Garcia-Beltran, Olimpo; Yanez, Osvaldo; Caballero, Julio; Galdamez, Antonio; Mena, Natalia; Nunez, Marco T.; Cassels, Bruce K.
Synthesis of coumarin derivatives as fluorescent probes for membrane and cell dynamics studies
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 76:79-86, APR 9 2014

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). (C) 2014 Elsevier Masson SAS. All rights reserved.

DOI:10.1016/j.ejmech.2014.02.016

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