Abstract:
A new synthesis of 2′-C-methyluridine phosphoramidite is presented. Special emphasis is dedicated to the improvement of the protection of the tertiary 2′-hydroxyl group. Comparison to previous protecting strategies and analysis of stability under 5′-DMTr removing conditions are discussed. The synthetic incorporation of this modified nucleoside into the catalytic core of a hammerhead ribozyme against the estrogen receptor α protein (ER-α), and transfection experiments in MCF-7 cell line are also presented. © 2010 Elsevier Ltd. All rights reserved.
Registro:
Documento: |
Artículo
|
Título: | 2-C-Methyluridine modified hammerhead ribozyme against the estrogen receptor |
Autor: | Pontiggia, R.; Pontiggia, O.; Simian, M.; Montserrat, J.M.; Engels, J.W.; Iribarren, A.M. |
Filiación: | INGEBI (CONICET), Vuelta de Obligado 2490-, 1428 Buenos Aires, Argentina Instituto de Oncología A. H. Roffo, UBA, Av. San Martín 5481, CABA, Argentina Instituto de Ciencias, Universidad Nacional de Gral. Sarmiento, J. M. Gutierrez 1150, Los Polvorines (B1613GSX), Prov. de Bs. As., Argentina Institute for Organic Chemistry and Chemical Biology, Johann Wolfgang Goethe-University, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany Laboratorio de Biotransformaciones, Universidad Nacional de Quilmes, Roque Saenz Peña 352, Roque Saenz Peña 352, Argentina
|
Palabras clave: | 2′-C-methyluridine; Estrogen receptor alpha; Modified ribozyme; estrogen receptor alpha; hammerhead ribozyme; hormone receptor blocking agent; hydroxyl group; phosphoramidous acid derivative; article; cell strain MCF 7; chemical modification; controlled study; drug stability; drug synthesis; enzyme active site; genetic transfection; receptor down regulation; Cell Line, Tumor; Humans; Oligonucleotides; Receptors, Estrogen; RNA, Catalytic; RNA, Messenger; Uridine |
Año: | 2010
|
Volumen: | 20
|
Número: | 9
|
Página de inicio: | 2806
|
Página de fin: | 2808
|
DOI: |
http://dx.doi.org/10.1016/j.bmcl.2010.03.060 |
Título revista: | Bioorganic and Medicinal Chemistry Letters
|
Título revista abreviado: | Bioorg. Med. Chem. Lett.
|
ISSN: | 0960894X
|
CODEN: | BMCLE
|
CAS: | 2'-C-methyluridine; Oligonucleotides; RNA, Catalytic; RNA, Messenger; Receptors, Estrogen; Uridine, 58-96-8; hammerhead ribozyme; locked nucleic acid
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0960894X_v20_n9_p2806_Pontiggia |
Referencias:
- Strobel, S.A., Cochrane, J.C., (2007) Curr. Opin. Chem. Biol., 11, p. 636
- Stoltenburg, R., Reinemann, C., Strehlitz, B., (2007) Biomol. Eng., 24, p. 381
- Corey, D.R., (2007) J. Clin. Invest., 117, p. 3615
- Kurreck, J., (2003) Eur. J. Biochem., 270, p. 1628
- Kaur, H., Ravindra Babu, B., Maiti, S., (2007) Chem. Rev., 107, p. 4672
- Gallo, M., Kretschmer-Kazemi Far, R., Scazakiel, G., Iribarren, A.M., (2005) Chem. Biodiv., 2, p. 198
- Gallo, M., Monteagudo, E., Cicero, D., Torres, H., Iribarren, A., (2001) Tetrahedron, 57, p. 5707
- Beigelman, L.N., Eromolinsky, B.S., Gurskaya, G.V., Tsapkina, E.N., Karpeisky, M.Y., Mikhailov, S.N., (1987) Carbohydr. Res., 166, p. 219
- Jenkins, S.R., Arison, B., Walton, E., (1968) J. Org. Chem., 33, p. 2490
- Walton, E., Jenkins, S.R., Nutt, R.F., Holly, F.W., (1969) J. Med. Chem., 12, p. 306
- Harry-O'kuru, R.E., Smith, J.M., Wolfe, M.S., (1997) J. Org. Chem., 62, p. 1754
- Al-Husani, A.H., Moore, H.W., (1985) J. Org. Chem., 50, p. 2597
- Yang, B.Y., Montgomery, R., (1996) Carbohydr. Res., 280, p. 27
- Gallo, M. Doctoral Thesis, Universidad de Buenos Aires, 2002; Beigelman, L., Karpeisky, A.M., Matulic-Adamic, J., Haeberli, P., Sweedler, D., Usman, N., (1995) Nucleic Acids Res., 23, p. 4434
- Scher, S., Kleba, C., Häner, R., Gauser, A., Engels, J.W., (1997) Bioorg. Med. Chem. Lett., 13, p. 1791
- Lavrovsky, Y., Tyagi, R.K., Chen, S., Song, C.S., Chatterjee, B., Roy, A.K., (1999) Mol. Endocrinol., 13, p. 925
- Pitsch, S., Weiss, P.A., Jenny, L., Stutz, A., Wu, X., (2001) Helv. Chim. Acta, 84, p. 3773
Citas:
---------- APA ----------
Pontiggia, R., Pontiggia, O., Simian, M., Montserrat, J.M., Engels, J.W. & Iribarren, A.M.
(2010)
. 2-C-Methyluridine modified hammerhead ribozyme against the estrogen receptor. Bioorganic and Medicinal Chemistry Letters, 20(9), 2806-2808.
http://dx.doi.org/10.1016/j.bmcl.2010.03.060---------- CHICAGO ----------
Pontiggia, R., Pontiggia, O., Simian, M., Montserrat, J.M., Engels, J.W., Iribarren, A.M.
"2-C-Methyluridine modified hammerhead ribozyme against the estrogen receptor"
. Bioorganic and Medicinal Chemistry Letters 20, no. 9
(2010) : 2806-2808.
http://dx.doi.org/10.1016/j.bmcl.2010.03.060---------- MLA ----------
Pontiggia, R., Pontiggia, O., Simian, M., Montserrat, J.M., Engels, J.W., Iribarren, A.M.
"2-C-Methyluridine modified hammerhead ribozyme against the estrogen receptor"
. Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 9, 2010, pp. 2806-2808.
http://dx.doi.org/10.1016/j.bmcl.2010.03.060---------- VANCOUVER ----------
Pontiggia, R., Pontiggia, O., Simian, M., Montserrat, J.M., Engels, J.W., Iribarren, A.M. 2-C-Methyluridine modified hammerhead ribozyme against the estrogen receptor. Bioorg. Med. Chem. Lett. 2010;20(9):2806-2808.
http://dx.doi.org/10.1016/j.bmcl.2010.03.060