Can thiolation render a low molecular weight polymer of just 20-kDa mucoadhesive?

Drug Development and Industrial Pharmacy

Volumn 42, Issue 5, 2016, Pages 686-693

  Mahmood, Arshad ^a   Bonengel, Sonja ^a   Laffleur, Flavia ^a   Ijaz, Muhammad ^a   Idrees, Muneeb Ahmad ^a   Hussain, Shah ^a   Huck, Christian W ^a   Matuszczak, Barbara ^a   Bernkop Schnürch, Andreas ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

Author keywords

Controlled release; Mucoadhesion; Poly (4 styrenesulfonic acid co maleic acid) cysteamine conjugate; Rheology; Thiomers

Indexed keywords

BUFFER; CODEINE; COPOLYMER; CYANAMIDE; MERCAPTAMINE; N HYDROXYSUCCINIMIDE; PHOSPHATE; POLYMER; THIOL GROUP; ADHESIVE AGENT; MALEIC ACID DERIVATIVE; N-HYDROXYSUCCINIMIDE; POLY(4-STYRENESULFONIC ACID-CO-MALEIC ACID); POLYSTYRENE DERIVATIVE; SUCCINIMIDE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL PHENOMENA; CONJUGATE; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; DRUG RELEASE; FLOW KINETICS; MOLECULAR WEIGHT; MUCOADHESION; PH; SUSTAINED DRUG RELEASE; THIOLATION; TOXICOLOGY; VISCOSITY; YOUNG MODULUS; ANIMAL; CACO-2 CELL LINE; CHEMISTRY; DRUG DELIVERY SYSTEM; HUMAN; INTESTINE MUCOSA; METABOLISM; PIG; TUMOR CELL LINE;

ADHESIVES; ANIMALS; CACO-2 CELLS; CARBODIIMIDES; CELL LINE, TUMOR; CYSTEAMINE; DRUG DELIVERY SYSTEMS; HUMANS; INTESTINAL MUCOSA; MALEATES; MOLECULAR WEIGHT; POLYMERS; POLYSTYRENES; RHEOLOGY; SUCCINIMIDES; SULFHYDRYL COMPOUNDS; SWINE; VISCOSITY;

EID: 84968624574     PISSN: 03639045     EISSN: 15205762     Source Type: Journal    
DOI: 10.3109/03639045.2015.1061538     Document Type: Article

References (34)

1. Grabovac V, Guggi D, Bernkop-Schnürch A. Comparison of the mucoadhesive properties of various polymers. Adv Drug Deliv Rev 2005;57:1713–23.
2. Huang Y, Leobandung W, Foss A, Peppas NA. Molecular aspects of muco-and bioadhesion: tethered structures and site-specific surfaces. J Control Release 2000;65:63–71.
3. Edsman K, Hägerström H. Pharmaceutical applications of mucoadhesion for the non-oral routes. J Pharm Pharmacol 2005;57:3–22.
4. Ahuja A, Khar RK, Ali J. Mucoadhesive drug delivery systems. Drug Dev Ind Pharm 1997;23:489–515.
5. Wang YY, Lai SK, Suk JS, et al. Addressing the PEG mucoadhesivity paradox to engineer nanoparticles that ‘‘slip’’ through the human mucus barrier. Angew Chem Int Ed 2008;47: 9726–9.
6. Imam ME, Hornof M, Valenta C, et al. Evidence for the interpenetration of mucoadhesive polymers into the mucous gel layer. STP Pharm Sci 2003;13:171–6.
7. Bertram U, Bodmeier R. In situ gelling, bioadhesive nasal inserts for extended drug delivery: in vitro characterization of a new nasal dosage form. Eur J Pharm Sci 2006;27:62–71.
8. Bernkop-Schnürch A, Clausen AE, Hnatyszyn M. Thiolated polymers: synthesis and in vitro evaluation of polymer–cysteamine conjugates. Int J Pharm 2001;226:185–94.
9. Li F, Luan Y, Liu X, et al. Characterization and aggregation behaviors of mixed DDAB/SDS solution with and without poly (4- styrenesulfonic acid-co-maleic acid) sodium. J Disper Sci Technol 2011;32:1624–33.
10. Nitanan T, Akkaramongkolporn P, Rojanarata T, et al. Neomycinloaded poly (styrene sulfonic acid-co-maleic acid) (PSSA-MA)/ polyvinyl alcohol (PVA) ion exchange nanofibers for wound dressing materials. Int J Pharm 2013;448:71–8.
11. Nitanan T, Akkaramongkolporn P, Rojanarata T, et al. Thermally crosslinkable poly (styrene sulfonic acid-co-maleic acid) (PSSAMA)/ polyvinyl alcohol (PVA) ion-exchange fibers. Polym Bull 2013;70:1431–44.
12. Laffleur F, Hintzen F, Rahmat D, et al. Enzymatic degradation of thiolated chitosan. Drug Dev Ind Pharm 2013;39:1531–9.
13. Hintzen F, Laffleur F, Sakloetsakun D, et al. In situ gelling properties of anionic thiomers. Drug Dev Ind Pharm 2012;38: 1479–85.
14. Schönbichler S, Bittner L, Pallua J, et al. Simultaneous quantification of verbenalin and verbascoside in Verbena officinalis by ATR-IR and NIR spectroscopy. J Pharm Biomed 2013;84: 97–102.
15. Hussain S, Güzel Y, Schönbichler SA, et al. Solid-phase extraction method for the isolation of plant thionins from European mistletoe, wheat and barley using zirconium silicate embedded in poly (styrene-co-divinylbenzene) hollow-monoliths. Analyt Bioanalyt Chem 2013;405:7509–21.
16. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983;65:55–63.
17. Dünnhaupt S, Barthelmes J, Thurner CC, et al. S-protected thiolated chitosan: synthesis and in vitro characterization. Carbohyd Polym 2012;90:765–72.
18. Laffleur F, Shahnaz G, Islambulchilar Z, Bernkop-Schnürch A. Design and in vitro evaluation of a novel polymeric excipient for buccal applications. Future Med Chem 2013;5:511–22.
19. Hintzen F, Hauptstein S, Perera G, Bernkop-Schnürch A. Synthesis and in vitro characterization of entirely S-protected thiolated pectin for drug delivery. Eur J Pharm Sci 2013;85:1266–73.
20. Sarti F, Müller C, Iqbal J, et al. Development and in vivo evaluation of an oral Vitamin B12 delivery system. Eur J Pharm Sci 2013;84: 132–7.
21. Maquelin K, Kirschner C, Choo-Smith L-P, et al. Identification of medically relevant microorganisms by vibrational spectroscopy. J Microbiol Methods 2002;51:255–71.
22. Barth A. The infrared absorption of amino acid side chains. Prog Biophys Mol Biol 2000;74:141–73.
23. Bhatia M, Ahuja M. Thiol modification of psyllium husk mucilage and evaluation of its mucoadhesive applications. Sci World J 2013; 2013:1–7.
24. Bernkop-Schnürch A. Thiomers: a new generation of mucoadhesive polymers. Adv Drug Deliv Rev 2005;57:1569–82.
25. Duchene D, Touchard F, Peppas N. Pharmaceutical and medical aspects of bioadhesive systems for drug administration. Drug Dev Ind Pharm 1988;14:283–318.
26. Shahnaz G, Perera G, Sakloetsakun D, et al. Synthesis, characterization, mucoadhesion and biocompatibility of thiolated carboxymethyl dextran–cysteine conjugate. J Control Release 2010;144: 32–8.
27. Kafedjiiski K, Jetti RK, Föger F, et al. Synthesis and in vitro evaluation of thiolated hyaluronic acid for mucoadhesive drug delivery. Int J Pharm 2007;343:48–58.
28. Leitner V, Marschütz M, Bernkop-Schnürch A. Mucoadhesive and cohesive properties of poly (acrylic acid)-cysteine conjugates with regard to their molecular mass. Eur J Pharm Sci 2003;18:89–96.
29. Iqbal J, Shahnaz G, Dünnhaupt S, et al. Preactivated thiomers as mucoadhesive polymers for drug delivery. Biomaterials 2012;33: 1528–35.
30. Llabot JM, Salman H, Millotti G, et al. Bioadhesive properties of poly (anhydride) nanoparticles coated with different molecular weights chitosan. J Microencapsul 2011;28:455–63.
31. Millotti G, Laffleur F, Perera G, et al. In vivo evaluation of thiolated chitosan tablets for oral insulin delivery. J Pharm Sci 2014;103: 3165–70.
32. Bertram U, Bodmeier R. Effect of polymer molecular weight and of polymer blends on the properties of rapidly gelling nasal inserts. Drug Dev Ind Pharm 2012;38:659–69.
33. Patel VM, Prajapati BG, Patel MM. Formulation, evaluation, and comparison of bilayered and multilayered mucoadhesive buccal devices of propranolol hydrochloride. AAPS PharmSciTech 2007;8: E147–54.
34. Andrews GP, Laverty TP, Jones DS. Mucoadhesive polymeric platforms for controlled drug delivery. Eur J Pharm Biopharm 2009; 71:505–18.