HEC-cysteamine conjugates: Influence of degree of thiolation on efflux pump inhibitory and permeation enhancing properties

International Journal of Pharmaceutics

Volumn 422, Issue 1-2, 2012, Pages 40-46

  Rahmat, Deni ^a   Sakloetsakun, Duangkamon ^b   Shahnaz, Gul ^a   Sarti, Federica ^a   Laffleur, Flavia ^a   Schnürch, Andreas Bernkop ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b KHON KAEN UNIVERSITY   (Thailand)

Author keywords

HEC cysteamine; In situ gelling; P gp inhibition; Permeation enhancing

Indexed keywords

FLUORESCEINISOTHIOCYANATE DEXTRAN 4; GELLING AGENT; GLUCOSE; GLYCOPROTEIN P; HYDROXYETHYLCELLULOSE; ISOTHIOCYANIC ACID DERIVATIVE; MERCAPTAMINE; PERIODATE SODIUM; RESAZURIN; RHODAMINE 123; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN CACO 2; CHEMICAL REACTION; CONTROLLED STUDY; CROSS LINKING; CYTOTOXICITY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG DETERMINATION; DRUG OXIDATION; DRUG PENETRATION; GELATION; HUMAN; HUMAN CELL; MOLECULAR INTERACTION; PRIORITY JOURNAL; THIOLATION; VISCOSITY;

BIOLOGICAL TRANSPORT; CACO-2 CELLS; CELLULOSE; CHEMISTRY, PHARMACEUTICAL; CYSTEAMINE; DEXTRANS; DISULFIDES; DRUG COMPOUNDING; FLUORESCEIN-5-ISOTHIOCYANATE; GELS; HUMANS; INTESTINAL MUCOSA; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; P-GLYCOPROTEIN; PERIODIC ACID; PERMEABILITY; RHODAMINE 123; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; TECHNOLOGY, PHARMACEUTICAL; VISCOSITY;

EID: 84655163964     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.10.024     Document Type: Article

References (29)

1. E.V. Batrakova, H. Han, V.Y. Alakhov, D.W. Miller, and A.V. Kabanov Effect of pluronic block copolymers on drug absorption in Caco-2 cell monolayers Pharm. Res. 6 1998 850 855 (Pubitemid 28307825)
2. A. Bernkop-Schnürch, C.E. Kast, and M.F. Richter Improvement in the mucoadhesive properties of alginate by the covalent attachment of cystein J. Control. Release 71 2001 277 285 (Pubitemid 32276047)
3. K.H. Bouhadir, D.S. Hausman, and D.J. Mooney Synthesis of cross-linked poly(aldehyde guluronate) hydrogels Polymer 40 1999 3575 3584 (Pubitemid 30122577)
4. A.E. Clausen, and A. Bernkop-Schnürch In vitro evaluation of the permeation-enhancing effect of thiolated polycarbophil J. Pharm. Sci. 89 2000 1253 1261
5. D. Dodou, P. Breedveld, and P.A. Wieringa Mucoadhesive in the gastrointestinal tract: revisiting the literature for novel applications Eur. J. Pharm. Biopharm. 60 2005 1 16 (Pubitemid 40545855)
6. D. Fischer, Y. Li, B. Ahlemeyer, J. Krieglstein, and T. Kissel In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis Biomaterial 24 2003 1121 1131 (Pubitemid 36069121)
7. F. Föger, H. Hoyer, K. Kafedjiiski, M. Thaurer, and A. Bernkop-Schnürch In vivo comparison of various polymeric and low molecular mass inhibitors of intestinal P-glycoprotein Biomaterial 27 2006 5855 5860 (Pubitemid 44287029)
8. A.F.S.A. Habeeb A sensitive method for localization of disulfide containing peptides in column effluents Anal. Biochem. 56 1973 60 65
9. J. Hombach, and A. Bernkop-Schnürch Chitosan solutions and particles: evaluation of their permeation enhancing potential on MDCK cells used as blood brain barrier model Int. J. Pharm. 376 2009 104 109
10. J. Hombach, T.F. Palmberger, and A. Bernkop-Schnürch Development and in vitro evaluation of a mucoadhesive vaginal delivery system for nystatin J. Pharm. Sci. 98 2009 555 564
11. J. Iqbal, J. Hombach, B. Matuszczak, and A. Bernkop-Schnürch Design and in vitro evaluation of a novel polymeric P-glycoprotein (P-gp) inhibitor J. Control. Release 147 2010 62 69
12. T. Ito, Y. Yeo, C.B. Highley, E. Bellas, C.A. Benitez, and D.S. Kohane The prevention of peritoneal adhesions by in situ cross-linking hydrogels of hyaluronic acid and cellulose derivatives Biomaterials 28 2007 975 983 (Pubitemid 44816378)
13. P. Jennings, C. Koppelstaetter, S. Aydin, T. Abberger, A.M. Wolf, G. Mayer, and W. Pfaller Cyclosporine A induces senescene in renal tubular epithelial cells AJP-Renal Physiol. 293 2007 831 838
14. K. Kafedjiiski, F. Föger, M. Werle, and A. Bernkop-Schnürch Synthesis and in vitro evaluation of a novel chitosan-glutathione conjugate Pharm. Res. 22 2005 1480 1488 (Pubitemid 41215888)
15. K.A. Kristiansen, A. Potthast, and B.E. Christensen Periodate oxidation of polysaccharides for modification of chemical and physical properties Carbohydr. Res. 345 2010 1264 1271
16. G. Millotti, C. Samberger, E. Fröhlich, and A. Bernkop-Schnürch Chitosan-graft-6-mercaptonicotinic acid: synthesis, characterization, and biocompatibility Biomacromolecules 10 2009 3023 3027
17. S. Miyazaki, W. Kubo, and D. Attwood Oral sustained delivery of theophilline using in-situ gelation of sodium alginate J. Control. Release 67 2000 275 280 (Pubitemid 30303841)
18. J. O'Brien, I. Wilson, T. Orton, and F. Pognan Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity Eur. J. Biochem. 267 2000 5421 5426
19. G.M. Pauletti, F.W. Okumu, and R.T. Borchardt Effect of size and charge on the passive diffusion of peptides across Caco-2 cell monolayers via the paracellular pathway Pharm. Res. 14 1997 164 168 (Pubitemid 27146358)
20. L. Peng, G.J. Calton, and J.W. Burnett Effect of borohydride reduction on antibodies Appl. Biochem. Biotechnol. 14 1987 91 99
21. D. Rahmat, S. Duangkamon, G. Shahnaz, G. Perera, R. Kaindl, and A. Bernkop-Schnürch Design and synthesis of a novel cationic thiomer Int. J. Pharm. 411 2011 10 17
22. D. Sakloetsakun, J. Hombach, and A. Bernkop-Schnürch In situ gelling properties of chitosan-thioglycolic acid conjugate in the presence of oxidizing agents Biomaterials 30 2009 6151 6157
23. D. Sakloetsakun, G. Millotti, A. Vetter, J. Iqbal, and A. Bernkop-Schnürch Thiolated chitosan: influence of various sulfhydryl ligands on permeation enhancing and P-gp inhibitory properties Drug Dev. Ind. Pharm. 37 2011 648 655
24. N.G.M. Schipper, S. Olsson, J. Hoogstraate, A. deBoer, K. Vrum, and P. Artursson Chitosan as absorption enhancers for poorly absorbable drugs 2: mechanism of absorption enhancement Pharm. Res. 14 1997 923 929 (Pubitemid 27326989)
25. Q. Shen, Y. Lin, T. Handa, M. Doi, M. Sugie, K. Wakayama, N. Okada, T. Fujita, and A. Yamamoto Modulation of intestinal P-glycoprotein function by polyethylene glycols and their derivatives by in vitro transport and in situ absorption studies Int. J. Pharm. 313 2006 49 56
26. M. Thanou, S. Henderson, A. Kydonieus, and C. Elson N-sulfonato-N,O- carboxymethylchitosan: a novel polymeric absorption enhancer for the oral delivery of macromolecules J. Control. Release 117 2007 171 178 (Pubitemid 46161881)
27. M. Tomita, M.J. Menconi, R.L. Delude, and M.P. Fink Polarized transport of hydrophilic compounds across rat colonic mucosa from serosa to mucosa is temperature dependent Gastroenterology 118 2000 535 554
28. M.V.S. Varma, Y. Ashokraj, C.S. Dey, and R. Panchagnula P-glycoprotein inhibitors and their screening: a perspective from bioavailability enhancement Pharmacol. Res. 48 2003 347 359 (Pubitemid 36945333)
29. V.J. Wacher, J.A. Silverman, Y. Zhang, and L.Z. Benet Role of P-glycoprotein and cytochrome P450 3A in limiting oral absorption of peptides and peptidomimetics J. Pharm. Sci. 87 1998 1322 1330