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Controlled synthesis of N,N,N-trimethyl chitosan for modulated bioadhesion and nasal membrane permeability.
Int J Biol Macromol. 2016 Jan; 82:933-44.IJ

Abstract

In an experiment to explore the bioadhesion, biocompatibility, and membrane permeation properties, the controlled synthesis of N,N,N-trimethyl chitosan (TMC) was carried out by two-step reductive methylation of chitosan (CHT). Methylation was confirmed by (1)H NMR (δ=3.1 ppm) and FTIR analysis (CH stretch at 1,485 cm(-1)). The TMC was further characterized by DSC, TGA, XRD, HR-TEM, SEM, and elemental analysis. Findings revealed improved solubility, enhanced viscosity, increased swelling index and higher molecular weight of TMC over CHT. Comparative evaluation validated increased bioadhesion potential, and improved ex vivo biocompatibility of TMC compared to CHT. Increased bioadhesion of TMC NPs over CHT NPs can be attributed to the strong electrostatic interactions between cationic amino groups with anionic sialic and sulfonic acid moieties contained in the mucin of the nasal mucus. Ex vivo biocompatibility studies suggested that the NP formulations of both biopolymers were biocompatible and could be applied safely on the nasal epithelium. Ex vivo permeation studies executed on excised cattle nasal mucosa illustrated improved permeability of TMC NPs over CHT NPs. In the author's opinion, two-step reductive methylation of CHT could be an attractive strategy to improve its solubility, bioadhesion, and permeation characteristics without affecting biocompatibility across the mucosal surfaces.

Authors+Show Affiliations

Industrial Pharmacy Laboratory, Department of Pharmaceutics, R. C. Patel Institute of Pharmaceutical Education and Research, Shirpur, Maharashtra, India. Electronic address: chandrakantpardeshi11@gmail.com.Department of Pharmaceutical Sciences, RTM Nagpur University, Nagpur, Maharashtra, India. Electronic address: vbelgamwar@gmail.com.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26562548

Citation

Pardeshi, Chandrakantsing V., and Veena S. Belgamwar. "Controlled Synthesis of N,N,N-trimethyl Chitosan for Modulated Bioadhesion and Nasal Membrane Permeability." International Journal of Biological Macromolecules, vol. 82, 2016, pp. 933-44.
Pardeshi CV, Belgamwar VS. Controlled synthesis of N,N,N-trimethyl chitosan for modulated bioadhesion and nasal membrane permeability. Int J Biol Macromol. 2016;82:933-44.
Pardeshi, C. V., & Belgamwar, V. S. (2016). Controlled synthesis of N,N,N-trimethyl chitosan for modulated bioadhesion and nasal membrane permeability. International Journal of Biological Macromolecules, 82, 933-44. https://doi.org/10.1016/j.ijbiomac.2015.11.012
Pardeshi CV, Belgamwar VS. Controlled Synthesis of N,N,N-trimethyl Chitosan for Modulated Bioadhesion and Nasal Membrane Permeability. Int J Biol Macromol. 2016;82:933-44. PubMed PMID: 26562548.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Controlled synthesis of N,N,N-trimethyl chitosan for modulated bioadhesion and nasal membrane permeability. AU - Pardeshi,Chandrakantsing V, AU - Belgamwar,Veena S, Y1 - 2015/11/10/ PY - 2015/09/10/received PY - 2015/10/22/revised PY - 2015/11/05/accepted PY - 2015/11/13/entrez PY - 2015/11/13/pubmed PY - 2016/10/14/medline KW - Chitosan KW - Methyl iodide (PubChem CID: 6328) KW - Mucoadhesion KW - N,N,N-Trimethyl chitosan KW - N-Methyl-2-pyrrolidinone (PubChem CID: 13387) KW - Nanoparticles KW - Nasal delivery KW - Polysaccharides KW - Reductive methylation KW - Sodium iodide (PubChem CID: 5238) SP - 933 EP - 44 JF - International journal of biological macromolecules JO - Int. J. Biol. Macromol. VL - 82 N2 - In an experiment to explore the bioadhesion, biocompatibility, and membrane permeation properties, the controlled synthesis of N,N,N-trimethyl chitosan (TMC) was carried out by two-step reductive methylation of chitosan (CHT). Methylation was confirmed by (1)H NMR (δ=3.1 ppm) and FTIR analysis (CH stretch at 1,485 cm(-1)). The TMC was further characterized by DSC, TGA, XRD, HR-TEM, SEM, and elemental analysis. Findings revealed improved solubility, enhanced viscosity, increased swelling index and higher molecular weight of TMC over CHT. Comparative evaluation validated increased bioadhesion potential, and improved ex vivo biocompatibility of TMC compared to CHT. Increased bioadhesion of TMC NPs over CHT NPs can be attributed to the strong electrostatic interactions between cationic amino groups with anionic sialic and sulfonic acid moieties contained in the mucin of the nasal mucus. Ex vivo biocompatibility studies suggested that the NP formulations of both biopolymers were biocompatible and could be applied safely on the nasal epithelium. Ex vivo permeation studies executed on excised cattle nasal mucosa illustrated improved permeability of TMC NPs over CHT NPs. In the author's opinion, two-step reductive methylation of CHT could be an attractive strategy to improve its solubility, bioadhesion, and permeation characteristics without affecting biocompatibility across the mucosal surfaces. SN - 1879-0003 UR - https://www.unboundmedicine.com/medline/citation/26562548/Controlled_synthesis_of_NNN_trimethyl_chitosan_for_modulated_bioadhesion_and_nasal_membrane_permeability_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0141-8130(15)30105-7 DB - PRIME DP - Unbound Medicine ER -