Abstract:
Thirty-seven brassinosteroid derivatives were tested for their antiviral activity against herpes simplex vires (HSV) type 1 and twenty-seven against HSV type 2, via a vires yield reduction assay. Most of the assayed compounds show selectivity indexes (SI) higher than those obtained with the reference drug, stigmasterol. The compounds that possessed a better structure-activity relationship are 6b [(22S,23S)-3β-bromo-5α ,22,23-trihydroxystigmastan-6-one], 7b [(22S,23S)-3β,5α ,22,23-tetrahydroxystigmastan-6-one] and 12b [(22S,23S)-5α-fluor-3β ,22,23-trihydroxy-stigmastan-6-one] with SI values of 100, 80 and 109 for HSV-1 and 71, 40 and 27 for HSV-2, respectively.
Registro:
Documento: |
Artículo
|
Título: | Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures |
Autor: | Talarico, L.B.; Ramírez, J.A.; Galagovsky, L.R.; Wachsman, M.B. |
Filiación: | Depto. de Quím. Orgán., Fac. de Ciencias Exactas y Naturales, Pabellón 2, 1428, Buenos Aires, Argentina
|
Palabras clave: | 2alpa,3alpha dihydroxy 6alpha fluoro 5alpha stigmast 22 ene; 2alpha,3alpha dihydroxystigmast 22 en 6 one; 2alpha,3alpha,22,23 tetrahydroxy 5alpha fluorostigmastan 6 one; 2alpha,3alpha,22,23 tetrahydroxy 5alpha stigmastan 6 one; 2alpha,3alpha,22,23 tetrahydroxy beta homo 7 oxastigmastan 6 one; 2alpha,3alpha,5alpha,22,23 pentahydroxystigmastan 6 one; 3 beta hydroxystigmasta 5,22 diene; 3alpha fluoro 22,23 dihydroxystigmastan 6 one; 3alpha,22,23 trihydroxy 5alpha stigmastan 6 one; 3alpha,5alpha,22,23 tetrahydroxystigmastan 6 one; 3beta acetoxy 22,23 dihydroxy 5alpha stigmastan 6 one; 3beta acetoxy 5alpha,22,23 trihydroxystigmastan 6 one; 3beta bromo 22,23 dihydroxy 5alpha stigmastan 6 one; 3beta bromo 5alpha chloro 6beta hydroxystigmast 22 ene; 3beta bromo 5alpha hydroxystigmast 22 en 6 one; 3beta bromo 5alpha,22,23 trihydroxystigmastan 6 one; 3beta fluoro 22,23 dihydroxystigmastan 6 one; 3beta fluoro 5alpha 22,23 dihydroxystigmastan 6 one; 3beta fluoro 5alpha chlorostigmast 22 en 6 one; 3beta,22,23 trihydroxy 5alpha stigmastan 6 one; 3beta,5alpha dihydroxystigmast 22 en 6 one; 3beta,5alpha,22,23 tetrahydroxystigmastan 6 one; 5alpha fluoro 3beta 22,23 trihydroxystigmastan 6 one; 5alpha fluorostigmasta 2,22 dien 6 one; 6beta hydroxy 5alpha stigmast 22 en 3 one; 9 (2 hydroxyethoxymetyl)guanine; brassinosteroid; stigmasta 4,22 dien 3 one; stigmasterol; unclassified drug; unindexed drug; animal cell; antiviral activity; article; cell culture; controlled study; drug selectivity; Herpes simplex virus 1; Herpes simplex virus 2; nonhuman; structure activity relation |
Año: | 2002
|
Volumen: | 11
|
Número: | 8
|
Página de inicio: | 434
|
Página de fin: | 444
|
Título revista: | Medicinal Chemistry Research
|
Título revista abreviado: | Med. Chem. Res.
|
ISSN: | 10542523
|
CODEN: | MCREE
|
CAS: | stigmasterol, 83-48-7
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico |
Referencias:
- Nakao, M., Hazama, M., Mayumi-Aono, A., Hinuma, S., Fujisawa, Y., Immunotherapy of acute and recurrent herpes simplex type 2 infection with an adjuvant-free form of recombinant glycoprotein D-interleukin-2 fusion protein (1984) J. Infect. Dis., 169, pp. 787-791
- Cassady, K.A., Whitley, R.J., New therapeutic approaches to the alphaherpesvirus infections (1997) J. Antimicrob. Chemother., 39, pp. 119-128
- Elion, G.B., Mechanism of action and selectivity of acyclovir (1982) Am. J. Med., 73 (SUPPL. 1A), pp. 7-13
- Helgstrand, E., Eriksson, B., Johansson, N.G., Lanneró, B., Larsson, A., Missiomi, A., Trisodium phosphonoformate, a new antiviral compound (1978) Science, 201, pp. 819-821
- Fisher, P.H., Chen, M.S., Prusoff, W.H., The incorporation of 5-iodo-5′-amino-2′,5-dideoxyuridine and 5-iodo-2′-deoxyuridine into herpes simplex virus DNA. Relationship between antiviral activity and effects on DNA structure (1980) Biochim. Biophys. Acta, 606, pp. 235-245
- Heidelberger, C., King, D., Trifluorothymidine (1979) Farmacol. Ther., 8, pp. 427-442
- Coen, D.M., Schaffer, P.A., Two distinct loci confer resistance to acycloguanosine in herpes simplex virus type 1 (1980) Proc. Natl. Acad. Sci. USA, 77, pp. 2265-2269
- Oliver, N.M., Collins, P., Van Der Meer, J., Vant Wout, J.W., Biological and biochemical characterization of clinical isolates of herpes simplex virus type 2 resistant to acyclovir (1989) Antimicrob. Agents Chemother., 33, pp. 635-640
- Sidwell, R.W., Ribavirin. In vitro antiviral activity (1980) Ribavirin, a Broad Spectrum Antiviral Agent, pp. 23-42. , Edited by R.A. Smith and W. Kirpatrick. Academic Press, New York
- 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 Chem. Chemother., 11, pp. 71-77
- Wachsman, M.B., Ramírez, J.A., Galagovsky, L.R., Coto, C.E., Antiviral activity of brassinosteroids derivatives against measles virus in cell cultures (2002) Antiviral Chem. Chemother., 13, pp. 61-66
- Clouse, S.D., Zurek, D., Molecular analysis of brassinolide action in plant growth and development (1991) Brassinosteroids: Chemistry, Bioactivity and Applications, pp. 122-140. , Edited by H.G. Cutler, T. Yokota and G. Adam, ACS Symposium Series 474. American Chemical Society, Washington DC
- Kamuro, Y., Takatsuto, S., Practical application of brassinosteroids in agricultural fields (1999) Brassinosteroids Steroidal Plant Hormones, pp. 223-241. , Edited by A. Sakurai, T. Yokota and S.D. Clouse. Springer-Verlag, Tokyo
- Ramírez, J., Gros, E., Galagovsky, L., Synthesis and bioactivity evaluation of brassinosteroid analogues (2000) Steroids, 65, pp. 329-337
- 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
- Teme Centurión, O.M., Galagovsky, L.R., Alternative synthesis of 24(S)-homoethylcastasterone from stigmasterol (1998) Anales Asoc. Quím. Argent., 86, pp. 104-109
- Fujioka, S., Sakurai, A., Brassinosteroids (1997) Nat. Prod. Rep., 14, pp. 1-10
- 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) Phytochem., 36, pp. 585-589
- Beadle, J.R., Kini, G.D., Aldern, K.A., Gardner, M.F., Wright, K.N., Richman, D.D., Hostetler, K.Y., Alkylthioglycerol prodrugs of foscarnet: Synthesis, oral bioavailability and structure-activity studies in human cytomegalovirus, herpes simplex virus type 1-infected cells (1998) Antiviral Chem. Chemother., 9, pp. 33-40
- Denizot, F., Lang, R., Rapid colorimetric assay for cell growth and survival (1986) J. Inmunol. Methods, 89, pp. 271-277
Citas:
---------- APA ----------
Talarico, L.B., Ramírez, J.A., Galagovsky, L.R. & Wachsman, M.B.
(2002)
. Structure-activity relationship studies in a set of new brassinosteroid derivatives assayed against herpes simplex virus type 1 and 2 in cell cultures. Medicinal Chemistry Research, 11(8), 434-444.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]
---------- CHICAGO ----------
Talarico, L.B., Ramírez, 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"
. Medicinal Chemistry Research 11, no. 8
(2002) : 434-444.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]
---------- MLA ----------
Talarico, L.B., Ramírez, 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"
. Medicinal Chemistry Research, vol. 11, no. 8, 2002, pp. 434-444.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]
---------- VANCOUVER ----------
Talarico, L.B., Ramírez, 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. Med. Chem. Res. 2002;11(8):434-444.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10542523_v11_n8_p434_Talarico [ ]