Design and in vitro evaluation of a novel polymeric excipient for buccal applications

Future Medicinal Chemistry

Volumn 5, Issue 5, 2013, Pages 511-522

  Laffleur, Flavia ^a   Shahnaz, Gul ^a   Islambulchilar, Ziba ^a   Bernkop Schnürch, Andreas ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

2 IMINOTHIOLANE; CHITOSAN; EXCIPIENT; MERCAPTONICOTINAMIDE; NICOTINAMIDE DERIVATIVE; POLYMER; THIOL GROUP; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CELL VIABILITY; CHEEK MUCOSA; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; CYTOTOXICITY; DISULFIDE BOND; DRUG ABSORPTION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG PENETRATION; DRUG RELEASE; DRUG SCREENING; DRUG SOLUBILITY; DRUG STABILITY; HUMAN; HUMAN CELL; HYDROGEN BOND; IN VITRO STUDY; MUCOADHESION; NONHUMAN; PRIORITY JOURNAL; TABLET DISINTEGRATION; TABLET HARDNESS; TENSILE STRENGTH; WATER TRANSPORT;

ADMINISTRATION, BUCCAL; ANIMALS; CACO-2 CELLS; CELL SURVIVAL; CHITIN; CHITOSAN; DRUG CARRIERS; EXCIPIENTS; HARDNESS; HUMANS; NIACINAMIDE; RHODAMINE 123; SULFHYDRYL COMPOUNDS; SWINE; TABLETS; WATER;

EID: 84876151940     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.13.33     Document Type: Article

References (40)

1. Langoth N, Kalbe J, Bernkop-Schnurch A. Development of buccal drug delivery systems based on a thiolated polymer. Int. J. Pharm. 252(1-2), 141-148 (2003).
2. Bouckaert S, Vakaet L, Remon JP. Influence of the buccal application site of a bioadhesive slow-release tablet on salivary miconazole concentrations in irradiated patients. Int. J. Pharm. 130(2), 257-260 (1996).
3. Laffleur F, Hintzen F, Rahmat D, Shahnaz G, Millotti G, Bernkop-Schnurch A. Enzymatic degradation of thiolated chitosan. Drug Dev. Ind. Pharm. doi:10.3109/0363904 5.2012.719901 (2012) (Epub ahead of print).
4. Shahnaz G, Vetter A, Barthelmes J et al. Thiolated chitosan nanoparticles for the nasal administration of leuprolide: bioavailability and pharmacokinetic characterization. Int. J. Pharm. 428(1-2), 164-170 (2012).
5. Laffleur F, Bernkop-Schnurch A. Thiomers: promising platform for macromolecular drug delivery. Future Med. Chem. 4(17), 2205-2216 (2012).
6. Dunnhaupt S, Barthelmes J, Iqbal J et al. In vivo evaluation of an oral drug delivery system for peptides based on S-protected thiolated chitosan. J. Control. Release 160(3), 477-485 (2012).
7. Dunnhaupt S, Barthelmes J, Rahmat D et al. S-protected thiolated chitosan for oral delivery of hydrophilic macromolecules: evaluation of permeation enhancing and efflux pump inhibitory properties. Mol. Pharm. 9(5), 1331-1341 (2012).
8. Dunnhaupt S, Barthelmes J, Thurner CC, Waldner C, Sakloetsakun D, Bernkop- Schnurch A. S-protected thiolated chitosan: synthesis and in vitro characterization. Carbohyd. Polym. 90(2), 765-772 (2012).
9. Solhi L, Schonbichler SA, Dunnhaupt S et al. Synthesis and in vitro characterization of a preactivated thiomer via polymerization reaction. Biomacromolecules 13(10), 3054-3063 (2012).
10. Forrest HS, Walker J. Chemotherapeutic agents of the sulphone type; 2 : 5-disubstituted derivatives of pyridine. J. Chem. Soc. 70, 1939-1945 (1948).
11. Carlsson J, Drevin H, Axen R. Protein thiolation and reversible protein-protein conjugation. N-Succinimidyl 3-(2-pyridyldithio)propionate, a new heterobifunctional reagent. Biochem. J. 173(3), 723-737 (1978).
12. Norris R, Brocklehurst K. A convenient method of preparation of high-activity urease from Canavalia ensiformis by covalent chromatography and an investigation of its thiol groups with 2,2́-dipyridyl disulphide as a thiol titrant and reactivity probe. Biochem. J. 159(2), 245-257 (1976).
13. Bernkop-Schnurch A, Kast CE, Richter MF. Improvement in the mucoadhesive properties of alginate by the covalent attachment of cysteine. J. Control. Release 71(3), 277-285 (2001).
14. Shahnaz G, Iqbal J, Rahmat D et al. Development and in vivo characterization of a novel peptide drug delivery system providing extended plasma half life. J. Control. Release 157(3), 375-382 (2012).
15. Bernkop-Schnurch A, Steininger S. Synthesis and characterisation of mucoadhesive thiolated polymers. Int. J. Pharm. 194(2), 239-247 (2000).
16. Jennings P, Koppelstaetter C, Pfaller W, Morin JP, Hartung T, Ryan MP. Assessment of a new cell culture perfusion apparatus for in vitro chronic toxicity testing. Part 2: toxicological evaluation. ALTEX 21(2), 61-66 (2004).
17. Rahmat D, Sakloetsakun D, Shahnaz G, Sarti F, Laffleur F, Schnurch AB. HEC-cysteamine conjugates: influence of degree of thiolation on efflux pump inhibitory and permeation enhancing properties. Int. J. Pharm. 422(1-2), 40-46 (2012).
18. Peh KK, Wong CF. Polymeric films as vehicle for buccal delivery: swelling, mechanical, and bioadhesive properties. J. Pharm. Sci. 2(2), 53-61 (1999).
19. Iqbal J, Shahnaz G, Dunnhaupt S, Muller C, Hintzen F, Bernkop-Schnurch A. Preactivated thiomers as mucoadhesive polymers for drug delivery. Biomaterials 33(5), 1528-1535 (2012).
20. Kafedjiiski K, Hoffer M, Werle M, Bernkop- Schnurch A. Improved synthesis and in vitro characterization of chitosan-thioethylamidine conjugate. Biomaterials 27(1), 127-135 (2006).
21. Wertz PW, Squier CA. Cellular and molecular basis of barrier function in oral epithelium. Crit. Rev. Ther. Drug Carrier Syst. 8(3), 237-269 (1991).
22. Bernkop-Schnurch A, Konig V, Leitner VM, Krauland AH, Brodnik I. Preparation and characterisation of thiolated poly(methacrylic acid)-starch compositions. Eur. J. Pharm. Biopharm. 57(2), 219-224 (2004).
23. Shahnaz G, Perera G, Sakloetsakun D, Rahmat D, Bernkop-Schnurch A. Synthesis, characterization, mucoadhesion and biocompatibility of thiolated carboxymethyl dextran-cysteine conjugate. J. Control. Release 144(1), 32-38 (2010).
24. Roldo M, Hornof M, Caliceti P, Bernkop- Schnurch A. Mucoadhesive thiolated chitosans as platforms for oral controlled drug delivery: synthesis and in vitro evaluation. Eur. J. Pharm. Biopharm. 57(1), 115-121 (2004).
25. Guggi D, Langoth N, Hoffer MH, Wirth M, Bernkop-Schnurch A. Comparative evaluation of cytotoxicity of a glucosamine- TBA conjugate and a chitosan-TBA conjugate. Int. J. Pharm. 278(2), 353-360 (2004).
26. Sakloetsakun D, Hombach JM, Bernkop- Schnurch A. In situ gelling properties of chitosan-thioglycolic acid conjugate in the presence of oxidizing agents. Biomaterials 30(31), 6151-6157 (2009).
27. Kast CE, Bernkop-Schnurch A. Thiolated polymers - thiomers: development and in vitro evaluation of chitosan-thioglycolic acid conjugates. Biomaterials 22(17), 2345-2352 (2001).
28. Bernkop-Schnurch A, Krauland AH, Leitner VM, Palmberger T. Thiomers: potential excipients for noninvasive peptide delivery systems. Eur. J. Pharm. Biopharm. 58(2), 253-263 (2004).
29. Barrett WC, DeGnore JP, Konig S et al. Regulation of PTP1B via glutathionylation of the active site cysteine 215. Biochemistry 38(20), 6699-6705 (1999).
30. Smart JD. Buccal drug delivery. Expert Opin. Drug Deliv. 2(3), 507-517 (2005).
31. Smart JD. Recent developments in the use of bioadhesive systems for delivery of drugs to the oral cavity. Crit. Rev. Ther. Drug Carrier Syst. 21(4), 319-344 (2004).
32. Zhang Y, Law Y, Chakrabarti S. Physical properties and compact analysis of commonly used direct compression binders. AAPS PharmSciTech 4(4), E62 (2003).
33. Mortazavi SA, Smart JD. An Investigation into the Role of Water-Movement and Mucus Gel Dehydration in Mucoadhesion. J. Control. Release 25(3), 197-203 (1993).
34. Duchene D, Ponchel G. Principle and investigation of the bioadhesion mechanism of solid dosage forms. Biomaterials 13(10), 709-714 (1992).
35. Guggi D, Marschutz MK, Bernkop-Schnurch A. Matrix tablets based on thiolated poly(acrylic acid): pH-dependent variation in disintegration and mucoadhesion. Int. J. Pharm. 274(1-2), 97-105 (2004).
36. Patel VF, Liu F, Brown MB. Advances in oral transmucosal drug delivery. J. Control. Release 153(2), 106-116 (2011).
37. Leitner VM, Walker GF, Bernkop-Schnurch A. Thiolated polymers: evidence for the formation of disulphide bonds with mucus glycoproteins. Eur. J. Pharm. Biopharm. 56(2), 207-214 (2003).
38. Smart JD. Lectin-mediated drug delivery in the oral cavity. Adv. Drug Deliv. Rev. 56(4), 481-489 (2004).
39. Cioffi EA, Bailey WF. Facile preparation of pyrylium and pyridinium bromides under neutral conditions. Tetrahedron Lett. 39(18), 2679-2680 (1998).
40. Welker E, Narayan M, Wedemeyer WJ, Scheraga HA. Structural determinants of oxidative folding in proteins. Proc. Natl Acad. Sci. USA 98(5), 2312-2316 (2001).