Synthesis and Activity Evaluation of 9-O-Substituted Berberine Derivatives Containing Polyamine Chain as Highly Selective Telomeric G-Quadruplex Stabilizing Ligands

doi:10.7503/cjcu20120327

Chem. J. Chinese Universities ›› 2012, Vol. 33 ›› Issue (10): 2217.doi: 10.7503/cjcu20120327

• Organic Chemistry • Previous Articles Next Articles

Synthesis and Activity Evaluation of 9-O-Substituted Berberine Derivatives Containing Polyamine Chain as Highly Selective Telomeric G-Quadruplex Stabilizing Ligands

MA Yan^1,2, HUANG Zhi-Shu²

1. Department of Medical Science, Shunde Polytechnic, Shunde 528333, China;
2. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510080, China

Received:2012-04-09 Online:2012-10-10 Published:2012-09-12

Abstract

Abstract:

A series of 9-O-substituted berberine derivatives(5a-5c) as telomeric quadruplex ligands was synthesized and evaluated. The interaction of berberine derivatives with telomeric G-quadruplex DNA was examined by CD spectroscopy, FRET-melting method, fluorescence titration assay and PCR-stop assay. The CD results indicated the derivatives were capable of inducing the formation of antiparallel G-quadruplex and the results from FRET-melting method clearly showed that derivatives with polyamine chain had high binding affinity and superior selectivity for telomeric G-quadruplex DNA over duplex. The PCR-stop assay results exhibited the inhibitory effect on the hybridization. All the results suggested the 9-O-substituted berberine derivatives were highly selective telomeric G-quadruplex DNA stabilizing ligands.

Key words: 9-O-Substituted berberine derivatives containing polyamine chain, Synthesis, Activity evaluation, Telomeric quadruplex DNA

CLC Number:

O629

TrendMD:

MA Yan, HUANG Zhi-Shu. Synthesis and Activity Evaluation of 9-O-Substituted Berberine Derivatives Containing Polyamine Chain as Highly Selective Telomeric G-Quadruplex Stabilizing Ligands[J]. Chem. J. Chinese Universities, 2012, 33(10): 2217.

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Synthesis and Activity Evaluation of 9-O-Substituted Berberine Derivatives Containing Polyamine Chain as Highly Selective Telomeric G-Quadruplex Stabilizing Ligands

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