Governing the DNA-binding mode of styryl dyes by the length of their alkyl substituents - from intercalation to major groove binding

被引：36

作者：

Berdnikova, Daria V. ^{[1
,2
,3
]}

Sosnin, Nikolai I. ^{[1
]}

Fedorova, Olga A. ^{[1
]}

Ihmels, Heiko ^{[2
,3
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilova Str 28, Moscow 119991, Russia

[2] Univ Siegen, Dept Chem Biol, Adolf Reichwein Str 2, D-57068 Siegen, Germany

[3] Univ Siegen, Ctr Micro & Nanochem & Engn, Adolf Reichwein Str 2, D-57068 Siegen, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 04期

基金：

俄罗斯科学基金会;

关键词：

FLUORESCENT-PROBES; CYANINE DYES; NUCLEIC-ACIDS; DUPLEX; AGGREGATION; DERIVATIVES; STACKING; GREEN;

D O I：

10.1039/c7ob02736b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of monomeric and homodimeric 4-alkoxystyryl(pyridinium) dyes was synthesized and their DNA-binding properties were investigated. We found that the length of the alkyl substituent has a crucial influence on the binding mode of the dyes, although the structure of the DNA-binding unit is the same for all compounds. Remarkably, mono- and bis-styryl derivatives comprising an oxodecyl chain represent the rare examples of small molecules that bind to the major groove of DNA. We have also demonstrated that the dyes, except the monostyryl dye with a bromopropyl substituent, form chiral aggregates in the presence of double-stranded DNA.

引用

页码：545 / 554

页数：10

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