TY - JOUR
T1 - Synthesis of coumarin derivatives as fluorescent probes for membrane and cell dynamics studies
AU - García-Beltrán, Olimpo
AU - Yañez, Osvaldo
AU - Caballero, Julio
AU - Galdámez, Antonio
AU - Mena, Natalia
AU - Nuñez, Marco T.
AU - Cassels, Bruce K.
N1 - Funding Information:
This work was supported by a postdoctoral fellowship from the Millennium Scientific Initiative (Grant P05-001-F ) and FONDECYT Grant # 1130141 . The authors thank Dr. M. Rosario Torres of the CAI Difracción de rayos-X, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Spain, for the intensity data collection.
PY - 2014/4/9
Y1 - 2014/4/9
N2 - 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).
AB - 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).
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U2 - 10.1016/j.ejmech.2014.02.016
DO - 10.1016/j.ejmech.2014.02.016
M3 - Article
C2 - 24576613
AN - SCOPUS:84896697682
SN - 0223-5234
VL - 76
SP - 79
EP - 86
JO - European Journal of Medicinal Chemistry
JF - European Journal of Medicinal Chemistry
ER -