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

Structure-activity Relationship Analysis Of 4'-bromo-[1,1'-biphenyl]-4- Yl 4-x-phenyl Methanone Derivatives And Activity Against Mycobacterium Tuberculosis

Principal Component Analysis (PCA) and Artificial Neural Network (ANN) were used to analyze the relationship between the structure and the activities of a series of nine biphenylphenyl methanone derivatives against Mycobacterium tuberculosis in vitro. Both PCA and ANN were able to classify these derivatives in two categories: low active and highly active compounds. Empirical and theoretical descriptors were used in the classification process. The descriptors selected by PCA indicated that the reactivity plays an important role in the determination of antimycobacterial activity of biphenylphenyl methanone derivatives (BPM). The BPM showed a moderate activity against the M. tuberculosis strain tested with the exception of chloride-, bromide- and nitroderivatives (when X = Cl, Br, NO2) which were the most actives against M. tuberculosis in vitro among all the methanones studied.491210251029(1998) The World Health Report, , World Health Organization, Geneva, SwitzerlandRastogi, N., Labrousse, V., Seng Goh, K., (1996) Curr. Microbiol., 33, p. 167De Conti, R., Gimenez, S.M.N., Haun, M., (1996) Eur. J. Med. Chem., 31, p. 1Collins, L.A., Franzblau, S.G., (1997) Antimicrob. Agents Chemother., 41, p. 1004Wold, S., Esbensen, K., Geladi, P., (1987) Chem. Intelligent Lab. Sys., 2, p. 37De Souza, A.D., Alderete, J.B., Sato, D.N., (1998) Proc. 14th Int. Conference Phys. Org. Chem., 14, p. 184. , Florianopolis, S.C., BrazilCosta, M.C.A., Gaudio, A.C., Takahata, Y., (1997) J. Mol Struct. (Theochem), 394, p. 291Hansch, C., Leo, A., Hoeckman, D., (1995) ACS Professional Reference Book, pp. 217-304. , Exploring QSAR, Washington, DCKarelson, K., Lobanov, V.S., Katritzky, A.R., (1996) Chem. Ber., 96, p. 1027Dewar, M.J.S., Zoebisch, E.G., Healy, E.F., (1985) J. Am. Chem. Soc., 107, p. 3902Gough, K.M., Belohorcova, K., Kaiser, K.L.E., (1994) Sci. Total. Environm., 142, p. 179Schalkoff, R., (1992) Pattern Recognition Statistical, Structural and Neural Approaches, , John Wiley & Sons, New YorkOinuma, H., Miyake, K., Yamanaka, M., (1988) J. Med. Chem., 33, p. 905Isu, Y., Nagashima, U., Aoyama, T., (1996) J. Chem. Inform. Comp. Sci., 36, p. 286Parr, R.G., Pearson, R.G., (1983) J. Am. Chem. Soc., 105, p. 7512Brown, R.E., Simas, A.M., (1982) Theor. Chim. Acta, 62, p. 1Abraham, M.H., Mc Gowan, J.C., (1987) Chromatografia, 23, p. 243Cartier, A., Rivail, J.L., (1987) Chem. Intelligent Lab. Sys., 1, p. 335Stewart, J.J.P., (1996) MOPAC 6.0 Manual, , Frank J. Seiler Research Laboratory, United States Air Force Academy, Colorado Springs, CODanon, Y., WinNN 0.97 Program, , copyright 1993-1995Yajko, D.M., Madej, J.J., Lancaster, M.V., (1995) J. Clin. Microbiol., 33, p. 2324Aoyama, T., Suzuki, Y., Ichikawa, H., (1990) J. Med. Chem., 33, p. 2583Ahmed, S.A., Gogal, R.M., Walsh, J.E., (1994) J. Immunol. Meth., 170, p. 211Klopman, G., Fercu, D., Jacob, J., (1996) J. Chem. Phys., 204, p. 181Karash, N., Terzioglu, N., Gürsoy, A., (1998) Arzneim.-Forsch./Drug Res., 48 (2), p. 75

Violacein/β-cyclodextrin Inclusion Complex Formation Studied By Measurements Of Diffusion Coefficient And Circular Dichroism

The formation of inclusion compounds between violacein and β-cyclodextrin was studied by diffusion and circular dichroism measurements. The present work was undertaken to explore the feasibility of the β-cyclodextrin in reducing the toxicity and enhancing the antitumoral efficacy of violacein by forming an inclusion complex. The results of the two experiments are in good agreement, suggesting the formation of 1 : 1 and 1 : 2 complexes. The diffusion coefficient measurements enabled estimates of the sizes of the complexes involved. From the circular dichroism and computational calculations it was possible to view a preference for inclusion of the most polar part of the molecule to form a 1 : 2 inclusion complex. We expect that this work proves the potential of these techniques to determining complex stoichiometry.3701/04/156774Bortolus, P., Monti, S., (1996) Advances in Photochemistry, 21, p. 1. , D. C. Neckers, D. H. Volman and G. von Bün Wiley-Interscience, New YorkLipkowitz, K.B., (1998) Chem. Rev., 98, p. 1829Dekharsky, M.V., Inoue, Y., (1998) Chem. Rev., 98, p. 1875Saenger, W., (1980) Angew. Chem. Int. Ed. Engl., 19, p. 344Parker, D., Kataky, R., (1997) J. Chem. Soc., Chem. Commun., 2, p. 141Connors, K.A., (1997) Chem. Rev., 97, p. 1325Stella, V.J., Rajewski, R.A., (1997) Pharm. Res., 14, p. 556Koehler, G., Grabner, G., Klein, C.T.H., Marconi, G., Mayer, B., Monti, S., Rechthaler, K., Wolschann, P., (1996) J. Incl. Phenom. Mol. Recognit. Chem., 25, p. 103Beezer, A.E., Mitchell, J.C., (1992) Andrews: Pestic. Sci., 35, p. 375Loh, W., Beezer, A.E., Mitchell, J.C., (1994) Lagmuir, 10, p. 3431Lino, A.C.S., Loh, W., J. Incl. Phenom. Mol. Recognit. Chem., p. 1998. , submittedCohen, A.G.Y., (1997) J. Org. Chem., 62, p. 120Li, M.-X., Li, N.-Q., Gu, Z.-N., Zhou, N.-H., Sun, Y.-L., Wu, Y.-Q., (1996) Electrochim. Acta., 41, p. 2877Manzanares, M.I., Solis, V., De Rossi, R.H., (1996) J. Electroanal. Chem., 407, p. 141Uekama, K., Otagiri, M., Kanie, Y., Tanaka, S., Ikeda, K., (1975) Chem. Pharm. Bull., 23, p. 1421Nakahara, H., Tanaka, H., Kukuda, K., Matsumoto, M., Tagaki, W., (1990) Thin Solid Films, p. 284Guo, R., Chang, J., Lin, S., Chen, R., Hu, J., Zhang, H., (1996) Guangpuxue Yu Guangpu Fenxi., 16, p. 38(1994) Chem. Abstr., 125, p. 86074Hamai, S., (1997) J. Incl. Phenom. Mol. Recognit. Chem., 27, p. 57Mayer, B., Marconi, G., Klein, C., Köhler, G., Wolschann, P., (1997) J. Incl. Phenom. Mol. Recognit. Chem., 29, p. 79Marconi, G., Mayer, B., (1997) Pure Appl. Chem., 69, p. 779Wu, Y., Jin, J., (1966) Sichuan Daxue Xuebao, Ziran Kexueban., 33, p. 560(1997) Chem. Abstr., 126, p. 317579Shen, X., Belletête, M., Durocher, G., (1998) J. Phys. Chem. B, 102, p. 1877Harada, A., Lin, J., Kamachi, M., (1992) Nature, 356, p. 325Harada, A., Lin, J., Kamachi, M., (1994) Nature, 370, p. 126Durán, N., Faljoni-Alario, A., (1980) An. Acad. Brasil. Ciên., 52, p. 287Rettori, D., Durán, N., (1998) World J. Microbiol. Biotechnol., 14, p. 685Haun, M., Pereira, M.F., Hoffmann, M.E., Riveros, R., Joyas, A., Campos, V., Durán, N., (1992) Biol. Res., 25, p. 21Durán, N., Antônio, R.V., Haun, M., Pilli, R.A., (1994) World J. Microbiol. Biotechnol., 10, p. 686Durán, N., Erazo, S., Campos, V., (1983) An. Acad. Brasil. Ciênc., 55, p. 231(1984) Chem. Abstr., 100, pp. 48417bDurán, N., Melo, P.S., Haun, M., (1996) Proc. XXV Annual Meeting Brazilian Biochemical Society, p. 150. , (Escritorio & Editorial, São Paulo, S.P., Brazil), Caxambu, M.G., Brazil O-24Durán, N., Melo, P.S., Haun, M., Proc. VIII Brazilian National Meeting in Virology, p. 1996. , (Brazilian Soc. Virology Publ., UNESP, Jaboticabal, S. P., Brazil), São Lourenço, M.G., BrazilMelo, P.S., Haun, M., Durán, N., (1997) FASEB J., 11 (SUPPL.), pp. A1418Durán, N., Haun, M., Brazilian Patent PI 9702918 (1997)Singh, U.V., Udupa, N., (1997) Indian J. Physiol. Pharmacol., 41, p. 171Singh, U.V., Udupa, N., (1997) Pharm. Sci., 3, p. 573Loh, W., Tonegutti, C.A., Volpe, P.L.O., (1993) J. Chem. Soc. Faraday Trans., 89, p. 113Akizadeth, A., Nieto De Castro, C.A., Wakeham, W.A., (1980) Int. J. Thermophys., 1, p. 243Price, W.E., Trickett, R.A., Harris, K.R., (1989) J. Chem. Soc. Faraday Trans. 1, 85, p. 3281Eastel, A.E., Woolf, L.A., (1989) J. Chem. Soc. Faraday Trans. 1, 80, p. 1287Noulty, R.A., Leaist, D.G., (1987) J. Chem. Eng. Data, 32, p. 418Grabner, G., Monti, S., Marconi, G., Mayer, B., Klein, C., Köhler, G., (1996) J. Phys. Chem., 100, p. 2006

Characterisation And Properties Of The Inclusion Complex Of 24-epibrassinolide With β-cyclodextrin

This paper reports the first study of an inclusion complex of a brassinosteroid with β-cyclodextrin. The formation of inclusion complexes between 24-epibrassinolide and β-cyclodextrin was confirmed by their physicochemical properties and the compounds were analysed by differential scanning calorimetry, powder X-ray diffraction, nuclear magnetic resonance spectrometry and scanning electron microscopy. Theoretical calculations using the MM+ HyperChem force field showed a preference for inclusion of the side chain of the epibrassinolide molecule into the β-cyclodextrin cavity to form a 1:1 inclusion complex, although complexes involving inclusion of the steroidal nucleus also possess a favourable interaction energy. Rice lamina inclination assay, employing IAC-103 and IAC-104 cultivars, showed an improved activity for the epibrassinolide-cyclodextrin complex compared to the epibrassinolide itself. The results suggest that brassinosteroid complexation with cyclodextrins may enhance the biological activity of these plant growth regulators.373233240Ahmed, S.M., Improvement of solubility and dissolution of 19-norprogesterone via inclusion complexation (1998) J. Inclusion Phenom. Mol. Rec. Chem., 30, pp. 111-125Alberts, E., Muller, B.W., Complexation of steroid-hormones with cyclodextrin derivatives. Substituent effects of the guest molecule on solubility and stability in aqueous-solution (1992) J. Pharm. Sci., 81, pp. 756-761Braun, P., Wild, A., The influence of brassinosteroids on growth and parameters of photosynthesis of wheat and mustard plants (1984) J. Plant Physiol., 116, pp. 189-196Brutti, C., Apostolo, N.M., Ferrerotti, S.A., Llorente, B.E., Krymkiewicz, N., Micropropagation of Cynara scolymus L. employing cyclodextrins to promote rhizogenesis (2000) Sci. 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Rel. Bioact. Mater., pp. 5006-5007. , Controlled Release Society, IncDurán, N., De Azevedo, M.B.M., Zullo, M.A.T., Salva, T.J.G., Alderete, J.B., (2000), Process of cyclodextrin/brassinosteroids formulation, for agricultural application, used as plant hormones, Brazilian Patent BR9906202-ADurzan, D.J., Ventimiglia, F.F., (2000), Cyclodextrin nutrients in plant tissue cultures, US Patent US 6087176 [Chem. Abstr. 133: 88976 (2000)]Fujioka, S., Noguchi, T., Takatsuto, S., Yoshida, S., Activity of brassinosteroids in the dwarf rice lamina inclination bioassay (1998) Phytochemistry, 49, pp. 1841-1848Fujioka, S., Sakurai, A., Biosynthesis and metabolism of brassinosteroids (1997) Physiol. Plant., 100, pp. 710-715Gosset, S., Gauvrit, C., (1992), Activity enhancement of benzamide herbicides by cyclodextrins. French 9222204 A1 [Chem. Abstr. 118: 75387 (1997)]Hayashi, T., Iijima, Y., Hoshino, A., Nakamura, M., (1998), Agents and method for flowering acceleration using cinnamic acid-cyclodextrin inclusion compounds Japanese Patent. Kokai Tokkyo Koho JP 10273404 A2 [Chem. Abstr. 129: 327304 (1999)]Huet, H., Jullien, M., The β-cyclodextrins delay the germination of the somatic embryos of carrot (Daucus carota L.) (1992) Acad. Sci., Ser. III, 314, pp. 171-177Ikekawa, N., Zhao, Y., Application of 24-epibrassinolide in agriculture (1991) Brassinosteroids: Chemistry, Bioactivity and Applications. ACS Symposium Series, 474, pp. 280-305. , Cutler H.G., Yokota T. and Adam G. (eds). American Chemical Society, Washington, DCKalinch, F.N., Mandava, N.B., Todhunter, J.A., Relationship of nucleic acid metabolism to brassinolide-induced responses in bean (1985) J. 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Springer-Verlag, BerlinMarzona, M., Carpignano, R., Quagliotto, P., Quantitative structure-stability relationships in the inclusion complexes of steroids with cyclodextrins (1992) Annal. Di Chim., 82, pp. 517-537Okii, M., (1993), Cyclodextrins for enhanced callus tissue culture of rice Japanese Patent. Kokai Tokkyo Koho JP 05292955 A2 [Chem. Abstr. 120: 1324504 (1997)]Rajagopalan, N., Chen, S.C., Chow, W.S., A study of the inclusion complex of amphotericin-B with cyclodextrin (1986) Int. J. Pharm., 29, pp. 161-168Sairam, P.K., Effect of homobrassinolide application on plant metabolism and grain yield under irrigated and moisture stress conditions of two wheat varieties (1994) Plant Growth Regul., 14, pp. 173-181Sakurai, A., Fujioka, S., The current status of physiology and biochemistry of brassinosteroids (1993) Plant Growth Regul., 13, pp. 147-159Sasse, J.M., Recent progress in brassinosteroid research (1997) Physiol. 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New anionic cobalt complexes using highly hindered bis-amides with varying donor abilities as ligands

Dalton Trans., 2007, 2135-214

Colorectal Cancer Chemoprevention By 2 β-cyclodextrin Inclusion Compounds Of Auraptene And 4′-geranyloxyferulic Acid

The inhibitory effects of novel prodrugs, inclusion complexes of 3-(4′-geranyloxy-3′-methoxyphenyl)-2-trans propenoic acid (GOFA) and auraptene (AUR) with b-cyclodextrin (CD), on colon carcinogenesis were investigated using an azoxymethane (AOM)/ dextran sodium sulfate (DSS) model. Male CD-1 (ICR) mice initiated with a single intraperitoneal injection of AOM (10 mg/kg body weight) were promoted by the addition of 1.5% (w/v) DSS to their drinking water for 7 days. They were then given a basal diet containing 2 dose levels (100 and 500 ppm) of GOFA/β-CD or AUR/β-CD for 15 weeks. At Week 18, the development of colonic adenocarcinoma was significantly inhibited by feeding with GOFA/β-CD at dose levels of 100 ppm (63% reduction in multiplicity, p < 0.05) and 500 ppm (83% reduction in the multiplicity, p < 0.001), when compared with the AOM/DSS group (multiplicity: 3.36 ± 3.34). In addition, feeding with 100 and 500 ppm (p < 0.01) of AUR/b-CD suppressed the development of colonic adenocarcinomas. The dietary administration with GOFA/β-CD and AUR/β-CD inhibited colonic inflammation and also modulated proliferation, apoptosis and the expression of several proinflammatory cytokines, such as nuclear factor-kappaB, tumor necrosis factor-α, Stat3, NF-E2-related factor 2, interleukin (IL)-6 and IL-1β, which were induced in the adenocarcinomas. Our findings indicate that GOFA/β-CD and AUR/β-CD, especially GOFA/β-CD, are therefore able to inhibit colitis-related colon carcinogenesis by modulating inflammation, proliferation and the expression of proinflammatory cytokines in mice. © 2009 UICC.1264830840Parkin, D.M., Bray, F., Ferlay, J., Pisani, P., Global cancer statistics, 2002 (2005) CA Cancer J Clin, 55, pp. 74-108(2006) Cancer fact sheet, (297). , WHO Media Center, WHOTanaka, T., Colorectal carcinogenesis: Review of human and experimental animal studies (2009) J Carcinog, 8, p. 5Balkwill, F., Mantovani, A., Inflammation and cancer: Back to Virchow? 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