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Gonzalez, M.M.; Rasse-Suriani, F.A.O.; Franca, C.A.; Diez, R.P.; Gholipour, Y.; Nonami, H.; Erra-Balsells, R.; Cabrerizo, F.M. "Photosensitized electron transfer within a self-assembled norharmane-2′-deoxyadenosine 5′-monophosphate (dAMP) complex" (2012) Organic and Biomolecular Chemistry. 10(47):9359-9372
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Abstract:

Norharmane is a compound that belongs to a family of alkaloids called β-carbolines (βCs). These alkaloids are present in a wide range of biological systems, playing a variety of significant photo-dependent roles. Upon UV-A irradiation, βCs are able to act as efficient photosensitizers. In this work, we have investigated the photosensitized oxidation of 2′-deoxyadenosine 5′-monophosphate (dAMP) by norharmane in an aqueous phase, upon UV-A (350 nm) irradiation. The effect of the pH was evaluated on both the interactions between norharmane and dAMP in the ground and electronic excited states, and on the dAMP photosensitized oxidation. A quite strong static interaction between norharmane and dAMP was observed, especially under those pH conditions where the protonated form of the alkaloid is present (pH < 7). Theoretical studies were performed to further characterize the static complex structure. The participation of reactive oxygen species (ROS) in the photosensitized reaction was also investigated and the photoproducts were characterized by means of UV-LDI-MS and ESI-MS. All the data provided herein indicate that electron transfer (Type I) within a self-assembled norharmane-dAMP complex is the operative mechanism in the dAMP photosensitization. © 2012 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Photosensitized electron transfer within a self-assembled norharmane-2′-deoxyadenosine 5′-monophosphate (dAMP) complex
Autor:Gonzalez, M.M.; Rasse-Suriani, F.A.O.; Franca, C.A.; Diez, R.P.; Gholipour, Y.; Nonami, H.; Erra-Balsells, R.; Cabrerizo, F.M.
Filiación:CIHIDECAR - CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2 3p, (1428) Buenos Aires, Argentina
Instituto de Investigaciones Biotecnológicas, Instituto Tecnológico de Chascomús (IIB-INTECH), Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Intendente Marino Km 8.2, CC 164 (7130) Chascomús, Argentina
CEQUINOR - CONICET, Facultad de Ciencias Exactas, Universidad Nacional, Plata calle 47 y 115, (1900) La Plata, Argentina
Plant Biophysics/Biochemistry Research Laboratory, College of Agriculture, Ehime University, 3-5-7 Tarumi, (790-8566) Matsuyama, Japan
Palabras clave:Aqueous phase; Carbolines; Complex structure; Deoxyadenosine; Electron transfer; Electronic excited state; Monophosphates; pH condition; Photoproducts; Photosensitized oxidation; Protonated; Reactive oxygen species; Self-assembled; Static interaction; Theoretical study; UV-LDI-MS; Cesium; Electric excitation; Electron transitions; Irradiation; Nitrogen compounds; Photosensitizers; Metabolites; 2' deoxy 5' adenosine monophosphate; 2'-deoxy-5'-adenosine monophosphate; beta carboline; deoxyadenosine phosphate; drug derivative; harmine; article; chemical structure; chemistry; electrospray mass spectrometry; light; oxidation reduction reaction; pH; Deoxyadenine Nucleotides; Harmine; Hydrogen-Ion Concentration; Light; Molecular Structure; Oxidation-Reduction; Spectrometry, Mass, Electrospray Ionization
Año:2012
Volumen:10
Número:47
Página de inicio:9359
Página de fin:9372
DOI: http://dx.doi.org/10.1039/c2ob26462e
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
CAS:beta carboline, 244-63-3; deoxyadenosine phosphate, 653-63-4; harmine, 343-27-1, 442-51-3; 2'-deoxy-5'-adenosine monophosphate, 653-63-4; Deoxyadenine Nucleotides; Harmine, 442-51-3; norharman, 244-63-3
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v10_n47_p9359_Gonzalez

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Citas:

---------- APA ----------
Gonzalez, M.M., Rasse-Suriani, F.A.O., Franca, C.A., Diez, R.P., Gholipour, Y., Nonami, H., Erra-Balsells, R.,..., Cabrerizo, F.M. (2012) . Photosensitized electron transfer within a self-assembled norharmane-2′-deoxyadenosine 5′-monophosphate (dAMP) complex. Organic and Biomolecular Chemistry, 10(47), 9359-9372.
http://dx.doi.org/10.1039/c2ob26462e
---------- CHICAGO ----------
Gonzalez, M.M., Rasse-Suriani, F.A.O., Franca, C.A., Diez, R.P., Gholipour, Y., Nonami, H., et al. "Photosensitized electron transfer within a self-assembled norharmane-2′-deoxyadenosine 5′-monophosphate (dAMP) complex" . Organic and Biomolecular Chemistry 10, no. 47 (2012) : 9359-9372.
http://dx.doi.org/10.1039/c2ob26462e
---------- MLA ----------
Gonzalez, M.M., Rasse-Suriani, F.A.O., Franca, C.A., Diez, R.P., Gholipour, Y., Nonami, H., et al. "Photosensitized electron transfer within a self-assembled norharmane-2′-deoxyadenosine 5′-monophosphate (dAMP) complex" . Organic and Biomolecular Chemistry, vol. 10, no. 47, 2012, pp. 9359-9372.
http://dx.doi.org/10.1039/c2ob26462e
---------- VANCOUVER ----------
Gonzalez, M.M., Rasse-Suriani, F.A.O., Franca, C.A., Diez, R.P., Gholipour, Y., Nonami, H., et al. Photosensitized electron transfer within a self-assembled norharmane-2′-deoxyadenosine 5′-monophosphate (dAMP) complex. Org. Biomol. Chem. 2012;10(47):9359-9372.
http://dx.doi.org/10.1039/c2ob26462e