Synthesis of coumarin derivatives as fluorescent probes for membrane and cell dynamics studies

Olimpo García-Beltrán; Osvaldo Yañez; Julio Caballero; Antonio Galdámez; Natalia Mena; Marco T. Nuñez; Bruce K. Cassels

doi:10.1016/j.ejmech.2014.02.016

Synthesis of coumarin derivatives as fluorescent probes for membrane and cell dynamics studies

Olimpo García-Beltrán, Osvaldo Yañez, Julio Caballero, Antonio Galdámez, Natalia Mena, Marco T. Nuñez, Bruce K. Cassels

Olimpo

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

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).

Original language	English
Pages (from-to)	79-86
Number of pages	8
Journal	European Journal of Medicinal Chemistry
Volume	76
DOIs	https://doi.org/10.1016/j.ejmech.2014.02.016
Publication status	Published - Apr 9 2014

Bibliographical note

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.

ASJC Scopus Subject Areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2014.02.016

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@article{202490298f094e8d8d654703874bb730,

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).",

author = "Olimpo Garc{\'i}a-Beltr{\'a}n and Osvaldo Ya{\~n}ez and Julio Caballero and Antonio Gald{\'a}mez and Natalia Mena and Nu{\~n}ez, {Marco T.} and Cassels, {Bruce K.}",

note = "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 Difracci{\'o}n de rayos-X, Facultad de Ciencias Qu{\'i}micas, Universidad Complutense de Madrid, Spain, for the intensity data collection. ",

year = "2014",

month = apr,

day = "9",

doi = "10.1016/j.ejmech.2014.02.016",

language = "English",

volume = "76",

pages = "79--86",

journal = "European Journal of Medicinal Chemistry",

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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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Synthesis of coumarin derivatives as fluorescent probes for membrane and cell dynamics studies

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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