaut, A ;

Toulmé, JJ ;

Rayner, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (24) :3144-3147

[5]

Bugaut A., 2004, ANGEW CHEM, V116, P3206

[6] SELEX and dynamic combinatorial chemistry interplay for the selection of conjugated RNA aptamers [J].

Bugaut, Anthony ;

Toulme, Jean-Jacques ;

Rayner, Bernard .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (22) :4082-4088

[7] Dynamic combinatorial chemistry [J].

Corbett, Peter T. ;

Leclaire, Julien ;

Vial, Laurent ;

West, Kevin R. ;

Wietor, Jean-Luc ;

Sanders, Jeremy K. M. ;

Otto, Sijbren .

CHEMICAL REVIEWS, 2006, 106 (09) :3652-3711

[8] G-quartets 40 years later:: From 5′-GMP to molecular biology and supramolecular chemistry [J].

Davis, JT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) :668-698

[9] A conserved quadruplex motif located in a transcription activation site of the human c-kit oncogene [J].

Fernando, Himesh ;

Reszka, Anthony P. ;

Huppert, Julian ;

Ladame, Sylvain ;

Rankin, Sarah ;

Venkitaraman, Ashok R. ;

Neidle, Stephen ;

Balasubramanian, Shankar .

BIOCHEMISTRY, 2006, 45 (25) :7854-7860

[10] Ligand amplification in a dynamic combinatorial glycopeptide library [J].

Hotchkiss, T ;

Kramer, HB ;

Doores, KJ ;

Gamblin, DP ;

Oldham, NJ ;

Davis, BG .

CHEMICAL COMMUNICATIONS, 2005, (34) :4264-4266

← 1 2 3 4 →