Cyclodextrin and phospholipid complexation in solubility and dissolution enhancement: A critical and meta-analysis

Expert Opinion on Drug Delivery

Volumn 11, Issue 8, 2014, Pages 1255-1272

  Semalty, Ajay ^a  

^a H N B GARHWAL UNIVERSITY   (India)

Author keywords

Complexation; Differential scanning calorimetry; Dissolution; Phospholipids; Solubility; X ray powder diffraction

Indexed keywords

CYCLODEXTRIN; DICLOFENAC; NARINGENIN; NIMESULIDE; PHOSPHOLIPID; QUERCETIN; RUTOSIDE;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG BIOAVAILABILITY; DRUG SOLUBILITY; EMULSION; FREEZE DRYING; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; NEBULIZATION; PERMEABILITY; PHYSICAL CHEMISTRY; PRECIPITATION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SCANNING ELECTRON MICROSCOPY; SPRAY DRYING; SUPERCRITICAL FLUID; SUSPENSION; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY; X RAY POWDER DIFFRACTION;

COMPLEXATION; DIFFERENTIAL SCANNING CALORIMETRY; DISSOLUTION; PHOSPHOLIPIDS; SOLUBILITY; X-RAY POWDER DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CYCLODEXTRINS; PHOSPHOLIPIDS; SOLUBILITY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; WATER; X-RAY DIFFRACTION;

EID: 84904597661     PISSN: 17425247     EISSN: 17447593     Source Type: Journal    
DOI: 10.1517/17425247.2014.916271     Document Type: Review

References (96)

1. Semalty A, Semalty M, Rawat MSM. Essentials of pharmaceutical technology. 1st edition. Pharma Med Press; Hyderabad, India: 2011. p. 4-5
2. Moneghini M, Kikig I, Perissutti B, et al. Characterization of nimesulide-b-cyclodextrin system prepared by supercritical fluid impregnation. Eur J Pharm Bioparm 2004;58:637-44
3. Pralhad T, Kumar R. Study of freezedried quercetin-cyclodextrin binary system by DSC, FTIR, X-ray diffraction and SEM analysis. J Pharm Biomed Anal 2004;34:333-9
4. Babu RJ, Pandit JK. Effect of cyclodextrin on the complexation and transdermal delivery of bupranolol through rat skin. Int J Pharm 2004;271:155-65
5. Rawat S, Jain SK. Solubility enhancement of celecoxib using betacyclodextrin inclusion complexes. Eur J Pharm Biopharm 2004;51:263-7
6. Sajeesh S, Sharma CP. Cyclodextrin-insulin complex encapsulated polymethacrylic acid based nanoparticles for oral insulin delivery. Int J Pharm 2006;325:147-54
7. Chen X, Chen R, Guo Z, et al. The preparation and stability of the inclusion complex of astaxanthin with beta-CD. Food Chem 2007;101:1580-4
8. Bhati LK, Tiwari G, Tiwari R, et al. Enhancement of complexation efficiency of meloxicam using binary and ternary solid systems: Formulation considerations. Am J Drug Discov Dev 2012;2(1):17-31
9. Connors KA. Complex formation. In: Gebbaro AR, Remington's pharmaceutical sciences. 18th edition. Mack Publishing Co, PA, USA; 1990
10. Magnusdottir M, Lofisson T. Cyclodextrins. J Incl Phenom Macrocycl Chem 2002;44:213-18
11. Rasheed A, Kumar A. Cyclodextrin as drug carrier molecule. Sci Pharm 2008;76:567-98
12. Loftsson T, Brewsteer ME, Masson M. Role of cyclodextrin in improving oral drug delivery. Am J Drug Deliv 2004;2(4):261-75
13. Irie T, Uekama K. Pharmaceutical application of cyclodextrin, toxicological issues and safety evaluation. J Pharm Sci 1997;85:147-62
14. Del VE. Cyclodextrins and their uses: A review. Process Biochem 2004;39:1033-46
15. Rinaki E, Valsami G, Macheras P. Quantitative biopharmaceutical classification system: The central role of dose/solubility ratio. Pharm Res 2003;20:1917
16. Vekama K. Design and evaluation of cyclodextrin based drug formulation. Chem Pharm Bull 2004;52:900-15
17. Wei QT, Wen H. Applications of complexation in the formulation of insoluble compounds. In: Liu R, editor. Water insoluble drug formulation. 2nd edition. CRC Press; London: 2008. p. 133-59
18. Szejtli J. Medicinal applications of cyclodextrins. Med Res Rev 1994;14:353-86
19. Connors KA. The stability of cyclodextrin complexes in solution. Chem Rev 1997;97:1325-57
20. Semalty A, Tanwar YS, Semalty M. Preparation and characterization of cyclodextrin inclusion complex of naringenin and critical comparison with phospholipid complexation for improving solubility and dissolution. J Thermal Anal Calorim 2014;115:2471-8
21. Borghetti GS, Lula IS, Sinisterra RD, et al. Quercetin/beta-cyclodextrin solid complexes prepared in aqueous solution followed by spray-drying or by physical mixture. AAPS PharmSciTech 2009;10(1):235-42
22. Patil JS, Kadam DV, Marapur SC, et al. Inclusion complex system; a novel technique to improve the solubility and bioavailability of poorly soluble drugs. Int J Pharm Sci 2010;2(2):29-32
23. Saravana KK, Sushma M, Prasanna RY. Dissolution enhancement of poorly soluble drugs by using complexation technique-A review. J Pharm Sci Res 2013;5(5):120-4
24. Friedrich H, Nada A, Bodmier R. Solid state and dissolution rate characterization of co-ground mixtures of nifedipine and hydrophilic carriers. Drug Dev Ind Pharm 2005;31:719-28
25. Sauceau M, Rodier E, Fages J. The preparation of inclusion complex of piroxicam with cyclodextrin by using supercritical carbon dioxide. J Supercritical Fluids 2008;47(2):326-32
26. Sunkara G, Kompella UB. Drug delivery application of supercritical fluid technology. Drug Dev Technol 2002;2:44-50
27. Semalty M, Panchpuri M, Singh D, et al. Cyclodextrin inclusion complex of racecadotril: Effect of drug-beta-cyclodextrin ratio and the method of complexation. Curr Drug Discov Tech 2014; In press
28. Haiyun D, Jianbin C, Guomei Z, et al. Preparation and spectral investigation on inclusion complex of beta-cyclodextrin with rutin. Spectrochim Acta Part A 2003;59:3421-9
29. Ficarra R, Tommasini S, Raneri D, et al. Study of flavonoids/beta- cyclodextrins inclusion complexes by NMR, FTIR, DSC, x-ray investigation. J Pharm Biomed Anal 2002;29:1005-14
30. Lantz AW, Rodriguez MA, Wetterer SM, et al. Estimation of association constants between oral malodor components and various native and derivatized cyclodextrins. Anal Chim Acta 2006;557:184-90
31. Rajendrakumar K, Madhusudan S, Pralhad T. Cyclodextrin complexes of valdecoxib: Properties and antiinflammatory activity in rat. Eur J Pharm Biopharm 2005;60:39-46
32. Loftsson T, Leeves N, Sigurjonsdottir JF, et al. Sustained drug delivery system based on a cationic polymer and an anionic drug/cyclodextrin complex. Pharmazie 2001;56:746-7
33. Rode T, Frauen M, Muller BW, et al. Complex formation of sericoside with hydrophilic cyclodextrins: Improvement of solubility and skin penetration in topical emulsion based formulations. Eur J Pharm Biopharm 2003;55:191-8
34. Loftsson T, Jarho P, Masson M, et al. Cyclodextrin in drug delivery. Expert Opin Drug Deliv 2005;2:335-51
35. Monnaert V, Betbeder D, Fenart L, et al. Effects of gamma-And hydroxypropylgamma-cyclodextrins on the transport of doxorubicin across an in vitro model of blood-brain barrier. J Pharmacol Exp Ther 2004;311:1115-20
36. Monnaert V, Tilloy S, Bricout H, et al. Behavior of alpha-, beta-, and gammacyclodextrins and their derivatives on an in vitro model of blood-brain barrier. J Pharmacol Exp Ther 2004;310:745-51
37. Tilloy S, Monnaert V, Fenart L, et al. Methylated b-cyclodextrin as P-gp modulators for deliverance of doxorubicin across an in vitro model of blood-brain barrier. Bioorg Med Chem Lett 2006;16(8):2154-7
38. Loftsson T, Masson M, Sigurjonsdottir JF. Methods to enhance the complexation efficiency of cyclodextrins. STP Pharm Sci 1999;9:237-42
39. Ammar HO, Salama HA, Ghorab M, et al. Implication of inclusion complexation of glimepiride in cyclodextrin-polymer systems on its dissolution, stability and therapeutic efficacy. Int J Pharm 2006;320:53-7
40. Cao F, Guo J, Ping Q. The physicochemical characteristics of freeze-dried scutellarin-cyclodextrin tetracomponent complexes. Drug Dev Ind Pharm 2005;31:747-56
41. Nair AB, Attimarad M, Al-Dhubiab BE, et al. Enhanced oral bioavailability of acyclovir by inclusion complex using hydroxypropyl-b-cyclodextrin. Drug Deliv 2013. [Epub ahead of print]
42. Guo B, Zhong S, Li N, et al. Dissolution enhancement of cefdinir with hydroxypropyl-beta-cyclodextrin. Drug Dev Ind Pharm 2013;39(11):1638-43
43. George S, Vasudevan D. Studies on the preparation, characterization, and solubility of 2-HP-beta-cyclodextrinmeclizine HCl inclusion complexes. J Young Pharm 2012;4(4):220-7
44. Dua K, Pabreja K, Ramana MV, et al. Dissolution behavior of beta-cyclodextrin molecular inclusion complexes of aceclofenac. J Pharm Bioallied Sci 2011;3(3):417-25
45. Swami G, Koshy MK, Pandey M, et al. Preparation and characterization of domperidone-beta-CD complexes prepared by kneading method. Int J Adv Pharm Sci 2010;1:68-74
46. Li J, Zhang X. Preparation and characterization of the inclusion complex of ofloxacin with beta-CD and HP-beta-CD. J Incl Phenom Macroc Chem 2010;69:173-9
47. Sathigri S, Chandha G, Lee YHP, et al. Physicochemical characterization of efavirenze-cyclodextrin inclusion complex. AAPS Pharm Sci Tech 2008;10(1):81-7
48. Brewster ME, Vandecruys R, Peeter J, et al. Comparative interaction of 2-hydroxypropyl-beta-cyclodextrin & sulfobutylether-beta-cyclodextrin with itraconazole: Phase-solubility behavior & stabilization of supersaturated drug solutions. Eur J Pharm Sciences 2008;34:94-103
49. Karathanos VT, Mourtzinos I, Yankopoular K, et al. Study of the solubility, antioxidant activity & structure of inclusion complex of vanillin with beta-cyclodextrin. Food Chem 2007;101:652-8
50. Gibaud S, Zirar SB, Mutzeahard P, et al. Melarsoprol-cyclodextrins inclusion complexes. Int J Pharm 2005;306:107-21
51. Zheng Y, Haworth IS, Zuo Z, et al. Physicochemical and structural characterization of quercetin-b-cyclodextrin complexes. J Pharm Sci 2005;94(5):1079-89
52. Mukherjee PK, Maiti K, Kumar V. Value added drug delivery systems with botanicals: Approach for dosage development from natural resources. Pharm Rev 2007;6:57-60
53. Samuni A, Chong PLG, Barenholz Y. Physical and chemical modifications of adriamycirdron complex by phospholipid bilayers. Cancer Res 1986;46:594-9
54. Tanhuanpaa K, Cheng KH, Anttonen K. Characteristics of pyrene phospholipid/gcyclodextrin complex. Biophys J 2001;81(9):1501-10
55. Bombardelli E, Spelta M. Phospholipid-polyphenol complexes: A new concept in skin care ingredients. Cosm Toil 1991;106(3):69-76
56. Vaizoglu O, Speiser PP. Pharmacosomes: A novel drug delivery system. Acta Pharm Suec 1986;23:163-72
57. Biju SS, Talegaonkar S, Mishra PR, et al. Vesicular systems: An overview. Indian J Pharm Sci 2006;68:141-53
58. Semalty A, Semalty M, Singh R, et al. Phytosome in herbal drug delivery: A review. Indian Drugs 2006;43:937-46
59. Canty DJ, Zeisel SH. Lecithin and choline in human health and disease. Nutr Rev 1994;52:327-39
60. Lieber CS, De Carl LM, Mak KM. Attenuation of alcohol-induced hepatic fibrosis by polyunsaturated lecithin. Hepatology 1990;12:1390-8
61. Lieber CS, Leo MA, Aleynik SI. Polyenylphosphatidylcholine decreases alcohol-induced oxidative stress in the baboon. Alcohol Clin Exp Res 1997;21:375-9
62. Kosina F, Budka K, Kolouch Z. Essential cholinephospholipids in the treatment of virus hepatitis. Cas Lek Cesk 1981;120:957-60
63. Gelenberg AJ, Dorer DJ, Wojcik JD. A crossover study of lecithin treatment of tardive dyskinesia. J Clin Psychiatry 1990;51:149-53
64. Growdon JH, Gelenberg AJ, Doller J. Lecithin can suppress tardive dyskinesia. New Eng J Med 1978;298:1029-30
65. Little A, Levy R, Chuaqui-Kidd P. Double-blind, placebo-controlled trial of high-dose lecithin in Alzheimer's disease. J Neur Neurosurg Psychol 1985;48:736-42
66. Hirsch MJ, Growdon JH, Wurtman RJ. Relations between dietary choline or lecithin intake, serum choline levels, and various metabolic indices. Metabolism 1978;27:953-60
67. Hanin I, Ansell GB. Lecithin. Technological, biological and therapeutic aspects. Plenum Press; New York and London: 1987
68. Cui F, Shi K, Zhang L, et al. Biodegradable nanoparticles loaded with insulin-phospholipid complex for oral delivery: Preparation, in vitro characterization and in vivo evaluation. J Control Release 2006;114:242-50
69. Yoo HS, Park TG. Biodegradable nanoparticles containing protein-fatty acid complex for oral delivery of salmon calcitonin. J Pharm Sci 2003;93:488-95
70. Singh D, Thakur B, Semalty M, et al. Baicalein-phospholipid complex: A novel drug delivery technology for phytotherapeutics. Curr Drug Discov Technol 2013;10(3):224-32
71. Singh D, Rawat MSM, Semalty A, et al. Chrysophanol-phospholipid complex. J Therm Anal Calorim 2013;111(3):2069-77
72. Semalty A, Semalty M, Singh D, et al. Phyto-phospholipid complex of catechin in value added herbal drug delivery. J Incl Phenom Macrocycl Chem 2012;73(1-4):377-86
73. Semalty A, Semalty M, Rawat BS, et al. Pharmacosomes: The lipid based novel drug delivery system. Exp Opin Drug Deliv 2009;6:599-612
74. Khazaeinia T, Jamali F. A comparison of gastrointestinal permeability induced by diclofenacphospholipid complex with diclofenac acid and its sodium salt. J Pharm Pharm Sci 2003;6(3):352-9
75. Li Y, Yang DJ, Chen SL, et al. Comparative physicochemical characterization of phospholipids complex of puerarin formulated by conventional and supercritical methods. Pharm Res 2007;25:563-77
76. Perrut M, Jung J, Leboeuf F. Enhancement of dissolution rate of polysoluble active ingredients by supercritical fluid processes. Part I: Micronization of neat particles. Int J Pharm 2005;288:3-10
77. Reverchon E, Della Porta G, Failivene MG. Progress parameters and morphology in amoxicillin micro and submicro particles generation by supercritical antisolvent precipitation. J Supercrit Fluids 2000;17:239-48
78. Warwick B, Dehghani F, Foster NR, et al Synthesis, purification, and micronization of pharmaceuticals using the gas antisolvent technique. Ind Eng Chem Res 2000;39:4571-3
79. Shi K, Cui F, Yu Y, et al. Preparation and characterization of a novel insulinphospholipid complex. Asian J Pharm Sci 2006;1(3-4):168-74
80. Bhattacharyya S, Ahammed SM, Saha BP, et al. The gallic acidphospholipid complex improved the antioxidant potential of gallic acid by enhancing its bioavailability. AAPS PharmSciTech 2013;14(3):1025-33
81. Rawat DS, Thakur BK, Semalty M, et al. Silymarin-phospholipid complexes: A drug delivery system in NDDS. Univ J Phytochem Ayurvedic Hights 2012;1(12):4-13
82. Singh D, Rawat MSM, Semalty A, et al. Quercetin-phospholipid complex: An amorphous pharmaceutical system in herbal drug delivery. Curr Drug Discov Tech 2012;9(1):17-24
83. Singh D, Rawat MSM, Semalty A, et al. Rutin-phospholipid complex: An innovative technique in novel drug delivery system-NDDS. Curr Drug Deliv 2012;9(3):305-14
84. Singh D, Rawat MSM, Semalty A, et al. Emodin-phospholipid complex: A potential of Herbal drug in the novel drug delivery system. J Therm Anal Calorim 2012;108(1):289-98
85. Singh D, Rawat MSM, Semalty A, et al. Gallic acid-phospholipid complex: Drug incorporation and physicochemical characterization. Lett Drug Des Discov 2011;8(3):284-91
86. Wu Z, Guo L, Deng L. Preparation and evaluation of a self-emulsifying drug delivery system of etoposide-phospholipid complex. Drug Dev Ind Pharm 2011;37:103-12
87. Semalty A, Semalty M, Singh D, et al. Preparation and characterization of phospholipid complexes of naringenin for effective drug delivery. J Incl Phenom Macrocycl Chem 2010;67:253-60
88. Fricker G, Kromp T, Wendel A, et al. Phospholipids and lipid-based formulations in oral drug delivery. Pharm Res 2010;27:1469-86
89. Semalty M, Semalty A, Singh D, et al. Development and characterization of aspirin-phospholipid complex for improved drug delivery. Int J Pharm Sci Nanotechnol 2010;3:946-53
90. Semalty A, Semalty M, Singh D, et al. Development and physicochemical evaluation of pharmacosomes of diclofenac. Acta Pharm 2009;59:335-44
91. Semalty A, Semalty M, Rawat BS, et al. Development and evaluation of pharmacosomes of aceclofenac. Indian J Pharm Sci 2010;72:571-5
92. Semalty A, Semalty M, Singh D, et al. The phyto-phospholipid complexesphytosomes: A potential therapeutic approach for herbal hepatoprotective drug delivery. Pharmacogenetics Rev 2007;1:369-74
93. Semalty A, Semalty M, Rawat MSM, et al. Supramolecular phospholipidspolyphenolic interactions: The PHYTOSOME strategy to improve the bioavailability of phytochemicals. Fitoterapia 2010;81:306-14
94. Manca ML, Zaru M, Ennas G, et al. Diclofenac-beta-cyclodextrin binary systems: Physicochemical characterization and in vitro dissolution and diffusion studies. AAPS Pharm Sci Tech 2005;6:3
95. Semalty A, Tanwar YS. Nimesulide-phosphatidylcholine complex for improvement of solubility and dissolution. Am J Drug Discov Dev 2014
96. Semalty A, Tanwar YS. Preparation and characterization of cyclodextrin inclusion complexes for improving solubility and dissolution of nimesulide. World J Pharm Sci 2014;2(1):72-8.