Literature review of cyclodextrins inclusion complexes characterization - Part I: Phase solubility diagram, dissolution and scanning electron microscopy

International Journal of Pharmaceutical Sciences Review and Research

Volumn 12, Issue 1, 2012, Pages 1-6

  Takahashi, Andrea Ikeda ^a   Veiga, Francisco José Baptista ^b   Ferraz, Humberto Gomes ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

Cyclodextrin; Dissolution; Phase solubility diagram; Scanning electron microscopy

Indexed keywords

CYCLODEXTRIN;

ACCURACY; ANALYTIC METHOD; CHEMICAL BOND; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); DISSOLUTION; EQUILIBRIUM CONSTANT; INTERMETHOD COMPARISON; MOLECULAR WEIGHT; PHASE SEPARATION; PHASE SOLUBILITY DIAGRAM; PHYSICAL CHEMISTRY; PRECIPITATION; PREDICTION; REVIEW; SCANNING ELECTRON MICROSCOPY; SENSITIVITY AND SPECIFICITY; STOICHIOMETRY;

EID: 84855481704     PISSN: None     EISSN: 0976044X     Source Type: Journal    
DOI: None     Document Type: Review

References (82)

1. Veiga FJB, Pecorelli CCMF, Ribeiro LSS. As ciclodextrinasem tecnologia farmacêutica.1 ed., Minerva Coimbra Editora, Coimbra, 2006, 228p.
2. Valle EMMD. Cyclodextrins and their uses: a review, Process Biochem., 39, 2004, 1033-1046.
3. Challa R, Ahuja A., Ali J, Khar RK, Cyclodextrin in drug delivery: An update review, AAPS Pharm. Sci. Tech., 6, 2005, E329-E357.
4. Brewster ME, Loftsson, T, Cyclodextrins as pharmaceutical solubilizers, Adv. Drug Delivery Rev., 59, 2007, 645-666.
5. Higuchi T, Connors, AK. Phase-solubility techniques, Adv. Anal. Chem. Instrum., 4, 1965, 117-212.
6. Carrier RL, Miller LA, Ahmed I, The utility of cyclodextrins for enhancing oral bioavailability, J. Controlled Release, 123, 2007, 78-99.
7. Loftsson T, Hreinsdóttir D, Másson M, Evaluation of cyclodextrinsolubilization of drugs, Int. J. Pharm., 302, 2005, 18-28.
8. Loftsson T, Hreinsdóttir D, Másson M, The complexation efficiency, J.Incl.Phenom. Macrocycl.Chem., 57, 2007, 545-542.
9. Araujo DR, Tsuneda SS, Cereda CMS, Carvalho FGF, Preté PSC, Fernandes SA, Yokaichiya F, Franco MKKD, Mazzaro I, Fraceto LF, Braga AFA, Paula E. Development and pharmacological evaluation of ropivacaine-2-hydroxypropyl-β-cyclodextrin inclusion complex, Eur. J. Pharm. Sci., 33, 2008, 60-71.
10. Jug M, Becirevic-Lacan M, Bengez S, Novel cyclodextrin-based film formulation intended for buccal delivery of atenolol, Drug Dev. Ind. Pharm., 35, 2009, 796-807.
11. Melo NFS, Grillo R, Rosa AH, Fraceto LF, Interaction between nitroheterocyclic compounds with β-cyclodextrins: Phase solubility and HPLC studies, J. Pharm. Biomed. Anal., 47, 2008, 865-869.
12. Tewes F, Brillault J, Couet W, Olivier JC, Formulation of rifampicin - cyclodextrin complexes for lung nebulization, J. Controlled Release, 129, 2008, 93-99.
13. Jullian C, Morales-Montecinos J, Zapata-Torres G, Aguilera B, Rodriguez J, Arán V, Olea-Azar C, Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins, Bioorg. Med. Chem., 16, 2008, 5078-5084.
14. Dahiya S, Pathak K, Influence of amorphous cyclodextrin derivatives on aceclofenac release from directly compressible tablets, Pharmazie, 62, 2007, 278-283.
15. Stancanelli R, Ficarra R, Cannavà C, Guardo M, Calabrò ML, Ficarra P, Ottanà R, Maccari R, Crupi V, Majolino D, Venuti V, UV-vis and FTIRATR characterization of 9-fluorenon-2-carboxyester/ (2- hydroxypropyl)-β-cyclodextrin inclusion complex, J. Pharm. Biomed. Anal., 47, 2008, 704-709.
16. Berbicz F, Nogueira AC, Neto AM, Natali MRM, Baesso ML, Matioli G, Use of photoacoustic spectroscopy in the characterization of inclusion complexes of benzophenone-3-hydroxypropyl-β- cyclodextrin and ex vivo evaluation of the percutaneous penetration of sunscreen, Eur. J. Pharm. Biopharm., 2011, doi: 10.1016/j.ejpb.2011.03.026.
17. Patil AL, Pore YV, Kuchekar BS, Late SG, Solid-state characterization and dissolution properties of bicalutamide-β-cyclodextrin inclusion complex, Pharmazie, 63, 2008, 282-285.
18. AlOmari AA, AlOmari MM, Badwan AA, AL-Sou'Od KA, Effect of cyclodextrins on the solubility and stability of candesartan cilexetil in solution and solid state, J. Pharm. Biom. Anal., 54, 2011, 503-509.
19. Hirlekar R, Kadam V, Preparation and characterization of inclusion complexes of carvedilol with methyl-β-cyclodextrin, J. Incl. Phenom. Macrocycl. Chem., 63, 2009, 219-224.
20. Aleem O, Kuchekar B, Pore Y, Late S, Effect of β-cyclodextrin and hydroxypropyl β-cyclodextrin complexation on physicochemical properties and antimicrobial activity of cefdinir, J. Pharm. Biomed. Anal., 47, 2008, 535-540.
21. Capello B, Di Maio C, Iervolino M, Miro A, Combined effect of hydroxypropyl methylcellulose and hydroxypropyl-β-cyclodextrin on physicochemical and dissolution properties of celecoxib, J. Incl. Phenom. Macrocycl. Chem., 59, 2007, 237-244.
22. AlOmari MM, El-Barghouthi MI, Zughul MB, Davies JED, Dipyridamole/β-cyclodextrincomplexation: Effect of buffer species, thermodynamics, and guest-host interactions probed by 1HNMR and molecular modeling studies, J. Incl. Phenom. Macrocycl. Chem., 64, 2009, 305-315.
23. Sathigari S, Chadha G, Lee YHP, Wright N, Parsons DL, Rangari VK, Fasina O, Babu RJ, Physicochemical characterization of efavirenzcyclodextrin inclusion complexes, AAPS Pharm. Sci. Tech., 10, 2009, 81-87.
24. Cappello B, Di Maio C, Iervolino M, Miro A, Calignano A, Etodolac/cyclodextrin formulations: Physicochemical characterization and in vivo pharmacological studies, Drug Dev. Ind. Pharm., 35, 2009, 877-886.
25. Shah M, Karekar P, Sancheti P, Vyas V, Pore Y, Effect of PVP K30 and/or L-Arginine on stability constant of Etoricoxib-HPβCD inclusion complex: preparation and characterization of Etoricoxib- HPβCD binary system, Drug Dev. Ind. Pharm., 35, 2009, 118-129.
26. Asbahr ACC, Franco L, Barison A, Silva CWP, Ferraz HG, Rodrigues LNC, Binary and ternary inclusion complexes of finasteride in HPβCD and polymers: Preparation and characterization, Bioorg. Med. Chem., 17, 2009, 2718-2723.
27. Dias K, Nikolau S, De Giovani WF, Synthesis and spectral investigation of Al(III) catechin/β-cyclodextrin and Al(III) quercetin/β-cyclodextrin inclusion compounds,Spectrochim. Acta, Part A, 70, 2008, 154-161.
28. Wang S, Ding Y, Yao Y, Inclusion complexes of fluorofenidone with β -cyclodextrin and hydroxypropyl-β-cyclodextrin, Drug Dev. Ind. Pharm., 35, 2009, 808-813.
29. Kim JK, Kim MS, Park JS, Kim CK, Thermo-reversible flurbiprofen liquid suppository with HP-β-CD as a solubility enhancer: improvement of rectal bioavailability, J. Incl. Phenom. Macrocycl. Chem., 64, 2009, 265-272.
30. Cirri M, Righi MF, Maestrelli F, Mura P, Valleri M, Development of glyburide fast-dissolving tablets based on the combined use of cyclodextrins and polymers, Drug Dev. Ind. Pharm., 35, 2009, 73-82.
31. Cho HJ, Balakrishnan P, Shim WS, Chung SJ, Shim CK, Kim DD, Characterization and in vitro evaluation of freeze-dried microparticles composed of granisetron-cyclodextrin complex and carboxymethylcellulose for intranasal delivery, Int. J. Pharm., 2010, 400, 59-65.
32. Messner M, Kurkov SV, Brewster ME, Jansook P, Loftsson T, Selfassembly of cyclodextrin complexes: Agregation of hydrocortisone/cyclodextrin complexes, Int. J. Pharm., 407, 2011, 174-183.
33. Grillo R, Melo NFS, Moraes CM, Lima R, Menezes CMS, Ferreira EI, Rosa AH, Fraceto LF. Study of the interaction between hydroxymethylnitrofurazone and 2-hydroxypropyl-β-cyclodextrin, J. Pharm. Biomed. Anal.,47, 2008, 295-302.
34. Di Cagno M, Stein PC, Skalko-Basnet N, Brandl M, Bauer-Brandl A, Solubilization of ibuprofen with β-cyclodextrin derivatives: Energetic and structural studies, J. Pharm. Biomed. Anal., 55, 2011, 446-451.
35. Beni S, Szakács Z, Csernák O, Barcza L, Noszál B, Cyclodextrin/imatinibcomplexation: Binding mode and charge dependent stabilities, Eur. J. Pharm. Sci., 30, 2007, 167-174.
36. Zhu XL, Wang HB, Chen Q, Yang WC, Yang GF, Preparation and characterization of inclusion complex of iprodione and β- cyclodextrin to improve fungicidal activity, J. Agric. Food Chem., 55, 2007, 3535-3539.
37. Hirlekar R, Kadam V, Preformulation Study of the Inclusion Complex Irbesartan-β-Cyclodextrin, AAPS Pharm. Sci. Tech., 10, 2009, 276-281.
38. Brewster ME, Vandecruys R, Peeters J, Neeskens P, Verreck G, Loftsson T, Comparative interaction of 2-hydroxypropyl-β-cyclodextrin and sulfobutylether-β-cyclodextrin with itraconazole: Phase-solubility behavior and stabilization of supersaturated drug solutions, Eur. J. Pharm. Sci., 34, 2008, 94-103.
39. Shinde VR, Shelake MR, Shetty SS, Chavan-Patil AB, Pore YV, Late SG, Enhanced solubility and dissolution rate of lamotrigine by inclusion complexation and solid dispersion technique, J. Pharm. Pharmacol., 60, 2008, 1121-1129.
40. Tatai A, Aigner Z, Eros I, Kata M, Preparation and investigation of mixtures containing lidocaine base and β-cyclodextrin, J. Incl. Phenom. Macrocycl. Chem.,59, 2007, 105-113.
41. Omar L, El-Barghouthi MI, Masoud NA, Abdoh AA, Al-Omari MM, Zughul MB, Badwan AA, Inclusion complexation of loratadine with natural and modified cyclodextrins:phase solubility and thermodynamic studies, J. Solution Chem., 36, 2007, 605-616.
42. Nacsa A, Berkesi O, Szabó-Révész P, Aigner Z, Achievement of pHindependence of poorly-soluble, ionizable loratadine by inclusion complex formation with dimethyl-b-cyclodextrin, J. Incl. Phenom. Macrocycl. Chem.,64, 2009, 249-254.
43. De Paula W, Denadai AML, Santoro MM, Braga ANG, Santos RAS, Sinisterra RD,Supramolecular interactions beween losartan and hydroxypropyl-β-CD: ESI mass-spectrometry, NMR techniques, phase solubility, isothermal titration calorimetry and antihypertensive studies, Int. J. Pharm., 404, 2011, 116-123.
44. Obaidat AA, Khanfar RA, Khawam MN, The effect of β-cyclodextrin on the solubility and dissolution rate of meloxicam and investigation of the driving force for complexation using molecular modeling, J. Incl. Phenom. Macrocycl. Chem., 63, 2009, 273-279.
45. Wang J, Cai Z, Investigation of inclusion complex of miconazole nitrate with β- cyclodextrin, Carbohydr. Polym., 72, 2008, 255-260.
46. Brun H, Paul M, Razzouq N, Binhas M, Gibaud S, Astier A, Cyclodextrin inclusion complexes of the central analgesic drug nefopam, Drug Dev. Ind. Pharm., 32, 2006, 1123-1134.
47. Figueiras A, Sarraguça JMG, Carvalho RA, Pais AACC, Veiga FJB, Interaction of omeprazole with a methylated derivative of β- cyclodextrin: Phase solubility, NMR spectroscopy and molecular simulation, Pharm. Res., 24, 2007, 377-389.
48. Maestrelli F, Cecchi M, Cirri M, Capasso G, Mennini N, Mura P, Comparative study of oxaprozin complexation with natural and chemically-modified cyclodextrins in solution and in the solid state, J. Incl. Phenom. Macrocycl., 63, 2009, 17-25.
49. Ghuzlaan A, AlOmari MM, Al-Sou'Od KA, Prednisone/cyclodextrin inclusion complexation: phase solubility, thermodynamic, physicochemical and computational analysis, J. Solution Chem., 38, 2009, 83-94.
50. Araujo MVG, Macedo OFL, Nascimento CC, Conegero LS, Barreto LS, Almeida LE, Costa-Jr NB, Gimenez IF, Characterization, phasesolubilityand molecular modelingofα- cyclodextrin/pyrimethamineinclusioncomplex,Spectrochim. Acta, Part A, 72, 2009, 165-170.
51. Wen X, Liu Z, Zhu T, Mass spectrometry and molecular modeling studies on the inclusion complexes between α, β-cyclodextrins and simvastatin, Chem. Phys. Lett., 405, 2005, 114-117.
52. Rajabi O, Tayyari F, Salari R, Tayyari SF, Study of interaction of spironolactone with hydroxypropyl-β-cyclodextrin in aqueous solution and in solid state, J. Mol. Struct., 878, 2008, 78-83.
53. Araújo MVG, Vieira EKB, Lázaro GS, Conegero LS, Ferreira OP, Almeida LE, Barreto LS, Costa-Jr NB, Gimenez IF, Sulfadiazine/hydroxypropyl-β-cyclodextrin host-guest system: Characterization, phase-solubility and molecular modeling, Bioorg. Med. Chem., 16, 2008, 5788-5794.
54. Anzai K, Mizoguchi J, Yanagi T, Hirayama F, Arima H, Uekama K, Improvement of dissolution properties of a new Helicobacter pylori eradicating agent (TG44) by inclusion complexation with β- cyclodextrin, Chem. Pharm. Bull., 55, 2007, 1466-1470.
55. Jug M, Kosalec I, Maestrelli F, Mura P, Analysis of triclosan inclusion complexes with β-cyclodextrin and its water-soluble polymeric derivative, J. Pharm. Biom. Anal., 54, 2011, 1030-1039.
56. Doiphode D, Gaikwad S, Pore Y, Kuchekar B, Late S, Effect of β- cyclodextrin complexation on physicochemical properties of zaleplon, J. Incl. Phenom. Macrocycl. Chem., 62, 2008, 43-50.
57. Eid EEM, Abdul AB, Suliman FEO, Sukari MA, Rasedee A, Fatah SS, Characterization of the inclusion complex of zerumbone with hydroxypropyl-β-cyclodextrin, Carbohydrate Polymers, 83, 2011, 1707-1714.
58. Hussei K, Türk M, Wahl MA, Comparative evaluation of ibuprofen/β- cyclodextrin complexes obtained by supercritical carbon dioxide and other conventional methods, Pharm. Res., 24, 2007, 585-592.
59. Jun SW, Kim MS, Kim JS, Park HJ, Lee S, Woo JS, Hwang SJ, Preparation and characterization of simvastatin/hydroxypropyl-β- cyclodextrin inclusion complex using supercritical antisolvent (SAS) process, Eur. J. Pharm. Biopharm., 66, 2007, 413-421.
60. Toropainen T, Velaga S, Heikkilä T, Matilainen L, Jarho P, Carlfors J, Lehto VP, Järvinen T, Järvinem K, Preparation of budesonide/γ- cyclodextrin complexes in supercritical fluids with a novel SEDS method. emulsion based formulations, J. Pharm. Sci., 95, 2006, 2235-2245.
61. Jug M, Maestrelli F, Bragagni M, Mura P, Preparation and solid-state characterization of bupivacaine hydrochloride cyclodextrin complexes aimed for bucal delivery, J. Pharm.Biom.Anal., 52, 2010, 9-18.
62. Swaminathan S, Pastero L, Serpe L, Trotta F, Vavia P, Aquilano D, Trotta M, Zara G, Cavalli R, Cyclodextrin-based nanosponges encapsulating camptothecin: Physicochemical characterization, stability and cytotoxity, Eur. J. Pharm. Biopharm., 74, 2010, 193-201.
63. Sinha VR, Anitha R, Ghosh S, Amita, Kumria R, Bhinge JR, Kumar M, Physicochemical characterization and in vitrodissolution behaviour of celecoxib-β-cyclodextrin inclusion complexes, Acta Pharm., 57, 2007, 47-60.
64. Zhang X, Zou M, Li S, Chen X, Zhong D, Bioavailability of clarithromycin cyclodextrin ternary complexes upon oral administration to healthy beagle dogs, Drug Dev. Ind. Pharm., 34, 2008, 163-171.
65. Rogers TL, Nelsen AC, Hu J, Brown JN, Sarkari M, Young TJ, Johnston KP, Williams III RO, A novel particle engineering technology to enhance dissolution of poorly water soluble drugs: spray-freezing into liquid, Eur. J. Pharm. Biopharm., 54, 2002, 271-280.
66. Onyeji CO, Omoruyi SI, Oladimeji FA, Dissolution properties and characterization of halofantrine-2-hydroxypropyl-β-cyclodextrin binary systems, Pharmazie, 62, 2007, 858-863.
67. Lee SY, Jung II, Kim JK, Lim GB, Ryu JH, Preparation of itraconazole/HP-β-CD inclusion complexes using supercritical aerosol solvent extraction system and their dissolution characteristics, J. Supercrit. Fluids.,44, 2008, 400-408.
68. Cirri M, Bragagni M, Mennini N, Mura P, Development of a new delivery system consisting in "drug - in cyclodextrin - in nanostructured lipid carriers" for ketoprofen topical delivery, Eur. J. Pharm. Biopharm., (2011), doi: 10.1016/j.ejpb.2011.07.015.
69. Nacsa A, Ambrus R, Berkesi O, Szabó-Révéz P, Aigner Z, Water-soluble loratadine inclusion complex: Analytical control of the preparation by microwave irradiation, J. Pharm. Biomed. Anal., 48, 2008, 1020-1023.
70. Szabados-Nacsa Á, Sipos P, Martinek T, Mándity I, Blazsó G, Balogh Á, Szabó-Révész P, Aigner Z, Physico-chemical characterization and in vitro/in vivo evaluation of loratadine:dimethyl-β-cyclodextrin inclusion complex, J. Pharm. Biom. Anal., 55, 2011, 294-300.
71. Patel RP, Patel MM, Solid-state characterization and dissolution properties of lovastatin hydroxypropyl-β-cyclodextrin inclusion complex, Pharm. Tech., 31, 2007, 72-82.
72. Corti G, Capasso G, Maestrelli F, Cirri M, Mura P, Physical-chemical characterization of binary systems of metformin hydrochloride with triacetyl-β-cyclodextrin, J. Pharm. Biomed. Anal., 45, 2007, 480-486.
73. Mura P, Bettinetti GP, Cirri M, Maestrelli F, Sorrenti M, Catenacci L, Solid-state characterization and dissolution properties of Naproxen- Arginine-Hydroxypropyl-β-cyclodextrin ternary system, Eur. J. Pharm. Biopharm., 59, 2005, 99-106.
74. Figueiras A, Carvalho RA, Ribeiro L, Torres-Labandeira JJ, Veiga FJB, Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified β-cyclodextrin, Eur. J. Pharm. Biopharm., 67, 2007, 531-539.
75. Zhang X, Wu D, Lai J, Lu Y, Yin Z, Wu W, Piroxicam/2-Hydroxypropyl- β-Cyclodextrin Inclusion Complex Prepared by a New Fluid-Bed Coating Technique, J. Pharm. Sci., 98, 2009, 665-675.
76. Ungaro F, Giovino C, Catanzano O, Miro A, Mele A, Quaglia F, LaRotonda MI, Use of cyclodextrins as solubilizing agents for simvastatin: Effect of hydroxypropyl-β-cyclodextrin on lactone/hydroxyacid aqueous equilibrium, Int. J. Pharm., 404, 2011, 49-56.
77. Vajna B, Farkas I, Farkas A, Pataki H, Nagy Z, Madarász J, Marosi G, Characterization of drug-cyclodextrin formulations using Raman mapping and multivariate curve resolution, J. Pharm. Biom. Anal., 56, 2011, 38-44.
78. Scalia S, Coppi G, Iannuccelli V, Microencapsulation of a cyclodextrin complex of the UV filter, butyl methoxydibenzoylmethane: In vivo skin penetration studies, J. Pharm. Biom. Anal., 54, 2011, 345-350.
79. Zhang X, Zhang Y, Zhong D, Chen Y, Li S, Investigation and Physicochemical characterization of clarithromycin-citric acidcyclodextrins ternary complexes, Drug Dev. Ind. Pharm., 33, 2007, 163-171.
80. Franco C, Schwingel L, Lula I, Sinisterra RD, Koester LS, Bassani VL, Studies on coumestrol/β-cyclodextrin association: Inclusion complex characterization, Int. J. Pharm., 369, 2009, 5-11.
81. Zoppi A, Garnero C, Linck YG, Chattah AK, Monti GA, Longhi MR, Enalapril:β-CD complex: Stability enhancement in solid state, Carbohydrate Polymers, 86, 2011, 716-721.
82. Ribeiro LSS, Ferreira DC, Veiga FJB, Phisicochemical investigation of the effects of water-soluble polymers on vinpocetinecomplexation with β-cyclodextrin and its sulfobutyl ether derivate is solution and solid state, Eur. J. Pharm. Sci., 20, 2003, 253-266.