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Vignoni, M.; Rasse-Suriani, F.A.O.; Butzbach, K.; Erra-Balsells, R.; Epe, B.; Cabrerizo, F.M. "Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines" (2013) Organic and Biomolecular Chemistry. 11(32):5300-5309
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Abstract:

It has been well documented that β-carboline alkaloids, particularly the 9-methyl derivatives, are efficient photosensitizers. However, structure-activity relationships are missing and the photochemical mechanisms involved in the DNA photodamage still remain unknown. In the present work, we examined the capability of three 9-methyl-β-carbolines (9-methyl- norharmane, 9-methyl-harmane and 9-methyl-harmine) to induce DNA damage upon UVA excitation at physiological pH. The type and extent of the damage was analyzed together with the photophysical and binding properties of the β-carboline derivatives investigated. The results indicate that even at neutral pH most of the DNA damage is generated from the protonated form of the excited β-carbolines in a type-I reaction. Oxidized purine residues are produced in high excess over oxidized pyrimidines, single-strand breaks and sites of base loss. In addition, the excited neutral form of the β-carbolines is responsible for significant generation of cyclobutane pyrimidine dimers (CPDs) by triplet-triplet-energy transfer. In the case of 9-methyl-norharmane, the yield of CPDs is increased in D2O, probably due to less rapid protonation in the deuterated solvent.© 2013 The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines
Autor:Vignoni, M.; Rasse-Suriani, F.A.O.; Butzbach, K.; Erra-Balsells, R.; Epe, B.; Cabrerizo, F.M.
Filiación: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 (B7130IWA) Chascomús, Argentina
Institute of Pharmacy and Biochemistry, University of Mainz, Staudingerweg 5, Mainz, Germany
CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, 3p, Ciudad Universitaria, (1428) Buenos Aires, Argentina
Palabras clave:Binding properties; Carboline derivatives; Cyclobutane pyrimidine dimers; Deuterated solvents; Photochemical mechanism; Physiological pH; Single-strand breaks; Structure activity relationships; Aromatic compounds; Binding energy; Energy transfer; pH; Photosensitizers; Protonation; Pyridine; DNA; 9 methyl beta carboline; 9-methyl-beta-carboline; calf thymus dna; carboline derivative; DNA; photosensitizing agent; virus DNA; animal; article; bacteriophage; cattle; chemical structure; chemistry; DNA damage; drug effect; genetics; ultraviolet radiation; Animals; Carbolines; Cattle; Corticoviridae; DNA; DNA Damage; DNA, Viral; Models, Molecular; Photosensitizing Agents; Ultraviolet Rays
Año:2013
Volumen:11
Número:32
Página de inicio:5300
Página de fin:5309
DOI: http://dx.doi.org/10.1039/c3ob40344k
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
CAS:9 methyl beta carboline, 2521-07-5; DNA, 9007-49-2; 9-methyl-beta-carboline; Carbolines; DNA, 9007-49-2; DNA, Viral; Photosensitizing Agents; calf thymus DNA, 91080-16-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v11_n32_p5300_Vignoni

Referencias:

  • Kearns, P.S., Coll, J.C., Rideout, J.A., (1995) J. Nat. Prod., 58, pp. 1075-1076
  • Hemmateenejad, B., Abbaspour, A., Maghami, H., Miri, R., Panjehshahin, M.R., (2006) Anal. Chim. Acta, 575, pp. 290-299
  • Kam, T.-S., Sim, K.-M., Koyano, T., Komiyama, K., (1999) Phytochemistry, 50, pp. 75-79
  • Kam, T.-S., Sim, K.-M., (1998) Phytochemistry, 47, pp. 145-147
  • Stachell, S.J., Stockwell, S.A., Van Vranken, D.L., (1999) Chem. Biol., 6, pp. 531-539
  • Siderhurst, M.S., James, D.M., Rithner, C.D., Dick, D.L., Bjostad, L.B., (2005) J. Econ. Entomol., 98, pp. 1669-1678
  • Susilo, R., Rommelspacher, H., (1987) Naunyn-Schmiedebergs Arch. Pharmacol., 335, pp. 70-76
  • Herraiz, T., Galisteo, J., (2003) J. Agric. Food Chem., 51, pp. 7156-7161
  • Spijkerman, R., Van Den Eijnden, R., Van De Mheen, D., Bongers, I., Fekkes, D., (2002) Eur. Neuropsychopharmacol., 12, pp. 61-71
  • Torreilles, J., Guérin, M.-C., Previero, A., (1985) Biochimie, 67, pp. 929-947
  • Pfau, W., Skog, K., (2004) J. Chromatogr., B: Biomed. Sci. Appl., 802, pp. 115-126
  • Breyer-Pfaff, U., Wiatr, G., Stevens, I., Jörg Gaertner, H., Mundle, G., Mann, K., (1996) Life Sci., 58, pp. 1425-1432
  • Shimoi, K., Miyamura, R., Mori, T., Todo, T., Ohtsuka, E., Wakabayashi, K., Kinae, N., (1996) Carcinogenesis, 17, pp. 1279-1283
  • Mori, T., Nakagawa, A., Kobayashi, N., Hashimoto, M.W., Wakabayashi, K., Shimoi, K., Kinae, N., (1998) J. Radiat. Res., 39, pp. 21-33
  • Chang, C.-C., Casteliazzi, M., Glover, T.W., Trosko, J.E., (1978) Cancer Res., 38, pp. 4527-4533
  • Shimoi, K., Kawabata, H., Tomita, I., (1992) Mutat. Res., 268, pp. 287-295
  • Hudson, J.B., Graham, E.A., Towers, G.H.N., (1986) Photochem. Photobiol., 43, pp. 21-26
  • Greiner, B., Fahndrich, C., Strauss, S., Rommelspacher, H., (1983) Naunyn-Schmiedebergs Arch. Pharmacol., 322, pp. 140-146
  • Fekkes, D., Bode, W.T., (1993) Life Sci., 52, pp. 2045-2054
  • Collins, M.A., Neafsey, E.J., (2000) Neurotoxic Factors in Parkinson's Disease and Related Disorders
  • Gearhart, D.A., Collins, M.A., Lee, J.M., Neafsey, E.J., (2000) Neurobiol. Dis., 7, pp. 201-211
  • Gearhart, D.A., Neafsey, E.J., Collins, M.A., (2002) Neurochem. Int., 40, pp. 611-620
  • Pavlovic, S., Schulze, G., Wernicke, C., Bonnet, R., Gille, G., Badiali, L., Kaminska, A., Rommelspacher, H., (2006) Neuroscience, 139, pp. 1525-1537
  • Hamann, J., Rommelspacher, H., Storch, A., Reichmann, H., Gille, G., (2006) J. Neurochem., 98, pp. 1185-1199
  • Hamann, J., Wernicke, C., Lehmann, J., Reichmann, H., Rommelspacher, H., Gille, G., (2008) Neurochem. Int., 52, pp. 688-700
  • 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
  • Gonzalez, M.M., Vignoni, M., Pellon-Maison, M., Ales-Gandolfo, M.A., Gonzalez-Baro, M.R., Erra-Balsells, R., Epe, B., Cabrerizo, F.M., (2012) Org. Biomol. Chem., 10, pp. 1807-1819
  • Gonzalez, M.M., Rasse-Suriani, F.A.O., Franca, C.A., Pis Diez, R., Gholipour, Y., Nonami, H., Erra-Balsells, R., Cabrerizo, F.M., (2012) Org. Biomol. Chem., pp. 9359-9372
  • Nonami, H., Orcoyen, M., Fukuyama, Y., Biondic, M.C., Erra-Balsells, R., (1998) An. Asoc. Quim., 86, pp. 81-89
  • Salditt, M., Braunstein, S.N., Camerini-Otero, R.D., Franklin, R.M., (1972) Virology, 48, pp. 259-262
  • Boiteux, S., O'Connor, T.R., Lederer, F., Gouyette, A., Laval, J., (1990) J. Biol. Chem., 265, pp. 3916-3922
  • Müller, E., Boiteux, S., Cunningham, R.P., Epe, B., (1990) Nucleic Acids Res., 18, pp. 5969-5973
  • Srere, P.A., Kosicki, G.W., Lumry, R., (1961) Biochim. Biophys. Acta, 50, pp. 184-185
  • Epe, B., Hegler, J., Lester, P., (1994) Methods Enzymol., 234, pp. 122-131
  • Epe, B., (2012) Photochem. Photobiol. Sci., 11, pp. 98-106
  • Häring, M., Rüdiger, H., Demple, B., Boiteux, S., Epe, B., (1994) Nucleic Acids Res., 22, pp. 2010-2015
  • Gonzalez, M.M., Salum, M.L., Gholipour, Y., Cabrerizo, F.M., Erra-Balsells, R., (2009) Photochem. Photobiol. Sci., 8, pp. 1139-1149
  • Gonzalez, M.M., Arnbjerg, J., Paula Denofrio, M., Erra-Balsells, R., Ogilby, P.R., Cabrerizo, F.M., (2009) J. Phys. Chem. A, 113, pp. 6648-6656
  • Taira, Z., Kanzawa, S., Dohara, C., Ishida, S., Matsumoto, M., Sakiya, Y., (1997) Jpn. J. Toxicol. Environ. Health, 43, pp. 83-91
  • Cadet, J., Sage, E., Douki, T., (2005) Mutat. Res., 571, pp. 3-17
  • Delatour, T., Douki, T., D'Ham, C., Cadet, J., (1998) J. Photochem. Photobiol., B, 44, pp. 191-198
  • Wood, P.D., Redmond, R.W., (1996) J. Am. Chem. Soc., 118, pp. 4256-4263
  • Bosca, F., Lhiaubet-Vallet, V., Cuquerella, M.C., Castell, J.V., Miranda, M.A., (2006) J. Am. Chem. Soc., 128, pp. 6318-6319
  • Foote, C.S., (1991) Photochem. Photobiol., 54, pp. 659-659
  • Krokan, H.E., Standal, R., Slupphaug, G., (1997) Biochem. J., 325, pp. 1-16
  • Mesaros, M., Tarzi, O.I., Erra-Balsells, R., Bilmes, G.M., (2006) Chem. Phys. Lett., 426, pp. 334-340
  • Draxler, S., Lippitsch, M.E., (1993) J. Phys. Chem., 97, pp. 11493-11496
  • Cao, R., Peng, W., Chen, H., Ma, Y., Liu, X., Hou, X., Guan, H., Xu, A., (2005) Biochem. Biophys. Res. Commun., 338, pp. 1557-1563
  • Paul, B.K., Guchhait, N., (2011) J. Phys. Chem. B, 115, pp. 11938-11949
  • Cabrerizo, F.M., Arnbjerg, J., Denofrio, M.P., Erra-Balsells, R., Ogilby, P.R., (2010) ChemPhysChem, 11, pp. 796-7980

Citas:

---------- APA ----------
Vignoni, M., Rasse-Suriani, F.A.O., Butzbach, K., Erra-Balsells, R., Epe, B. & Cabrerizo, F.M. (2013) . Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines. Organic and Biomolecular Chemistry, 11(32), 5300-5309.
http://dx.doi.org/10.1039/c3ob40344k
---------- CHICAGO ----------
Vignoni, M., Rasse-Suriani, F.A.O., Butzbach, K., Erra-Balsells, R., Epe, B., Cabrerizo, F.M. "Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines" . Organic and Biomolecular Chemistry 11, no. 32 (2013) : 5300-5309.
http://dx.doi.org/10.1039/c3ob40344k
---------- MLA ----------
Vignoni, M., Rasse-Suriani, F.A.O., Butzbach, K., Erra-Balsells, R., Epe, B., Cabrerizo, F.M. "Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines" . Organic and Biomolecular Chemistry, vol. 11, no. 32, 2013, pp. 5300-5309.
http://dx.doi.org/10.1039/c3ob40344k
---------- VANCOUVER ----------
Vignoni, M., Rasse-Suriani, F.A.O., Butzbach, K., Erra-Balsells, R., Epe, B., Cabrerizo, F.M. Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines. Org. Biomol. Chem. 2013;11(32):5300-5309.
http://dx.doi.org/10.1039/c3ob40344k