High-throughput phase-distribution method to determine drug-cyclodextrin binding constants

Journal of Pharmaceutical Sciences

Volumn 98, Issue 1, 2009, Pages 229-238

  Chen, Zhi ^a   Lu, Dujuan ^a   Weber, Stephen C ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Binding constant; Complexation; Cyclodextrin; Distribution; High throughput technologies; Solubility

Indexed keywords

2 HYDROXYPROPYL BETA CYLODEXTRIN; 2,6 O DIMETHYL BETA CYCLODEXTRIN; ALPHA CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; ECONAZOLE; HEPTAKIS(2,3,6 O TRIMETHYL) BETA CYCLODEXTRIN; HYDROXYETHYL BETA CYCLODEXTRIN; MICONAZOLE; POLYVINYLCHLORIDE; SEBACIC ACID; SEBACIC ACID DIOCTYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; DRUG BINDING; DRUG DISTRIBUTION; DRUG FORMULATION; DRUG SOLUBILITY; HIGH THROUGHPUT SCREENING;

EID: 58149267688     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21396     Document Type: Article

References (40)

1. Loftsson T, Hreinsdottir D, Masson M. 2005. Evaluation of cyclodextrin solubilization of drugs. Int J Pharm 302:18-28.
2. Das NG, Das SK. 2006. Formulation of poorly soluble drugs. Drug Delivery Report Spring/Summer: 52-55.
3. Hedges AR. 1998. Industrial applications of cyclodextrins. Chem Rev 98:2035-2044.
4. Uekama K, Hirayama F, Irie T. 1998. Cyclodextrin drug carrier systems. Chem Rev 98:2045-2076.
5. Loftsson T, Brewster ME, Masson M. 2004. Role of cyclodextrins in improving oral drug delivery. Am J Drug Deliv 2:261-275.
6. Hirsch W, Fried V, Altman L. 1985. Effect of cyclodextrins on sparingly soluble salts. J Pharm Sci 74:1123-1125.
7. Bodor N, Buchwald P. 2003. Theoretical insights into the formation, structure, and energetics of some cyclodextrin complexes. J Inclusion Phenomena Macrocyclic Chem 44:9-14.
8. Rao VM, Stella VJ. 2003. When can cyclodextrins be considered for solubilization purposes? J Pharm Sci 92:927-932.
9. Lipinski CA. 2001. Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods 44:235-249.
10. Chen J, Ohnmacht CM, Hage DS. 2004. Characterization of drug interactions with soluble β-cyclodextrin by high-performance affinity chromatography, J Chromatogr A 1033:115-126.
11. Schou C, Heegaard NHH. 2006. Recent applications of affinity interactions in capillary electrophoresis. Electrophoresis 27:44-59.
12. Schipper BR, Ramstad T. 2005. Determination of the binding constant between alprostadil and alpha-cyclodextrin by capillary electrophoresis: Implications for a freeze-dried formulation. J Pharm Sci 94:1528-1537.
13. Karakasyan C, Taverna M, Millot M-C. 2004. Determination of binding constants of hydrophobically end-capped poly(ethylene glycol)s with beta-cyclodextrin by affinity capillary electrophoresis. J Chromatogr A 1032:159-164.
14. Rundlett KL, Armstrong DW. 2001. Methods for the determination of binding constants by capillary electrophoresis. Electrophoresis 22:1419-1427.
15. Sideris EE, Georgiou CA, Koupparis MA, Macheras PE. 1994. Automated flow-injection serial dynamic dialysis technique in the study of drug binding with cyclodextrins. Anal Chim Acta 289:87-95.
16. Beni S, Szakacs Z, Csernak O, Barcza L, Noszal B. 2007. Cyclodextrin/imatinib complexation: Binding mode and charge dependent stabilities. Eur J Pharm Sci 30:167-174.
17. Archontaki HA, Vertzoni MV, Athanassiou-Malaki MH. 2002. Study on the inclusion complexes of bromazepam with β- and β-hydroxypropyl- cyclodextrins. J Pharm Biomed Anal 28:761-769.
18. Koopmans C, Ritter H. 2007. Color change of N-isopropylacrylamide copolymer bearing reichardts dye as optical sensor for lower critical solution temperature and for host-guest interaction with β-cyclodextrin. J Am Chem Soc 129:3502-3503.
19. Sheehy PM, Ramstad T. 2005. Determination of the molecular complexation constant between alprostadil and alpha-cyclodextrin by conductometry. J Pharm Biomed Anal 39:877-885.
20. Kahle C, Holzgrabe U. 2004, Determination of binding constants of cyclodextrin inclusion complexes with amino acids and dipeptides by potentiometric titration. Chirality 16:509-515.
21. Higuchi T, Connors KA. 1965. Phase-solubility techniques. Advan Anal Chem Instr 4:117-212.
22. Loukas YL. 1997. Inclusion complexation of unstable guests with cyclodextrins: Improved kinetic studies for the calculation of the binding constants in guest-cyclodextrin systems. Pharm Sci 3:343-346.
23. Loukas YL, Vraka V, Gregoriadis G. 1996. Use of a nonlinear least-squares model for the kinetic determination of the stability constant of cyclodextrin inclusion complexes. Int J Pharm 144: 225-231.
24. Masson M, Sigurdardottir BV, Matthiasson K, Loftsson T. 2005. Investigation of drug-cyclodextrin complexes by a phase-distribution method: Some theoretical and practical considerations. Chem Pharm Bull 53:958-964.
25. Eli W, Chen W, Xue Q. 2000. Determination of association constants of cyclodextrin-nonionic surfactant inclusion complexes by a partition coefficient method. J Inclusion Phenomena Macrocyclic Chem 38:37-43.
26. Senisterra GA, Markin E, Yamazaki K, Hui R, Vedadi M, Awrey DE. 2006. Screening for ligands using a generic and high-throughput light-scattering-based assay. J Biomol Screen 11:940-948.
27. Hallikas O, Taipale J. 2006. High-throughput assay for determining specificity and affinity of protein-DNA binding interactions. Nat Protoc 1:215-222.
28. Li S, Sun L, Chung Y, Weber SG. 1999. Artificial receptor-facilitated solid-phase microextraction of barbiturates. Anal Chem 71:2146-2151.
29. Valenta JN, Dixon RP, Hamilton AD, Weber SG. 1994. Enhanced extraction of phenobarbital from serum with a designed artificial receptor. Anal Chem 66:2397-2403.
30. Chen Z, Weber SG. 2007. High-throughput method for lipophilicity measurement. Anal Chem 79:1043-1049.
31. Chen Z, Yang Y, Werner S, Wipf P, Weber SG. 2006. A screening method for chiral selectors that does not require covalent attachment. J Am Chern Soc 128:2208-2209.
32. Mura P, Faucci MT, Manderioli A, Bramanti G. 2001. Multicomponent systems of econazole with hydroxyacids and cyclodextrins. J Inclusion Phenomena Macrocyclic Chem 39:131-138.
33. Guillaume YC, Peyrin E. 1999. Symmetry breaking during the formation of β-cyclodextrin-imidazole inclusion compounds: Capillary electrophoresis study. Anal Chem 71:2046-2052.
34. Pedersen M, Bjerregaard S, Jacobsen J, Rommelmayer Larsen A, Mehlsen Sorensen A. 1998. An econazole β-cyclodextrin inclusion complex: An unusual dissolution rate, supersaturation, and biological efficacy example. Int J Pharm 165:57-68.
35. Pedersen M. 1994. Isolation and antimycotic effect of a genuine miconazole-β-cyclodextrin complex. Eur J Pharm Biopharm 40:19-23.
36. El-Barghouthi MI, Masoud NA, Al-Kafawein JK, Abdoh AA. 2006. Inclusion complexation of itraconazole with β- and 2-hydroxypropyl-β- cyclodextrins in aqueous solutions. Russ J Phys Chem 80:1050-1055.
37. Peeters J, Neeskens P, Tollenaere JP, Van Remoortere P, Brewster ME. 2002. Characterization of the interaction of 2-hydroxypropyl-β-cyclo- dextrin with itraconazole at pH 2, 4, and 7. J Pharm Sci 91:1414-1422.
38. Miyake K, Irie T, Arima H, Hirayama F, Uekama K, Hirano M, Okamaoto Y. 1999. Characterization of itraconazole/2-hydroxypropyl-beta-cyclodextrin inclusion complex in aqueous propylene glycol solution. Int J Pharm 179:237-245.
39. Pedersen M, Edelsten M, Nielsen VF, Scarpellini A, Skytte S, Slot C. 1993. Formation and antimycotic effect of cyclodextrin inclusion complexes of econazole and miconazole. Int J Pharm 90:247-254.
40. Poole SK, Poole CF. 2003. Separation methods for estimating octanol-water partition coefficients. J Chromatogr B Anal Technol Biomed Life Sci 797:3-19.