Navegar

Colección

Datos Estadísticas

Artículo

Robaldo, L.; Izzo, F.; Dellafiore, M.; Proietti, C.; Elizalde, P.V.; Montserrat, J.M.; Iribarren, A.M. "Influence of conformationally restricted pyrimidines on the activity of 10-23 DNAzymes" (2012) Bioorganic and Medicinal Chemistry. 20(8):2581-2586
El editor solo permite decargar el artículo en su versión post-print desde el repositorio. Por favor, si usted posee dicha versión, enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

The catalytic core of a 10-23 DNAzyme was modified introducing conformationally restricted nucleosides such as (2′R)-, (2′S)-2′-deoxy-2′-C-methyluridine, (2′R)-, (2′S)-2′-deoxy-2′-C-methylcytidine, 2,2′-anhydrouridine and LNA-C, in one, two or three positions. Catalytic activities under pseudo first order conditions were compared at different Mg 2+ concentrations using a short RNA substrate. At low Mg 2+ concentrations, triple modified DNAzymes with similar kinetic performance to that displayed by the non-modified control were identified. In the search for a partial explanation of the obtained results, in silico studies were carried out in order to explore the conformational behavior of 2′-deoxy-2′-C-methylpyrimidines in the context of a loop structure, suggesting that at least partial flexibility is needed for the maintenance of activity. Finally, the modified 2′-C-methyl DNAzyme activity was tested assessing the inhibition of Stat3 expression and the decrease in cell proliferation using the human breast cancer cell line T47D. © 2012 Published by Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Influence of conformationally restricted pyrimidines on the activity of 10-23 DNAzymes
Autor:Robaldo, L.; Izzo, F.; Dellafiore, M.; Proietti, C.; Elizalde, P.V.; Montserrat, J.M.; Iribarren, A.M.
Filiación:INGEBI (CONICET), Vuelta de Obligado 2490-(1428), Buenos Aires, Argentina
IBYME, Vuelta de Obligado 2490-(1428), Buenos Aires, Argentina
Instituto de Ciencias, Universidad Nacional de Gral. Sarmiento, J.M. Gutierrez 1150c, Los Polvorines, (B1613GSX), Prov. de Bs. As., Argentina
Laboratorio de Biotransformaciones, Universidad Nacional de Quilmes, Roque Saenz Peña 352, (1876) Bernal, Prov. de Bs. As., Argentina
Palabras clave:2′-C-Methylnucleosides; Deoxyribozymes; DNA structures; DNAzymes; Modified nucleosides; 2' deoxy 2' c methyl pyrimidine derivative; 2' deoxy 2' c methylcytidine; 2' deoxy 2' c methyluridine; 2' methylcytidine; deoxyribozyme; pyrimidine derivative; short hairpin RNA; STAT3 protein; unclassified drug; article; breast cancer; cancer cell; catalysis; cell proliferation; concentration response; controlled study; enzyme activity; enzyme inhibition; enzyme kinetics; enzyme modification; enzyme stability; enzyme structure; enzyme synthesis; human; human cell; nucleic acid synthesis; protein conformation; protein expression; Antineoplastic Agents; Biocatalysis; Cell Proliferation; DNA, Catalytic; DNA, Single-Stranded; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Enzyme Activation; Humans; Molecular Conformation; Pyrimidines; STAT3 Transcription Factor; Structure-Activity Relationship; Tumor Cells, Cultured
Año:2012
Volumen:20
Número:8
Página de inicio:2581
Página de fin:2586
DOI: http://dx.doi.org/10.1016/j.bmc.2012.02.047
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:deoxyribozyme, 206668-15-7; Antineoplastic Agents; DNA, Catalytic; DNA, Single-Stranded; Pyrimidines; RNA-cleaving DNA 10-23; STAT3 Transcription Factor; STAT3 protein, human
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v20_n8_p2581_Robaldo

Referencias:

  • Strobel, S.A., Cochrane, J.C., (2007) Curr. Opin. Chem. Biol., 11, p. 636
  • Santoro, S.W., Joyce, G.F., (1997) Proc. Natl. Acad. Sci. U.S.A., 94, p. 4262
  • Baum, D.A., Silverman, S.K., (2008) Cell. Mol. Life Sci., 65, p. 2156
  • Breaker, R.R., Joyce, G.F., (1994) Chem. Biol., 1, p. 223
  • Hollestein, M., Hipólito, C.J., Lam, C.H., Perrin, D.M., (2009) Nucleic Acids Res., 37, p. 1638
  • Hollestein, M., Hipólito, C.J., Lam, C.H., Perrin, D.M., (1988) ChemBiochem, 2009, p. 10
  • Purtha, W.E., Coppins, R.L., Smalley, M.K., Silverman, S.K., (2005) J. Am. Chem. Soc., 127, p. 13124
  • Cuenoud, B., Szostak, J.W., (1995) Nature, 375, p. 611
  • Wang, W., Billen, L.P., Yi, Y., (2002) Chem. Biol., 9, p. 507
  • Pradeepkumar, P.I., Höbartner, C., Baum, D.A., Silverman, S.K., (2008) Angew. Chem., Int. Ed., 47, p. 1753
  • Chandra, M., Silverman, S.K., (2008) J. Am. Chem. Soc., 130, p. 2936
  • Li, Y., Sen, D., (1996) Nat. Struct. Biol., 3, p. 743
  • Bhindi, R., Fahmy, R.G., Lowe, H.C., Chesterman, C.N., Dass, C.R., Cairns, M.J., Saravolac, E.G., Kachigian, L.M., (2007) Am. J. Phatol., 171, p. 1079
  • Zaborowska, A., Schubert, S., Kurreck, J., Erdmann, V.A., (2005) FEBS Lett., 579, p. 554
  • Joyce, G.F., (2001) Methods Enzymol., 341, p. 503
  • Nowakowski, J., Shim, P., Prasad, G.S., Stout, C.D., Joyce, G.F., (1999) Nat. Struct. Biol., 6, p. 151
  • Nowakowski, J., Shim, P.J., Stout, D., Joyce, G.F., (2000) J. Mol. Biol., 300, p. 93
  • Nowakowski, J., Shim, P.J., Joyce, G.F., Stout, C.D., (1885) Acta Cryst. Sect. D Biol. Crystallogr., 1999, p. 55
  • Kenward, M., Dorfman, D.D., (2009) Biophys. J., 97, p. 2785
  • Sun, L.-Q., Cairns, M.J., Gerlach, W.L., Witherington, C., Wang, L., King, A., (1999) J. Biol. Chem., 274, p. 17236
  • Lu, Z.-X., Ye, M., Yan, G.-R., Li, Q., Tang, M., Lee, L.M., Sun, L.-Q., Cao, Y., (2005) Cancer Gene Ther., 12, p. 647
  • Vester, B., Lundberg, L.B., Sorensen, M.D., Babu, B.R., Douthwaite, S.S., Wengel, J., (2002) J. Am. Chem. Soc., 124, p. 13682
  • Schubert, F., Gül, D.C., Grunert, H.-P., Zeichhardt, H., Erdmann, V.A., Kurreck, J., (2003) Nucleic Acids Res., 31, p. 5982
  • Reyes-Gutierrez, P., Álvarez-Sala, L.M., (2009) Oligonucleotides, 19, p. 233
  • Lam, C.H., Perrin, D.M., (2010) Bioorg. Med. Chem. Let., 20, p. 5119
  • Nawrot, B., Widera, K., Wojcik, M., Rebowska, B., Nowak, G., Stec, W.J., (2007) FEBS J., 274, p. 1062
  • Smuga, D., Majchrazak, K., Sochacka, E., Naurot, B., (2010) New J. Chem., 34, p. 934
  • Wang, B., Cao, L., Chiuman, W., Li, Y., Xi, Z., (2010) Biochemistry, 49, p. 7553
  • Cicero, D.O., Neuner, P.J.S., Franzese, O., D'Onofrio, C., Iribarren, A.M., (1994) Bioorg. Med. Chem. Lett., 4, p. 861
  • Caballero, G., Gallo, M., Montserrat, J.M., Iribarren, A.M., (2002) Helv. Chim. Acta, 85, p. 1284
  • Cicero, D.O., Iribarren, A.M., Bazzo, R., (1994) Appl. Magn. Reson., 7, p. 95
  • Robaldo, L., Montserrat, J.M., Iribarren, A.M., (2010) Bioorg. Med. Chem. Lett., 20, p. 4367
  • Iribarren, A.M., Cicero, D.O., Neuner, P.J., (1994) Antisense Res. Develop., 4, p. 95
  • Darnell Jr., J.E., (2002) Nat. Rev. Cancer, 2, p. 740
  • Haura, E.B., Turkson, J., Jove, R., (2005) Nat. Clin. Pract. Oncol., 2, p. 315
  • Yu, H., Pardoll, D., Jove, R., (2009) Nat. Rev. Cancer, 9, p. 798
  • Yue, P., Turkson, J., (2009) Expert Opin. Investig. Drugs, 18, p. 45
  • Inghirami, G., Chiarle, R., Simmons, W.J., Piva, R., Schlessinger, K., Levy, D.E., (2005) Cell Cycle, 4, p. 1131
  • Huang, Y., Qiu, J., Dong, S., Redell, M.S., Poli, V., Mancini, M.A., Tweardy, D.J., (2007) J. Biol. Chem., 282, p. 34958
  • Niu, G., Shain, K.H., Huang, M., Ravi, R., Bedi, A., Dalton, W.S., Jove, R., Yu, H., (2001) Cancer Res., 61, p. 3276
  • Proietti, C., Salatino, M., Rosemblit, C., Carnevale, R., Pecci, A., Kornblihtt, A.R., Molinolo, A.A., Elizalde, P.V., (2005) Mol. Cell Biol., 25, p. 4826
  • Gritsko, T., Williams, A., Turkson, J., Kaneko, S., Bowman, T., Huang, M., Nam, S., Jove, R., (2006) Clin. Cancer Res., 12, p. 11
  • Ling, X., Arlinghaus, R.B., (2005) Cancer Res., 65, p. 2532
  • Proietti, C.J., Rosemblit, C., Beguelin, W., Rivas, M.A., Diaz Flaque, M.C., Charreau, E.H., Schillaci, R., Elizalde, P.V., (2009) Mol. Cell Biol., 29, p. 1249
  • Zhao, W., Jaganathan, S., Turkson, J., (2010) J. Biol. Chem., 285, p. 35855
  • Song, H., Wang, R., Wang, S., Lin, J., (2005) Proc. Natl. Acad. Sci. U.S.A., 102, p. 4700
  • Pedranzini, L., Dechow, T., Berishaj, M., Comenzo, R., Zhou, P., Azare, J., Bornmann, W., Bromberg, J., (2006) Cancer Res., 66, p. 9714
  • Pontiggia, R., Pontiggia, O., Simian, M., Montserrat, J.M., Engels, J.W., Iribarren, A.M., (2010) Bioorg. Med. Chem. Lett., 20, p. 2806
  • Zaborowska, Z., Fürste, J.P., Erdmann, V.A., Kurreck, J., (2002) J. Biol. Chem., 277, p. 40617
  • Robins, M.J., Wilson, J.S., Hansske, F.K., (1983) J. Am. Chem. Soc., 105, p. 4059
  • Hansske, F., Majed, D., Robins, M.J., (1984) Tetrahedron, 40, p. 125
  • Gallo, M., Monteagudo, E., Ciccero, D.O., Torres, H.N., Iribarren, A.M., (2001) Tetrahedron, 57, p. 5707
  • Cicero, D.O., Gallo, M., Neuner, P.J., Iribarren, A.M., (2001) Tetrahedron, 57, p. 7613
  • Dran, G., Luthy, I.A., Molinolo, A.A., Montecchia, F., Charreau, E.H., Pasqualini, C.D., Lanari, C., (1995) Breast Cancer Res. Treat., 35, p. 173

Citas:

---------- APA ----------
Robaldo, L., Izzo, F., Dellafiore, M., Proietti, C., Elizalde, P.V., Montserrat, J.M. & Iribarren, A.M. (2012) . Influence of conformationally restricted pyrimidines on the activity of 10-23 DNAzymes. Bioorganic and Medicinal Chemistry, 20(8), 2581-2586.
http://dx.doi.org/10.1016/j.bmc.2012.02.047
---------- CHICAGO ----------
Robaldo, L., Izzo, F., Dellafiore, M., Proietti, C., Elizalde, P.V., Montserrat, J.M., et al. "Influence of conformationally restricted pyrimidines on the activity of 10-23 DNAzymes" . Bioorganic and Medicinal Chemistry 20, no. 8 (2012) : 2581-2586.
http://dx.doi.org/10.1016/j.bmc.2012.02.047
---------- MLA ----------
Robaldo, L., Izzo, F., Dellafiore, M., Proietti, C., Elizalde, P.V., Montserrat, J.M., et al. "Influence of conformationally restricted pyrimidines on the activity of 10-23 DNAzymes" . Bioorganic and Medicinal Chemistry, vol. 20, no. 8, 2012, pp. 2581-2586.
http://dx.doi.org/10.1016/j.bmc.2012.02.047
---------- VANCOUVER ----------
Robaldo, L., Izzo, F., Dellafiore, M., Proietti, C., Elizalde, P.V., Montserrat, J.M., et al. Influence of conformationally restricted pyrimidines on the activity of 10-23 DNAzymes. Bioorg. Med. Chem. 2012;20(8):2581-2586.
http://dx.doi.org/10.1016/j.bmc.2012.02.047