Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures
Twenty-seven brassinosteroid derivatives were tested for antiviral activity against measles virus (MV) via a virus-yield reduction assay. Compounds 6b [(22S,23S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one], 1d [(22R,23R)-2α,3α,22,23-tetrahydroxy-β-Homo-7-oxa- stigmastan-6-one], 8a [(22R,23R)-3β-fl...
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| Formato: | Capítulo de libro |
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International Medical Press Ltd
2002
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 08166caa a22008537a 4500 | ||
|---|---|---|---|
| 001 | PAPER-20442 | ||
| 003 | AR-BaUEN | ||
| 005 | 20250903104851.0 | ||
| 008 | 190411s2002 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0036462250 | |
| 024 | 7 | |2 cas |a ribavirin, 36791-04-5 | |
| 030 | |a ACCHE | ||
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 100 | 1 | |a Wachsman, M.B. | |
| 245 | 1 | 0 | |a Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures |
| 260 | |b International Medical Press Ltd |c 2002 | ||
| 270 | 1 | 0 | |m Wachsman, M.B.; Laboratorio de Virología, Departamento de Quimica Biologica, Universidad de Buenos Aires, Buenos Aires, Argentina; email: wachsman@qb.fcen.uba.ar |
| 504 | |a Banks, G., Fernandez, H., Clinical use of ribavirin in measles, a summarized review (1980) Clinical Applications of Ribavirin, pp. 203-209. , Edited by AD Smith, E Knight & JAD Smith. New York: Academic Press | ||
| 504 | |a Barnard, D.L., Stowell, V.D., Seley, K.L., Hegde, V.R., Das, S.R., Rajappan, V.P., Schneller, S.W., Sidwell, R.W., Inhibition of measles virus replication by 5′-norcarbocyclic adenosine analogues (2001) Antiviral Chemistry & Chemotherapy, 12, pp. 241-250 | ||
| 504 | |a Cutts, F.T., Henao-Restrepo, A.M., Olive, J.M., Measles elimination: Progress and challenges (1999) Vaccine, 17, pp. S47-S52 | ||
| 504 | |a De Clerq, E., Cools, M., Balzarini, J., Snoeck, R., Andrei, G., Hosoya, M., Shigeta, S., Matsuda, A., Antiviral activities of 5,ethyl-1-β-D-ribofuranosylimidazole-4-carboxamide and related compounds (1991) Antimicrobial Agents and Chemotherapy, 35, pp. 679-684 | ||
| 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 Forni, A.L., Schluger, N.W., Roberts, R.B., Severe measles pneumonitis in adults: Evaluation of clinical characteristics and therapy with intravenous ribavirin (1994) Clinical Infectious Disease, 19, pp. 454-462 | ||
| 504 | |a Gururangen, S.R., Stevens, R.F., Morris, D.J., Ribavirin response in measles pneumonia (1990) Journal of Infectious Disease, 20, pp. 219-221 | ||
| 504 | |a McMorris, T.C., Patil, T.A., Chavez, R.G., Baker, M.E., Clouse, S.D., Synthesis and biological activity of 28-homobrassinolide and analogues (1994) Phytochemistry, 36, pp. 585-589 | ||
| 504 | |a Ramírez, J., Gros, E., Galagovsky, L., Synthesis and bioactivity evaluation of brassinosteroid analogues (2000) Steroids, 65, pp. 329-337 | ||
| 504 | |a Ramírez, J., Gros, E., Galagovsky, L., Synthesis of analogues of 28-homocastasterone, 28-homotyphasterol and 28-homoteasterone. Effects of heteroatom substituents at C-5 on bioactivity (2000) Tetrahedron, 56, pp. 6171-6180 | ||
| 504 | |a Ross, L.A., Kwang, S.K., Mason W.H., Jr., Gomperts, E., Successful treatment of disseminated measles in a patient with acquired immunodeficiency syndrome: Consideration of antiviral and passive immunotherapy (1984) American Journal of Medicine, 88, pp. 313-314 | ||
| 504 | |a Shigeta, S., Mori, S., Baba, M., Ito, M., Honzumi, K., Nakamura, K., Oshitani, H., De Clerq, E., Antiviral activities of ribavirin, 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide and 6′-(R)-6′-C-methylneplanocin A against several ortho and paramyxoviruses (1992) Antimicrobial Agents and Chemotherapy, 36, pp. 435-439 | ||
| 504 | |a Stogner, S.W., King, J.W., Black-Payne, C., Bocchini, J., Ribavirin and intravenous immune globulin therapy for measles pneumonia in HIV infection (1993) Southern Medical Journal, 141, pp. 1415-1418 | ||
| 504 | |a Teme Centurión, O.M., Galagovsky, L.R., Alternative synthesis of 24(S)-homoethylcastasterone from stigmasterol (1998) Anales de la Asociación Química Argentina, 86, pp. 104-109 | ||
| 504 | |a Wachsman, M.B., Lopez, E.M.F., Ramirez, J.A., Galagovsky, L.R., Coto, C.E., Antiviral effect of brassinosteroids against herpes virus and arenaviruses (2000) Antiviral Chemistry & Chemotherapy, 11, pp. 71-77 | ||
| 504 | |a Wyde, P.R., Moore-Poveda, D.K., De Clercq, E., Neyts, J., Matsuda, A., Minikawa, N., Guzmán, E., Gilbert, B.E., Use of cotton rats to evaluate the efficacy of antivirals in treatment of measles virus infections (2000) Antimicrobial Agents and Chemotherapy, 44, pp. 1146-1152 | ||
| 506 | |2 openaire |e Política editorial | ||
| 520 | 3 | |a Twenty-seven brassinosteroid derivatives were tested for antiviral activity against measles virus (MV) via a virus-yield reduction assay. Compounds 6b [(22S,23S)-3β-bromo-5α,22,23-trihydroxystigmastan-6-one], 1d [(22R,23R)-2α,3α,22,23-tetrahydroxy-β-Homo-7-oxa- stigmastan-6-one], 8a [(22R,23R)-3β-fluoro-22,23-dihydroxystigmastan-6-one], 9b [(22S,23S)-3β-fluoro-5α,22,23-trihydroxystigmastan-6-one] and 10b [(22S,23S)-5α-fluor-3β,22,23-trihydroxystigmastan-6-one], with selectivity indexes (SI) of 40, 57, 31, 37 and 53, are the derivatives with good antiviral activity against MV. These SI values are higher than those obtained with ribavirin (used as reference drug). A comparative analysis of 50% cytotoxic concentration (CC50) values, using confluent non-growing cells, gives and indication of structure-activity relationship. According to their degree of cytotoxicity the compounds were divided in three groups: low, intermediate and high cytotoxicity. By observing the chemical structures of compounds belonging to the first group we can see that less cytotoxic activities are related to the presence of a 3β-hydroxy group on C-3 (ring A) and a double bond between C-22 and C-23 (side chain). The replacement of a 5α-hydroxy group by a 5α-fluoro group enhances cytotoxicity. Halogenated brassinosteroid derivatives in C-3 position are more cytotoxic than those with an acetoxy group in the same position. For compounds 1d, 6b, 10b and ribavirin, cytotoxicity measurements were also done with replicating cells; CC50 values were low, but they still competed favourably with ribavirin against MV. |l eng | |
| 593 | |a Laboratorio de Virología, Departamento de Quimica Biologica, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 593 | |a Departamento de Quimica Organica, Universidad de Buenos Aires, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ANTIVIRAL/BRASSINOSTEROIDS DERIVATIVES |
| 690 | 1 | 0 | |a MEASLES VIRUS |
| 690 | 1 | 0 | |a PARAMYXOVIRIDAE |
| 690 | 1 | 0 | |a 2ALPHA,3ALPHA,22,23 TETRAHYDROXY BETA HOMO 7 OXASTIGMASTAN 6 ONE |
| 690 | 1 | 0 | |a 3BETA BROMO 5ALPHA,22,23 TRIHYDROXYSTIGMASTAN 6 ONE |
| 690 | 1 | 0 | |a 3BETA FLUORO 22,23 DIHYDROXYSTIGMASTAN 6 ONE |
| 690 | 1 | 0 | |a 3BETA FLUORO 5ALPHA,22,23 TRIHYDROXYSTIGMASTAN 6 ONE |
| 690 | 1 | 0 | |a 5ALPHA FLUORO 3BETA,22,23 TRIHYDROXYSTIGMASTAN 6 ONE |
| 690 | 1 | 0 | |a BRASSINOSTEROID |
| 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 CELL CULTURE |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CONCENTRATION RESPONSE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a CYTOTOXICITY |
| 690 | 1 | 0 | |a DRUG BINDING |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a MEASLES |
| 690 | 1 | 0 | |a MEASLES VIRUS |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PRIORITY JOURNAL |
| 690 | 1 | 0 | |a STRUCTURE ACTIVITY RELATION |
| 700 | 1 | |a Ramírez, Javier Alberto | |
| 700 | 1 | |a Galagovsky, L.R. | |
| 700 | 1 | |a Coto, C.E. | |
| 773 | 0 | |d International Medical Press Ltd, 2002 |g v. 13 |h pp. 61-66 |k n. 1 |p Antiviral Chem. Chemother. |x 09563202 |t Antiviral Chemistry and Chemotherapy | |
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| 856 | 4 | 0 | |u https://doi.org/10.1177/095632020201300105 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_09563202_v13_n1_p61_Wachsman |y Handle |
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