Artículos de revistas
Free 2-propen-1-amine Derivative And Inclusion Complexes With β-cyclodextrin: Scanning Electron Microscopy, Dissolution, Cytotoxicity And Antimycobacterial Activity
Registro en:
Journal Of The Brazilian Chemical Society. , v. 15, n. 5, p. 682 - 689, 2004.
1035053
2-s2.0-9644258589
Autor
De Souza A.O.
Santos Jr. R.R.
Sato D.N.
De Azevedo M.M.M.
Ferreira D.A.
Melo P.S.
Haun M.
Silva C.L.
Duran N.
Institución
Resumen
Inclusion complexes and physical mixtures of isomeric mixture of E/Z (50:50) of 3-(4′-bromo-[1,1′-biphenyl]-4-yl)-3-(4-bromophenyl)-N,N- dimethyl-2-propen-1-amine (BBAP) and β-cyclodextrin (β-CD) in the molar proportion of 1:1 and 1:2 were analyzed by scanning electron microscopy. The dissolution behavior of BBAP and of the inclusion complexes were also evaluated for six hours. By scanning electron microscopy (SEM), it was possible to observe an inclusion complex formed between BBAP and β-CD by co-evaporation, either in the molar proportion of 1:1 or 1:2. In the physical mixtures, no complex was observed as previously detected by physicochemical analysis. The dissolution studies showed that the inclusion complexes BBAP/β-CD 1:1 and 1:2 released respectively 49.07 ± 1.48 and 40.26 ± 3.90% of BBAP during six hours. Free BBAP was less soluble than the inclusion complex and reached 9.00 ± 0.75% of dissolution. Biological assays, such as cytotoxicity to J774 macrophages and to a permanent lung fibroblast cell line (V79), indicated that the BBAP does not exhibit any additional toxic effect with the β-CD complexes. However, the complexes were less cytotoxic to V79 cells than the free form. The BBAP/β-CD inclusion complexes were more effective (MIC) than the free compound on several mycobacteria strains. Similar behavior was observed for BBAP/β-CD complexes and rifampicin, a front-line antitubercular drug, on M. tuberculosis H37Rv growing inside J774 macrophages. 15 5 682 689 Bibby, D.C., Davies, N.M., Tucker, I.G., (2000) Int. J. Pharm., 197, p. 1 De Souza, A.O., Sato, D.N., Aily, D.C.G., Durán, N., (1998) J. Antimicrob. Chemother., 42, p. 407 Pereira, D.G., De Castro, S.L., Durán, N., (1998) Acta Tropica, 69, p. 205 De Souza, A.O., Santos Júnior, R.R., Ferreira-Júlio, J.F., Rodrigues, J.A., Melo, P.S., Haun, M., Sato, D.N., Durán, N., (2001) Eur. J. Med. Chem., 36, p. 843 De Souza, A.O., Hemerly, F.P., Busollo, A.C., Melo, P.S., Machado, G.M.C., Miranda, C.C., Santa-Rita, R.M., Durán, N., (2002) J. Antimicrob. Chemother., 50, p. 629 De Conti, R., Gimenez, S.M.N., Haun, M., Pilli, R.A., De Castro, S.L., Durán, N., (1996) Eur. J. Med. Chem., 31, p. 915 De Souza, A.O., Santos Jr., R.R., Sato, D.N., Lima, H.O.S., Andrade-Santana, M.H., Alderete, J.B., Faljoni-Alario, A., Durán, N., (2000) Abstracts of the 29 a Reunião Anual Da Sociedade Brasileira de Bioquímica, , Caxambu, Brazil Higuchi, T., Connors, K.A., (1965) Adv. Anal. Chem. Instrum., 4, p. 117 Collins, L.A., Franzblau, S.G., (1997) Antimicrob. Agents Chemother., 41, p. 1004 Oh, Y.K., Nix, D.E., Straubinger, R.M., (1995) Antimicrob Agents Chemother., 39, p. 2104 Cingi, M.R., De Angelis, I., Fortunati, E., Reggiani, D., Bianchi, V., Tiozzo, R., Zucco, F., (1991) Toxicol. In Vitro, 5, p. 119 Denizot, F., Lang, R., (1986) J. Immun. Methods, 89, p. 271 Borenfreund, E., Puerner, J.A., (1984) J. Tiss. Cult. Meth., 9, p. 7 Melo, P.S., Maria, S.S., Vidal, B.C., Haun, M., Durán, N., (2000) In Vitro Cell Rev. Biol. Animal, 36, p. 539 Melo, P.S., Durán, N., Haun, M., (2001) Toxicology, 159, p. 135 Shrivastava, R., John, G.W., Rispat, G., Chevalier, A., Massingham, R., (1991) ATLA - Alt. Lab. Anim., 19, p. 393