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

Eduardo Soriano; Cory Holder; Andrew Levitz; Maged Henary

doi:10.3390/molecules21010023

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

Molecules. 2015 Dec 24;21(1):E23. doi: 10.3390/molecules21010023.

Authors

Eduardo Soriano¹, Cory Holder², Andrew Levitz³, Maged Henary^{4

5}

Affiliations

¹ Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. esoriano1@gsu.edu.
² Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. cholder1@gsu.edu.
³ Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. alevitz1@gsu.edu.
⁴ Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. mhenary1@gsu.edu.
⁵ Center for Diagnostics and Therapeutics, Georgia State University, Petit Science Center, 100 Piedmont Ave SE, Atlanta, GA 30303, USA. mhenary1@gsu.edu.

Abstract

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.

Keywords: DFT calculations; DNA grooves; cyanine dye; optical properties; synthesis; unsymmetrical.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbocyanines / chemical synthesis*
Carbocyanines / chemistry
Computational Biology / methods
Fluorescent Dyes / chemical synthesis*
Fluorescent Dyes / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Nucleic Acids / chemistry*
Optical Phenomena

Substances

Carbocyanines
Fluorescent Dyes
Nucleic Acids