Inclusion complexes of HP-β-cyclodextrin with agomelatine: Preparation, characterization, mechanism study and in vivo evaluation

Carbohydrate Polymers

Volumn 147, Issue , 2016, Pages 415-425

  Liao, Yunhui ^a   Zhang, Xuefei ^a   Li, Chenglin ^a   Huang, Yanjuan ^a   Lei, Ming ^a   Yan, Mina ^a   Zhou, Yuefang ^a   Zhao, Chunshun ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

Absorption; Agomelatine; Hydroxypropyl cyclodextrin inclusion complex; Inclusion mechanism; Molecular modeling studies; Pharmacokinetics

Indexed keywords

ABSORPTION; BIOCHEMISTRY; MOLECULAR MODELING; NAPHTHALENE; PHARMACOKINETICS; SOLUBILITY;

AGOMELATINE; CYCLODEXTRIN INCLUSION COMPLEXES; MOLECULAR MODELING STUDIES; ORAL BIOAVAILABILITIES; PHARMACOKINETIC STUDIES; PHARMACOLOGICAL EFFECTS; STRUCTURAL CHARACTERIZATION; THERMODYNAMIC STUDIES;

CYCLODEXTRINS;

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ACETAMIDE DERIVATIVE; AGOMELATINE;

ANIMAL; AREA UNDER THE CURVE; CHEMISTRY; DIFFERENTIAL SCANNING CALORIMETRY; FREEZE DRYING; INTESTINE; METABOLISM; MOLECULAR DOCKING; RAT; SOLUBILITY;

2-HYDROXYPROPYL-BETA-CYCLODEXTRIN; ACETAMIDES; ANIMALS; AREA UNDER CURVE; CALORIMETRY, DIFFERENTIAL SCANNING; FREEZE DRYING; INTESTINES; MOLECULAR DOCKING SIMULATION; RATS; SOLUBILITY;

EID: 84964412507     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2016.04.022     Document Type: Article

References (50)

1. U. Berg, N. Bladh, and A. Hjelmencrantz Structure and dynamic stability of cyclodextrin inclusion complexes with 1,4-disubstituted bicyclo[2.2.2]octanes Journal of the Chemical Society Perkin Transactions 2 9 2001 1850 1857
2. 1H NMR spectroscopic study of the interaction between cyclodextrins and bicyclo[3.3.1]nonanes Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 26 4 1996 209 218
3. P.A.P. Cevallos, M.P. Buera, and B.E. Elizalde Encapsulation of cinnamon and thyme essential oils components (cinnamaldehyde and thymol) in β-cyclodextrin: effect of interactions with water on complex stability Journal of Food Engineering 99 1 2010 70 75
4. S. Chakraborty, S. Basu, A. Lahiri, and S. Basak Inclusion of chrysin in β-cyclodextrin nanocavity and its effect on antioxidant potential of chrysin: a spectroscopic and molecular modeling approach Journal of Molecular Structure 977 1-3 2010 180 188
5. S. Chaudhuri, S. Chakraborty, and P.K. Sengupta Encapsulation of serotonin in β-cyclodextrin nano-cavities: fluorescence spectroscopic and molecular modeling studies Journal of Molecular Structure 975 1-3 2010 160 165
6. Coquerel, G., Linol, J., & Souvie, J.-C. (2009). Crystalline form III of agomelatine, a process for its preparation and pharmaceutical compositions containing it. Google Patents.
7. Y.J. Dang, H.Z. Feng, L. Zhang, C.H. Hu, and C.Y. Zhu In situ absorption in rat intestinal tract of solid dispersion of annonaceous acetogenins Gastroenterology Research and Practice 2012 2012 879676
8. C. De Bodinat, B. Guardiola-Lemaitre, E. Mocaër, P. Renard, C. Muñoz, and M.J. Millan Agomelatine, the first melatonergic antidepressant: discovery, characterization and development Nature Reviews Drug Discovery 9 8 2010 628 642
9. K. Demyttenaere Agomelatine: a narrative review European Neuropsychopharmacology 21 2011 S703 S709
10. C. Desai, and B. Prabhakar Nano-amorphous composites of cilostazol-HP-β-CD inclusion complexes: physicochemical characterization, structure elucidation, thermodynamic studies and in vitro evaluation Journal of Inclusion Phenomena and Macrocyclic Chemistry 81 1-2 2014 175 191
11. C. Desai, and B. Prabhakar Nano-amorphous composites of cilostazol-HP-β-CD inclusion complexes: physicochemical characterization, structure elucidation, thermodynamic studies and in vitro evaluation Journal of Inclusion Phenomena and Macrocyclic Chemistry 81 1-2 2015 175 191
12. N. Devasari, C.P. Dora, C. Singh, S.R. Paidi, V. Kumar, M.E. Sobhia, and et al. Inclusion complex of erlotinib with sulfobutyl ether-beta-cyclodextrin: preparation, characterization, in silico, in vitro and in vivo evaluation Carbohydrate Polymers 134 2015 547 556
13. W. Du, Y. Zhou, Y. Gong, and C. Zhao Investigation of physicochemical properties and in-vitro in-vivo evaluation of agomelatine polymorphs Asian Journal of Pharmaceutical Sciences 8 3 2013 181 190
14. S. Gould, and R.C. Scott 2-Hydroxypropyl-beta-cyclodextrin (HP-beta-CD): a toxicology review Food and Chemical Toxicology 43 10 2005 1451 1459
15. T. Higuchi, and K.A. Connors Phase-solubility techniques Advances in Analytical Chemistry and Instrumentation 4 2 1965 117 212
16. Y. Hu, L. Zheng, C. Qian, and W. Yu Absorption in small intestinal tract of ion drug-phenolsulfonphthalein Journal of China Pharmaceutical University 27 6 1996 355 359
17. Y.Y. Hwang, D.C. Shin, Y.S. Nam, and B.-K. Cho Characterization, stability, and pharmacokinetics of sibutramine/β-cyclodextrin inclusion complex Journal of Industrial and Engineering Chemistry 18 4 2012 1412 1417
18. G. Jadhav, and P. Vavia Physicochemical, in silico and in vivo evaluation of a danazol-β-cyclodextrin complex International Journal of Pharmaceutics 352 1 2008 5 16
19. R. Jain, S. Duvvuri, V. Kansara, N.K. Mandava, and A.K. Mitra Intestinal absorption of novel-dipeptide prodrugs of saquinavir in rats International Journal of Pharmaceutics 336 2 2007 233 240
20. C. Jullian, S. Miranda, G. Zapata-Torres, F. Mendizabal, and C. Olea-Azar Studies of inclusion complexes of natural and modified cyclodextrin with (+)catechin by NMR and molecular modeling Bioorganic and Medicinal Chemistry 15 9 2007 3217 3224
21. C. Jullian, J. Morales-Montecinos, G. Zapata-Torres, B. Aguilera, J. Rodriguez, V. Aran, and et al. Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins Bioorganic and Medicinal Chemistry 16 9 2008 5078 5084
22. E. Junquera, and E. Aicart Thermodynamic analysis of the binding of a hepatoprotectant drug, thioctic acid, by β-cyclodextrin Journal of Pharmaceutical Sciences 88 6 1999 626 631
23. J.-S. Kim, S. Mitchell, P. Kijek, Y. Tsume, J. Hilfinger, and G.L. Amidon The suitability of an in situ perfusion model for permeability determinations: utility for BCS class I biowaiver requests Molecular Pharmaceutics 3 6 2006 686 694
24. H. Lennernäs Human intestinal permeability Journal of Pharmaceutical Sciences 87 4 1998 403 410
25. H. Li, X. Zhao, Y. Ma, G. Zhai, L. Li, and H. Lou Enhancement of gastrointestinal absorption of quercetin by solid lipid nanoparticles Journal of Controlled Release 133 3 2009 238 244
26. Z. Liao, Q. Ping, W. Xiao, and X. Liang The study in situ on rat intestinal absorption of the active components in Guizhifuling capsule The Chinese Journal of Natural Medicines 3 2005 303 307
27. J. Liu, L. Qiu, J. Gao, and Y. Jin Preparation, characterization and in vivo evaluation of formulation of baicalein with hydroxypropyl-β-cyclodextrin International Journal of Pharmaceutics 312 1 2006 137 143
28. H. Liu, G. Yang, Y. Tang, D. Cao, T. Qi, Y. Qi, and et al. Physicochemical characterization and pharmacokinetics evaluation of beta-caryophyllene/beta-cyclodextrin inclusion complex International Journal of Pharmaceutics 450 1-2 2013 304 310
29. M. Liu, W. Cao, Y. Sun, and Z. He Preparation, characterization and in vivo evaluation of formulation of repaglinide with hydroxypropyl-beta-cyclodextrin International Journal of Pharmaceutics 477 1-2 2014 159 166
30. T. Loftsson, and D. Duchene Cyclodextrins and their pharmaceutical applications International Journal of Pharmaceutics 329 1 2007 1 11
31. T. Loftsson, D. Hreinsdóttir, and M. Masson Evaluation of cyclodextrin solubilization of drugs International Journal of Pharmaceutics 302 1 2005 18 28
32. S.-X. Ma, W. Chen, X.-D. Yang, N. Zhang, S.-J. Wang, L. Liu, and et al. Alpinetin/hydroxypropyl-β-cyclodextrin host-guest system: preparation, characterization, inclusion mode, solubilization and stability Journal of Pharmaceutical and Biomedical Analysis 67-68 2012 193 200
33. H.C. Marques, J. Hadgraft, and I. Kellaway Studies of cyclodextrin inclusion complexes. I. The salbutamol-cyclodextrin complex as studied by phase solubility and DSC International Journal of Pharmaceutics 63 3 1990 259 266
34. B.S. Muñoz, M. Martin, B. Del Castillo, J. Menendez, L. Vazquez, and D. Lerner Analytical applications of retinoid-cyclodextrin inclusion complexes. 1. Characterization of a retinal-beta-cyclodextrin complex Journal of Pharmaceutical and Biomedical Analysis 14 8-10 1996 909 915
35. M.V. Ol'khovich, A.V. Sharapova, S.N. Lavrenov, S.V. Blokhina, and G.L. Perlovich Inclusion complexes of hydroxypropyl-β-cyclodextrin with novel cytotoxic compounds: solubility and thermodynamic properties Fluid Phase Equilibria 384 2014 68 72
36. M.M. Omari, A.A. Badwan, M.B. Zughul, J. Eric, and D. Davies Fexofenadine/cyclodextrin inclusion complexation: phase solubility, thermodynamic, physicochemical, and computational analysis Drug Development and Industrial Pharmacy 33 11 2007 1205 1215
37. T. Pralhad, and K. Rajendrakumar Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis Journal of Pharmaceutical and Biomedical Analysis 34 2 2004 333 339
38. N. Rajendiran, and G. Venkatesh Micrometer size rod formed by secondary self assembly of omeprazole with α- and β-cyclodextrins Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 137 2015 832 840
39. D. Salvatierra, C. Díez, and C. Jaime Host/guest interactions and NMR spectroscopy. A computer program for association constant determination Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 27 3 1997 215 231
40. H.-J. Schneider, F. Hacket, V. Rüdiger, and H. Ikeda NMR studies of cyclodextrins and cyclodextrin complexes Chemical Reviews 98 5 1998 1755 1786
41. F. Semcheddine, N.E.I. Guissi, X. Liu, Z. Wu, and B. Wang Effects of the preparation method on the formation of true nimodipine SBE-β-CD/HP-β-CD inclusion complexes and their dissolution rates enhancement AAPS PharmSciTech 16 3 2014 704 715
42. J. Stappaerts, J. Brouwers, P. Annaert, and P. Augustijns In situ perfusion in rodents to explore intestinal drug absorption: challenges and opportunities International Journal of Pharmaceutics 478 2 2015 665 681
43. B.H. Stewart, O.H. Chan, N. Jezyk, and D. Fleisher Discrimination between drug candidates using models for evaluation of intestinal absorption Advanced Drug Delivery Reviews 23 1 1997 27 45
44. 1H NMR studies on host-guest interaction of paeonol and two of its isomers with β-cyclodextrin International Journal of Pharmaceutics 316 1 2006 7 13
45. C.A. Ventura, I. Giannone, D. Paolino, V. Pistara, A. Corsaro, and G. Puglisi Preparation of celecoxib-dimethyl-beta-cyclodextrin inclusion complex: characterization and in vitro permeation study European Journal of Medicinal Chemistry 40 7 2005 624 631
46. L.-F. Yin, S.-J. Huang, C.-L. Zhu, S.-H. Zhang, Q. Zhang, X.-J. Chen, and et al. In vitro and in vivo studies on a novel solid dispersion of repaglinide using polyvinylpyrrolidone as the carrier Drug Development and Industrial Pharmacy 38 11 2012 1371 1380
47. J.-Q. Zhang, D. Wu, K.-M. Jiang, D. Zhang, X. Zheng, C.-P. Wan, and et al. Preparation, spectroscopy and molecular modelling studies of the inclusion complex of cordycepin with cyclodextrins Carbohydrate Research 406 2015 55 64
48. Y.H. Zhao, M.H. Abraham, J. Le, A. Hersey, C.N. Luscombe, G. Beck, and et al. Evaluation of rat intestinal absorption data and correlation with human intestinal absorption European Journal of Medicinal Chemistry 38 3 2003 233 243
49. S.-L. Zheng, J.-M. Chen, W.-X. Zhang, and T.-B. Lu Structures of polymorphic agomelatine and its cocrystals with acetic acid and ethylene glycol Crystal Growth & Design 11 2 2011 466 471
50. Y. Zhou, W. Chu, M. Lei, J. Li, W. Du, and C. Zhao Application of a continuous intrinsic dissolution-permeation system for relative bioavailability estimation of polymorphic drugs International Journal of Pharmaceutics 473 1-2 2014 250 258