title: Benz[c,d]indolium-containing Monomethine Cyanine Dyes: Synthesis and Photophysical Properties.
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.
authors.affiliation: Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. esoriano1@gsu.edu.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Soriano
authors.affiliation: Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. cholder1@gsu.edu.
authors.forename: Cory
authors.initials: C
authors.lastname: Holder
authors.affiliation: Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. alevitz1@gsu.edu.
authors.forename: Andrew
authors.initials: A
authors.lastname: Levitz
authors.affiliation: Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA. mhenary1@gsu.edu.|Center for Diagnostics and Therapeutics, Georgia State University, Petit Science Center, 100 Piedmont Ave SE, Atlanta, GA 30303, USA. mhenary1@gsu.edu.
authors.forename: Maged
authors.initials: M
authors.lastname: Henary
mesh_terms: D002232:Carbocyanines / Q000138:chemical synthesis* / Q000737:chemistry; D019295:Computational Biology / Q000379:methods; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009696:Nucleic Acids / Q000737:chemistry*; D055620:Optical Phenomena
chemical_list: D002232:Carbocyanines; D005456:Fluorescent Dyes; D009696:Nucleic Acids
keywords: DFT calculations; DNA grooves; cyanine dye; optical properties; synthesis; unsymmetrical