Synthesis and G-quadruplex binding studies of new 4-N-methylpyridinium porphyrins

被引：56

作者：

Goncalves, Diana P. N. ^{[1
]}

Ladame, Sylvain ^{[1
]}

Balasubramanian, Shankar ^{[1
]}

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

机构：

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 17期

关键词：

D O I：

10.1039/b608494j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of cationic porphyrins carrying 1 - 3 meso-N-pyridinium groups has been synthesised, and their binding to G-quadruplex DNA has been explored by surface plasmon resonance (SPR) and circular dichroism spectroscopy. Two trans substituents appear to be sufficient for tight binding; preferential binding to the anti-parallel intramolecular human telomeric DNA was observed for the A(2) trans and A(3) porphyrins. The A(2) trans is able to induce the formation of an anti-parallel G-quadruplex in a K+ free solution, mimicking the effect of a molecular chaperone.

引用

页码：3337 / 3342

页数：6

共 32 条

[1] PYRROMETHANES AND PORPHYRINS THEREFROM [J].

ARSENAULT, GP ;

BULLOCK, E ;

MACDONALD, SF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (16) :4384-4389

[2]

BALAGURUMOORTHY P, 1994, J BIOL CHEM, V269, P21858

[3] Verification of antiparallel G-quadruplex structure in human telomeres by using two-photon excitation fluorescence lifetime imaging microscopy of the 3,6-bis(1-methyl-4-vinylpyridinium)carbazole diiodide molecule [J].

Chang, CC ;

Chu, JF ;

Kao, FJ ;

Chiu, YC ;

Lou, PJ ;

Chen, HC ;

Chang, TC .

ANALYTICAL CHEMISTRY, 2006, 78 (08) :2810-2815

[4] 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

[5] 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

[6] Rational synthesis of meso-substituted porphyrins bearing one nitrogen heterocyclic group [J].

Gryko, D ;

Lindsey, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2249-2252

[7] Structure of a G-quadruplex-ligand complex [J].

Haider, SM ;

Parkinson, GN ;

Neidle, S .

JOURNAL OF MOLECULAR BIOLOGY, 2003, 326 (01) :117-125

[8] Interactions of TMPyP4 and TMPyP2 with quadruplex DNA. Structural basis for the differential effects on telomerase inhibition [J].

Han, FXG ;

Wheelhouse, RT ;

Hurley, LH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3561-3570

[9] Selective interactions of cationic porphyrins with G-quadruplex structures [J].

Han, HY ;

Langley, DR ;

Rangan, A ;

Hurley, LH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :8902-8913

[10] Prevalence of quadruplexes in the human genome [J].

Huppert, JL ;

Balasubramanian, S .

NUCLEIC ACIDS RESEARCH, 2005, 33 (09) :2908-2916

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