title: Excited state dynamics of brightly fluorescent second generation epicocconone analogues.
abstract: The natural product epicocconone, owing to its unique fluorescence properties, has been developed into a range of products used in biotechnology, especially proteomics. However, its weak green fluorescence in its native state, while advantageous for proteomics applications, is a disadvantage in other applications that require two-color readouts. Here we report the photophysical characterization of two brightly fluorescent analogues of epicocconone. These analogues, with naphthyl or pyridyl groups replacing the heptatriene chain, resulted in bright fluorescence in both the native state and the long Stokes shifted enamine. Time-resolved fluorescence studies and DFT calculations were carried out to understand the excited state processes involved in fluorescence. Results showed the p-chloro group on the pyridyl is responsible for the high fluorescence of the native fluorophore. The application of one of these compounds for staining electrophoresis gels is exemplified.
authors.forename: Soumit
authors.initials: S
authors.lastname: Chatterjee
authors.forename: Peter
authors.initials: P
authors.lastname: Karuso
authors.affiliation: ‡Normandie Univ, COBRA, UMR 6014 et FR 3038, CNRS, Univ Rouen, INSA Rouen, 1 rue Tesnières, 76821 Mont-Saint-Aignan, Cedex, France.
authors.forename: Agathe
authors.initials: A
authors.lastname: Boulangé
authors.affiliation: ‡Normandie Univ, COBRA, UMR 6014 et FR 3038, CNRS, Univ Rouen, INSA Rouen, 1 rue Tesnières, 76821 Mont-Saint-Aignan, Cedex, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Franck
authors.affiliation: §Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India.
authors.forename: Anindya
authors.initials: A
authors.lastname: Datta
mesh_terms: D001578:Benzopyrans / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D054879:Halogenation; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D009284:Naphthols / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D013050:Spectrometry, Fluorescence
chemical_list: D001578:Benzopyrans; D005456:Fluorescent Dyes; D005663:Furans; D007659:Ketones; D009284:Naphthols; D011725:Pyridines; C477464:epicocconone