Parte de libro

Wachsman, M.B.; Castilla, V. "Antiviral Properties of Brassinosteroids" (2012) Brassinosteroids: Practical Applications in Agriculture and Human Health:57-71
Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor

Abstract:

In this chapter, we reviewed the antiviral activity of natural and synthetic brassinosteroids (BRs). Brassinolide and other natural BRs such as 28-homocastasterone present a broad antiviral spectrum against RNA and DNA viruses. Since the concentration of BRs in the plant tissue is very low, isolation of these compounds from plant sources is impractical, and they had to be obtained by chemical synthesis. The antiviral activity of a group of synthetic analogues against Herpes Simplex Type 1 and 2 (HSV-1 and HSV-2), Measles (MV), Vesicular Stomatitis Virus (VSV), Polio Virus (PV) and Arena Viruses was also determined. Several of the tested compounds showed selectivity indexes 10-to 18-fold higher than ribavirin, a broad spectrum antiviral compound, for Junín Virus (JUNV), a moderate activity against HSV-1/HSV-2 and good anti-MV, anti-PV and anti-VSV activity, with antiviral selectivity Index (SI) values also higher than ribavirin, a reference drug. Structure activity relationship Studies were performed in order to determine which stereochemistry, type and position of functional groups are needed to develop a potent and selective class of viral inhibitors. The antiviral mode of action of the BRs against HSV, JUNV and VSV was also investigated. For all assayed viruses, the antiviral compounds adversely affect virus protein synthesis and mature viral particle formation. © 2011 Bentham Science Publishers. All rights reserved.

Registro:

Documento: Parte de libro
Título:Antiviral Properties of Brassinosteroids
Autor:Wachsman, M.B.; Castilla, V.
Filiación:Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 4, C1428EGA, Buenos Aires, Argentina
Palabras clave:Herpes simplex virus; Junín virus; Measles virus; Poliovirus; Ribavirin; Vesicular stomatitis
Año:2012
Página de inicio:57
Página de fin:71
DOI: http://dx.doi.org/10.2174/978160805298111201010057
Título revista:Brassinosteroids: Practical Applications in Agriculture and Human Health
Título revista abreviado:Brassinosteroids: Pract. Appl. in Agric. and Human Health
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_97816080_v_n_p57_Wachsman

Referencias:

  • Elion, G.B., Mechanism of action and selectivity of acyclovir (1982) Am J Med, 73 (SUPPL. 1A), pp. 7-13
  • De Clercq, E., Highlights in the discovery of antiviral drugs: A personal retrospective (2010) J Med Chem, 53, pp. 1438-1450
  • De Clercq, E., Anti-HIV drugs: 25 compounds approved within 25 years after the discovery of HIV (2009) Int J Antimicrob Agents, 33, pp. 307-320
  • Treanor, J., Falsey, A., Respiratory viral infections in the elderly (1999) Antiviral Res, 44, pp. 79-102
  • Shigeta, S., Approaches to antiviral chemotherapy for acute respiratory infections (1998) Antiviral Chem Chemother, 9, pp. 93-107
  • Dixon, R.A., Natural products and plant disease resistance (2001) Nature, 411, pp. 843-847
  • Grove, M.D., Spencer, G.F., Rohwedder, W.K., Brassinolide, a plant growth-promoting steroid isolated from Brassica napus pollen (1979) Nature, 281, pp. 216-217
  • Mandava, N.B., Plant growth-promoting brassinosteroids (1988) Ann Rev Plant Physiol Plant Mol Biol, 39, pp. 23-52
  • Bajguz, A., Tretyn, A., The chemical characteristic and distribution of brassinosteroids in plants (2003) Phytochem, 62, pp. 1027-1046
  • Kohen, F.F., Gunasekera, M., Cross, S.S., New antiviral sterol disulfate ortho esters from the marine sponge Petrosia weinbergi (1991) J Org Chem, 56, pp. 1322-1325
  • Sun, H.H., Cross, S.S., Gunasekera, M., Koehn, F.F., Weinbersterol disulfates A and B, antiviral steroid sulfates from the sponge Petrosia weinbergi (1991) Tetrahedron, 47, pp. 1185-1190
  • Comin, M.J., Maier, M.S., Roccatagliata, A.J., Pujol, C.A., Damonte, E.B., Evaluation of the antiviral activity of natural sulfated polyhydroxysteroids and their synthetic derivatives and analogs (1999) Steroids, 64, pp. 335-340
  • Arthan, D., Svasti, J., Kittakoop, P., Pittayakhachonwut, D., Tanticharoen, M., Thebtaranonth, Y., Antiviral isoflavonoid sulfate and steroidal glycosides from the fruits of Solanum torvum (2002) Phytochem, 59, pp. 459-463
  • Acosta, E.G., Bruttomesso, A.C., Bisceglia, J.A., Wachsman, M.B., Galagovsky, L.R., Castilla, V., Dehydroepiandrosterone, epiandrosterone and synthetic derivatives inhibit Junin virus replication in vitro (2008) Virus Res, 135, pp. 203-212
  • Romanutti, C., Bruttomesso, A.C., Castilla, V., Bisceglia, J.A., Galagovsky, L.R., Wachsman, M.B., In vitro antiviral activity of dehydroepiandrosterone and its synthetic derivatives against vesicular stomatitis virus (2009) Vet J, 182, pp. 327-335
  • Romanutti, C., Bruttomesso, A.C., Castilla, V., Galagovsky, L.R., Wachsman, M.B., Anti-adenovirus activity of epiandrosterone and dehydroepiandrosterone derivatives (2010) Chemotherapy, 56, pp. 158-165
  • Henderson, E., Yang, J., Schwartz, A., Dehydroepiandrosterone (DHEA) and synthetic DHEA analogs are modest inhibitors of HIV-1 IIIB replication (1992) AIDS Res Human Retrovir, 8, pp. 625-631
  • Diallo, K., Loemba, H., Oliveira, M., Mavoungou, D.D., Wainberg, M.A., Inhibition of human immunodeficiency virus type-1 (HIV-1) replication by immunor (IM28), a new analog of dehydroepiandrosterone (2000) Nucleos Nucleot Nucleic Acids, 19, pp. 2019-2024
  • Mavoungou, D., Poaty-mavoungou, V., Akoume, M., Ongali, B., Mavoungou, E., Inhibition of human immunodeficiency virus type-1 (HIV-1) glycoprotein-mediated cell-cell fusion by immunor (IM28) (2005) Virol J, 11, pp. 9-10
  • Chang, C.C., Ou, Y.C., Rang, S.L., Chen, C.J., Antiviral effect of dehydroepiandrosterone on Japonese Encephalitis virus infection (2005) J Gen Virol, 86, pp. 2513-2523
  • Wachsman, M.B., López, E.M., Ramírez, J.A., Galagovsky, L.R., Coto, C.E., Antiviral effect of brassinosteroids against herpes virus and arenaviruses (2000) Antivir Chem Chemother, 11, pp. 71-77
  • Wachsman, M.B., Ramirez, J.A., Galagovsky, L.R., Coto, C.E., Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures (2002) Antivir Chem Chemother, 13, pp. 61-66
  • Talarico, L.B., Ramirez, J.A., Galagovsky, L.R., Wachsman, M.B., Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures (2002) Med Chem Res, 11, pp. 434-444
  • Wachsman, M.B., Castilla, V., Talarico, L.B., Ramirez, J.A., Galagovsky, L.R., Coto, C.E., Antiherpetic mode of action of (22S,23S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one in vitro (2004) Int J Antimicrob Agents, 23, pp. 524-527
  • Wachsman, M.B., Ramírez, J.A., Talarico, L.B., Galagovsky, L.R., Coto, C.E., Antiviral activity of natural and synthetic brassinosteroids (2004) Curr Med Chem.- Anti-Infective Agents, 3, pp. 163-179
  • Castilla, V., Ramírez, J.A., Coto, C.E., Plant and animal steroids a new hope to search for antiviral agents (2010) Curr Med Chem, 17, pp. 1858-1873
  • Cutts, F.T., Henao-restrepo, A.M., Olive, J.M., Measles elimination: progress and challenges (1999) Vaccine, 17, pp. S47-S52
  • Weissenbacher, M.C., Laguens, R.P., Coto, C.E., Argentine hemorrhagic fever (1987) Curr Top Microbiol Immunol, 134, pp. 79-116
  • Collett, M.S., Neyts, J., Modlin, J.F., A case for developing antiviral drugs against polio (2008) Antivir Res, 79, pp. 179-187
  • Rodriguez, L.L., Emergence and re-emergence of vesicular stomatitis in the United States (2002) Virus Res, 85, pp. 211-219
  • Whitley, R.J., Roizman, B., Herpes simplex virus infections (2001) The Lancet, 357, pp. 1513-1518
  • Denizot, F., Lang, R., Rapid colorimetric assay for cell growth and survival (1986) J Immunol Methods, 89, pp. 271-277
  • Romanutti, C., Castilla, V., Coto, C.E., Wachsman, M.B., Antiviral effect of a synthetic brassinosteroid on the replication of vesicular stomatitis virus in Vero cells (2007) Int J Antimicrob Agents, 29, pp. 311-316
  • Talarico, L.B., Castilla, V., Ramirez, J.A., Galagovsky, L.R., Wachsman, M.B., Synergistic in vitro interactions between (22S,23S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one and acyclovir or foscarnet against herpes simplex virus type 1 (2006) Chemotherapy, 52, pp. 38-42
  • Castilla, V., Larzábal, M., Sgalippa, N.A., Wachsman, M.B., Coto, C.E., Antiviral mode of action of a synthetic brassinosteroid against Junin virus replication (2005) Antiviral Res, 68, pp. 88-95
  • Khripach, V., Zhabinskii, V., De Groot, A., Twenty years of brassinosteroids: Steroidal plant hormones warrant better crops for the XXI century (2000) Ann Bot, 86, pp. 441-447
  • Michelini, F.M., Ramírez, J.A., Berra, A., Galagovsky, L.R., Alché, L.E., In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues (2004) Steroids, 69, pp. 713-720
  • Michelini, F.M., Berra, A., Alché, L.E., The in vitro immunomodulatory activity of a synthetic brassinosteroid analogue would account for the improvement of herpetic stromal keratitis in mice (2008) J Steroid Biochem Mol Biol, 108, pp. 164-170
  • Michelini, F.M., Ramírez, J.A., Berra, A., Galagovsky, L.R., Alché, L.E., Anti-herpetic and anti-inflammatory activities of two new synthetic 22,23-dihydroxylated stigmastane derivatives (2008) J. Steroid Biochem Mol Biol, 111, pp. 111-116
  • Ramírez, J.A., Bruttomesso, A.C., Michelini, F.M., Acebedo, S.L., Alché, L.E., Galagovsky, L.R., Syntheses of immunomodulating androstanes and stigmastanes: comparison of their TNF-alpha inhibitory activity (2007) Bioorg Med Chem, 15, pp. 7538-7544
  • Mauch, D.H., Nagler, K., Schumacher, S., CNS synaptogenesis promoted by glia-derived cholesterol (2001) Science, 294, pp. 1354-1357
  • Schaller, H., The role of sterols in plant growth and development (2003) Prog Lipid Res, 42, pp. 163-175
  • Karlova, R., De Vries, S.C., Advances in understanding brassinosteroid signaling (2006) Sci STKE, 354, pp. pe36
  • Ashida, K., Goto, K., Zhao, Y., Dehydroepiandrosterone negatively regulates the p38 mitogen-activated protein kinase pathway by a novel mitogen-activated protein kinase phosphatase (2005) Biochim Biophys Acta, 1728, pp. 84-94
  • Ziegler, C.G., Sicard, F., Sperber, S., Ehrhart-bornstein, M., Bornstein, S.R., Krug, A.W., DHEA reduces NGF-mediated cell survival in serum-deprived PC12 cells (2006) Ann N Y Acad Sci, 1073, pp. 306-311
  • Schümann, M., Dobbelstein, M., Adenovirus induced extracellular signal-regulated kinase phosphorylation during the late phase of infection enhances viral protein levels and virus progeny (2006) Cancer Res, 66, pp. 1282-1288

Citas:

---------- APA ----------
Wachsman, M.B. & Castilla, V. (2012) . Antiviral Properties of Brassinosteroids. Brassinosteroids: Practical Applications in Agriculture and Human Health, 57-71.
http://dx.doi.org/10.2174/978160805298111201010057
---------- CHICAGO ----------
Wachsman, M.B., Castilla, V. "Antiviral Properties of Brassinosteroids" . Brassinosteroids: Practical Applications in Agriculture and Human Health (2012) : 57-71.
http://dx.doi.org/10.2174/978160805298111201010057
---------- MLA ----------
Wachsman, M.B., Castilla, V. "Antiviral Properties of Brassinosteroids" . Brassinosteroids: Practical Applications in Agriculture and Human Health, 2012, pp. 57-71.
http://dx.doi.org/10.2174/978160805298111201010057
---------- VANCOUVER ----------
Wachsman, M.B., Castilla, V. Antiviral Properties of Brassinosteroids. Brassinosteroids: Pract. Appl. in Agric. and Human Health. 2012:57-71.
http://dx.doi.org/10.2174/978160805298111201010057