Artículo

Cabrera, R.; Filevich, O.; García-Acosta, B.; Athilingam, J.; Bender, K.J.; Poskanzer, K.E.; Etchenique, R."A Visible-Light-Sensitive Caged Serotonin" (2017) ACS Chemical Neuroscience. 8(5):1036-1042
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Serotonin, or 5-hydroxytryptamine (5HT), is an important neurotransmitter in the nervous system of both vertebrates and invertebrates. Deficits in 5HT signaling are responsible for many disabling psychiatric conditions, and its molecular machinery is the target of many pharmaceuticals. We present a new 5HT phototrigger, the compound [Ru(bpy)2(PMe3)(5HT)]2+, where PMe3 is trimethylphosphine. As with other ruthenium-bipyridyl based caged compounds, [Ru(bpy)2(PMe3)(5HT)]2+ presents activity in the visible region of the spectrum. We characterize and discuss the photochemical properties of the caged compound, and demonstrate its use by modulating the excitability of mouse prefrontal principal neurons. © 2017 American Chemical Society.

Registro:

Documento: Artículo
Título:A Visible-Light-Sensitive Caged Serotonin
Autor:Cabrera, R.; Filevich, O.; García-Acosta, B.; Athilingam, J.; Bender, K.J.; Poskanzer, K.E.; Etchenique, R.
Filiación:Departamento de Química Inorgánica, Analítica y Química Física, INQUIMAE, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, CONICET, Ciudad Universitaria Pabellón 2, EHA Buenos Aires, AR1428, Argentina
Ciclo Básico Común, Universidad de Buenos Aires, Buenos Aires, 1053, Argentina
Laboratorio de Neurobiología Molecular, BIOMED, Pontificia Universidad Católica Argentina, CONICET, Buenos Aires, C1107AFB, Argentina
Kavli Institute for Fundamental Neuroscience, UCSF Weill Institute for Neuroscience, San Francisco, CA, United States
Department of Neurology, University of California, San Francisco, San Francisco, CA 94143, United States
Department of Biochemistry and Biophysics, University of California, San Francisco, San Francisco, CA 94143, United States
Palabras clave:neurophysiology; phototriggers; Ruthenium complex; serotonin; serotonin; ruthenium; serotonin; animal cell; Article; light absorption; mouse; nerve cell excitability; nonhuman; pH; photochemistry; photolysis; photosensitivity; priority journal; proton nuclear magnetic resonance; pyramidal nerve cell; quantum yield; animal; chemistry; drug effects; light; metabolism; nerve cell; prefrontal cortex; Animals; Light; Mice; Neurons; Prefrontal Cortex; Ruthenium; Serotonin
Año:2017
Volumen:8
Número:5
Página de inicio:1036
Página de fin:1042
DOI: http://dx.doi.org/10.1021/acschemneuro.7b00083
Handle:http://hdl.handle.net/20.500.12110/paper_19487193_v8_n5_p1036_Cabrera
Título revista:ACS Chemical Neuroscience
Título revista abreviado:ACS Chem. Neurosci.
ISSN:19487193
CODEN:ACNCD
CAS:serotonin, 50-67-9; ruthenium, 7440-18-8; Ruthenium; Serotonin
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_19487193_v8_n5_p1036_Cabrera

Referencias:

  • Adams, S.R., Kao, J.P., Grynkiewicz, Y., Minta, G.A., Tsien, R.Y., Biologically useful chelators that release Ca2+ upon illumination (1988) J. Am. Chem. Soc., 110, pp. 3212-3220
  • Barth, A., Corrie, J.E., Characterization of a new caged proton capable of inducing large pH jumps (2002) Biophys. J., 83, pp. 2864-2871
  • Filevich, O., Carrone, G., Andino Pavlovsky, V., Etchenique, R., Fast Optical pH Manipulation and Imaging (2012) Anal. Chem., 84, pp. 5618-5624
  • Ellis-Davies, G.C.R., Matsuzaki, M., Paukert, M., Kasai, H., Bergles, D.E., 4-Carboxymethoxy-5,7-Dinitroindolinyl-Glu: An Improved Caged Glutamate for Expeditious Ultraviolet and Two-Photon Photolysis in Brain Slices (2007) J. Neurosci., 27 (25), pp. 6601-6604
  • Belov, V.N., Wurm, C.A., Boyarskiy, V.P., Jakobs, S., Hell, S.W., (2010) Angew. Chem., Int. Ed., 49, pp. 3520-3523
  • Del Mármol, J., Filevich, O., Etchenique, R., A Ruthenium-Rhodamine Complex as an Activatable Fluorescent Probe (2010) Anal. Chem., 82, pp. 6259-6264
  • Filevich, O., Salierno, M., Etchenique, R., A caged nicotine with nanosecond range kinetics and visible light sensitivity (2010) J. Inorg. Biochem., 104, pp. 1248-1251
  • Hayashi, K., Hashimoto, K., Kusaka, N., Yamazoe, A., Fukaki, H., Tasaka, M., Nozaki, H., Caged gene-inducer spatially and temporally controls gene expression and plant development in transgenic Arabidopsis plant (2006) Bioorg. Med. Chem. Lett., 16, pp. 2470-2474
  • Young, D.D., Deiters, A., Photochemical Activation of Protein Expression in Bacterial Cells (2007) Angew. Chem., Int. Ed., 46, pp. 4290-4292
  • Shestopalov, I.A., Sinha, S., Chen, J.K., Light-controlled gene silencing in zebrafish embryos (2007) Nat. Chem. Biol., 3, pp. 650-651
  • Chou, C., Deiters, A., Light-Activated Gene Editing with a Photocaged Zinc-Finger Nuclease (2011) Angew. Chem., Int. Ed., 50, pp. 6839-6842
  • Mayer, G., Heckel, A., Biologically active molecules with a "light switch (2006) Angew. Chem., Int. Ed., 45, pp. 4900-4921
  • Patchornik, A., Amit, B., Woodward, R.B., Photosensitive protecting groups (1970) J. Am. Chem. Soc., 92, pp. 6333-6335
  • Wieboldt, R., Gee, K.R., Niu, L., Ramesh, D., Carpenter, B.K., Hess, G.P., Photolabile precursors of glutamate: Synthesis, photochemical properties, and activation of glutamate receptors on a microsecond time scale (1994) Proc. Natl. Acad. Sci. U. S. A., 91 (19), pp. 8752-8756
  • Canepari, M., Nelson, L., Papageorgiou, G., Corrie, J.E.T., Ogden, D., Photochemical and pharmacological evaluation of 7-nitroindolinyl-and 4-methoxy-7-nitroindolinyl-amino acids as novel, fast caged neurotransmitters (2001) J. Neurosci. Methods, 112, pp. 29-42
  • 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), pp. 2384-2388
  • 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, pp. 418-422
  • 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
  • Yang, X., Rode, D.L., Peterka, D.S., Yuste, R., Rothman, S.M., Optical control of focal epilepsy in vivo with caged γ-aminobutyric acid (2012) Ann. Neurol., 71 (1), pp. 68-75
  • Chalifoux, J.R., Carter, A.G., GABAB Receptor Modulation of Voltage-Sensitive Calcium Channels in Spines and Dendrites (2011) J. Neurosci., 31 (11), pp. 4221-4232
  • Nikolenko, V., Yuste, R., Zayat, L., Baraldo, L.M., Etchenique, R., Two-photon uncaging of neurochemicals using inorganic metal complexes, Chem (2005) Chem. Commun., pp. 1752-1754
  • 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
  • Araya, R., Andino-Pavlovsky, V., Yuste, R., Etchenique, R., Two-Photon Optical Interrogation of Individual Dendritic Spines with Caged Dopamine, ACS Chem (2013) ACS Chem. Neurosci., 4 (8), pp. 1163-1167
  • Poskanzer, K.E., Yuste, R., Astrocytic regulation of cortical UP states (2011) Proc. Natl. Acad. Sci. U. S. A., 108, pp. 18453-18458
  • Garner, R.N., Gallucci, J.C., Dunbar, K.R., Turro, C., [Ru(bpy)2(5-cyanouracil)2] 2+ as a Potential Light-Activated Dual-Action Therapeutic Agent (2011) Inorg. Chem., 50, pp. 9213-9215
  • Knoll, J.D., Turro, C., Control and Utilization of Ruthenium and Rhodium Metal Complex Excited States for Photoactivated Cancer Therapy (2015) Coord. Chem. Rev., 282-283, pp. 110-126
  • Bahreman, A., Cuello-Garibo, J.A., Bonnet, S., Yellow-light sensitization of a ligand photosubstitution reaction in a ruthenium polypyridyl complex covalently bound to a rhodamine dye (2014) Dalton Trans., 43, pp. 4494-4505
  • Da Rocha, Z.N., Marchesi, M.S., Molin, J.C., Lunardi, C.N., Miranda, K.M., Bendhack, L.M., Ford, P.C., Da Silva, R.S., The inducing NO-vasodilation by chemical reduction of coordinated nitrite ion in cis-[Ru(NO)2L(bpy)2]+ complex (2008) Dalton Trans., pp. 4282-4287
  • Franco, L.P., Cicillini, S.A., Biazzotto, J.C., Schiavon, M.A., Mikhailovsky, A., Burks, P., Garcia, J., Da Silva, R.S., Photoreactivity of a quantum dot-ruthenium nitrosyl conjugate (2014) J. Phys. Chem. A, 118, pp. 12184-12191
  • Blundell, J.E., Serotonin and appetite (1984) Neuropharmacology, 23, pp. 1537-1551
  • Pigott, T.A., Seay, S.M., A review of the efficacy of selective serotonin reuptake inhibitors in obsessive-compulsive disorder (1999) J. Clin. Psychiatry, 60, pp. 101-106
  • Gillette, R., Evolution and Function in Serotonergic Systems (2006) Integr. Comp. Biol., 46, pp. 838-846
  • Palma-Cerda, F., Auger, C., Crawford, D.J., Hodgson, A.C.C., Reynolds, S.J., Cowell, J.K., Swift, K.A.D., Ogden, D., New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups (2012) Neuropharmacology, 63, pp. 624-634
  • Corrie, J.E.T., Desantis, A., Katayama, Y., Khodakhah, K., Messenger, J.B., Ogden, D.C., Trentham, D.R., Postsynaptic Activation at the Squid Giant Synapse by Photolytic Release of L-Glutamate from A 'Caged' L-Glutamate (1993) J. Physiol., 465, pp. 1-8
  • Vandenberg, L.N., Blackiston, D.J., Rea, A.C., Dore, T.M., Levin, M., Left-right patterning in Xenopus conjoined twin embryos requires serotonin signaling and gap junctions (2014) Int. J. Dev. Biol., 58, pp. 799-809
  • Rea, A.C., Vandenberg, L.N., Ball, R.E., Snouffer, A.A., Hudson, A.G., Zhu, Y., McLain, D.E., Dore, T.M., Light Activated Serotonin for Exploring Its Action in Biological Systems (2013) Chem. Biol., 20, pp. 1536-1546
  • Breitinger, H.-G.A., Wieboldt, R., Ramesh, D., Carpenter, B.K., Hess, G.P., Synthesis and Characterization of Photolabile Derivatives of Serotonin for Chemical Kinetic Investigations of the Serotonin 5-HT3 Receptor (2000) Biochemistry, 39, pp. 5500-5508
  • Boahen, Y.O., MacDonald, G.M., A concise approach to caged serotonin for Fourier transform infrared (FT-IR) difference photolysis studies (2005) J. Ghana Sci. Assoc., 7, pp. 54-59
  • Zayat, L., Salierno, M., Etchenique, R., Ruthenium(II) Bipyridyl Complexes as Photolabile Caging Groups for Amines (2006) Inorg. Chem., 45, pp. 1728-1731
  • McLain, D.E., Rea, A.C., Widegren, M.B., Dore, T.M., Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation (2015) Photochem. Photobiol. Sci., 14, pp. 2151-2158
  • Avesar, D., Gulledge, A.T., Selective serotonergic excitation of callosal projection neurons (2012) Front. Neural Circuits, 6, p. 12
  • Dembrow, N.C., Chitwood, R.A., Johnston, D., Projection-specific neuromodulation of medial prefrontal cortex neurons (2010) J. Neurosci., 30, pp. 16922-16937
  • Pinnick, D.V., Durham, B., Photosubstitution Reactions of Ru(bpy)2XYn+ Complexes (1984) Inorg. Chem., 23, pp. 1440-1445
  • Filevich, O., Etchenique, R., RuBiGABA-2: A hydrophilic caged GABA with long wavelength sensitivity (2013) Photochem. Photobiol. Sci., 12, pp. 1565-1570
  • Viala, C., Coudret, C., An Expeditious Route to cis-Ru(bpy)2Cl2 (bpy: 2,2′-bipyridine) Using Carbohydrate as Reducers (2006) Inorg. Chim. Acta, 359, pp. 984-989
  • Gee, S., Ellwood, I., Patel, T., Luongo, F., Deisseroth, K., Sohal, V.S., Synaptic activity unmasks dopamine D2 receptor modulation of a specific class of layer v pyramidal neurons in prefrontal cortex (2012) J. Neurosci., 32, pp. 4959-4971
  • Seong, H.J., Carter, A.G., D1 receptor modulation of action potential firing in a subpopulation of layer 5 pyramidal neurons in the prefrontal cortex (2012) J. Neurosci., 32, pp. 10516-10521

Citas:

---------- APA ----------
Cabrera, R., Filevich, O., García-Acosta, B., Athilingam, J., Bender, K.J., Poskanzer, K.E. & Etchenique, R. (2017) . A Visible-Light-Sensitive Caged Serotonin. ACS Chemical Neuroscience, 8(5), 1036-1042.
http://dx.doi.org/10.1021/acschemneuro.7b00083
---------- CHICAGO ----------
Cabrera, R., Filevich, O., García-Acosta, B., Athilingam, J., Bender, K.J., Poskanzer, K.E., et al. "A Visible-Light-Sensitive Caged Serotonin" . ACS Chemical Neuroscience 8, no. 5 (2017) : 1036-1042.
http://dx.doi.org/10.1021/acschemneuro.7b00083
---------- MLA ----------
Cabrera, R., Filevich, O., García-Acosta, B., Athilingam, J., Bender, K.J., Poskanzer, K.E., et al. "A Visible-Light-Sensitive Caged Serotonin" . ACS Chemical Neuroscience, vol. 8, no. 5, 2017, pp. 1036-1042.
http://dx.doi.org/10.1021/acschemneuro.7b00083
---------- VANCOUVER ----------
Cabrera, R., Filevich, O., García-Acosta, B., Athilingam, J., Bender, K.J., Poskanzer, K.E., et al. A Visible-Light-Sensitive Caged Serotonin. ACS Chem. Neurosci. 2017;8(5):1036-1042.
http://dx.doi.org/10.1021/acschemneuro.7b00083