Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities

被引:66
作者
Chen, WH [1 ]
Pang, JY
Qin, Y
Peng, Q
Cai, ZW
Jiang, ZH
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Peoples R China
[2] Hong Kong Baptist Univ, Sch Chinese Med, Kowloon, Hong Kong, Peoples R China
[3] Hong Kong Baptist Univ, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1016/j.bmcl.2004.10.098
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
This communication describes the facile synthesis of five novel berberine dimers and their strong affinities toward double-stranded DNA. These berberine dimers were synthesized in 37-84% yields from the reaction of berberrubine with dihaloalkanes of varying lengths, and fully characterized by HRMS and H-1 NMR. Compared with the monomeric parent berberine, these dimers showed greatly enhanced binding affinities up to approximately 100-fold, with two double helical oligodeoxynucleotides, d(AAGAATTCTT)(2) and d(TAAGAATTCTTA)(2), which was investigated by means of fluorescence spectrometry. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2689 / 2692
页数:4
相关论文
共 20 条
[1]   METALS AND DNA - MOLECULAR LEFT-HANDED COMPLEMENTS [J].
BARTON, JK .
SCIENCE, 1986, 233 (4765) :727-734
[2]   Spectrometric studies of cytotoxic protoberberine alkaloids binding to double-stranded DNA [J].
Chen, WH ;
Qin, Y ;
Cai, ZW ;
Chan, CL ;
Luo, GA ;
Jiang, ZH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (05) :1859-1866
[3]   Study on noncovalent complexes of cytotoxic protoberberine alkaloids with double-stranded DNA by using electrospray ionization mass spectrometry [J].
Chen, WH ;
Chan, CL ;
Cai, ZW ;
Luo, GA ;
Jiang, ZH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (19) :4955-4959
[4]   DNA STRAND SCISSION BY (-)-EPICATECHIN AND PROCYANIDIN-B2 [J].
CHRISEY, LA ;
BONJAR, GHS ;
HECHT, SM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :644-646
[5]   Spectrofluorometric determination of DNA and RNA with berberine [J].
Gong, GQ ;
Zong, ZX ;
Song, YM .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1999, 55 (09) :1903-1907
[6]   Antibacterial activity and structure-activity relationships of berberine analogs [J].
Iwasa, K ;
Kamigauchi, M ;
Ueki, M ;
Taniguchi, M .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (06) :469-478
[7]   Cytotoxicity and DNA binding properties of the plant alkaloid burasaine [J].
Kluza, J ;
Baldeyrou, B ;
Colson, P ;
Rasoanaivo, P ;
Mambu, L ;
Frappier, F ;
Bailly, C .
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2003, 20 (4-5) :383-391
[8]   BERBERINE - COMPLEX WITH DNA [J].
KREY, AK ;
HAHN, FE .
SCIENCE, 1969, 166 (3906) :755-&
[9]   Protonated forms of poly[d(G-C)] and poly(dG).poly(dC) and their interaction with berberine [J].
Kumar, GS ;
Das, S ;
Bhadra, K ;
Maiti, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (23) :4861-4870
[10]   Ultratight DNA binding of a new bisintercalating anthracycline antibiotic [J].
Leng, FF ;
Priebe, W ;
Chaires, JB .
BIOCHEMISTRY, 1998, 37 (07) :1743-1753