Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties

Molecules

Eduardo Soriano¹  Cory Holder¹  Andrew Levitz¹  Maged Henary¹ 

[1] Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA;

关键词: cyanine dye;    unsymmetrical;    synthesis;    optical properties;    DFT calculations;    DNA grooves;   

DOI  :  10.3390/molecules21010023

来源: mdpi

【 摘 要 】

Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.