Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization

Mostrar otras versiones (1)

β-Carbolines (βCs) are a group of alkaloids present in many plants and animals. It has been suggested that these alkaloids participate in a variety of significant photosensitized processes. Despite their well-established natural occurrence, the main biological role of these alkaloids and the mechani...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autor principal: Gonzalez, M.M
Otros Autores: Vignoni, M., Pellon-Maison, M., Ales-Gandolfo, M.A, Gonzalez-Baro, M.R, Erra-Balsells, R., Epe, B., Cabrerizo, F.M
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2012
Acceso en línea:Registro en Scopus
DOI
Handle
Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
LEADER 12695caa a22017297a 4500
001 PAPER-23472
003 AR-BaUEN
005 20230518205510.0
008 190411s2012 xx ||||fo|||| 00| 0 eng|d
024 7 |2 scopus  |a 2-s2.0-84857213249 
024 7 |2 cas  |a DNA, 9007-49-2; thymidine, 50-89-5; Carbolines; DNA, 9007-49-2; Photosensitizing Agents; Reactive Oxygen Species; Thymidine, 50-89-5 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a OBCRA 
100 1 |a Gonzalez, M.M. 
245 1 0 |a Photosensitization of DNA by β-carbolines: Kinetic analysis and photoproduct characterization 
260 |c 2012 
270 1 0 |m Epe, B.; Institute of Pharmacy and Biochemistry, University of Mainz, Staudingerweg 5, D-55099 Mainz, Germany; email: epe@uni-mainz.de 
506 |2 openaire  |e Política editorial 
504 |a Hemmateenejad, B., Abbaspour, A., Maghami, H., Miri, R., Panjehshahin, M.R., (2006) Anal. Chim. Acta, 575, pp. 290-299 
504 |a Kam, T.S., Sim, K.M., Koyano, T., Komiyama, K., (1999) Phytochemistry, 50, pp. 75-79 
504 |a Kam, T.S., Sim, K.M., (1998) Phytochemistry, 47, pp. 145-147 
504 |a Kearns, P.S., Cou, J.C., Rideout, J.A., (1995) J. Nat. Prod., 58, pp. 1075-1076 
504 |a Stachel, S.J., Stockwell, S.A., Van Vranken, D.L., (1999) Chem. Biol., 6, pp. 531-539 
504 |a Siderhurst, M.S., James, D.M., Rithner, C.D., Dick, D.L., Bjostad, L.B., (2005) J. Econ. Entomol., 98, pp. 1669-1678 
504 |a Adachi, J., Mizoi, Y., Naito, T., Ogawa, Y., Uetani, Y., Ninomiya, I., (1991) J. Nut., 121, pp. 646-652 
504 |a Herraiz, T., Galisteo, J., (2003) J. Agric. Food Chem., 51, pp. 7156-7161 
504 |a De Meester, C., (1995) Mutat. Res., Rev.Genet. Toxicol., 339, pp. 139-153 
504 |a Pfau, W., Skog, K., (2004) J. Chromatogr., B: Anal. Technol. Biomed. Life Sci., 802, pp. 115-126 
504 |a Spijkerman, R., Van Den Eijnden, R., Van De Mheen, D., Bongers, I., Fekkes, D., (2002) Eur. Neuropsychopharmacol., 12, pp. 61-71 
504 |a Torreilles, J., Guerin, M., Previero, A., (1985) Biochimie, 67, pp. 929-947 
504 |a Breyer-Pfaff, U., Wiatr, G., Stevens, I., Gaertner, H., Mundle, G., Mann, K., (1996) Life Sci., 58, pp. 1425-1432 
504 |a Downum, K.R., (1992) New Phytol., 122, pp. 401-420 
504 |a Mori, T., Nakagawa, A., Kobayashi, N., Hashimoto, M.W., Wakabayashi, K., Shimoi, K., Kinae, N., (1998) J. Radiat. Res., 39, pp. 21-33 
504 |a Shimoi, K., Kawabata, H., Tomita, I., (1992) Mutat. Res., Fundam. Mol. Mech. Mutagen., 268, pp. 287-295 
504 |a Chang, C., Castellazzi, M., Glover, T., Trosko, J., (1978) Cancer Res., 38, pp. 4527-4533 
504 |a Shimoi, K., Miyamura, R., Mori, T., Todo, T., Ohtsuka, E., Wakabayashi, K., Kinae, N., (1996) Carcinogenesis, 17, pp. 1279-1283 
504 |a Hudson, J.B., Graham, E.A., Towers, G.H.N., (1986) Photochem. Photobiol., 43, pp. 21-26 
504 |a Gonzalez, M.M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baró, M.R., Erra-Balsells, R., Cabrerizo, F.M., (2010) Org. Biomol. Chem., 8, pp. 2543-2552 
504 |a Will, O., Gocke, E., Eckert, I., Schulz, I., Pflaum, M., Mahler, H.C., Epe, B., (1999) Mutat. Res., Fundam. Mol. Mech. Mutagen., 435, pp. 89-101 
504 |a Mahler, H.C., Schulz, I., Adam, W., Grimm, G.N., Saha-Möller, C.R., Epe, B., (2001) Mutat. Res., Fundam. Mol. Mech. Mutagen., 461, pp. 289-299 
504 |a Nonami, H., Orcoyen, M., Fukuyama, Y., Biondic, M.C., Erra-Balsells, R., (1998) An. Asoc. Quim., 86, pp. 81-89 
504 |a Salditt, M., Braunstein, S.N., Camerini-Otero, R.D., Franklin, R.M., (1972) Virology, 48, pp. 259-262 
504 |a Boiteux, S., O'Connor, T.R., Lederer, F., Gouyette, A., Laval, J., (1990) J. Biol. Chem., 265, pp. 3916-3922 
504 |a Müller, E., Boiteux, S., Cunningham, R.P., Epe, B., (1990) Nucleic Acids Res., 18, pp. 5969-5973 
504 |a Braun, A.M., Maurette, M.T., Oliveros, E., (1991) Photochemical Technology, 2, pp. 85-88 
504 |a Kuhn, H.J., Braslavsky, S.E., Schmidt, R., (2004) Pure Appl. Chem., 76, pp. 2105-2146 
504 |a Colmenarejo, G., Bfircena, M., Gutierrez-Alonso, M.C., Montero, F., Orellana, G., (1995) FEBS Lett., 374, pp. 426-428 
504 |a Bauer, W., Vinograd, J., (1968) J. Mol. Biol., 33, pp. 141-171 
504 |a Buxton, G.V., Greenstock, C.L., Helman, W.P., Ross, A.B., (1988) J. Phys. Chem. Ref. Data, 17, pp. 513-886 
504 |a Atkinson, R., (1995) Active Oxygen in Chemistry, p. 289. , C. S. Foote, J. S. Valentine, A. Greenberg and J. F. Liebman (ed.), 2, Chapman & Hall, London 
504 |a Lakowicz, J.R., (2006) Principles of Fluorescence Spectroscopy, pp. 278-285. , Springer, New York 
504 |a Petroselli, G., Dántola, M.L., Cabrerizo, F.M., Lorente, C., Braun, A.M., Oliveros, E., Thomas, A.H., (2009) J. Phys. Chem. A, 113 (9), pp. 1794-1799 
504 |a Epe, B., Hegler, J., (1994) Methods Enzymol., 234, pp. 122-131 
504 |a Epe, B., (2012) Photochem. Photobiol. Sci., 11, pp. 98-106 
504 |a Tomas Vert, F., Zabala Sanchez, I., Olba Torrent, A., (1984) J. Photochem., 26, pp. 285-294 
504 |a Varela, A.P., Miguel, M.D.G., Maanita, A.L., Burrows, H.D., Becker, R.S., (1995) J. Phys. Chem., 99, pp. 16093-16100 
504 |a Kishikawa, H., Jiang, Y.-R., Goodisman, J., Dabrowiak, J.C., (1991) J. Am. Chem. Soc., 113, pp. 5434-5440 
504 |a Gonzalez, M.M., Salum, M.L., Gholipour, Y., Cabrerizo, F.M., Erra-Balsells, R., (2009) Photochem. Photobiol. Sci., 8, pp. 1139-1149 
504 |a Gonzalez, M.M., Arnbjerg, J., Denofrio, M.P., Erra-Balsells, R., Ogilby, P.R., Cabrerizo, F.M., (2009) J. Phys. Chem. A, 113, pp. 6648-6656 
504 |a Cabrerizo, F.M., Arnbjerg, J., Denofrio, M.P., Erra-Balsells, R., Ogilby, P.R., (2010) ChemPhysChem, 11, pp. 796-798 
504 |a Briviba, K., Klotz, L.O., Sies, H., (1997) Biol. Chem., 378, pp. 1259-1265 
504 |a Ogilby, P.R., Foote, C.S., (1983) J. Am. Chem. Soc., 105, pp. 3423-3430 
504 |a García-Zubiri, I.X., Burrows, H.D., Seixas De Melo, J.S., Pina, J., Monteserín, M., Tapia, M.J., (2007) Photochem. Photobiol., 83, pp. 1455-1464 
504 |a Taira, Z., Kanzawa, S., Dohara, C., Ishida, S., Matsumoto, M., Sakiya, Y., (1997) Jap. J. Toxicol. Environ. Health, 43, pp. 83-91 
504 |a García-Zubiri, I.X., Burrows, H.D., Seixas De Melo, J.S., Monteserín, M., Arroyo, A., Tapia, M.J., (2008) J. FluoreSc, 18, pp. 961-972 
504 |a Sakurovs, R., Ghiggino, K.P., (1982) J. Photochem., 18, pp. 1-8 
504 |a Cadet, J., Sage, E., Douki, T., (2005) Mutat. Res., Fundam. Mol. Mech. Mutagen., 571, pp. 3-17 
504 |a Delatour, T., Douki, T., D'Ham, C., Cadet, J., (1998) J. Photochem. Photobiol., B, 44, pp. 191-198 
504 |a Wood, P.D., Redmond, R.W., (1996) J. Am. Chem. Soc., 118, pp. 4256-4263 
504 |a Foote, C.S., (1991) Photochem. Photobiol., 54, p. 659 
504 |a Duarte, V., Gasparutto, D., Jaquinod, M., Cadet, J., (2000) Nucleic Acids Res., 28, pp. 1555-1563 
504 |a Häring, M., Rüdiger, H., Demple, B., Boiteux, S., Epe, B., (1994) Nucleic Acids Res., 22, pp. 2010-2015 
504 |a Epe, B., (1995) Rev. Physiol., Biochem., Pharmacol., 127, pp. 223-249 
504 |a Pflaum, M., Will, O., Mahler, H.-C., Epe, B., (1998) Free Radic. Res., 29, pp. 585-594 
504 |a Srere, P., Kosicki, G.W., Lumry, R., (1961) Biochim. Biophys. Acta, 50, pp. 184-185 
504 |a Cuquerella, M.C., Lhiaubet-Vallet, V., Bosca, F., Miranda, M.A., (2011) Chem. Sci., 2, pp. 1219-1232 
504 |a Bosca, F., Lhiaubet-Vallet, V., Cuquerella, M.C., Castell, J.V., Miranda, M.A., (2006) J. Am. Chem. Soc., 128, pp. 6318-6319 
504 |a Lhiaubet-Vallet, V., Cuquerella, M.C., Castell, J.V., Bosca, F., Miranda, M.A., (2007) J. Phys. Chem. B, 111, pp. 7409-7414 
504 |a Varela, A.P., Burrows, H.D., Douglas, P., Da Graa Miguel, M., (2001) J. Photochem. Photobiol., A, 146, pp. 29-36 
504 |a Tarzi, O.I., Ponce, M.A., Cabrerizo, F.M., Bonesi, S.M., Erra-Balsells, R., (2005) ARKIVOC, 7, pp. 295-310 
504 |a Biondic, M.C., Erra-Balsells, R., (1994) J. Photochem. Photobiol., A, 77, pp. 149-159 
520 3 |a β-Carbolines (βCs) are a group of alkaloids present in many plants and animals. It has been suggested that these alkaloids participate in a variety of significant photosensitized processes. Despite their well-established natural occurrence, the main biological role of these alkaloids and the mechanisms involved are, to date, poorly understood. In the present work, we examined the capability of three important βCs (norharmane, harmane and harmine) and two of its derivatives (N-methyl-norharmane and N-methyl-harmane) to induce DNA damage upon UV-A excitation, correlating the type and extent of the damage with the photophysical characteristics and DNA binding properties of the compounds. The results indicate that DNA damage is mostly mediated by a direct type-I photoreaction of the protonated βCs after non-intercalative electrostatic binding. Reactive oxygen species such as singlet oxygen and superoxide are not involved to a major extent, as indicated by the only small influence of D 2O and of superoxide dismutase on damage generation. An analysis with repair enzymes revealed that oxidative purine modifications such as 8-oxo-7,8-dihydroguanine, sites of base loss and single-strand breaks (SSB) are generated by all βCs, while only photoexcited harmine gives rise to the formation of cyclobutane pyrimidine dimers as well. © 2012 The Royal Society of Chemistry.  |l eng 
593 |a CIHIDECAR-CONICET, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 3p, (1428) Buenos Aires, Argentina 
593 |a INIFTA-CONICET, Universidad Nacional de la Plata, Casilla de Correo 16, Sucursal 4, (1900) La Plata, Argentina 
593 |a INIBIOLP-CONICET, Universidad Nacional de la Plata, calle 60 y 120, (1900), La Plata, Argentina 
593 |a IIB-INTECH-CONICET, Universidad Nacional de San Martín, Intendente Marino km 8, 2 CC 164, (B7130IWA), Chascomús Buenos Aires, Argentina 
593 |a Institute of Pharmacy and Biochemistry, University of Mainz, Staudingerweg 5, D-55099 Mainz, Germany 
690 1 0 |a 8-OXO-7 ,8-DIHYDROGUANINE 
690 1 0 |a CARBOLINES 
690 1 0 |a CYCLOBUTANE PYRIMIDINE DIMERS 
690 1 0 |a DNA DAMAGES 
690 1 0 |a DNA-BINDING PROPERTIES 
690 1 0 |a ELECTROSTATIC BINDING 
690 1 0 |a HARMANE 
690 1 0 |a KINETIC ANALYSIS 
690 1 0 |a PHOTOPHYSICAL 
690 1 0 |a PHOTOPRODUCTS 
690 1 0 |a PHOTOREACTIONS 
690 1 0 |a PROTONATED 
690 1 0 |a REACTIVE OXYGEN SPECIES 
690 1 0 |a REPAIR ENZYMES 
690 1 0 |a SINGLE-STRAND BREAKS 
690 1 0 |a SINGLET OXYGEN 
690 1 0 |a SUPER OXIDE DISMUTASE 
690 1 0 |a SUPEROXIDES 
690 1 0 |a ANIMALS 
690 1 0 |a BINDING ENERGY 
690 1 0 |a BUTANE 
690 1 0 |a DNA 
690 1 0 |a METABOLITES 
690 1 0 |a NITROGEN COMPOUNDS 
690 1 0 |a OXYGEN 
690 1 0 |a PYRIDINE 
690 1 0 |a CESIUM 
690 1 0 |a CARBOLINE DERIVATIVE 
690 1 0 |a DNA 
690 1 0 |a PHOTOSENSITIZING AGENT 
690 1 0 |a REACTIVE OXYGEN METABOLITE 
690 1 0 |a THYMIDINE 
690 1 0 |a ARTICLE 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a CHEMISTRY 
690 1 0 |a KINETICS 
690 1 0 |a PHOTOCHEMISTRY 
690 1 0 |a CARBOLINES 
690 1 0 |a DNA 
690 1 0 |a KINETICS 
690 1 0 |a MOLECULAR STRUCTURE 
690 1 0 |a PHOTOCHEMICAL PROCESSES 
690 1 0 |a PHOTOSENSITIZING AGENTS 
690 1 0 |a REACTIVE OXYGEN SPECIES 
690 1 0 |a THYMIDINE 
700 1 |a Vignoni, M. 
700 1 |a Pellon-Maison, M. 
700 1 |a Ales-Gandolfo, M.A. 
700 1 |a Gonzalez-Baro, M.R. 
700 1 |a Erra-Balsells, R. 
700 1 |a Epe, B. 
700 1 |a Cabrerizo, F.M. 
773 0 |d 2012  |g v. 10  |h pp. 1807-1819  |k n. 9  |p Org. Biomol. Chem.  |x 14770520  |w (AR-BaUEN)CENRE-2303  |t Organic and Biomolecular Chemistry 
856 4 1 |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-84857213249&doi=10.1039%2fc2ob06505c&partnerID=40&md5=bcffc05ae27ecd39647da62f28e2505d  |y Registro en Scopus 
856 4 0 |u https://doi.org/10.1039/c2ob06505c  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_14770520_v10_n9_p1807_Gonzalez  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v10_n9_p1807_Gonzalez  |y Registro en la Biblioteca Digital 
961 |a paper_14770520_v10_n9_p1807_Gonzalez  |b paper  |c PE 
962 |a info:eu-repo/semantics/article  |a info:ar-repo/semantics/artículo  |b info:eu-repo/semantics/publishedVersion 
999 |c 84425 

Ejemplares similares