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Molecules 2018, 23(2), 226; https://doi.org/10.3390/molecules23020226

Synthesis and Optical Properties of Near-Infrared meso-Phenyl-Substituted Symmetric Heptamethine Cyanine Dyes

1
Department of Chemistry, Georgia State University, 50 Decatur St., Atlanta, GA 30303, USA
2
Center for Diagnostics and Therapeutics, Georgia State University, Petit Science Center, 100 Piedmont Ave SE, Atlanta, GA 30303, USA
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 27 November 2017 / Revised: 18 January 2018 / Accepted: 20 January 2018 / Published: 24 January 2018
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF) probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds. View Full-Text
Keywords: heptamethine cyanine dyes; absorbance; fluorescence; NIRF; physiochemical properties; HSA binding heptamethine cyanine dyes; absorbance; fluorescence; NIRF; physiochemical properties; HSA binding
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Levitz, A.; Marmarchi, F.; Henary, M. Synthesis and Optical Properties of Near-Infrared meso-Phenyl-Substituted Symmetric Heptamethine Cyanine Dyes. Molecules 2018, 23, 226.

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