The conformational characteristics of Congo red, Evans blue and Trypan blue

被引:39
作者
Skowronek, M
Roterman, I
Konieczny, L
Stopa, B
Rybarska, J
Piekarska, B
Górecki, A
Król, M
机构
[1] Jagiellonian Univ, Coll Med, Dept Biostat & Med Informat, PL-31501 Krakow, Poland
[2] Jagiellonian Univ, Coll Med, Inst Biochem, PL-31034 Krakow, Poland
[3] Stanislaw Staszic Univ Min & Met, Krakow, Poland
来源
COMPUTERS & CHEMISTRY | 2000年 / 24卷 / 3-4期
关键词
Congo red; Evans blue; Trypan blue;
D O I
10.1016/S0097-8485(99)00089-3
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The structures of the closely related bis-azo dyes Evans blue, Trypan blue and Congo red, which appeared to have different self-assembly properties and correspondingly different abilities to form complexes with amyloids and some other proteins, were compared in this work. Ab initio and semi-empirical methods were used to find the optimal structures and partial charge distributions of the dyes. The optimal structures were searched using different widely used programs. The structures of Congo red and evans blue were found to be planar, except for the torsion on the central diphenyl bond connecting the two halves of the dye. Both symmetrical parts of the molecules appeared very close to planarity. However, Trypan blue exhibits non planarity on the di-azo bonds, as well as on the central bond between the symmetrical parts of the dye. In a consequence, the non planarity of this molecule is higher than in the case of its isomer, Evans blue and co ngo red as well. The extra rotation around the azo bonds extorted by the close proximity of the sulfonic groups may be the direct cause of its poor self-assembling and complexation properties versus Evans blue. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:429 / 450
页数:22
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