title: Synthesis of coumarin derivatives as fluorescent probes for membrane and cell dynamics studies.
abstract: Three coumarin-derived fluorescent probes, 3-acetyl-7-[(6-bromohexyl)oxy]-2H-chromen-2-one (FM1), 7-[(6-bromohexyl)oxy]-4-methyl-2H-chromen-2-one (FM2) and ethyl 2-{7-[(6-bromohexyl)oxy]-2-oxo-2H-chromen-4-yl}acetate (FM3), are described, with their photophysical constants. The compounds were tested in preliminary studies employing epifluorescence microscopy demonstrating that they allow the imaging of human neuroblastoma SH-SY5Y cell membranes. The structure of FM3 was confirmed by X-ray crystallographic analysis. Molecular dynamics (MD) simulations were used to characterize the localization and interactions of the studied compounds with a lipid bilayer model of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC).
authors.affiliation: Department of Chemistry, Faculty of Sciences, University of Chile, Santiago, Chile; Facultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 Calle 67, Ibagué, Colombia. Electronic address: ojgarciab@ug.uchile.cl.
authors.forename: Olimpo
authors.initials: O
authors.lastname: García-Beltrán
authors.affiliation: Centro de Bioinformática y Simulación Molecular, Facultad de Ingeniería, Universidad de Talca, 2 Norte 685, Casilla 721, Talca, Chile.
authors.forename: Osvaldo
authors.initials: O
authors.lastname: Yañez
authors.affiliation: Centro de Bioinformática y Simulación Molecular, Facultad de Ingeniería, Universidad de Talca, 2 Norte 685, Casilla 721, Talca, Chile.
authors.forename: Julio
authors.initials: J
authors.lastname: Caballero
authors.affiliation: Department of Chemistry, Faculty of Sciences, University of Chile, Santiago, Chile.
authors.forename: Antonio
authors.initials: A
authors.lastname: Galdámez
authors.affiliation: Department of Biology, Faculty of Sciences, University of Chile, Santiago, Chile.
authors.forename: Natalia
authors.initials: N
authors.lastname: Mena
authors.affiliation: Department of Biology, Faculty of Sciences, University of Chile, Santiago, Chile.
authors.forename: Marco T
authors.initials: MT
authors.lastname: Nuñez
authors.affiliation: Department of Chemistry, Faculty of Sciences, University of Chile, Santiago, Chile.
authors.forename: Bruce K
authors.initials: BK
authors.lastname: Cassels
mesh_terms: D045744:Cell Line, Tumor; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry*; D006801:Humans; D056004:Molecular Dynamics Simulation; D009447:Neuroblastoma / Q000473:pathology
chemical_list: D003374:Coumarins; D005456:Fluorescent Dyes; C030123:coumarin
keywords: Cell membranes; Coumarins; Molecular dynamics; Probes