Macrocyclic and helical oligoamides as a new class of g-quadruplex ligands

被引:155
作者
Shirude, Pravin S.
Gillies, Elizabeth R.
Ladame, Sylvain
Godde, Frederic
Shin-Ya, Kazuo
Huc, Ivan
Balasubramanian, Shankar
机构
[1] Univ Bordeaux 1, Inst Europeen Chim & Biol, CNRS, UMR 5248, F-33607 Pessac, France
[2] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England
[3] Natl Inst Adv Ind Sci & Technol, Chem Biol Team, BIRC, Tokyo 1008921, Japan
关键词
D O I
10.1021/ja073775h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A planar trimeric macrocyclic oligoamide of 8-amino-2-quinoline carboxylic acid, bearing ammonium side chains, stabilizes the human telomeric G-quadruplex more strongly than the potent ligand telomestatin. Furthermore, a helical oligoamide tetramer also binds strongly to G-quadruplexes and is a new structural class of quadruplex ligand that appears to interact enantioselectively.
引用
收藏
页码:11890 / +
页数:3
相关论文
共 29 条
[1]   Mutated telomeres sensitize tumor cells to anticancer drugs independently of telomere shortening and mechanisms of telomere maintenance [J].
Cerone, M. A. ;
Londono-Vallejo, J. A. ;
Autexier, C. .
ONCOGENE, 2006, 25 (56) :7411-7420
[2]   An intramolecular G-quadruplex structure with mixed parallel/antiparallel G-strands formed in the human BCL-2 promoter region in solution [J].
Dai, JX ;
Dexheimer, TS ;
Chen, D ;
Carver, M ;
Ambrus, A ;
Jones, RA ;
Yang, DZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1096-1098
[3]   Porphyrin derivatives for telomere binding and telomerase inhibition [J].
Dixon, IM ;
Lopez, F ;
Estève, JP ;
Tejera, AM ;
Blasco, MA ;
Pratviel, G ;
Meunier, B .
CHEMBIOCHEM, 2005, 6 (01) :123-132
[4]   Chiral induction in quinoline-derived oligoamide foldamers:: Assignment of helical handedness and role of steric effects [J].
Dolain, C ;
Jiang, H ;
Léger, JM ;
Guionneau, P ;
Huc, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (37) :12943-12951
[5]   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
[6]   Development and biological assessment of fully water-soluble helical aromatic amide foldamers [J].
Gillies, Elizabeth R. ;
Deiss, Frederique ;
Staedel, Cathy ;
Schmitter, Jean-Marie ;
Huc, Ivan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (22) :4081-4084
[7]   Amphipathic helices from aromatic amino acid oligomers [J].
Gillies, Elizabeth R. ;
Dolain, Christel ;
Leger, Jean-Michel ;
Huc, Ivan .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21) :7931-7939
[8]   Interaction of telomestatin with the telomeric single-strand overhang [J].
Gomez, D ;
Paterski, R ;
Lemarteleur, T ;
Shin-ya, K ;
Mergny, JL ;
Riou, JF .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (40) :41487-41494
[9]   4-STRANDED NUCLEIC-ACID STRUCTURES 25 YEARS LATER - FROM GUANOSINE GELS TO TELOMER DNA [J].
GUSCHLBAUER, W ;
CHANTOT, JF ;
THIELE, D .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1990, 8 (03) :491-511
[10]   Prevalence of quadruplexes in the human genome [J].
Huppert, JL ;
Balasubramanian, S .
NUCLEIC ACIDS RESEARCH, 2005, 33 (09) :2908-2916