Rapamycin-cyclodextrin complexation: Improved solubility and dissolution rate

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 70, Issue 1-2, 2011, Pages 167-175

  Abdur Rouf, M ^a   Vural, Imran ^b   Bilensoy, Erem ^b   Hincal, Atilla ^b   Erol, Dilek Demir ^a  

^a YEDITEPE UNIVERSITY   (Turkey)

^b HACETTEPE UNIVERSITY   (Turkey)

Author keywords

Cyclodextrin; Dissolution; Rapamycin; Sirolimus

Indexed keywords

EID: 79955990118     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9885-2     Document Type: Article

References (33)

1. H Baker A Sidorowicz SN Sehgal 1978 Rapamycin (AY-22, 989), a new antifungal antibiotic. III. In vitro and in vivo evaluation J. Antibiot. (Tokyo) 31 539 545 1:CAS:528:DyaE1MXjsFU%3D (Pubitemid 8402848)
2. RR Martel J Klicius S Galet 1977 Inhibition of the immune response by rapamycin, a new antifungal antibiotic Can. J. Physiol. Pharmacol. 55 48 51 10.1139/y77-007 1:CAS:528:DyaE2sXltFWrsLs%3D (Pubitemid 8061941)
3. SJ Collier 1989 Immunosuppressive drugs Curr. Opin. Immunol. 2 854 858 10.1016/0952-7915(89)90169-6 1:CAS:528:DyaK3MXlvFOnu78%3D (Pubitemid 20354641)
4. FJ Dumont MJ Staruch SL Koprak MR Melino NH Sigal 1990 Distinct mechanisms of suppression of murine T cell activation by the related macrolides FK-506 and rapamycin J. Immunol. 144 251 258 1:CAS:528:DyaK3cXptFCgsA%3D%3D (Pubitemid 20030485)
5. AM Woltman SW van der Kooij PJ Coffer R Offringa MR Daha C van Kooten 2003 Rapamycin specifically interferes with GMCSF signaling in human dendritic cells, leading to apoptosis via increased p27KIP1 expression Blood 101 1439 1445 10.1182/blood-2002-06-1688 1:CAS:528:DC%2BD3sXht1agurY%3D (Pubitemid 36182518)
6. CP Eng SN Sehgal C Vezina 1984 Activity of rapamycin (AY-22, 989) against transplanted tumors J. Antibiot. (Tokyo) 37 1231 1237 1:CAS:528: DyaL2cXmt1ahsLo%3D (Pubitemid 14015835)
7. R Yatscoff 1996 Pharmacokinetics of rapamycin Transplant Proc. 28 970 973 1:CAS:528:DyaK28XjtVGltrY%3D (Pubitemid 26138500)
8. Rapamune® Label and Patient Information, Wyeth Pharmaceuticals Inc. Philadelphia, PA 19101. http://www.accessdata.fda.gov/drugsatfda-docs/label/ 2004/21083s017,21110s020lbl.pdf (2010). Accessed 29 June 2010
9. De, T., Trieu, V., Yim, Z., Cordia, J., Yang, A., Beals, B., Ci, S., Louie, L., Desai, N.: Nanoparticle albumin-bound (nab) rapamycin as an anticancer agent [abstract]. In: Proceedings of the 98th Annual Meeting of the American Association for Cancer Research, Los Angeles, Meeting Abstracts, 14-18 April 2007
10. AY Alemdar D Sadi VC McAlister I Mendez 2004 Liposomal formulations of tacrolimus and rapamycin increase graft survival and fiber outgrowth of dopaminergic grafts Cell Transplant. 13 263 271 10.3727/000000004783983936 (Pubitemid 38620968)
11. MA Rouf I Vural J-M Renoir AA Hincal 2009 Development and characterization of liposomal formulations for rapamycin delivery and investigation of their antiproliferative effect on MCF7 cells J. Liposome Res. 19 4 322 331 10.3109/08982100902963043 1:CAS:528:DC%2BD1MXhtlektbvJ
12. G Buech E Bertelmann U Pleyer I Siebenbrodt HH Borchert 2007 Formulation of sirolimus eye drops and corneal permeation studies J. Ocul. Pharmacol. Ther. 23 292 303 10.1089/jop.2006.130 1:CAS:528:DC%2BD2sXntVKqs7k%3D (Pubitemid 46986611)
13. ML Forrest CY Won AW Malick GS Kwon 2006 In vitro release of the mTOR inhibitor rapamycin from poly(ethylene glycol)-b-poly(epsilon-caprolactone) micelles J. Control Release 110 370 377 10.1016/j.jconrel.2005.10.008 1:CAS:528:DC%2BD2MXhtlert7nJ (Pubitemid 41827491)
14. NN Kipshidze TR Porter G Dangas H Yazdi F Tio F Xie D Hellinga R Wolfram R Seabron R Waksman A Abizaid G Roubin S Iyer A Colombo MB Leon JW Moses P Iversen 2005 Novel site-specific systemic delivery of Rapamycin with perfluorobutane gas microbubble carrier reduced neointimal formation in a porcine coronary restenosis model Catheter Cardiovasc. Interv. 64 389 394 10.1002/ccd.20285 (Pubitemid 40322056)
15. PS Brara M Moussavian MA Grise JP Reilly M Fernandez RA Schatz PS Teirstein 2003 Pilot trial of oral rapamycin for recalcitrant restenosis Circulation 107 1722 1724 10.1161/01.CIR.0000066282.05411.17 (Pubitemid 36418349)
16. GM Ray JJ Nawarskas WH Frishman 2006 The paclitaxel-eluting stent in percutaneous coronary intervention: part II: Comparison with the sirolimus-eluting stent, economics, and unanswered questions Cardiol. Rev. 14 143 150 10.1097/01.crd.0000214683.72810.87 (Pubitemid 44350385)
17. NM Pires BL Hoeven van, der MR de Vries LM Havekes BJ van Vlijmen WE Hennink PH Quax JW Jukema 2005 Local perivascular delivery of anti-restenotic agents from a drug-eluting poly(epsilon-caprolactone) stent cuff Biomaterials 26 5386 5394 10.1016/j.biomaterials.2005.01.063 1:CAS:528:DC%2BD2MXivFKru70%3D (Pubitemid 40462353)
18. JE Sousa AG Sousa MA Costa AC Abizaid F Feres 2003 Use of rapamycin-impregnated stents in coronary arteries Trans. Proc. 35 165S 170S 10.1016/S0041-1345(03)00215-X 1:CAS:528:DC%2BD3sXksFGqtbY%3D (Pubitemid 36547939)
19. X Wang SS Venkatraman FY Boey JS Loo LP Tan 2006 Controlled release of sirolimus from a multilayered PLGA stent matrix Biomaterials 27 5525 5588
20. L Szente J Szejtli 1999 Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development Adv. Drug Deliv. Rev. 36 17 38 10.1016/S0169-409X(98)00092-1 1:CAS:528:DyaK1MXksFegtw%3D%3D (Pubitemid 29074474)
21. R Challa A Ahuja J Ali RK Khar 2005 Cyclodextrins in drug delivery: an updated review AAPS Pharm. Sci. Tech. 6 E329 E357 10.1208/pt060243 (Pubitemid 41631739)
22. T Higuchi KA Connors 1965 Phase-solubility techniques Adv. Anal. Chem. Instrum. 4 117 212 1:CAS:528:DyaF2MXktlGitrg%3D
23. H Nogami T Nagai Y Yotsuyanagi 1969 Dissolution phenomena of organic medicinals involving simultaneous phase change Chem. Pharm. Bull. 17 499 509 1:CAS:528:DyaF1MXktlegtL8%3D
24. G Trapani A Latrofa M Franco MR Pantaleo E Sanna F Massa F Tuveri G Liso 2000 Complexation of zolpidem with 2-hydroxypropyl -, methyl -, and 2-hydroxypropyl-γ-cyclodextrin: effect on aqueous solubility, dissolution rate, and ataxic activity in rat J. Pharm. Sci. 89 1443 1451 10.1002/1520-6017(200011)89:11<1443::AID-JPS7>3.0.CO;2-Q 1:CAS:528:DC%2BD3cXnvVygtr8%3D
25. GM Ferron WD Conway WJ Jusko 1997 Lipophilic benzamide and anilide derivatives as high-performance liquid chromatography internal standards: application to sirolimus(rapamycin) determination J. Chromatog. B 703 243 251 10.1016/S0378-4347(97)00415-5 1:CAS:528:DyaK1cXktlaqtg%3D%3D (Pubitemid 28011264)
26. DW Holt T Lee K Jones A Johnston 1997 Validation of an assay for routine monitoring of sirolimus using HPLC with mass spectrometric detection Clin. Chem. 46 1179 1183
27. K Uekama 1985 Pharmaceutical applications of methylated cyclodextrins Pharm. Int. 6 61 65 1:CAS:528:DyaL2MXitV2hsrY%3D (Pubitemid 15144297)
28. L Liu Q-X GUO 2002 The driving forces in the inclusion complexation of cyclodextrins J. Incl. Phenom. Macrocycl. Chem. 42 1 14 10.1023/A:1014520830813 1:CAS:528:DC%2BD38XivFymsrc%3D (Pubitemid 38075810)
29. F Otero-Espinar S Anguiano-Igea J Garcia-Gonzalez J Vila-Jato J Blanco-Mendez 1992 Interaction of naproxen with b-cyclodextrin in solution and in the solid state Int. J. Pharm. 79 149 157 10.1016/0378-5173(92)90106-C 1:CAS:528:DyaK38XhsFylu7c%3D
30. Kacso, I., Borodi, G., Farcas, S. I., and Bratu, I: Inclusion compound of vitamin B13 in β-Cyclodextrin. J. Phys.: Conference Series 182 (2009). doi: 10.1088/1742-6596/182/1/012009
31. M Hassan M Suleiman N Najib 1990 Improvement of the in vitro dissolution characteristics of famotidine by inclusion in b-cyclo-dextrin Int. J. Pharm. 58 19 24 10.1016/0378-5173(90)90282-9 1:CAS:528:DyaK3cXhs1CrtL4%3D (Pubitemid 20034223)
32. HC Marques J Hadgraft I Kallaway 1990 Studies of cyclodextrin inclusion complexes. I. The salbutamol-cyclodextrin complex as studied by phase solubility and DSC Int. J. Pharm. 63 259 266 10.1016/0378-5173(90)90132-N
33. J Szejtli 1994 Medicinal applications of cyclodextrins Med. Res. Rev. 14 353 386 10.1002/med.2610140304 1:CAS:528:DyaK2cXls1ekt7o%3D (Pubitemid 24142073)