Thiolated chitosan as mucoadhesive polymers for buccal drug delivery
Article Sidebar
Main Article Content
Abstract
Buccal mucosa has been interested for local and systemic drug delivery due to the avoidance of gastrointestinal enzyme degradation and hepatic first pass metabolism. However, buccal drug delivery needs to be designed as mucoadhesive dosage forms by mucoadhesive polymers. Chitosan is a natural mucoadhesive polymer. The positive amino groups of chitosan interact with anionic substructures in mucus layer to form electrostatic mucoadhesive interaction which are non-specific and suffer short retention time. Thus, the chitosan derivarives have been synthesized to enhance mucoadhesive property. Thiolated chitosan is chitosan polymer, having thiol (-SH) bearing side chains. The thiol groups can form disulfide bonds or covalent bonds with cysteine-rich subdomains of mucus glycoproteins and hence the improvement of chemical interactions. This covalent interaction exhibits the much higher mucoadhesive property than the electrostatic interaction of chitosan. Various thiolated chitosan are synthesized such as chitosan-cysteine conjugate, chitosan-thioglycolic acid, chitosan-thioethylamidine and chitosan-4-thio-butylamidine by the formation amide or amidine bonds with thiol bearing compounds. The mucoadhesive force and time of thiolated chitosan are higher than unmodified chitosan. Furthermore, the mucoadhesive property depends on the amount of thiol group in the polymer chains which is determined by Ellman’s reagent. Recently, thiolated chitosan has been used as mucoadhesive polymer to develop wafers, xerogels and tablets for buccal drug delivery.
Article Details
In the case that some parts are used by others The author must Confirm that obtaining permission to use some of the original authors. And must attach evidence That the permission has been included
References
Ayensu I, Mitchell JC, Boateng JS. In vitro characterisation of chitosan based xerogels for potential buccal delivery of proteins. Carbohyd Polym 2012;89:935–941.
Bernkop-Schnürch A, Hornof M, Guggi D. Thiolated chitosans. Eur J Pharm Biopharm 2004;57:9–17.
Bernkop-Schnürch A. Thiomers: A new generation of mucoadhesive polymers. Adv Drug Deliver Rev 2005;57(11):1569–1582.
Boateng JS, Ayensu I. Preparation and characterization of laminated thiolated chitosan-based freeze-dried wafers for potential buccal delivery of macromolecules. Drug Dev Ind Pharm 2014;40(5):611–618.
Dünnhaupt 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 2012a;160(3):477–485.
Dünnhaupt S, Barthelmes J, Thurner CC, et al. S-protected thiolated chitosan: Synthesis and in vitro characterization. Carbohyd Polym 2012b;90(2):765–772.
Hauptstein S, Bonengel N, Griessinger J, et al. Synthesis and characterization of pH tolerant and mucoadhesive (thiol–polyethylene glycol) chitosan graft polymer for drug delivery. J Pharm Sci 2014;103:594–601.
Hearnden V, Sankar V, Hull K, et al. New developments and opportunities in oral mucosal drug delivery for local and systemic disease. Adv Drug Deliver Rev 2012;64:16–28.
Kafedjiiski K, Föger F, Werle M, et al. Synthesis and in vitro evaluation of a novel hitosan–glutathione conjugate. Pharm Res 2005a;22(9):1480–1488.
Kafedjiiski K, Hofferb M, Werlec M, et al. Improved synthesis and in vitro characterization of chitosan–thioethylamidine conjugate. Biomaterials 2006;27:127–135.
Kafedjiiski K, Krauland AH, Hoffer MH, et al. Synthesis and in vitro evaluation of a novel thiolated chitosan. Biomaterials 2005b;26:819–826.
Laffleur F. Mucoadhesive polymers for buccal drug delivery. Drug Dev Ind Pharm. 2014;40(5):591–598.
Langoth N, Kahlbacher H, Schöffmann G, et al. Thiolated chitosans: Design and in vivo evaluation of a mucoadhesive buccal peptide drug delivery system. Pharm Res 2006;23(3):573–579.
Maculotti K, Genta I, Perugini P, et al. Preparation and in vitro evaluation of thiolated chitosan microparticles. J Microencapsul 2005;22(5):459–470.
Mortazavian E, Dorkoosh FA, Rafiee-Tehrani M. Design, characterization and ex vivo evaluation of chitosan film integrating of insulin nanoparticles composed of thiolated chitosan derivative for buccal delivery of insulin. Drug Dev Ind Pharm. 2014;40(5):691–698
Moussa SA, Farouk AF, Opwis K, et al. Production, characterization and antibacterial activity of Mucor rouxii DSM-119 chitosan. J Textile Sci Engg 2011;1:105.
Naz K, Shahnaz G, Ahmed M, et al. Formulation and in vitro characterization of thiolated buccoadhesive film of fluconazole. AAPS PharmSciTech 2016; DOI: 10.1208/s12249-016-0607-y.
Rao NGR, Shravani B, Reddy MS. Overview on buccal drug delivery system. J Pharm Sci & Res 2013;5(4):80–88.
Roldo M, Hornof M, Caliceti P, et al. Mucoadhesive thiolated chitosans as platforms for oral controlled drug delivery: synthesis and in vitro evaluation. Eur J Pharm Biopharm 2004;57:115–121.
Russo E, Selmin F, Baldassari S, et al. A focus on mucoadhesive polymers and their application in buccal dosage forms. J Drug Deliv Sci Tec 2016;32:113–125.
Salamat-Miller N, Chittchang M, Johnston TP. The use of mucoadhesive polymers in buccal drug delivery. Adv Drug Deliver Rev 2005;57(11):1666–1691.
Samprasit W, Rojanarata T, Akkaramongkolporn P, et al. Fabrication and in vitro/in vivo performance of mucoadhesive electrospun nanofiber mats containing α-mangostin. AAPS PharmSciTech 2015;16(5):1140–1152.
Schmitz T, Grabovac V, Palmberger TF, et al. Synthesis and characterization of a chitosan-N-acetyl cysteine conjugate. Int J Pharm 2008;347:79–85.
Sogias IA, Williams AC, Khutoryanskiy VV. Why is chitosan mucoadhesive?. Biomacromolecules 2008;9:1837–1842.
Sreenivas SA, Pai KV. Thiolated Chitosans: Novel polymers for mucoadhesive drug delivery – A review. Trop J Pharm Res 2008;7(3):1077-1088.
Sudhakar Y, Kuotsu K, Bandyopadhyay AK. Buccal bioadhesive drug delivery — A promising option for orally less efficient drugs. J Control Release 2006;114:15–40.
Tonglairoum P, Ngawhirunpat T, Rojanarata T. et al., Fabrication o fmucoadhesive chitosan coated polyvinylpyrrolidone/cyclodextrin/clotrimazole sandwich patches for oral candidiasis. Carbohyd Polym 2015;132:173–179.
Tonglalroum P, Opanasopit P. Thiomers: a new generation mucoadhesive polymer for tranmucosal drug delivery systems. TBPS. 2013;8(1):19–27.