title: Synthesis of mucoadhesive thiolated gelatin using a two-step reaction process.
abstract: Using a novel two-step approach, the thiolation of gelatin for mucoadhesive drug delivery has been achieved. The initial step involved the amination of native gelatin via an amine to carboxylic acid coupling reaction with ethylene diamine, followed by thiolation with Traut's reagent. The resulting thiolated product showed an increase in thiol content of up to 10-fold in comparison with control gelatin samples. Improved cohesion and mucoadhesion in comparison with unmodified and control gelatin samples was also observed. This reaction process was observed to be influenced by both the temperature and the pH of the amination reaction, affecting both amine content and product yield. Swelling ability, cohesion and mucoadhesion were all observed to be strongly dependent on the thiol content of the samples but also, importantly, the molecular weight (MW) of the gelatin used. Gelatin with a MW of 20-25 kDa proved to be optimal in creating this novel mucoadhesive gelatin material.
authors: Pharmaceutical and Molecular Biotechnology Research Centre, Department of Chemical and Life Sciences, Waterford Institute of Technology, Waterford, Ireland. Electronic address: 20052625@mail.wit.ie.
authors: Sarah
authors: S
authors: Duggan
authors: Pharmaceutical and Molecular Biotechnology Research Centre, Department of Chemical and Life Sciences, Waterford Institute of Technology, Waterford, Ireland.
authors: Orla
authors: O
authors: O'Donovan
authors: Pharmaceutical and Molecular Biotechnology Research Centre, Department of Chemical and Life Sciences, Waterford Institute of Technology, Waterford, Ireland.
authors: Eleanor
authors: E
authors: Owens
authors: Pharmaceutical and Molecular Biotechnology Research Centre, Department of Chemical and Life Sciences, Waterford Institute of Technology, Waterford, Ireland.
authors: Wayne
authors: W
authors: Cummins
authors: Pharmaceutical and Molecular Biotechnology Research Centre, Department of Chemical and Life Sciences, Waterford Institute of Technology, Waterford, Ireland.
authors: Helen
authors: H
authors: Hughes
mesh_terms: D000268:Adhesiveness; D000586:Amination / Q000187:drug effects; D000818:Animals; D002417:Cattle; D003432:Cross-Linking Reagents / Q000737:chemistry / Q000494:pharmacology; D016503:Drug Delivery Systems; D005029:Ethylenediamines / Q000737:chemistry / Q000494:pharmacology; D005780:Gelatin / Q000737:chemistry* / Q000378:metabolism; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D007096:Imidoesters / Q000737:chemistry / Q000494:pharmacology; D007202:Indicators and Reagents / Q000737:chemistry / Q000494:pharmacology; D007413:Intestinal Mucosa / Q000378:metabolism*; D008855:Microscopy, Electron, Scanning; D008970:Molecular Weight; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013499:Surface Properties; D034421:Sus scrofa; D014867:Water / Q000032:analysis
chemical_list: D003432:Cross-Linking Reagents; D005029:Ethylenediamines; D007096:Imidoesters; D007202:Indicators and Reagents; D011108:Polymers; D013438:Sulfhydryl Compounds; D014867:Water; C031234:ethylenediamine; C005905:methyl 4-mercaptobutyrimidate; D005780:Gelatin
keywords: Amination; Ethylene diamine; Gelatin; Mucoadhesion; Thiolation; Traut’s reagent; Two-step reaction