A coumarinylaldoxime as a specific sensor for Cu2+ and its biological application

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

doi:10.1016/j.tetlet.2013.12.033

A coumarinylaldoxime as a specific sensor for Cu²⁺ and its biological application

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

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

22 Scopus citations

Abstract

In this Letter we present a new probe, (E)-7-(diethylamino)-2-oxo-2H- chromene-3-carbaldehyde oxime (JB), which can detect Cu²⁺ ions in HEPES buffer under physiological conditions. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu²⁺ complex formed is 2:1. Possible interference with other analytes was examined, and the decrease of the fluorescence of JB at 510 nm when it reacts with Cu²⁺ was shown to be highly selective. This probe accumulates in the plasmalemma of human neuroblastoma SH-SY5Y cells. Molecular dynamics (MD) simulations revealed that JB interacts with the lipid bilayer at the level of the glycerol moieties.

Original language	English
Pages (from-to)	873-876
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2013.12.033
State	Published - 22 Jan 2014
Externally published	Yes

Keywords

Coumarin derivative
Cu-selectivity
Fluorescent probe
Lipid bilayer
Molecular dynamics

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This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.tetlet.2013.12.033

Cite this

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title = "A coumarinylaldoxime as a specific sensor for Cu2+ and its biological application",

abstract = "In this Letter we present a new probe, (E)-7-(diethylamino)-2-oxo-2H- chromene-3-carbaldehyde oxime (JB), which can detect Cu2+ ions in HEPES buffer under physiological conditions. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu2+ complex formed is 2:1. Possible interference with other analytes was examined, and the decrease of the fluorescence of JB at 510 nm when it reacts with Cu2+ was shown to be highly selective. This probe accumulates in the plasmalemma of human neuroblastoma SH-SY5Y cells. Molecular dynamics (MD) simulations revealed that JB interacts with the lipid bilayer at the level of the glycerol moieties.",

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T1 - A coumarinylaldoxime as a specific sensor for Cu2+ and its biological application

AU - García-Beltrán, Olimpo

AU - Cassels, Bruce K.

AU - Mena, Natalia

AU - Nuñez, Marco T.

AU - Yañez, Osvaldo

AU - Caballero, Julio

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Y1 - 2014/1/22

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AB - In this Letter we present a new probe, (E)-7-(diethylamino)-2-oxo-2H- chromene-3-carbaldehyde oxime (JB), which can detect Cu2+ ions in HEPES buffer under physiological conditions. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu2+ complex formed is 2:1. Possible interference with other analytes was examined, and the decrease of the fluorescence of JB at 510 nm when it reacts with Cu2+ was shown to be highly selective. This probe accumulates in the plasmalemma of human neuroblastoma SH-SY5Y cells. Molecular dynamics (MD) simulations revealed that JB interacts with the lipid bilayer at the level of the glycerol moieties.

KW - Coumarin derivative

KW - Cu-selectivity

KW - Fluorescent probe

KW - Lipid bilayer

KW - Molecular dynamics

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