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Lang, K.L.; Silva, I.T.; Zimmermann, L.A.; MacHado, V.R.; Teixeira, M.R.; Lapuh, M.I.; Galetti, M.A.; Palermo, J.A.; Cabrera, G.M.; Bernardes, L.S.C.; Simões, C.M.O.; Schenkel, E.P.; Caro, M.S.B.; Durán, F.J. "Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives" (2012) Bioorganic and Medicinal Chemistry. 20(9):3016-3030
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Abstract:

Two cucurbitacins, dihydrocucurbitacin B (1) and cucurbitacin B (2), which can be obtained in large amounts from the roots of Wilbrandia ebracteata and from the fruits of Luffa operculata, respectively, were used as starting materials for the preparation of a library of 29 semi-synthetic derivatives. The structural changes that were performed include the removal, modification or permutation of functional groups in rings A and B as well as in the side chain. All new semisynthetic compounds, as well as 1 and 2, were tested in vitro for their cytotoxic effects on non-small-cell lung cancer cells (A549 cells). Some of these compound displayed potent to moderate activity against A549 tumor cells, especially those cucurbitacin B derivatives which were modified at ring A. © 2012 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives
Autor:Lang, K.L.; Silva, I.T.; Zimmermann, L.A.; MacHado, V.R.; Teixeira, M.R.; Lapuh, M.I.; Galetti, M.A.; Palermo, J.A.; Cabrera, G.M.; Bernardes, L.S.C.; Simões, C.M.O.; Schenkel, E.P.; Caro, M.S.B.; Durán, F.J.
Filiación:Programa de Pós-Graduaão em Química, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil
Programa de Pós-Graduaão em Farmácia, Universidade Federal de Santa Catarina, Florianópolis, SC, Brazil
UMYMFOR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Argentina
Palabras clave:Cucurbitacins; Cytotoxic activity; Semisynthesis; Triterpenoids; 16 oxo dihydrocucurbitacin b; 2 bromo dihydrocucurbitacin b; 2 deoxy dihydrocucurbitacin b; 2,16 dideoxy dihydrocucurbitacin b; cucurbitacin; cucurbitacin b derivative; dihydrocucurbitacin b; Luffa operculata extract; plant extract; unclassified drug; Wilbrandia ebracteata extract; article; cell viability; chemical modification; chemical reaction; concentration response; controlled study; Cucurbitaceae; drug cytotoxicity; drug screening; drug specificity; drug structure; drug synthesis; fruit; human; human cell; IC 50; in vitro study; luffa operculata; lung non small cell cancer; plant root; structure activity relation; structure analysis; Wilbrandia ebracteata; Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Cucurbitaceae; Fruit; Humans; Luffa; Plant Roots; Triterpenes; Luffa operculata; Wilbrandia ebracteata
Año:2012
Volumen:20
Número:9
Página de inicio:3016
Página de fin:3030
DOI: http://dx.doi.org/10.1016/j.bmc.2012.03.001
Título revista:Bioorganic and Medicinal Chemistry
Título revista abreviado:Bioorg. Med. Chem.
ISSN:09680896
CODEN:BMECE
CAS:Antineoplastic Agents; Triterpenes; cucurbitacin B, 6199-67-3; dihydrocucurbitacin B
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09680896_v20_n9_p3016_Lang

Referencias:

  • Butler, M.S., (2008) Nat. Prod. Rep., 25, p. 475
  • Ganesan, A., (2008) Curr. Opin. Chem. Biol., 12, p. 306
  • Harvey, A.L., (2008) Drug Disc. Today, 13, p. 894
  • Lam, K.S., (2007) Trends Microbiol., 15, p. 279
  • Newman, D.J., Cragg, G.M., (2007) J. Nat. Prod., 70, p. 461
  • Chin, Y.-W., Balunas, M.J., Chai, H.B., Kinghorn, A.D., (2006) AAPS J., 8, p. 239
  • Wermuth, C.G., (2008) The Practice of Medicinal Chemistry, , Elsevier Academic Press
  • Miró, M., (1995) Phytother. Res., 9, p. 159
  • Valente, L.M.M., (2004) Quím. Nova, 27, p. 944
  • Chen, J.C., Chiu, M.H., Nie, R.L., Cordell, G.A., Qiu, S.X., (2005) Nat. Prod. Rep., 22, p. 386
  • Lee, K.-H., (2010) J. Nat. Prod., 73, p. 500
  • Lee, D.H., Iwanski, G.B., Thoennissen, N.H., (2010) Sci. World J., 10, p. 413
  • Dinan, L., Harmatha, J., Lafont, R., (2001) J. Chromatogr. A, 935, p. 105
  • Ríos, J.L., Escandell, J.M., Recio, M.C., (2005) Stud. Natural Prod. Chem., 32, p. 429
  • Lee, D.H., Thoennissen, N.H., Goff, C., Iwanski, G.B., Forscher, C., Doan, N.B., Said, J.W., Koeffler, P., (2011) Cancer Lett., 306, p. 161
  • Lavie, D., Glotter, E., (1971) Fortschr. Chem. Org. Naturst., 29, p. 307
  • Thoennissen, N.H., Iwanski, G.B., Doan, N.B., Okamoto, R., Lin, P., Abbassi, S., Song, J.H., Koeffler, P., (2009) Cancer Res., 69, p. 5876
  • Siqueira, J.M., Peters, R.R., Gazola, A.C., Krepsky, P., Farias, M.R., Rae, G.A., Brum-Fernandes, A.J., Ribeiro-Do-Valle, R.M., (2007) Life Sci., 80, p. 1382
  • Yang, L., Wu, S., Zhang, Q., Liu, F., Wu, P., (2007) Cancer Lett., 256, p. 267
  • Sun, J., Blaskovich, M.A., Jove, R., Livingston, S.K., Coppola, D., Sebti, S.M., (2005) Oncogene, 24, p. 3236
  • Blaskovich, M.A., Sun, J.Z., Cantor, A., Turkson, J., Jove, R., Sebti, S.M., (2003) Cancer Res., 63, p. 1270
  • Jayaprakasan, B., Seeram, N.P., Nair, M.G., (2003) Cancer Lett., 189, p. 11
  • Duncan, M.D., Duncan, K.L.K., (1997) J. Surg. Res., 69, p. 55
  • Yu, H., Jove, R., (2004) Nature Rev. Cancer., 4, p. 97
  • Fletcher, S., Drewry, J.A., Shahani, V.M., Page, B.D.G., Gunning, P.T., (2009) Biochem. Cell Biol., 87, p. 825
  • Siddiquee, K.Z., Turkson, J., (2008) Cell. Res., 18, p. 254
  • Haritunians, T., Gueller, S., Zhang, L., Badr, R., Yin, D., Xing, H., Fung, M.C., Koeffler, H.P., (2008) Leukemia Res., 32, p. 1366
  • Wakimoto, N., Yin, D., O'kelly, J., Haritunians, T., Karlan, B., Said, J., Xing, H., Koeffler, H.P., (2008) Cancer Sci., 99, p. 1793
  • Yin, D., Wakimoto, N., Xing, H., Lu, D., Huynh, T., Wang, X., Black, K.L., Koeffler, H.P., (2008) Int. J. Cancer., 123, p. 1364
  • Knecht, D.A., Lafleur, R.A., Kahsai, A.W., Argueta, C.E., Beshir, A.B., Fenteany, G., (2010) PLoS ONE., 5, p. 14039
  • Duncan, K.L.K., Duncan, M.D., Alley, M.C., Sausville, E.A., (1996) Biochem. Pharmacol., 52, p. 1553
  • Dinan, L., Whiting, P., Girault, J.-P., Lafont, R., Dhadialla, T.S., Cress, D.E., Mugat, B., Lepesant, J.-A., (1997) Biochem. J., 327, p. 643
  • Maloney, K.N., Fujita, M., Eggert, U.S., Schroeder, F.C., Field, C.M., Mitchison, T.M., Clardy, J., (2008) J. Nat. Prod., 71, p. 1927
  • Ryu, S.Y., Choi, S.U., Lee, S.H., Lee, C.O., No, Z., Ahn, J.W., (1995) Arch. Pharm. Res., 18 (1), p. 60
  • Bartalis, J., Halaweish, F.T., (2011) Bioorg. Med. Chem., 19, p. 2757. , publications and patents cited therein
  • Jung, M.E., Lui, R.M., (2010) J. Org. Chem., 75, p. 7146
  • Schenkel, E.P., Farias, M.R., Mayer, R., Breitmaier, E., Rucker, G., (1992) Phytochemistry, 31, p. 1329
  • Farias, M.R., Schenkel, E.P., Mayer, R., Rücker, G., (1993) Planta Med., 59, p. 272
  • Santos, R.I., Santos, M.A., Dos Schenkel, E.P., (1996) Int. J. Pharmacog., 34, p. 300
  • Lang, K.L., Guimarães, T.R., Rocha MacHado, V., Zimmermann, L.A., Silva, I.T., Teixeira, M.R., Durán, F.J., Schenkel, E.P., (2011) Planta Med., 77, p. 1648
  • Wen, X., Zhang, P., Liu, J., Zhang, L., Wu, X., Ni, P., Sun, H., (2006) Bioorg. Med. Chem. Lett., 16, p. 722
  • Wen, X., Xia, J., Cheng, K., Zhang, L., Zhang, P., Liu, J., Zhang, L., Sun, H., (2007) Bioorg. Med. Chem. Lett., 17, p. 5777
  • Hartung, J., Hünig, S., Kneuer, R., Schwarz, M., Wenner, H., (1997) Synthesis, 12, p. 1433
  • Drögemüller, M., Flessner, T., Jautelat, R., Scholz, U., Winterfeldt, E., (1998) Eur. J. Org. Chem., 12, p. 2811
  • Barton, D.H.R., Jang, D.O., Jaszberenyi, J.C., (1993) Tetrahedron, 49, p. 7193
  • Seyden-Penne, J., (1997) Reductions by the Alumino- And Borohydrides in Organic Synthesis, , Wiley-VCH France
  • Králíková, S., Budesinsky, M., Tomecková, I., Rosenberg, I., (2006) Tetrahedron, 62, p. 9742
  • Veleiro, A.S., Rosenstein, R.E., Jaliffa, C.O., Grilli, M.L., Speroni, F., Burton, G., (2003) Bioorg. Med. Chem. Lett., 13, p. 343
  • Gemal, A.L., Luche, J.L., (1981) J. Am. Chem. Soc., 18, p. 5454
  • Weyermann, P., Keese, R., (2011) Tetrahedron, 67, p. 3874
  • Alvarez-Manzaneda, E.J., Chahboun, R., Cabrera Torres, E., Alvarez, E., Alvarez-Manzaneda Roldán, R., Haidour, A., Ramos, J., (2005) Tetrahedron Lett., 46, p. 1075
  • Jayaprakasam, B., Seeram, N.P., Nair, M.G., (2003) Cancer Lett., 189, p. 11
  • Durán, F.J., Ghini, A.A., Coirini, H., Burton, G., (2006) Tetrahedron, 62, p. 4762
  • Cuia, J., Fana, L., Huanga, L., Liub, H., Zhoub, A., (2009) Steroids, 74, p. 62
  • Itharat, A., Houghton, P.J., Houghton, E., Burke, P.J., Sampson, J.H., Raman, A., (2004) J. Ethnopharmacol., 90, p. 33
  • Monks, A., Scudiero, D., Skehan, P., Shoemaker, R., Paull, K., Vistica, D., Hose, C., Boyd, M.J., (1991) Nat. Cancer Inst., 83, p. 757
  • Mosmann, T., (1983) J. Immunol. Methods, 65, p. 55
  • Liu, T., Zhang, M., Zhang, H., Sun, C., Deng, Y., (2008) Eur. Arch. Otorhinol., 265, p. 1225
  • Duangmano, S., Dakeng, S., Jiratchariyakul, S., Suksamrarn, A., Smith, D., Patmasiriwat, P., (2010) Int. J. Mol. Sci., 11, p. 5323
  • Chan, K.T., Meng, F.Y., Li, Q., Ho, C.Y., Lam, T.S., To, Y., Lee, W.H., Toh, M., (2010) Cancer Lett., 294, p. 118
  • Iwanski, G.B., Lee, D.H., En-Gal, S., Doan, N.B., Castor, B., Vogt, M., Toh, M., Koeffler, P., (2010) Brit. J. Pharm., 160, p. 998
  • Sadzuka, Y., Hatakeyama, H., Sonobe, T., (2010) Int. J. Pharm., 383, p. 186
  • Liu, T., Peng, H., Zhang, M., Deng, Y., Wu, Z., (2010) Eur. J. Pharm. Sci., 641, p. 15
  • Dang, G.V., Rode, B.M., Stuppner, H., (1994) Eur. J. Pharm. Sci., 2, p. 331
  • Chen, C., Qiang, S., Lou, L., Zhao, W., (2009) J. Nat. Prod., 72, p. 824
  • Fang, X., Phoebe, C.H., Pezzuto, J.M., Fong, H.H.S., Farnsworth, N.R., Yellin, B., Hecht, S.M., (1984) J. Nat. Prod., 47, p. 988
  • Kanchanapoom, T., Kasaia, R., Yamasakia, K., (2002) Phytochemistry, 59, p. 215
  • Matsuda, H., Nakashima, S., Abdel-Halim, O.B., Morikawa, T., Yoshikawa, M., (2010) Chem. Pharm. Bull., 58, p. 747
  • Wu, P.L., Lin, F.W., Wu, T.S., Kuoh, C.S., Lee, K.H., Lee, S.J., (2004) Chem. Pharm. Bull., 52, p. 345
  • Velde, V., Lavie, D., (1983) Tetrahedron, 39, p. 317

Citas:

---------- APA ----------
Lang, K.L., Silva, I.T., Zimmermann, L.A., MacHado, V.R., Teixeira, M.R., Lapuh, M.I., Galetti, M.A.,..., Durán, F.J. (2012) . Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives. Bioorganic and Medicinal Chemistry, 20(9), 3016-3030.
http://dx.doi.org/10.1016/j.bmc.2012.03.001
---------- CHICAGO ----------
Lang, K.L., Silva, I.T., Zimmermann, L.A., MacHado, V.R., Teixeira, M.R., Lapuh, M.I., et al. "Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives" . Bioorganic and Medicinal Chemistry 20, no. 9 (2012) : 3016-3030.
http://dx.doi.org/10.1016/j.bmc.2012.03.001
---------- MLA ----------
Lang, K.L., Silva, I.T., Zimmermann, L.A., MacHado, V.R., Teixeira, M.R., Lapuh, M.I., et al. "Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives" . Bioorganic and Medicinal Chemistry, vol. 20, no. 9, 2012, pp. 3016-3030.
http://dx.doi.org/10.1016/j.bmc.2012.03.001
---------- VANCOUVER ----------
Lang, K.L., Silva, I.T., Zimmermann, L.A., MacHado, V.R., Teixeira, M.R., Lapuh, M.I., et al. Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives. Bioorg. Med. Chem. 2012;20(9):3016-3030.
http://dx.doi.org/10.1016/j.bmc.2012.03.001