Host-guest system of 4-nerolidylcatechol in 2-hydroxypropyl-β- cyclodextrin: Preparation, characterization and molecular modeling

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 64, Issue 1-2, 2009, Pages 23-35

  Soares, Líllian Amélia ^a   Leal, Ana Flávia Vasconcelos Borges ^a   Fraceto, Leonardo Fernandes ^b   Maia, Elaine Rose ^c   Resck, Inês Sabioni ^c   Kato, Massuo Jorge ^d   De Sousa Gil, Eric ^a   De Sousa, Aparecido Ribeiro ^e   Da Cunha, Luiz Carlos ^a   Rezende, Kênnia Rocha ^a  

^a FEDERAL UNIVERSITY OF GOIÁS   (Brazil)

^b SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^c UNIVERSITY OF BRASILIA   (Brazil)

^d UNIVERSITY OF SÃO PAULO   (Brazil)

^e FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

2 Hydroxypropyl cyclodextrin; 4 Nerolidylcatechol; 1H NMR and molecular dynamics; Inclusion complex

Indexed keywords

EID: 67349157553     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9532-y     Document Type: Article

References (42)

1. CD Ropke VV da Silva CZ Kera DV Miranda RL de Almeida TC Sawada SBM Barros 2006 In vitro and in vivo inhibition of skin matrix metalloproteinases by pothomorphe umbellata root extract Photochem. Photobiol. 82 2 439 442
2. CD Ropke TM Kaneko RM Rodrigues VV Silva S Barros TCH Sawada MJ Kato SBM Barros 2002 Evaluation of percutaneous absorption of 4-nerolidylcathecol from four topical formulations Int. J. Pharm. 249 1-2 109 116 (Pubitemid 35333437)
3. CD Ropke RR Meirelles VV Silva TCH Sawada SBM Barros 2003 Pothomorphe umbellata extract prevents α-tocopherol depletion after UV-irradiation Photochem. Photobiol. 78 5 436 439
4. CD Ropke TCH Sawada VV da Silva NS Michalany SBM Barros 2005 Photoprotective effect of Pothomorphe umbellata root extract against ultraviolet radiation induced chronic skin damage in the hairless mouse Clin. Exp. Dermatol. 30 3 272 276 (Pubitemid 40547702)
5. Barros, S.B.M., Ropke, C.D.: Use of Pothomorphe umbellata extract, composition on basis of Pothomorphe umbellata extract and method of application on the Pothomorphe umbellata extract. (Fundação de Amparo a Pesquisa do Estado de São Paulo-FAPESP, Brazil; Universidade de São Paulo-USP). PCT Int. Appl. (2004), CODEN: PIXXD2 WO 2004026323 A1
6. FF Perazzo GHB Souza W Lopes LGV Cardoso JCT Carvalho NPD Nanayakkara JK Bastos 2005 Anti-inflammatory and analgesic properties of water-ethanolic extract from Pothomorphe umbellata (Piperaceae) aerial parts J. Ethnopharmacol. 99 2 215 220 (Pubitemid 40724396)
7. E Mongelli F Desmarchelier J Coussio G Ciccia 1995 Antimicrobial activity and interaction with DNA of medicinal plants from the Peruvian Amazon region Rev. Argent. Microbiol. 27 4 199 203
8. E Mongelli A Romano C Desmarchelier J Coussio G Ciccia 1999 A cytotoxic catechol derivative from Pothomorphe peltata inhibits topoisomerase I activity Planta Med. 65 4 376 378 (Pubitemid 29249919)
9. MC Valadares KR Rezende ER Pereira MC Sousa B Gonçalves JC de Assis MJ Kato 2007 Protective effects of 4-nerolidylcatechol against genotoxicity induced by cyclophosphamide Food Chem. Toxicol. 45 10 1975 1978 (Pubitemid 47238212)
10. MA Vandelli G Salvioli A Mucci R Panini L Malmusi 1995 2-Hydroxypropyl-β-cyclodextrin complexation with ursodeoxycholic acid Int. J. Pharm. 118 1 77 83
11. CM Fernandes MT Vieira FJB Veiga 2002 Physicochemical characterization and in vitro dissolution behavior of nicardipine-cyclodextrins inclusion compounds Eur. J. Pharm. Sci. 15 1 79 88 (Pubitemid 34136971)
12. HA Archontaki MV Vertzoni MH Athanassiou-Malaki 2002 Study on the inclusion complexes of bromazepam with β- and β-hydroxypropyl- cyclodextrins J. Pharm. Biomed. Anal. 28 3-4 761 769 (Pubitemid 34465642)
13. D Duchêne D Wouessidjewe 1990 Pharmaceutical uses of cyclodextrins and derivatives Drug Dev. Ind. Pharm. 16 17 2487 2499
14. F Leroy-Lechat D Wouessidjewe JP Andreux F Puisieux D Duchêne 1994 Evaluation of the cytotoxicity of cyclodextrins and hydroxypropylated derivatives Int. J. Pharm. 101 1-2 97 103 (Pubitemid 24028534)
15. ME Davis ME Brewster 2004 Cyclodextrin-based pharmaceutics: past, present and future Nat. Rev. Drug Discov. 3 12 1023 1035 (Pubitemid 39642365)
16. W Hirsch V Fried L Altman 1985 Effect of cyclodextrins on sparingly soluble salts J. Pharm. Sci. 74 10 1123 1125 (Pubitemid 15231339)
17. KR Rezende SBM Barros 2004 Quantification of 4-nerolidylchatecol of Pothomorphe umbellata (Piperaceae) in rat plasma samples by HPLC UV Braz. J. Pharm. Sci. 40 3 373 380 (Pubitemid 40039516)
18. KR Gustafson JH Cardellina JB McMahon LK Pannell GM Cragg MR Boyd 1992 The peltatolls, nove HIV-inhibitory catechol derivates from P. peltata J. Org. Chem. 57 10 2809 2811
19. T Higuchi KA Connors 1965 Phase solubility techniques Adv. Anal. Chem. Instrum. 4 117 212
20. P Job 1928 Formation and stability of inorganic complexes in solution Ann. Chim. 9 113 203
21. ML Calabro S Tommasini P Donato D Ranieri R Stancanelli P Ficarra R Ficarra C Costa S Catania C Rustichelli G Gamberini 2004 Effects of α- and β-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones J. Pharm. Biomed. Anal. 35 2 364 367 (Pubitemid 38520130)
22. Materials Studio Software and Insight II Software, Accelrys, 9685 Scranton Road, San Diego, CA 92121-3752, USA
23. MJ Hwang TP Stockfisch AT Hagler 1994 Derivation of Class II force fields. 2. Derivation and characterization of a Class II force field, CFF93, for the alkyl functional group and alkane molecules J. Am. Chem. Soc. 116 6 2515 2525 (Pubitemid 24980771)
24. H Sun SJ Mumby JR Maple AT Hagler 1994 An ab initio CFF93 all-atom force field for polycarbonates J. Am. Chem. Soc. 116 7 2978 2987 (Pubitemid 24980835)
25. Abola, E.E., Bernstein, F.C., Bryant, S.H., Koetzle, T.F., Weng, J., Allen, F.H., Bergerhoff, G., Sievers, R.: Protein Data Bank. In Allen, F.H., Bergerhoff, G., Sievers, R. (eds.) Crystallographic Databases-Information Content, Software Systems, Scientific Applications. Data Commission of International Union of Crystallography, Cambridge (1987)
26. Berman, H.M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T.N., Weissig, H., Shindyalov, I.N., Bourne, P.E.: The protein Data Bank. Nucleic Acids Res. 28, 235-242 (2000) http://www.rcsb.org/PDB. Accessed 12 June 2008 (Pubitemid 30047768)
27. AJ Sharff LE Rodseth FA Quiocho 1993 Refined 1.8-.ANG. structure reveals the mode of binding of beta-cyclodextrin to the maltodextrin binding protein Biochemistry 32 40 10553 10559 (Pubitemid 23327786)
28. ML Connolly 1983 Solvent-accessible surfaces of proteins and nucleic acids Science 221 4612 709 713
29. ML Connolly 1992 Shape distributions of protein topography Biopolymers 32 9 1215 1236
30. T Loftsson EM Brewster 1996 Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization Int. J. Pharm. Sci. 85 10 1017 1025 (Pubitemid 26338912)
31. JA Imonigie DH Macartney 1993 Effects of cyclodextrin inclusion on the kinetics on the outer-sphere oxidation of 4-tert-butylcatechol by transition metal complexes in acidic aqueous media Inorg. Chem. 32 6 1007 1012
32. HH Tønnesen M Másson T Loftsson 2002 Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability Int. J. Pharm. 244 1-2 127 135 (Pubitemid 35245453)
33. J Blanco JL Vila-Jato F Otero S Anguiano 1991 Influence of method of preparation on inclusion complexes of naproxen with different cyclodextrins Drug. Dev. Ind. Pharm. 17 7 943 945
34. J Pitha J Milecki H Fales L Pannell K Uekama 1986 Hydroxypropyl-β- cyclodextrin: preparation and characterization; effects on solubility of drugs Int. J. Pharm. 29 1 73 82 (Pubitemid 16162498)
35. CA Ventura S Tirendi G Puglisi E Bousquet L Panza 1997 Solid-state properties of powders in the formulation and processing of solid dosage forms Int. J. Pharm. 14 1 1 13
36. JL Sacoman KM Monteiro A Possenti GM Figueira MA Foglio JE Carvalho 2008 Cytotoxicity and antitumoral activity of dichloromethane extract and its fractions from Pothomorphe umbellata Braz. J. Med. Biol. Res. 41 5 411 415
37. S Gibaud SB Zirar P Mutzenhardt I Fries A Astier 2005 Melarsoprol-cyclodextrins inclusion complexes Int. J. Pharm. 306 1-2 107 121 (Pubitemid 41643145)
38. T Xinyi S Lindenbaum 1991 Studies on complexation between β-cyclodextrin and bile salts Int. J. Pharm. 74 1-2 127 135
39. FJB Veiga CM Fernandes RA Carvalho CFGC Geraldes 2001 Molecular modeling and 1H-NMR: ultimate tools for the investigation of tolbutamide: β-cyclodextrin and tolbutamide: hydropropyl-β-cyclodextrin complexes Chem. Pharm. Bull. 49 10 1251 1256 (Pubitemid 33035631)
40. EM Martin Del Valle 2004 Cyclodextrins and their uses: a review Process Biochem. 39 9 1033 1046 (Pubitemid 38527174)
41. MVG Araujo EKB Vieira GS Lázaro LS Conegero OP Ferreira LE Almeida LS Barreto NBC Costa Junior IF Gimenez 2007 Inclusion complexes of pyrimethamine in 2-hydroxypropyl-β-cyclodextrin: characterization, phase solubility and molecular modelling Bioorg. Med. Chem. 15 17 5752 5759 (Pubitemid 47044973)
42. Soares, L.A.: Preparação e caracterização do complexo de inclusão do 4-nerolidilcatecol em hidroxipropil-β- ciclodextrina. M.Sc. Thesis, Universidade Federal de Goiás, Goiânia, GO (2007)