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

Résultat de recherche › examen par les pairs

52 Citations (Scopus)

Résumé

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.

Langue d'origine	English
Pages (de-à)	5280-5283
Nombre de pages	4
Journal	Tetrahedron Letters
Volume	53
Numéro de publication	39
DOI	https://doi.org/10.1016/j.tetlet.2012.07.082
Statut de publication	Published - sept. 26 2012

Financement

Bailleurs de fonds	Numéro du bailleur de fonds
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

Accès au document

10.1016/j.tetlet.2012.07.082

Autres fichiers et liens

Citer

García-Beltrán, O., Mena, N., Friedrich, L. C., Netto-Ferreira, J. C., Vargas, V., Quina, F. H., Núñez, M. T., & Cassels, B. K. (2012). Design and synthesis of a new coumarin-based 'turn-on' fluorescent probe selective for Cu ⁺² Tetrahedron Letters, 53(39), 5280-5283. https://doi.org/10.1016/j.tetlet.2012.07.082

@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",

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day = "26",

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

language = "English",

volume = "53",

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journal = "Tetrahedron Letters",

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TY - JOUR

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

N2 - 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.

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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