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Synthesis of chitosan iodoacetamides via carbodiimide coupling reaction: Effect of degree of substitution on the hemostatic properties.
Carbohydr Polym 2020; 229:115522CP

Abstract

Uncontrolled hemorrhage continues to be the leading cause of death from traumatic injuries both in the battlefield and in the civilian life. Chitosan is among the very few materials that have made the short list of military recommended field-deployable hemostatic dressings. However, the detailed mechanism of its action is still not fully understood. Moreover, in the cases when patients developed coagulopathy, the efficacy of the dressings rely solely on those mechanisms that work outside of the regular blood coagulation cascade. In addition to the well-known erythrocyte agglutination, we proposed to use the reactive N-iodoacetyl group on a new chitosan derivative to accelerate hemostasis. In this paper, we describe the synthesis of chitosan iodoacetamide (CI) with considerations of the stoichiometry among the reagents, the choice of solvent, the pH of the reaction medium, and the reaction time. The reaction was confirmed by FT-IR, 1H and 13C NMR, elemental analysis, iodine content analysis, and SEM-EDS. Water contact angle measurements and Erythrocyte Sedimentation Rate (ESR) method were used to evaluate the hemostatic potential of the newly synthesized CI as a function of their degree of substitution (DS). The range of DS was 5.9% to 27.8% for CI. The mid-range of DS gave the best results for the ESR. CIs exhibit favorable cytocompatibilities up to DS 18.7 compared to the generic unmodified chitosan. In general, the biocompatibility of chitosan iodoacetamide slightly declined with increasing the iodide content up to DS 21.5 owing to its affinity to SH groups of cells.

Authors+Show Affiliations

Department of Textile Engineering Chemistry & Science, North Carolina State University, Raleigh, NC 27695-8301, United States.Department of Textile Engineering Chemistry & Science, North Carolina State University, Raleigh, NC 27695-8301, United States; Pre-treatment and Finishing of Cellulosic Fibers Dept., Textile Research Division, National Research Centre (Scopus Affiliation ID 60014618), Dokki, Giza, Egypt.Pre-treatment and Finishing of Cellulosic Fibers Dept., Textile Research Division, National Research Centre (Scopus Affiliation ID 60014618), Dokki, Giza, Egypt.Department of Textile Engineering Chemistry & Science, North Carolina State University, Raleigh, NC 27695-8301, United States. Electronic address: shudson@ncsu.edu.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31826420

Citation

Shen, Jialong, et al. "Synthesis of Chitosan Iodoacetamides Via Carbodiimide Coupling Reaction: Effect of Degree of Substitution On the Hemostatic Properties." Carbohydrate Polymers, vol. 229, 2020, p. 115522.
Shen J, Nada AA, Abou-Zeid NY, et al. Synthesis of chitosan iodoacetamides via carbodiimide coupling reaction: Effect of degree of substitution on the hemostatic properties. Carbohydr Polym. 2020;229:115522.
Shen, J., Nada, A. A., Abou-Zeid, N. Y., & Hudson, S. M. (2020). Synthesis of chitosan iodoacetamides via carbodiimide coupling reaction: Effect of degree of substitution on the hemostatic properties. Carbohydrate Polymers, 229, p. 115522. doi:10.1016/j.carbpol.2019.115522.
Shen J, et al. Synthesis of Chitosan Iodoacetamides Via Carbodiimide Coupling Reaction: Effect of Degree of Substitution On the Hemostatic Properties. Carbohydr Polym. 2020 Feb 1;229:115522. PubMed PMID: 31826420.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of chitosan iodoacetamides via carbodiimide coupling reaction: Effect of degree of substitution on the hemostatic properties. AU - Shen,Jialong, AU - Nada,Ahmed Ali, AU - Abou-Zeid,Nabil Yousrie, AU - Hudson,Samuel M, Y1 - 2019/10/31/ PY - 2018/10/29/received PY - 2019/08/23/revised PY - 2019/10/22/accepted PY - 2019/12/13/entrez PY - 2019/12/13/pubmed PY - 2019/12/13/medline KW - Carbohydrates KW - Chitosan iodoacetamide KW - Hemorrhages KW - Topical hemostatic dressings SP - 115522 EP - 115522 JF - Carbohydrate polymers JO - Carbohydr Polym VL - 229 N2 - Uncontrolled hemorrhage continues to be the leading cause of death from traumatic injuries both in the battlefield and in the civilian life. Chitosan is among the very few materials that have made the short list of military recommended field-deployable hemostatic dressings. However, the detailed mechanism of its action is still not fully understood. Moreover, in the cases when patients developed coagulopathy, the efficacy of the dressings rely solely on those mechanisms that work outside of the regular blood coagulation cascade. In addition to the well-known erythrocyte agglutination, we proposed to use the reactive N-iodoacetyl group on a new chitosan derivative to accelerate hemostasis. In this paper, we describe the synthesis of chitosan iodoacetamide (CI) with considerations of the stoichiometry among the reagents, the choice of solvent, the pH of the reaction medium, and the reaction time. The reaction was confirmed by FT-IR, 1H and 13C NMR, elemental analysis, iodine content analysis, and SEM-EDS. Water contact angle measurements and Erythrocyte Sedimentation Rate (ESR) method were used to evaluate the hemostatic potential of the newly synthesized CI as a function of their degree of substitution (DS). The range of DS was 5.9% to 27.8% for CI. The mid-range of DS gave the best results for the ESR. CIs exhibit favorable cytocompatibilities up to DS 18.7 compared to the generic unmodified chitosan. In general, the biocompatibility of chitosan iodoacetamide slightly declined with increasing the iodide content up to DS 21.5 owing to its affinity to SH groups of cells. SN - 1879-1344 UR - https://www.unboundmedicine.com/medline/citation/31826420/Synthesis_of_chitosan_iodoacetamides_via_carbodiimide_coupling_reaction:_Effect_of_degree_of_substitution_on_the_hemostatic_properties L2 - https://linkinghub.elsevier.com/retrieve/pii/S0144-8617(19)31190-7 DB - PRIME DP - Unbound Medicine ER -