Green synthesis of quaternized chitosan nanogel using emulsion-photopolymerization as redox-responsive drug carrier

We report the green synthesis of trimethyl chitosan-functionalized poly(2-hydroxyethyl methacrylate) (PHEMA-TMC) nanogels via surfactant-free emulsion photopolymerization. TMC, a quaternized derivative of chitosan, was synthesized through methylation of chitosan, resulting in quaternary and tertiary...

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Published in:	Carbohydrate polymers Vol. 304; p. 120495
Main Authors:	Lekjinda, Kritsadayut, Sunintaboon, Panya
Format:	Journal Article
Language:	English
Published:	England Elsevier Ltd 15-03-2023
Subjects:	Amines Chitosan - pharmacology Disulfides Drug Carriers Emulsions Nanogel Nanogels Oxidation-Reduction PHEMA Polyhydroxyethyl Methacrylate Redox-responsive Riboflavin Trimethyl chitosan Visible light-induced surfactant-free emulsion polymerization Riboflavin PHEMA Visible light-induced surfactant-free emulsion polymerization Nanogel Trimethyl chitosan Redox-responsive
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Abstract	We report the green synthesis of trimethyl chitosan-functionalized poly(2-hydroxyethyl methacrylate) (PHEMA-TMC) nanogels via surfactant-free emulsion photopolymerization. TMC, a quaternized derivative of chitosan, was synthesized through methylation of chitosan, resulting in quaternary and tertiary amine groups as the main substitution products. TMC tertiary amine moiety and riboflavin (RF) acted as a redox photo-initiating system to generate free radicals for the polymerization under light irradiation. The effects of polymerization parameters such as irradiation time, concentrations of TMC and RF were investigated using MBA as crosslinker. Under the optimal condition of 1 % TMC, 4 % HEMA, 0.8 μM RF, 5 % MBA, and 4 h of polymerization time, the cationic PHEMA-TMC nanogel was synthesized with 76 % monomer conversion and an average diameter of about 106 nm. Moreover, the disulfide-crosslinked PHEMA-TMC nanogel was also synthesized using the disulfide dimethacrylate crosslinker, which exhibited a redox-induced degradation and release of encapsulated melatonin, potentially useful as a redox-responsive drug delivery carrier. [Display omitted]
AbstractList	We report the green synthesis of trimethyl chitosan-functionalized poly(2-hydroxyethyl methacrylate) (PHEMA-TMC) nanogels via surfactant-free emulsion photopolymerization. TMC, a quaternized derivative of chitosan, was synthesized through methylation of chitosan, resulting in quaternary and tertiary amine groups as the main substitution products. TMC tertiary amine moiety and riboflavin (RF) acted as a redox photo-initiating system to generate free radicals for the polymerization under light irradiation. The effects of polymerization parameters such as irradiation time, concentrations of TMC and RF were investigated using MBA as crosslinker. Under the optimal condition of 1 % TMC, 4 % HEMA, 0.8 μM RF, 5 % MBA, and 4 h of polymerization time, the cationic PHEMA-TMC nanogel was synthesized with 76 % monomer conversion and an average diameter of about 106 nm. Moreover, the disulfide-crosslinked PHEMA-TMC nanogel was also synthesized using the disulfide dimethacrylate crosslinker, which exhibited a redox-induced degradation and release of encapsulated melatonin, potentially useful as a redox-responsive drug delivery carrier. We report the green synthesis of trimethyl chitosan-functionalized poly(2-hydroxyethyl methacrylate) (PHEMA-TMC) nanogels via surfactant-free emulsion photopolymerization. TMC, a quaternized derivative of chitosan, was synthesized through methylation of chitosan, resulting in quaternary and tertiary amine groups as the main substitution products. TMC tertiary amine moiety and riboflavin (RF) acted as a redox photo-initiating system to generate free radicals for the polymerization under light irradiation. The effects of polymerization parameters such as irradiation time, concentrations of TMC and RF were investigated using MBA as crosslinker. Under the optimal condition of 1 % TMC, 4 % HEMA, 0.8 μM RF, 5 % MBA, and 4 h of polymerization time, the cationic PHEMA-TMC nanogel was synthesized with 76 % monomer conversion and an average diameter of about 106 nm. Moreover, the disulfide-crosslinked PHEMA-TMC nanogel was also synthesized using the disulfide dimethacrylate crosslinker, which exhibited a redox-induced degradation and release of encapsulated melatonin, potentially useful as a redox-responsive drug delivery carrier. [Display omitted]
ArticleNumber	120495
Author	Sunintaboon, Panya Lekjinda, Kritsadayut
Author_xml	– sequence: 1 givenname: Kritsadayut surname: Lekjinda fullname: Lekjinda, Kritsadayut – sequence: 2 givenname: Panya surname: Sunintaboon fullname: Sunintaboon, Panya email: panya.sun@mahidol.ac.th
BackLink	https://www.ncbi.nlm.nih.gov/pubmed/36641180$$D View this record in MEDLINE/PubMed
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Keywords	Riboflavin PHEMA Visible light-induced surfactant-free emulsion polymerization Nanogel Trimethyl chitosan Redox-responsive
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Snippet	We report the green synthesis of trimethyl chitosan-functionalized poly(2-hydroxyethyl methacrylate) (PHEMA-TMC) nanogels via surfactant-free emulsion...
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StartPage	120495
SubjectTerms	Amines Chitosan - pharmacology Disulfides Drug Carriers Emulsions Nanogel Nanogels Oxidation-Reduction PHEMA Polyhydroxyethyl Methacrylate Redox-responsive Riboflavin Trimethyl chitosan Visible light-induced surfactant-free emulsion polymerization
Title	Green synthesis of quaternized chitosan nanogel using emulsion-photopolymerization as redox-responsive drug carrier
URI	https://dx.doi.org/10.1016/j.carbpol.2022.120495 https://www.ncbi.nlm.nih.gov/pubmed/36641180 https://search.proquest.com/docview/2765778630
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