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

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

6 Citas (Scopus)

Resumen

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).

Idioma original	Inglés
Páginas (desde-hasta)	79-86
Número de páginas	8
Publicación	European Journal of Medicinal Chemistry
Volumen	76
DOI	https://doi.org/10.1016/j.ejmech.2014.02.016
Estado	Publicada - 9 abr. 2014
Publicado de forma externa	Sí

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@article{ea21ad9cd1bd462fbb1b3c6ed6567953,

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).",

keywords = "Cell membranes, Coumarins, Molecular dynamics, Probes",

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.}",

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",

issn = "0223-5234",

}

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.

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).

KW - Cell membranes

KW - Coumarins

KW - Molecular dynamics

KW - Probes

UR - http://www.scopus.com/inward/record.url?scp=84896697682&partnerID=8YFLogxK

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 -

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

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