Synthesis and photophysics of benzazole based triazoles with amino acid-derived pendant units. Multiparametric optical sensors for BSA and CT-DNA in solution

被引：20

作者：

Debia, Natali P. ^{[1
]}

Rodriguez, Juan J. P. ^{[1
]}

da Silveira, Carolina H. ^{[2
]}

Chaves, Otavio A. ^{[3
]}

Iglesias, Bernardo A. ^{[2
]}

Rodembusch, Fabiano S. ^{[1
]}

Ludtke, Diogo S. ^{[1
]}

机构：

[1] UFRGS Univ Fed Rio Grande do Sul, Inst Quim, Av Bento Goncalves 9500, BR-91501970 Porto Alegre, RS, Brazil

[2] UFSM Univ Fed Santa Maria, LBMP Lab Bioinorgan & Mat Porfirin, Av Roraima 1000, BR-97105900 Santa Maria, RS, Brazil

[3] SENAI Innovat Inst Green Chem, Rua Morals & Silva 53, BR-20271030 Rio De Janeiro, RJ, Brazil

来源：

JOURNAL OF MOLECULAR LIQUIDS | 2020年 / 309卷

关键词：

Amino acid-derived triazole; Fluorescent sensor; Protein detection; DNA intercalation; Docking studies; BOVINE SERUM-ALBUMIN; AZIDE-ALKYNE CYCLOADDITION; MOLECULAR DOCKING; HYDROXYPHENYL BENZAZOLES; FLUORESCENCE LIFETIME; BINDING PROPERTIES; ETHIDIUM-BROMIDE; TERMINAL ALKYNES; SPECTROSCOPY; NMR;

D O I：

10.1016/j.molliq.2020.113092

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Herein we report the synthesis of a series of amino acid-derived triazoles by an organocatalytic cycloaddition reaction between azides and carbonyl compounds, catalyzed by a simple amine.These compounds present absorption maxima located in the UV-B ascribed to fully spin and symmetry allowed electronic transitions and a main fluorescence emission in the UV-A (similar to 380 nm) with a relatively large Stokes shift (5700 cm(-1)). No significant solvatochromism was observed in both ground and excited states. Unexpectedly, the benzoxazole derivatives presented much higher fluorescence quantum yield values (40-80%) of compared to the sulfur analogues (3-6%). In addition, the DNA binding assays indicated that these compounds presented strong interaction with CT-DNA, which could be attributed to pi-stacking and intermolecular hydrogen-bonding. The interaction of the benzazoles with bovine serum albumin (BSA) was also investigated, where a suppression mechanism was observed. In each case, docking was performed to better understand the observed interactions. (C) 2020 Elsevier B.V. All rights reserved.

引用

页数：17