Synthesis and in vitro characterization of a novel S-protected thiolated alginate

Carbohydrate Polymers

Volumn 124, Issue , 2015, Pages 1-7

  Hauptstein, Sabine ^a   Dezorzi, Stefanie ^a   Prüfert, Felix ^a   Matuszczak, Barbara ^a   Bernkop Schnürch, Andreas ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ALGINATE; AMINATION; AMINO ACIDS; BIOCOMPATIBILITY; COVALENT BONDS;

AQUEOUS ENVIRONMENT; DEGREE OF MODIFICATION; DISULFIDE BOND FORMATION; MERCAPTONICOTINIC ACID; MUCOADHESIVE PROPERTIES; OXIDATIVE RING-OPENING; PRIMARY AMINO GROUPS; REDUCTIVE AMINATION;

POLYMERS;

ADHESIVE AGENT; ALGINIC ACID; CYSTEINE; NICOTINIC ACID DERIVATIVE;

ANALOGS AND DERIVATIVES; ANIMAL; CACO 2 CELL LINE; CHEMISTRY; HUMAN; OXIDATION REDUCTION REACTION; SYNTHESIS; VISCOSITY;

ADHESIVES; ALGINATES; ANIMALS; CACO-2 CELLS; CYSTEINE; HUMANS; NICOTINIC ACIDS; OXIDATION-REDUCTION; VISCOSITY;

EID: 84923600690     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.01.049     Document Type: Article

References (35)

1. T.M. Allen, and P.R. Cullis Drug delivery systems: Entering the mainstream Science 303 5665 2004 1818 1822
2. G.P. Andrews, T.P. Laverty, and D.S. Jones Mucoadhesive polymeric platforms for controlled drug delivery European Journal of Pharmceutics and Biopharmceutics 71 3 2009 505 518
3. E.W. Baxter, and A.B. Reitz Reductive aminations of carbonyl compounds with borohydride and borane reducing agents Organic Reactions 59 1 2004 1 714
4. A. Bernkop-Schnürch Thiomers: A new generation of mucoadhesive polymers Advanced Drug Delivery Reviews 57 11 2005 1569 1582
5. A. Bernkop-Schnürch, C.E. Kast, and M.F. Richter Improvement in the mucoadhesive properties of alginate by the covalent attachment of cysteine Journal of Controlled Release: Official Journal of the Controlled Release Society 71 3 2001 277 285
6. A. Bernkop-Schnürch, V. Schwarz, and S. Steininger Polymers with thiol groups: A new generation of mucoadhesive polymers? Pharmaceutical Research 16 6 1999 876 881
7. A. Bernkop-Schnürch, and S. Steininger Synthesis and characterisation of mucoadhesive thiolated polymers International Journal of Pharmacy 194 2 2000 239 247
8. D. Bruneel, and E. Schacht Chemical modification of pullulan: 1. Periodate oxidation Polymer 34 12 1993 2628 2632
9. M. Davidovich-Pinhas, O. Harari, and H. Bianco-Peled Evaluating the mucoadhesive properties of drug delivery systems based on hydrated thiolated alginate Journal of Controlled Release: Official Journal of the Controlled Release Society 136 1 2009 38 44
10. S. Dünnhaupt, J. Barthelmes, J. Iqbal, G. Perera, C.C. Thurner, and H. Friedl In vivo evaluation of an oral drug delivery system for peptides based on S-protected thiolated chitosan Journal of Controlled Release: Official Journal of the Controlled Release Society 160 3 2012 477 485
11. S. Dünnhaupt, J. Barthelmes, D. Rahmat, K. Leithner, C.C. Thurner, and H. Friedl S-Protected thiolated chitosan for oral delivery of hydrophilic macromolecules: Evaluation of permeation enhancing and efflux pump inhibitory properties Molecular Pharmaceutics 9 5 2012 1331 1341
12. S. Dünnhaupt, J. Barthelmes, C.C. Thurner, C. Waldner, D. Sakloetsakun, and A. Bernkop-Schnürch S-protected thiolated chitosan: Synthesis and in vitro characterization Carbohydrate Polymers 90 2 2012 765 772
13. R. Freter, E.R. Pohl, J.M. Wilson, and D.J. Hupe Role of the central thiol in determining rates of the thiol-disulfide interchange reaction The Journal of Organic Chemistry 44 11 1979 1771 1774
14. J.F. Goodwin, and S.Y. Choi Quantification of protein solutions with trinitrobenzenesulfonic acid Clinical Chemistry 16 1 1970 24 31
15. A. Greimel, M. Werle, and A. Bernkop-Schnürch Oral peptide delivery: In-vitro evaluation of thiolated alginate/poly(acrylic acid) microparticles Journal of Pharmacy and Pharmacology 59 9 2007 1191 1198
16. E.E. Hassan, and J.M. Gallo A simple rheological method for the in vitro assessment of mucin-polymer bioadhesive bond strength Pharmaceutical Research 7 5 1990 491 495
17. S. Hauptstein, S. Bonengel, J. Griessinger, and A. Bernkop-Schnürch Synthesis and characterization of pH tolerant and mucoadhesive (thiol-polyethylene glycol) chitosan graft polymer for drug delivery Journal of Pharmaceutical Sciences 103 2 2014 594 601
18. S. Hauptstein, C. Müller, S. Dünnhaupt, F. Laffleur, and A. Bernkop-Schnürch Preactivated thiomers: Evaluation of gastroretentive minitablets International Journal of Pharmacy 456 2 2013 473 479
19. F. Hintzen, S. Hauptstein, G. Perera, and A. Bernkop-Schnürch Synthesis and in vitro characterization of entirely S-protected thiolated pectin for drug delivery European Journal of Pharmacy and Biopharmaceuticals 85 3 Pt B 2013 1266L 1273
20. F. Hintzen, F. Laffleur, D. Sakloetsakun, K. Leithner, and A. Bernkop-Schnürch In situ gelling properties of anionic thiomers Drug Development and Industrial Pharmacy 38 12 2012 1479 1485
21. J. Iqbal, G. Shahnaz, S. Dünnhaupt, C. Müller, F. Hintzen, and A. Bernkop-Schnürch Preactivated thiomers as mucoadhesive polymers for drug delivery Biomaterials 33 5 2012 1528 1535
22. 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 6 2007 975 983
23. A.B. Jindal, M.N. Wasnik, and H.A. Nair Synthesis of thiolated alginate and evaluation of mucoadhesiveness, cytotoxicity and release retardant properties Indian Journal of Pharmaceutical Sciences 72 6 2010 766 774
24. C. Le-Tien, M. Millette, M. Lacroix, and M.A. Mateescu Modified alginate matrices for the immobilization of bioactive agents Biotechnology and Applied Biochemistry 39 Pt 2 2004 189L 198
25. V.M. Leitner, G.F. Walker, and A. Bernkop-Schnürch Thiolated polymers: Evidence for the formation of disulphide bonds with mucus glycoproteins European Journal of Pharmceutics and Biopharmceutics 56 2 2003 207 214
26. C. Muller, D. Rahmat, F. Sarti, K. Leithner, and A. Bernkop-Schnürch Immobilization of 2-mercaptoethylamine on oxidized chitosan: A substantially mucoadhesive and permeation enhancing polymer Journal of Materials Chemistry 22 9 2012 3899 3908
27. T.F. Palmberger, K. Albrecht, B. Loretz, and A. Bernkop-Schnürch Thiolated polymers: Evaluation of the influence of the amount of covalently attached l-cysteine to poly(acrylic acid) European Journal of Pharmceutics and Biopharmceutics 66 3 2007 405 412
28. J.A. Plumb Cell sensitivity assays: The MTT assay Methods in Molecular Medicine 28 1999 25 30
29. D. Quintanar-Guerrero, R. Villalobos-García, E. Alvarez-Colín, and J.M. Cornejo-Bravo In vitro evaluation of the bioadhesive properties of hydrophobic polybasic gels containing N,N-dimethylaminoethyl methacrylate-co-methyl methacrylate Biomaterials 22 9 2001 957 961
30. D. Rahmat, D. Sakloetsakun, G. Shahnaz, G. Perera, R. Kaindl, and A. Bernkop-Schnürch Design and synthesis of a novel cationic thiolated polymer International Journal of Pharmacy 411 1-2 2011 10 17
31. J. Siepmann, and N.A. Peppas Modeling of drug release from delivery systems based on hydroxypropyl methylcellulose (HPMC) Advanced Drug Delivery Reviews 48 2-3 2001 139 157
32. J.D. Smart The basics and underlying mechanisms of mucoadhesion Advanced Drug Delivery Reviews 57 11 2005 1556 1568
33. H.H. Tønnesen, and J. Karlsen Alginate in drug delivery systems Drug Development and Industrial Pharmacy 28 6 2002 621 630
34. X. Wang, J. Iqbal, D. Rahmat, and A. Bernkop-Schnürch Preactivated thiomers: Permeation enhancing properties International Journal of Pharmacy 438 1-2 2012 217 224
35. T.W. Wong Alginate graft copolymers and alginate-co-excipient physical mixture in oral drug delivery Journal of Pharmacy and Pharmacology 63 12 2011 1497 1512