The influence of cosolvent on the complexation of HP-β-cyclodextrins with oleanolic acid and ursolic acid

AAPS PharmSciTech

Volumn 10, Issue 4, 2009, Pages 1137-1144

  Li, Rui ^a   Quan, Peng ^b   Liu, Dong Fei ^a   Wei, Fang Di ^a   Zhang, Qing ^a   Xu, Qun Wei ^a  

^a NANJING MEDICAL UNIVERSITY   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Ethanol; Hydroxypropyl cyclodextrin; Oleanolic acid; Solubilization; Ursolic acid

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ALCOHOL; OLEANOLIC ACID; SOLVENT; URSOLIC ACID; WATER;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG SOLUBILITY; DRUG STRUCTURE; EVAPORATION; FILTRATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATHEMATICAL MODEL; PREDICTION;

AUTOMATIC DATA PROCESSING; BETA-CYCLODEXTRINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ETHANOL; OLEANOLIC ACID; SOLUBILITY; TRITERPENES;

EID: 75549090973     PISSN: None     EISSN: 15309932     Source Type: Journal    
DOI: 10.1208/s12249-009-9317-z     Document Type: Article

References (27)

1. J Liu 2005 Oleanolic acid and ursolic acid: research perspectives J Ethnopharmacol 100 92 94 10.1016/j.jep.2005.05.024 1:CAS:528: DC%2BD2MXmvVKnsbw%3D 15994040 (Pubitemid 41073528)
2. RA Prentis Y Lis SR Walker 1988 Pharmaceutical innovation by the seven UK-owned pharmaceutical companies (1964-1985) Br J Clin Pharmacol 25 387 396 1:STN:280:DyaL1c7ptlShtQ%3D%3D 3358900
3. T Loftsson P Jarho M Másson T Järvinen 2005 Cyclodextrins in drug delivery Expert Opin Drug Deliv 2 335 351 10.1517/17425247.2.1.335 1:CAS:528:DC%2BD2MXjsFantrY%3D 16296758 (Pubitemid 41130887)
4. Y Ozkan T Atay N Dikmen A Isimer HY Aboul-Enein 2000 Improvement of water solubility and in vitro dissolution rate of gliclazide by complexation with β-cyclodextrin Pharm Acta Helv 74 365 370 10.1016/S0031-6865(99)00063-1 1:CAS:528:DC%2BD3cXislaqs7s%3D 10812935 (Pubitemid 30227321)
5. S Tommasini D Raneri R Ficarra ML Calabro R Stancanelli P Ficarra 2004 Improvement in solubility and dissolution rate of flavonoids by complexation β-cyclodextrin J Pharm Biomed Anal 35 379 387 10.1016/S0731-7085(03)00647-2 1:CAS:528:DC%2BD2cXivVWrtLw%3D 15063470 (Pubitemid 38520131)
6. F Hirayama K Uekama 1999 Cyclodextrin-based controlled drug release system Adv Drug Deliv Rev 36 125 141 10.1016/S0169-409X(98)00058-1 1:CAS:528:DyaK1MXksFensw%3D%3D 10837712 (Pubitemid 29074480)
7. T Hara H Arima F Hirayama K Uekama 2006 Enhanced bioavailability of a new thiazolidine derivative FPFS-410, an antidiabetic and lipid-lowering drug, after oral administration of its hydroxypropyl-β-cyclodextrin complex to bile duct-cannulated rats J Pharm Sci 95 1771 1782 10.1002/jps.20655 1:CAS:528:DC%2BD28XnvF2itLg%3D 16795019 (Pubitemid 44229584)
8. L Wang X Jiang W Xu C Li 2007 Complexation of tanshinone IIA with 2-hydroxypropyl-b-cyclodextrin: effect on aqueous solubility, dissolution rate, and intestinal absorption behavior in rats Int J Pharm 341 58 67 10.1016/j.ijpharm.2007.03.046 1:CAS:528:DC%2BD2sXot1Cls7g%3D 17482783 (Pubitemid 47090205)
9. T Loftsson ME Brewster 1996 Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization J Pharm Sci 85 1017 1025 10.1021/js950534b 1:CAS:528:DyaK28XlsFSrsr4%3D 8897265 (Pubitemid 26338912)
10. CQ Yang LY Ding YL Lin HY Wu C Wang 2005 The phase-solubility study of the enhanced solubility of oleanolic acid by inclusion with HP-β-CD Chinese Traditional Patent Medicine 27 888 889
11. T Loftsson M Másson 2004 The effects of water-soluble polymers on cyclodextrins and cyclodextrin solubilization of drugs J Drug Deliv Sci Technol 14 35 43 1:CAS:528:DC%2BD2cXks1Kgtrw%3D
12. T Loftsson M Másson JF Sigurjónsdóttir 1999 Methods to enhance the complexation efficiency of cyclodextrins ST P Pharma Sci 9 237 242 1:CAS:528:DyaK1MXlsleiu7s%3D
13. E Rytting KA Lentz XQ Chen F Qian S Venkatesh 2004 A quantitative structure-property relationship for predicting drug solubility in PEG 400/water cosolvent systems Pharm Res 21 237 244 10.1023/B:PHAM.0000016237.06815.7a 1:CAS:528:DC%2BD2cXhtlWqt7w%3D 15032304 (Pubitemid 38221968)
14. N Bodor J Drustrup W Wu 2000 Effect of cyclodextrins on the solubility and stability of a novel soft corticosteroid, loteprednol etabonate Pharmazie 55 206 209 1:CAS:528:DC%2BD3cXhvFajurg%3D 10756542
15. Y He P Li SH Yalkowsky 2003 Solubilization of fluasterone in cosolvent/cyclodextrin combinations Int J Pharm 264 25 34 10.1016/S0378-5173(03) 00389-2 1:CAS:528:DC%2BD3sXmvF2ksL0%3D 12972333 (Pubitemid 37297631)
16. ME Brewster T Loftsson 2007 Cyclodextrins as pharmaceutical solubilizers Adv Drug Deliv Rev 59 645 666 10.1016/j.addr.2007.05.012 1:CAS:528: DC%2BD2sXpsFGks7g%3D 17601630 (Pubitemid 47299263)
17. T Higuchi KA Connors 1965 Phase-solubility techniques Adv Anal Chem Instrum 4 117 212 1:CAS:528:DyaF2MXktlGitrg%3D
18. T Loftsson D Hreinsdóttir M Másson 2005 Evaluation of cyclodextrin solubilization of drugs Int J Pharm 302 18 28 10.1016/j.ijpharm. 2005.05.042 1:CAS:528:DC%2BD2MXpvVWju7w%3D 16099118 (Pubitemid 41244817)
19. JW Millard FA Alvarez-nunez SH Yalkowsky 2002 Solubilization by cosolvents: establishing useful constants for the log-linear model Int J Pharm 245 153 166 10.1016/S0378-5173(02)00334-4 1:CAS:528:DC%2BD38XntFygsrc%3D 12270252 (Pubitemid 35299901)
20. P Li L Zhao SH Yalkowsky 1999 Combined effect of cosolvent and cyclodextrin on solubilization of nonpolar drugs J Pharm Sci 88 1107 1111 10.1021/js990159d 1:CAS:528:DyaK1MXmtVOns7c%3D 10564056 (Pubitemid 29526293)
21. P Quan DF Liu R Li Q Zhang Y Qian QW Xu 2009 The effects of water-soluble polymers on hydroxypropyl-β-cyclodextrin solubilization of oleanolic acid and ursolic acid J Incl Phenom Macro 63 181 188 10.1007/s10847-008-9505-6 1:CAS:528:DC%2BD1MXpvVCjsw%3D%3D
22. K Okimoto RA Rajewski K Uekama JA Jona VJ Stella 1996 The interaction of charged and uncharged drugs with neutral (HP-β-CD) and anionically charged (SBE7-β-CD) β-cyclodextrins Pharm Res 13 256 264 10.1023/A: 1016047215907 1:CAS:528:DyaK28Xht1Oku74%3D 8932446 (Pubitemid 26072147)
23. Moffat AC, Osselton MD, Widdop B, editors. Clarke's analysis of drugs and poisons. London: Pharmaceutical Press; 2004.
24. Yalkowsky SH. Solubility and solubilization in aqueous media. Washington: American Chemical Society; 1999.
25. T Loftsson M Másson ME Brewster 2004 Self-association of cyclodextrins and cyclodextrin complexes J Pharm Sci 93 1091 1099 10.1002/jps.20047 1:CAS:528:DC%2BD2cXjsFKisLo%3D 15067686 (Pubitemid 38529683)
26. L García-Río P Hervés JR Leis JC Mejuto J Pérez-Juste P Rodríguez-Dafonte 2006 Evidence for complexes of different stoichiometries between organic solvents and cyclodextrins Org Biomol Chem 4 1038 1048 10.1039/b513214b 16525548 (Pubitemid 43383350)
27. C Martin F Sanchez R Jimenez R Prado P Perez-Tejeda P Lopez-Cornejo 2006 Salt and solvent effects on the kinetics and thermodynamics of the inclusion of the ruthenium complex [Ru(NH3)5(4,4′-bpy)]2+ in β-cyclodextrin J Phys Chem B 110 12959 12963 10.1021/jp060659c 1:CAS:528:DC%2BD28XlsFarsLY%3D 16805599 (Pubitemid 44115628)