Abstract:
We have devised a new caged GABA based on ruthenium bipyridyl coordination chemistry. This phototrigger delivers GABA upon irradiation with wavelengths up to 532 nm undergoing heterolytic photocleavage, in a clean and very fast (a few nanoseconds) photoreaction. With an absorptivity coefficient εMAX = 5300 M-1 cm-1 at 447 nm and a quantum efficiency φ ∼ 0.09, RuBiGABA-2 is among the most active caged-GABAs, especially at long wavelengths. This highly hydrophilic caged GABA can be synthesized in a simple one-pot reaction. The synthesis, chemical characterization and photochemical properties are presented. Finally, the usefulness of this caged compound is demonstrated by photodelivering free GABA on leech motoneurons. © 2013 The Royal Society of Chemistry and Owner Societies.
Registro:
Documento: |
Artículo
|
Título: | RuBiGABA-2: A hydrophilic caged GABA with long wavelength sensitivity |
Autor: | Filevich, O.; Etchenique, R. |
Filiación: | Departamento de Química Inorgánica, Analítica y Química Física, Universidad de Buenos Aires, Pabellón 2, (C1428EHA) Buenos Aires, Argentina
|
Palabras clave: | 2,2' bipyridine; 4 aminobutyric acid; bis(bipyridyl)ruthenium(II); drug derivative; GABAergic receptor affecting agent; organometallic compound; phosphine derivative; 2,2' bipyridine; 4 aminobutyric acid; GABAergic receptor affecting agent; organometallic compound; phosphine derivative; animal; article; chemical phenomena; chemistry; cytology; drug effect; ganglion; leech; light; photolysis; analogs and derivatives; drug effects; 2,2'-Dipyridyl; Animals; GABA Agents; gamma-Aminobutyric Acid; Ganglia; Hydrophobic and Hydrophilic Interactions; Leeches; Light; Organometallic Compounds; Phosphines; Photolysis; 2,2'-Dipyridyl; Animals; GABA Agents; gamma-Aminobutyric Acid; Ganglia; Hydrophobic and Hydrophilic Interactions; Leeches; Light; Organometallic Compounds; Phosphines; Photolysis |
Año: | 2013
|
Volumen: | 12
|
Número: | 9
|
Página de inicio: | 1565
|
Página de fin: | 1570
|
DOI: |
http://dx.doi.org/10.1039/c3pp25248e |
Título revista: | Photochemical and Photobiological Sciences
|
Título revista abreviado: | Photochem. Photobiol. Sci.
|
ISSN: | 1474905X
|
CODEN: | PPSHC
|
CAS: | 2,2' bipyridine, 366-18-7; 4 aminobutyric acid, 28805-76-7, 56-12-2; 2,2'-Dipyridyl, 551W113ZEP; GABA Agents; Organometallic Compounds; Phosphines; bis(bipyridyl)ruthenium(II); gamma-Aminobutyric Acid, 56-12-2; 2,2'-Dipyridyl; bis(bipyridyl)ruthenium(II); GABA Agents; gamma-Aminobutyric Acid; Organometallic Compounds; Phosphines
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v12_n9_p1565_Filevich |
Referencias:
- Mayer, G., Heckel, A., Biologically active molecules with a light switch (2006) Angew. Chem., Int. Ed., 45, p. 4900
- Marquele-Oliveira, F., De Almeida Santana, D.C., Fleury Taveira, S., Vermeulena, D.M., De Oliveira, A.R.M., Da Silva, R.S., Lopez, R.F.V., Development of nitrosyl ruthenium complex-loaded lipid carriers for topical administration: Improvement in skin stability and in nitric oxide release by visible light irradiation (2010) J. Pharm. Biomed. Anal., 53, p. 843
- Campagna, S., Puntoriero, F., Nastasi, F., Bergamini, G., Balzani, V., Photochemistry and photophysics of coordination compounds: Ruthenium (2007) Top. Curr. Chem., 280, p. 117
- Schatzschneider, U., Photoactivated biological activity of transition-metal complexes (2010) Eur. J. Inorg. Chem., 10, p. 1451
- Ganguly, K., Schinder, A.F., Wong, S.T., Poo, M., GABA itself promotes the developmental switch of neuronal GABAergic responses from excitation to inhibition (2001) Cell, 105, p. 521
- Rial Verde, E.M., Zayat, L., Etchenique, R., Yuste, R., Photorelease of GABA with visible light using an inorganic caging group (2008) Front. Neural Circuits, 2, p. 2
- Schachter, S.C., Vagus nerve stimulation: Where are we? (2002) Curr. Opin. Neurol., 2, p. 201
- Kramer, R.H., Fortin, D.L., Trauner, D., New photochemical tools for controlling neuronal activity (2009) Curr. Opin. Neurobiol., 19, p. 544
- Ellis-Davies, G.C.R., Caged compounds: Photorelease technology for control of cellular chemistry and physiology (2007) Nat. Methods, 4, p. 619
- Brasen, J.C., Dewitt, S., Hallett, M.B., A reporter of UV intensity delivered to the cytosol during photolytic uncaging (2010) Biophys. J., 98, p. 25
- http://www.ascentscientific.com, Ascent Scientific Ltd (UK), products RuBiGABA and RuBiGlutamate; Zayat, L., Noval, M.G., Campi, J., Calero, C.I., Calvo, D.J., Etchenique, R., A new inorganic photolabile protecting group for highly efficient visible light GABA uncaging (2007) ChemBioChem, 17, p. 2035
- Fino, E., Araya, R., Peterka, D.S., Salierno, M., Etchenique, R., Yuste, R., RuBi-glutamate: Two-photon and visible-light photoactivation of neurons and dendritic spines (2009) Front. Neural Circuits, 3, p. 2
- Ciesienski, K.L., Franz, K.J., Keys for unlocking photolabile metal-containing cages (2011) Angew. Chem., Int. Ed., 50, p. 814
- Salierno, M., Marceca, E., Peterka, D.S., Yuste, R., Etchenique, R., A fast ruthenium polypyridine cage complex photoreleases glutamate with visible or IR light in one and two photon regimes (2010) J. Inorg. Biochem., 104, p. 418
- Nicholls, J.G., Purves, D., Monosynaptic chemical and electrical connections between sensory and motor cells in the central nervous system of the leech (1970) J. Physiol., 209, p. 647
- Cline, H.T., Evidence for GABA as a neurotransmitter in the leech (1986) J. Neurosci., 6, p. 2848
- Gee, K.R., Wieboldt, J.R., Hess, G.P., Synthesis and photochemistry of a new photolabile derivative of GABA. Neurotransmitter release and receptor activation in the microsecond time region (1994) J. Am. Chem. Soc., 116, p. 8366
- Papageorgiou, G., Corrie, J.E.T., Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors (2007) Tetrahedron, 63, p. 9668
- Matsuzaki, M., Hayama, T., Kasai, H., Ellis-Davies, G.C.R., Two-photon uncaging of γ-aminobutyric acid in intact brain tissue (2010) Nat. Chem. Biol., 6, p. 255
- Papageorgiou, G., Ogden, D., Kelly, G., Corrie, J.E.T., Synthetic and photochemical studies of substituted 1-acyl-7- nitroindolines (2005) Photochem. Photobiol. Sci., 4, p. 887
- Senda, N., Momotake, A., Arai, T., Synthesis and photocleavage of 7-[{bis(carboxymethyl)amino}coumarin-4-yl] methyl-caged neurotransmitters (2007) Bull. Chem. Soc. Jpn., 80 (12), p. 2384
- Lopes-Dos-Santos, V., Campi, J., Filevich, O., Ribeiro, S., Etchenique, R., In vivo photorelease of GABA in the mouse cortex (2011) Braz. J. Med. Biol. Res., 44, p. 688
Citas:
---------- APA ----------
Filevich, O. & Etchenique, R.
(2013)
. RuBiGABA-2: A hydrophilic caged GABA with long wavelength sensitivity. Photochemical and Photobiological Sciences, 12(9), 1565-1570.
http://dx.doi.org/10.1039/c3pp25248e---------- CHICAGO ----------
Filevich, O., Etchenique, R.
"RuBiGABA-2: A hydrophilic caged GABA with long wavelength sensitivity"
. Photochemical and Photobiological Sciences 12, no. 9
(2013) : 1565-1570.
http://dx.doi.org/10.1039/c3pp25248e---------- MLA ----------
Filevich, O., Etchenique, R.
"RuBiGABA-2: A hydrophilic caged GABA with long wavelength sensitivity"
. Photochemical and Photobiological Sciences, vol. 12, no. 9, 2013, pp. 1565-1570.
http://dx.doi.org/10.1039/c3pp25248e---------- VANCOUVER ----------
Filevich, O., Etchenique, R. RuBiGABA-2: A hydrophilic caged GABA with long wavelength sensitivity. Photochem. Photobiol. Sci. 2013;12(9):1565-1570.
http://dx.doi.org/10.1039/c3pp25248e