title: Epicocconone-Hemicyanine Hybrids: Near Infrared Fluorophores for Protein Staining and Cell Imaging.
abstract: The development of new near infrared (NIR) dyes is crucial for diverse applications and especially bioimaging, as they absorb and emit light in the "therapeutic window" (650-950 nm). We report here a new family of NIR fluorophores that has been obtained by hybridising hemicyanines with epicocconone. Emission wavelengths of these hybrid dyes is in the range 715-795 nm and is combined with large Stokes' shifts (75-95 nm). The absorption and emission wavelength can be modulated according to the hemicyanine moiety and adding sulfonic acid moieties enhances water solubility. We demonstrate their application in the sensitive detection of proteins in gel electrophoresis and the staining of specific cellular organelles in confocal microscopy. These results are particularly encouraging and bring forward a new fluorescent skeleton for chemical biology.
authors.affiliation: Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia.
authors.forename: Peter
authors.identifier: http://orcid.org/0000-0002-0217-6021
authors.initials: P
authors.lastname: Karuso
authors.affiliation: Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia.
authors.forename: Wendy
authors.initials: W
authors.lastname: Loa Kum Cheung
authors.affiliation: Normandie Univ., CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014 & FR 3038), 76000, Rouen, France.|Present address: Univ. Bordeaux, ISM (CNRS-UMR 5255), 351 Cours de la Libération, Talence, 33405 Cedex, France.
authors.forename: Philippe A
authors.initials: PA
authors.lastname: Peixoto
authors.affiliation: Normandie Univ., CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014 & FR 3038), 76000, Rouen, France.|Present address: AQUISTAIN, Domaine du Haut-Carré, Bâtiment C5, 351 Cours de la Libération, 33400, Talence, France.
authors.forename: Agathe
authors.initials: A
authors.lastname: Boulangé
authors.affiliation: Normandie Univ., CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014 & FR 3038), 76000, Rouen, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Franck
mesh_terms: D000818:Animals; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry*; D002232:Carbocyanines / Q000138:chemical synthesis / Q000737:chemistry*; D002417:Cattle; D045744:Cell Line, Tumor; D004591:Electrophoresis, Polyacrylamide Gel; D005456:Fluorescent Dyes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008856:Microscopy, Fluorescence; D011506:Proteins / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry; D019265:Spectroscopy, Near-Infrared; D013194:Staining and Labeling
chemical_list: D001578:Benzopyrans; D002232:Carbocyanines; D005456:Fluorescent Dyes; D005663:Furans; D007659:Ketones; D011506:Proteins; C000601156:tetramethylene hemicyanine; D012710:Serum Albumin, Bovine; C477464:epicocconone
keywords: cyanine; epicocconone; fluorescent probes; imaging agents; protein staining