Effect of cyclodextrin complexation on the liposome permeability of a model hydrophobic weak acid

Pharmaceutical Research

Volumn 25, Issue 11, 2008, Pages 2505-2515

  Joguparthi, Vijay ^a,b   Anderson, Bradley D ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

Camptothecins; Controlled drug delivery; Cyclodextrin complexation; DB 67; Hydroxypropyl cyclodextrin; Liposomes; Membrane transport

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; 7 TERT BUTYLDIMETHYLSILYL 10 HYDROXYCAMPTOTHECIN; DB 67; LIPOSOME; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; COMPLEX FORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDRATION; HYDROPHOBICITY; IONIZATION; LIGHT SCATTERING; MEMBRANE BINDING; MEMBRANE PERMEABILITY; MEMBRANE TRANSPORT; OSMOLALITY; PARTICLE SIZE; PH; PRIORITY JOURNAL;

BETA-CYCLODEXTRINS; BIOLOGICAL TRANSPORT; CAMPTOTHECIN; CHEMISTRY, PHARMACEUTICAL; EXCIPIENTS; HYDROGEN-ION CONCENTRATION; HYDROPHOBICITY; LIPID BILAYERS; LIPOSOMES; ORGANOSILICON COMPOUNDS; PERMEABILITY;

EID: 53849088181     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-008-9664-6     Document Type: Article

References (26)

1. A. A. Gabizon 2002 Liposomal drug carrier systems in cancer chemotherapy: current status and future prospects J. Drug Target 10 535 538
2. D. D. Lasic B. Ceh M. C. Stuart L. Guo P. M. Frederik Y. Barenholz 1995 Transmembrane gradient driven phase transitions within vesicles: lessons for drug delivery Biochim Biophys Acta 1239 145 156
3. E. Maurer-Spurej K. F. Wong N. Maurer D. B. Fenske P. R. Cullis 1999 Factors influencing uptake and retention of amino-containing drugs in large unilamellar vesicles exhibiting transmembrane pH gradients Biochim. Biophys. Acta 1416 1 10
4. R. P. Hertzberg M. J. Caranfa S. M. Hecht 1989 On the mechanism of topoisomerase I inhibition by camptothecin: evidence for binding to an enzyme-DNA complex Biochemistry 28 4629 4638
5. V. Joguparthi B. D. Anderson 2008 Liposomal delivery of hydrophobic weak acids: enhancement of drug retention using a high intraliposomal pH J. Pharm. Sci. 97 433 454
6. V. Joguparthi T. X. Xiang B. D. Anderson 2008 Liposome transport of hydrophobic drugs: gel phase lipid bilayer permeability and partitioning of the lactone form of a hydrophobic camptothecin, DB-67 J. Pharm. Sci. 97 400 420
7. V. Joguparthi S. Feng B. D. Anderson 2008 Determination of intraliposomal pH and its effect on membrane partitioning and passive loading of a hydrophobic camptothecin, DB-67 Int. J. Pharm. 352 17 28
8. B. McCormack G. Gregoriadis 1994 Entrapment of cyclodextrin-drug complexes into liposomes: potential advantages in drug delivery J. Drug Target 2 449 454
9. B. McCormack G. Gregoriadis 1996 Comparative studies of the fate of free and liposome-entrapped hydroxypropyl-b-cyclodextrin/drug complexes after intravenous injection into rats: implications in drug delivery Biochim. Biophys. Acta 1291 237 244
10. H. Chen J. Gao F. Wang W. Liang 2007 Preparation, characterization and pharmacokinetics of liposomes-encapsulated cyclodextrins inclusion complexes for hydrophobic drugs Drug Deliv. 14 201 208
11. D. G. Fatouros K. Hatzidimitriou S. G. Antimisiaris 2001 Liposomes encapsulating prednisolone and prednisolone-cyclodextrin complexes: comparison of membrane integrity and drug release Eur. J. Pharm. Sci. 13 287 296
12. Y. Hagiwara H. Arima Y. Miyamoto F. Hirayama K. Uekama 2006 Preparation and pharmaceutical evaluation of liposomes entrapping salicylic acid/gamma-cyclodextrin conjugate Chem. Pharm. Bull (Tokyo) 54 26 32
13. F. Maestrelli M. L. Gonzalez-Rodriguez A. M. Rabasco P. Mura 2006 Effect of preparation technique on the properties of liposomes encapsulating ketoprofen-cyclodextrin complexes aimed for transdermal delivery Int. J. Pharm. 312 53 60
14. G. Piel M. Piette V. Barillaro D. Castagne B. Evrard L. Delattre 2006 Betamethasone-in-cyclodextrin-in-liposome: the effect of cyclodextrins on encapsulation efficiency and release kinetics Int. J. Pharm. 312 75 82
15. I. I. Salem N. Duzgunes 2003 Efficacies of cyclodextrin-complexed and liposome-encapsulated clarithromycin against Mycobacterium avium complex infection in human macrophages Int. J. Pharm. 250 403 414
16. P. Hatzi S. Mourtas P. G. Klepetsanis S. G. Antimisiaris 2007 Integrity of liposomes in presence of cyclodextrins: effect of liposome type and lipid composition Int. J. Pharm. 333 167 176
17. S. L. Niu B. J. Litman 2002 Determination of membrane cholesterol partition coefficient using a lipid vesicle-cyclodextrin binary system: effect of phospholipid acyl chain unsaturation and headgroup composition Biophys. J. 83 3408 3415
18. H. Ohvo J. P. Slotte 1996 Cyclodextrin-mediated removal of sterols from monolayers: effects of sterol structure and phospholipids on desorption rate Biochemistry 35 8018 8024
19. J. Nishijo H. Mizuno 1998 Interactions of cyclodextrins with DPPC liposomes. Differential scanning calorimetry studies Chem. Pharm. Bull. (Tokyo) 46 120 124
20. G. Puglisi M. Fresta C. Ventura 1996 Interaction of natural and modified b-cyclodextrins with biological membrane model of dipalmitoylphosphatidylcholine J. Colloid Interface Sci. 180 542 547
21. J. Nishijo S. Shiota K. Mazima Y. Inoue H. Mizuno J. Yoshida 2000 Interactions of cyclodextrins with dipalmitoyl, distearoyl, and dimyristoyl phosphatidyl choline liposomes. A study by leakage of carboxyfluorescein in inner aqueous phase of unilamellar liposomes Chem. Pharm. Bull. (Tokyo) 48 48 52
22. G. Piel M. Piette V. Barillaro D. Castagne B. Evrard L. Delattre 2007 Study of the relationship between lipid binding properties of cyclodextrins and their effect on the integrity of liposomes Int. J. Pharm. 338 35 42
23. J. Fassberg V. J. Stella 1992 A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues J. Pharm. Sci. 81 676 684
24. P. S. Uster T. M. Allen B. E. Daniel C. J. Mendez M. S. Newman G. Z. Zhu 1996 Insertion of poly(ethylene glycol) derivatized phospholipid into pre-formed liposomes results in prolonged in vivo circulation time FEBS Lett. 386 243 246
25. T. X. Xiang B. D. Anderson 2002 Stable supersaturated aqueous solutions of silatecan 7-t-butyldimethylsilyl-10-hydroxycamptothecin via chemical conversion in the presence of a chemically modified b-cyclodextrin Pharm. Res. 19 1215 1222
26. J. R. Silvius M. J. Zuckermann 1993 Interbilayer transfer of phospholipid-anchored macromolecules via monomer diffusion Biochemistry 32 3153 3161