Physico-chemical Characterization Of The Inclusion Complex Between A 2-propen-1-amine Derivative And β-cyclodextrin

Inclusion complexes and physical mixtures were prepared with 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 different proportions. In this study, theoretical calculations using Molecular Mechanics MM+ force field were applied to predict the structures of the inclusion complexes formed by interaction of BBAP and b-cyclodextrin. Circular dichroism, differential thermal analysis (DTA), X-ray diffraction and 13C CP/MAS NMR methods were used to characterize the inclusion complexes and provide information about the stoichiometry of the inclusion complexes. The combined spectroscopy techniques indicate the formation of a complex of BBAP/β-CD in the molar proportion of 1:1 and 1:2 by co-evaporation and no complexation was detected in the physical mixture of the compounds. © 2006 Sociedad Chilena de Química β-.503115127Bibby, D.C., Davies, N.M., Tucker, I.G., (2000) Int. J. Pharm., 197, p. 1Connors, K.A., (1995) J. Pharm. Sci., 84, p. 843Connors, K.A., Paulson, A., Toledo-Velasquez, D.J., (1988) J. Org. Chem., 53, p. 2123Dollo, G., Le Corre, P., Chollet, M., Chevanne, F., Bertault, M., Burgot, J.-L., Le Verge, R., (1999) J. Pharm. Sci., 88, p. 889Mucci, A., Schenetti, L., Vandelli, M.A., Ruozi, B., Forni, F., (1999) J. Chem. Research, (S), p. 414Keipert, S., Fedder, J., Bohm, A., Hanke, B., (1996) Int. J. Pharm., 142, p. 153Nigam, S., Durocher, G., (1999) J. Photochem. Photobiol. A: Chem., 103, p. 143De Souza, A.O., Sato, D.N., Aily, D.C.G., Duran, N., (1998) J. Antimicrob. Chemother., 42, p. 407Pereira, D.G., De Castro, S.L., Durán, N., (1998) Acta Tropica, 69, p. 205De 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. 843De 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. 629De Conti, R., Gimenez, S.M.N., Haun, M., Pilli, R.A., De Castro, S.L., Durán, N., (1996) N. Eur. J. Med. Chem., 31, p. 915De Azevedo, M.B.M., Alderete, J.B., Lino, A.C.S., Loh, W., Faljoni-Alario, A., Durán, N., (2000) J. Incl. Phenom. Macrocyclic. Chem., 37, p. 67Zhou, D., Wu, Y., Xu, Q., Yang, L., Bai, C., (2000) Z. Tan. J. Incl. Phenom. Macrocyclic. Chem., 37, p. 273Ammar, H.O., Ghorab, M., El-Nahhas, S.A., Emara, I.H., Makram, T.S., (1999) Pharmazie, 54, p. 142Muñoz De La Pena, A., Ndou, T.T., Zung, J.B., Warner, I.M., (1991) J. Phys. Chem., 95, p. 3330Smith, V.K., Ndou, T.T., Warner, I.M., (1994) J. Phys. Chem., 98, p. 8627Blanco, M., Coello, J., Iturriaga, H., Maspoch, S., Pérez-Maseda, C., (2000) Anal. Chim. Acta, 407, p. 233Ohashi, M., Kasatani, K., Shinohara, H., Sato, H., (1990) J. Am. Chem. Soc., 112, p. 5824Harata, K., Uedaria, H., (1975) Bull. Chem. Soc. Jpn., 48, p. 375Schellman, J.A., (1968) Acc. Chem. Res., 1, p. 144Bettinetti, G.P., Gonzzaniga, A., Mura, P., Giordano, F., Setti, M., (1992) Drug Dev. Ind. Pharm., 18, p. 39Mura, P.P., Faucci, M.T., Parrini, P.L., Furlanetto, S., Pinzauti, S., (1999) Int. J. Pharm., 179, p. 117Cunha-Silva, L., Teixeira-Dias, J.J.C., (2002) J. Phys. Chem., 106, p. 3323Lai, S., Locci, E., Piras, A., Porcedda, S., Lai, A., Marangiu, B., (2003) Carbohydr. Res., 338, p. 222