In vitro antiviral activity of dehydroepiandrosterone and its synthetic derivatives against vesicular stomatitis virus
In this work the antiviral activity of 20 dehydroepiandrosterone (DHEA) analogs with different substituents at positions C-3, C-15, C-16 and C-17 were evaluated against vesicular stomatitis virus (VSV) in Vero cell cultures. The selectivity indexes (SI) obtained with DHEA and epiandrosterone (EA) we...
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2009
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| LEADER | 12560caa a22014897a 4500 | ||
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| 003 | AR-BaUEN | ||
| 005 | 20230518203812.0 | ||
| 008 | 190411s2009 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-69949111854 | |
| 024 | 7 | |2 cas |a epiandrosterone, 481-29-8; prasterone, 53-43-0; ribavirin, 36791-04-5; Antiviral Agents; Dehydroepiandrosterone, 53-43-0; RNA, Viral | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a VTJRF | ||
| 100 | 1 | |a Romanutti, C. | |
| 245 | 1 | 3 | |a In vitro antiviral activity of dehydroepiandrosterone and its synthetic derivatives against vesicular stomatitis virus |
| 260 | |c 2009 | ||
| 270 | 1 | 0 | |m Wachsman, M.B.; Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon 2, Piso 4, C1428EGA Buenos Aires, Argentina; email: wachsman@qb.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Barr, J.N., Whelan, S.P.J., Wertz, G.W., Transcriptional control of the RNA-dependent RNA polymerase of vesicular stomatitis virus (2002) Biochimica et Biophysica Acta, 1577, pp. 337-353 | ||
| 504 | |a Bradley, W., Kraus, L., Good, R., Day, N., Dehydroepiandrosterone inhibits replication of feline immunodeficiency virus in chronically infected cells (1995) Veterinary Immunology and Immunopathology, 46, pp. 159-168 | ||
| 504 | |a Bruttomesso, A.C., Gros, E.G., Ponce, M.A., Balsells, R.E., Photooxygenation of pregnanes (2004) Helvetic Chimica Acta, 87, pp. 2987-3003 | ||
| 504 | |a Cantlon, J.D., Gordy, P.W., Bowen, R.A., Immune responses in mice, cattle and horses to a DNA vaccine for vesicular stomatitis (2000) Vaccine, 18, pp. 2368-2374 | ||
| 504 | |a Chang, C.C., Ou, Y.C., Rang, S.L., Chen, C.J., Antiviral effect of dehydroepiandrosterone on Japanese Encephalitis virus infection (2005) Journal of General Virology, 86, pp. 2513-2523 | ||
| 504 | |a Defaye, G., Chambaz, E.M., Synthesis of 15β-hydroxylated derivatives of dehydroisoandrosterone and isoandrosterone (1978) Tetrahedron Letters, 19, pp. 3849-3850 | ||
| 504 | |a Denizot, F., Lang, R., Rapid colorimetric assay for cell growth and survival (1986) Journal of Immunological Methods, 89, pp. 271-277 | ||
| 504 | |a 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) Nucleosides Nucleotides Nucleic Acids, 19, pp. 2019-2024 | ||
| 504 | |a Flanagan, E.B., Zamparo, J.M., Ball, L.A., Rodriguez, L.L., Wertz, G.W., Rearrangement of the genes of vesicular stomatitis virus eliminates clinical disease in the natural host: new strategy for vaccine development (2001) Journal of Virology, 75, pp. 6107-6114 | ||
| 504 | |a Graci, J.D., Cameron, C.E., Mechanisms of action of ribavirin against distinct viruses (2006) Reviews in Medical Virology, 16, pp. 37-48 | ||
| 504 | |a Henderson, E., Yang, J., Schwartz, A., Dehydroepiandrosterone (DHEA) and synthetic DHEA analogs are modest inhibitors of HIV-1 IIIB replication (1992) AIDS Research and Human Retroviruses, 8, pp. 625-631 | ||
| 504 | |a Iwasaki, M., The Reformatsky reaction of 17-ketosteroids with ethyl α-bromopropionate (1967) Steroids, 9, pp. 373-386 | ||
| 504 | |a Johnson, W.S., Gastambide, B., Pappo, R., The action of lead tetra-acetate on an enol acetate. Their interconversion and rearrangement (1957) Journal of the American Chemical Society, 79, pp. 1991-1994 | ||
| 504 | |a Leeds, N.S., Fukushima, D.K., Gallagher, T.F., Studies of steroid ring D epoxides of enol acetates; a new synthesis of estriol and of androstane-3β,16α,17β-triol (1954) Journal of the American Chemical Society, 76, pp. 2943-2948 | ||
| 504 | |a Letchworth, G.J., Rodriguez, L.L., Barrera, J.D.C., Vesicular stomatitis (1999) The Veterinary Journal, 157, pp. 239-260 | ||
| 504 | |a Loria, R.M., Inge, T.H., Cook, S.S., Szakal, A.K., Regelson, W., Protection against acute lethal viral infections with the native steroid dehydroepiandrosterone (DHEA) (1988) Journal of Medical Virology, 26, pp. 301-314 | ||
| 504 | |a Loria, R.M., Padgett, D.A., Androstenediol regulates systemic resistance against lethal infections in mice (1992) Archives of Virology, 127, pp. 103-115 | ||
| 504 | |a 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) Virology Journal, 11, pp. 9-10 | ||
| 504 | |a McElroy, M.C., Basset, H.F., The development of oral lesions in lambs naturally infected with orf virus (2007) The Veterinary Journal, 174, pp. 673-674 | ||
| 504 | |a Numazawa, M., Osawa, Y., Improved synthesis of 16 alpha-hydroxylated androgens: intermediates of estriol formation in pregnancy (1978) Steroids, 32, pp. 519-527 | ||
| 504 | |a Numazawa, M., Nagaoka, M., Stereospecific synthesis of 16α-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism (1982) Journal of Organic Chemistry, 47, pp. 4024-4029 | ||
| 504 | |a Padgett, D.A., Loria, R.M., Sheridan, J.F., Steroid hormone regulation of antiviral immunity (1997) Journal of Neuroimmunology, 78, pp. 203-311 | ||
| 504 | |a Pedersen, N.C., North, T.W., Rigg, R., Reading, C., Higgins, J., Leutenegger, C., Henderson, G.L., 16alpha-Bromo-epiandrosterone therapy modulates experimental feline immunodeficiency virus viremia: initial enhancement leading to long-term suppression (2003) Veterinary Immunology and Immunopathology, 94, pp. 133-148 | ||
| 504 | |a Rodriguez, L.L., Emergence and re-emergence of vesicular stomatitis in the United States (2002) Virus Research, 85, pp. 211-219 | ||
| 504 | |a 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) International Journal of Antimicrobial Agents, 29, pp. 311-316 | ||
| 504 | |a Rose, J.K., Whitt, M.A., Rhabdoviridae: the viruses and their replication (2001) Fundamental Virology 4, pp. 665-688. , Knipe D.M., and Howley P.M. (Eds), Lippincott Williams & Wilkins, Philadelphia, USA | ||
| 504 | |a Sondheimer, F., Burstein, S., Mechoulam, R., Syntheses in the cardiac aglycone field III. The conversion of a 14α- to a 14β- hydroxy group in the androstane series. The ultraviolet spectra of ρ15-androstene-17-ones (1960) Journal of the American Chemical Society, 82, pp. 3209-3212 | ||
| 504 | |a Wachsman, M.B., López, E.M.F., Ramírez, J.A., Galagovsky, L.R., Coto, C.E., Antiviral effect of brassinosteroids against herpes virus and arenaviruses (2000) Antiviral Chemistry and Chemotherapy, 11, pp. 71-77 | ||
| 504 | |a Wachsman, M.B., Ramírez, J.A., Talarico, L.B., Galagovsky, L.R., Coto, C.E., Antiviral activity of natural and synthetic brassinosteroids (2004) Current Medicinal Chemistry - Anti-Infective Agents, 3, pp. 163-179 | ||
| 504 | |a Yoneda, M., Wada, K., Katayama, K., Nakajima, N., Blumberg, R., Nakajima, A., A novel therapy for acute hepatitis utilizing dehydroepiandrosterone in the murine model of hepatitis (2004) Biochemistry and Pharmacology, 68, pp. 2283-2289 | ||
| 520 | 3 | |a In this work the antiviral activity of 20 dehydroepiandrosterone (DHEA) analogs with different substituents at positions C-3, C-15, C-16 and C-17 were evaluated against vesicular stomatitis virus (VSV) in Vero cell cultures. The selectivity indexes (SI) obtained with DHEA and epiandrosterone (EA) were 50 and 72.6, respectively. The work showed that the compounds 21-norpregna-5,17(20)-dien-3β,16α-diyl-diacetate, 17,17-ethylendioxyandrostan-5,15-dien-3β-ol and 3β-hydroxypregn-17(20)-en-16-one had higher SI values than ribavirin, which was used as a reference drug. The antiviral mode of action of DHEA was also investigated against VSV replication in Vero cells, and time of addition experiments showed that DHEA mainly affected a late event in the virus growth cycle. Analysis of RNA and protein synthesis indicated that DHEA adversely affected positive strand RNA synthesis and viral mature particle formation. © 2008 Elsevier Ltd. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Umweltbundesamt, EX-190/04 | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, PICT 12307/02 | ||
| 536 | |a Detalles de la financiación: This work was supported by grants from the Universidad de Buenos Aires, UBA, EX-190/04, X 046 and Agencia Nacional de Promoción Científica y Técnica (ANPCYT) PICT 12307/02. | ||
| 593 | |a Laboratorio de Virología, Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon 2, Piso 4, C1428EGA Buenos Aires, Argentina | ||
| 593 | |a Departamento de Química Orgánica, UMYMFOR, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellon 2, Piso 4, C1428EGA Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ANTIVIRAL |
| 690 | 1 | 0 | |a DEHYDROEPIANDROSTERONE ANALOGS |
| 690 | 1 | 0 | |a DHEA |
| 690 | 1 | 0 | |a EA |
| 690 | 1 | 0 | |a VESICULAR STOMATITIS VIRUS |
| 690 | 1 | 0 | |a 1 BETA DEXTRO RIBOFURANOSIL 1 2 4 TRIAZOLE 3 CARBOXAMIDE |
| 690 | 1 | 0 | |a 16ALPHA HYDROXYPRASTERONE |
| 690 | 1 | 0 | |a 17 OXO 5ALPHA ANDROSTAN 3BETA,16ALPHA YLDIACETATE |
| 690 | 1 | 0 | |a 17 OXO 5ALPHA ANDROSTAN 3BETA,16BETA YLDIACETATE |
| 690 | 1 | 0 | |a 17 OXOANDROST 5 EN 3BETA YL ACETATE |
| 690 | 1 | 0 | |a 17 OXOANDROST 5 EN 3BETA YLACETAE |
| 690 | 1 | 0 | |a 17 OXOANDROST 5 EN 3BETA,16ALPHA DIYLDIACETATE |
| 690 | 1 | 0 | |a 17 OXOANDROST 5 EN 3BETA,16BETA YLDIACETATE |
| 690 | 1 | 0 | |a 17,17 ETHYLENDIOXY 3BETA ANDROSTANYL ACETATE |
| 690 | 1 | 0 | |a 17,17 ETHYLENDIOXYANDROST 5 EN 3BETA OL |
| 690 | 1 | 0 | |a 17,17 ETHYLENDIOXYANDROST 5,15 DIEN 3BETA OL |
| 690 | 1 | 0 | |a 17,17 ETHYLENDIOXYANDROSTAN 16ALPHA BROMO 3BETA OL |
| 690 | 1 | 0 | |a 17,17 ETHYLENDIOXYANDROSTAN 3BETA OL |
| 690 | 1 | 0 | |a 17,17 ETHYLENDIOXYANDROSTAN 5,15 DIEN 3BETA OL |
| 690 | 1 | 0 | |a 21 NORPREGNA 5,17(20) DIEN 3BETA,16ALPHA DIYLDIACETATE |
| 690 | 1 | 0 | |a 3BETA 6ALPHA DIHYDROXY 17 ANDROSTANONE |
| 690 | 1 | 0 | |a 3BETA HYDROXYPREGN 17(20) EN 16 ONE |
| 690 | 1 | 0 | |a 3BETA,15ALPHA DIHYDROXY 5ALPHA ANDROSTAN 17 ONE |
| 690 | 1 | 0 | |a 3BETA,15BETA DIHYDROXY 5ALPHA ANDROSTAN 17 ONE |
| 690 | 1 | 0 | |a 3BETA,16ALPHA DIHYDROXY 5ALPHA ANDROSTAN 17 ONE |
| 690 | 1 | 0 | |a ANDROSTA 5,16 DIEN 3BETA,17 DIYLDIACETATE |
| 690 | 1 | 0 | |a ANTIVIRUS AGENT |
| 690 | 1 | 0 | |a EPIANDROSTERONE |
| 690 | 1 | 0 | |a PRASTERONE |
| 690 | 1 | 0 | |a PRASTERONE DERIVATIVE |
| 690 | 1 | 0 | |a RIBAVIRIN |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ANIMAL CELL |
| 690 | 1 | 0 | |a ANTIVIRAL ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a DRUG MECHANISM |
| 690 | 1 | 0 | |a GROWTH INHIBITION |
| 690 | 1 | 0 | |a IN VITRO STUDY |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PROTEIN SYNTHESIS |
| 690 | 1 | 0 | |a RNA SYNTHESIS |
| 690 | 1 | 0 | |a VERO CELL |
| 690 | 1 | 0 | |a VESICULAR STOMATITIS VIRUS |
| 690 | 1 | 0 | |a VIROGENESIS |
| 690 | 1 | 0 | |a VIRUS PARTICLE |
| 690 | 1 | 0 | |a VIRUS REPLICATION |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a ANTIVIRAL AGENTS |
| 690 | 1 | 0 | |a CERCOPITHECUS AETHIOPS |
| 690 | 1 | 0 | |a DEHYDROEPIANDROSTERONE |
| 690 | 1 | 0 | |a FLUORESCENT ANTIBODY TECHNIQUE, INDIRECT |
| 690 | 1 | 0 | |a REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION |
| 690 | 1 | 0 | |a RNA, VIRAL |
| 690 | 1 | 0 | |a VERO CELLS |
| 690 | 1 | 0 | |a VESICULAR STOMATITIS |
| 690 | 1 | 0 | |a VESICULOVIRUS |
| 690 | 1 | 0 | |a VIRUS REPLICATION |
| 690 | 1 | 0 | |a VESICULAR STOMATITIS VIRUS |
| 700 | 1 | |a Bruttomesso, A.C. | |
| 700 | 1 | |a Castilla, V. | |
| 700 | 1 | |a Bisceglia, J.A. | |
| 700 | 1 | |a Galagovsky, L.R. | |
| 700 | 1 | |a Wachsman, M.B. | |
| 773 | 0 | |d 2009 |g v. 182 |h pp. 327-335 |k n. 2 |p Vet. J. |x 10900233 |t Veterinary Journal | |
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