Design and synthesis of a new coumarin-based 'turn-on' fluorescent probe selective for Cu +2

Olimpo García-Beltrán; Natalia Mena; Leidi C. Friedrich; José Carlos Netto-Ferreira; Víctor Vargas; Frank H. Quina; Marco T. Núñez; Bruce K. Cassels

doi:10.1016/j.tetlet.2012.07.082

Design and synthesis of a new coumarin-based 'turn-on' fluorescent probe selective for Cu ⁺²

Olimpo García-Beltrán, Natalia Mena, Leidi C. Friedrich, José Carlos Netto-Ferreira, Víctor Vargas, Frank H. Quina, Marco T. Núñez, Bruce K. Cassels

Olimpo

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

52 Citations (Scopus)

Abstract

The novel coumarin-based 'turn-on' fluorescent probe (E)-3-(2,5- dimethoxybenzylideneamino)-7-hydroxy-2H-chromen-2-one (MGM) was designed, synthesized, and characterized. This compound shows high selectivity for Cu ⁺², combined with a large fluorescence enhancement upon binding to Cu ²⁺. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu ²⁺ complex formed is 2:1. Preliminary studies employing epifluorescence microscopy demonstrated that Cu ⁺² could be imaged in human neuroblastoma SH-SY5Y cells treated with MGM.

Original language	English
Pages (from-to)	5280-5283
Number of pages	4
Journal	Tetrahedron Letters
Volume	53
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2012.07.082
Publication status	Published - Sept 26 2012

Bibliographical note

Funding Information:
This work was supported by the Millennium Scientific Initiative (Grant P05-001-F) and by the Instituto Nacional de Ciência e Tecnologia do Meio Ambiente-USP (Brazil). JCNF thanks the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) for a Visiting Professor Fellowship. FHQ and LCF acknowledge fellowship support from the CNPq-Brazil.

Funding

This work was supported by the Millennium Scientific Initiative (Grant P05-001-F) and by the Instituto Nacional de Ciência e Tecnologia do Meio Ambiente-USP (Brazil). JCNF thanks the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) for a Visiting Professor Fellowship. FHQ and LCF acknowledge fellowship support from the CNPq-Brazil.

Funders	Funder number
CNPq-Brazil
Instituto Nacional de Ciência e Tecnologia do Meio Ambiente-USP
Fundação de Amparo à Pesquisa do Estado de São Paulo

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2012.07.082

Cite this

@article{fdd7697819d0468184fc2b7fd70d030e,

title = "Design and synthesis of a new coumarin-based 'turn-on' fluorescent probe selective for Cu +2 ",

abstract = "The novel coumarin-based 'turn-on' fluorescent probe (E)-3-(2,5- dimethoxybenzylideneamino)-7-hydroxy-2H-chromen-2-one (MGM) was designed, synthesized, and characterized. This compound shows high selectivity for Cu +2, combined with a large fluorescence enhancement upon binding to Cu 2+. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu 2+ complex formed is 2:1. Preliminary studies employing epifluorescence microscopy demonstrated that Cu +2 could be imaged in human neuroblastoma SH-SY5Y cells treated with MGM.",

author = "Olimpo Garc{\'i}a-Beltr{\'a}n and Natalia Mena and Friedrich, {Leidi C.} and Netto-Ferreira, {Jos{\'e} Carlos} and V{\'i}ctor Vargas and Quina, {Frank H.} and N{\'u}{\~n}ez, {Marco T.} and Cassels, {Bruce K.}",

note = "Funding Information: This work was supported by the Millennium Scientific Initiative (Grant P05-001-F) and by the Instituto Nacional de Ci{\^e}ncia e Tecnologia do Meio Ambiente-USP (Brazil). JCNF thanks the Funda{\c c}{\~a}o de Amparo {\`a} Pesquisa do Estado de S{\~a}o Paulo (FAPESP) for a Visiting Professor Fellowship. FHQ and LCF acknowledge fellowship support from the CNPq-Brazil. ",

year = "2012",

month = sep,

day = "26",

doi = "10.1016/j.tetlet.2012.07.082",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Design and synthesis of a new coumarin-based 'turn-on' fluorescent probe selective for Cu +2

AU - García-Beltrán, Olimpo

AU - Mena, Natalia

AU - Friedrich, Leidi C.

AU - Netto-Ferreira, José Carlos

AU - Vargas, Víctor

AU - Quina, Frank H.

AU - Núñez, Marco T.

AU - Cassels, Bruce K.

N1 - Funding Information: This work was supported by the Millennium Scientific Initiative (Grant P05-001-F) and by the Instituto Nacional de Ciência e Tecnologia do Meio Ambiente-USP (Brazil). JCNF thanks the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) for a Visiting Professor Fellowship. FHQ and LCF acknowledge fellowship support from the CNPq-Brazil.

PY - 2012/9/26

Y1 - 2012/9/26

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AB - The novel coumarin-based 'turn-on' fluorescent probe (E)-3-(2,5- dimethoxybenzylideneamino)-7-hydroxy-2H-chromen-2-one (MGM) was designed, synthesized, and characterized. This compound shows high selectivity for Cu +2, combined with a large fluorescence enhancement upon binding to Cu 2+. Benesi-Hildebrand and Job plots demonstrate that the stoichiometry of the Cu 2+ complex formed is 2:1. Preliminary studies employing epifluorescence microscopy demonstrated that Cu +2 could be imaged in human neuroblastoma SH-SY5Y cells treated with MGM.

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