Spectroscopic, Molecular Modeling, and NMR-Spectroscopic Investigation of the Binding Mode of the Natural Alkaloids Berberine and Sanguinarine to Human Telomeric G-Quadruplex DNA

被引：101

作者：

Bessi, Irene ^{[1
,2
,3
]}

Bazzicalupi, Carla ^{[4
]}

Richter, Christian ^{[1
]}

Jonker, Hendrik R. A. ^{[1
]}

Saxena, Krishna ^{[1
]}

Sissi, Claudia ^{[5
]}

Chioccioli, Matteo ^{[2
,3
]}

Bianco, Sara ^{[5
]}

Bilia, Anna Rita

Schwalbe, Harald ^{[1
]}

Gratteri, Paola ^{[2
,3
]}

机构：

[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, Ctr Biomol Magnet Resonance, D-60438 Frankfurt, Germany

[2] Univ Firenze, Dept Pharmaceut Sci, QSAR, I-50019 Florence, Italy

[3] Univ Firenze, Dept Pharmaceut Sci, Lab Mol Modeling Cheminformat, I-50019 Florence, Italy

[4] Univ Firenze, Dept Chem Ugo Schiff, I-50019 Florence, Italy

[5] Univ Padua, Dept Pharmaceut Sci, I-35100 Padua, Italy

来源：

ACS CHEMICAL BIOLOGY | 2012年 / 7卷 / 06期

关键词：

OPLS POTENTIAL FUNCTIONS; WATER SUPPRESSION; STRUCTURAL BASIS; DYNAMICS; FIELD; POLYMORPHISM; RECOGNITION; ASSOCIATION; DERIVATIVES; ABSORPTION;

D O I：

10.1021/cb300096g

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

G-quadruplex structures can be formed at the single-stranded overhang of telomeric DNA, and ligands able to stabilize this structure have recently been identified as potential anticancer drugs. Among the potential G-quadruplex binders, we have studied the binding ability of berberine and sanguinarine, two members of the alkaloid family, an important class of natural products long known for medicinal purpose. Our spectroscopic (CD, NMR, and fluorescence) studies and molecular modeling approaches revealed binding modes at ligand-complex stoichiometries >1:1 and ligand self-association induced by DNA for the interactions of the natural alkaloids berberine and sanguinarine with the human telomeric G-quadruplex DNA.

引用

页码：1109 / 1119

页数：11

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