Ultrabright and Serum-Stable Squaraine Dyes
- 18 August 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 63 (17), 9436-9445
- https://doi.org/10.1021/acs.jmedchem.0c00617
Abstract
Highly stable symmetric and asymmetric squaraine fluorophores have been synthesized featuring an internal salt bridge between a quaternary ammonium cation and the central oxycyclobutenolate ring of the chromophore. Some of our newly synthesized symmetric and asymmetric compounds display increased molar absorptivity, quantum yield in serum, and thermal/photochemical stability over previously reported squaraine-based dyes. Consequently, both classes show great promise in resurfacing the normal environment-labile squaraine dyes as novel imaging agents and scaffolds for fluorescence sensing. Furthermore, incorporating a covalent attachment point away from the conjugated system allows for biological tagging applications without disturbing the optimum optical characteristics of the newly designed fluorophore.Funding Information
- National Institute of Biomedical Imaging and Bioengineering (R01-EB022230)
- Georgia State University
- Brains and Behavior Seed Grant
- Health Innovation Platform Grant
- Georgia Research Alliance Venture Grant Phase 1
This publication has 22 references indexed in Scilit:
- A sensitive colorimetric and fluorescent sensor based on imidazolium-functionalized squaraines for the detection of GTP and alkaline phosphatase in aqueous solutionChemical Communications, 2014
- An intermolecular hydrogen-bonding effect on spectral and photophysical properties of 6-aminocoumarin in protic solventsPhotochemical & Photobiological Sciences, 2013
- The Role of π Bridges in High‐Efficiency DSCs Based on Unsymmetrical SquarainesChemistry – A European Journal, 2012
- Bright Near‐Infrared Fluorophores Based on Squaraines by Unexpected Halogen EffectsAngewandte Chemie, 2011
- Potential diagnostic value of fluorescein angiography and color Doppler imaging in primary open-angle glaucoma.European Journal of Ophthalmology, 2010
- Synthesis and characterization of squaric acid based NIR dyes for their application towards dye-sensitized solar cellsJournal of Photochemistry and Photobiology A: Chemistry, 2010
- Functionalization of Boron Dipyrrin (BODIPY) Dyes through Iridium and Rhodium Catalysis: A Complementary Approach to α‐ and β‐Substituted BODIPYsChemistry – A European Journal, 2009
- Phenylethynyl-BODIPY Oligomers: Bright Dyes and Fluorescent Building BlocksOrganic Letters, 2008
- A new synthesis of symmetric boraindacene (BODIPY) dyesChemical Communications, 2008
- A new spectrofluorimetric microdetermination of nitrite in water after derivatization with 4-methyl-7-aminocoumarinTalanta, 1996