New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties
Novel imidazole derivatives of the low molecular weight chitosan N-(2-hydroxypropyl)-1H-1,2,3-triazol-4-yl)methyl)-1-methyl-1H-imidazol-3-ium chitosan chloride (NMIC) were synthesized using copper-catalyzed azide–alkyne cycloaddition (CuAAC). The degrees of substitution (DSs) for the new derivatives...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-07-01
|
| Series: | Biomimetics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2313-7673/8/3/302 |
| _version_ | 1797590100771602432 |
|---|---|
| author | Natalia Drozd Alexey Lunkov Balzhima Shagdarova Alla Il’ina Valery Varlamov |
| author_facet | Natalia Drozd Alexey Lunkov Balzhima Shagdarova Alla Il’ina Valery Varlamov |
| author_sort | Natalia Drozd |
| collection | DOAJ |
| description | Novel imidazole derivatives of the low molecular weight chitosan N-(2-hydroxypropyl)-1H-1,2,3-triazol-4-yl)methyl)-1-methyl-1H-imidazol-3-ium chitosan chloride (NMIC) were synthesized using copper-catalyzed azide–alkyne cycloaddition (CuAAC). The degrees of substitution (DSs) for the new derivatives were 18–76%. All chitosan derivatives (2000 µg/mL) were completely soluble in water. The antimicrobial activity of the new compounds against <i>E. coli</i> and <i>S. epidermidis</i> was studied. The effect of chitosan derivatives on blood and its components was studied. NMIC samples (DS 34–76%) at a concentration <10 μg/mL had no effect on blood and plasma coagulation. Chitosan derivatives (DS 18–76%) at concentrations of ≥83 μg/mL in blood and ≥116.3 μg/mL in plasma resulted in a prolongation of the clotting time of blood and plasma, positively related to the DS. At concentrations up to 9.1 μg/mL, NMIC did not independently provoke platelet aggregation. The degree of erythrocyte hemolysis upon contact with NMIC samples (2.5–2500 μg/mL) was below 4%. The inhibition of blood/plasma coagulation indicates the promising use of the studied samples to modify the surface of medical materials in order to achieve thromboresistance. |
| first_indexed | 2024-03-11T01:15:38Z |
| format | Article |
| id | doaj.art-6c3d20fc92674ea5a7f036a51622657a |
| institution | Directory Open Access Journal |
| issn | 2313-7673 |
| language | English |
| last_indexed | 2024-03-11T01:15:38Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomimetics |
| spelling | doaj.art-6c3d20fc92674ea5a7f036a51622657a2023-11-18T18:29:50ZengMDPI AGBiomimetics2313-76732023-07-018330210.3390/biomimetics8030302New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial PropertiesNatalia Drozd0Alexey Lunkov1Balzhima Shagdarova2Alla Il’ina3Valery Varlamov4National Medical Center for Hematology, 4, Novoi Zykovsky Prospect, Moscow 125167, RussiaInstitute of Bioengineering, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect, 33, Build. 2, Moscow 119071, RussiaInstitute of Bioengineering, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect, 33, Build. 2, Moscow 119071, RussiaInstitute of Bioengineering, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect, 33, Build. 2, Moscow 119071, RussiaInstitute of Bioengineering, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect, 33, Build. 2, Moscow 119071, RussiaNovel imidazole derivatives of the low molecular weight chitosan N-(2-hydroxypropyl)-1H-1,2,3-triazol-4-yl)methyl)-1-methyl-1H-imidazol-3-ium chitosan chloride (NMIC) were synthesized using copper-catalyzed azide–alkyne cycloaddition (CuAAC). The degrees of substitution (DSs) for the new derivatives were 18–76%. All chitosan derivatives (2000 µg/mL) were completely soluble in water. The antimicrobial activity of the new compounds against <i>E. coli</i> and <i>S. epidermidis</i> was studied. The effect of chitosan derivatives on blood and its components was studied. NMIC samples (DS 34–76%) at a concentration <10 μg/mL had no effect on blood and plasma coagulation. Chitosan derivatives (DS 18–76%) at concentrations of ≥83 μg/mL in blood and ≥116.3 μg/mL in plasma resulted in a prolongation of the clotting time of blood and plasma, positively related to the DS. At concentrations up to 9.1 μg/mL, NMIC did not independently provoke platelet aggregation. The degree of erythrocyte hemolysis upon contact with NMIC samples (2.5–2500 μg/mL) was below 4%. The inhibition of blood/plasma coagulation indicates the promising use of the studied samples to modify the surface of medical materials in order to achieve thromboresistance.https://www.mdpi.com/2313-7673/8/3/302chitosanchitosan derivativesclick chemistryhemocompatibility |
| spellingShingle | Natalia Drozd Alexey Lunkov Balzhima Shagdarova Alla Il’ina Valery Varlamov New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties Biomimetics chitosan chitosan derivatives click chemistry hemocompatibility |
| title | New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties |
| title_full | New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties |
| title_fullStr | New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties |
| title_full_unstemmed | New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties |
| title_short | New N-Methylimidazole-Functionalized Chitosan Derivatives: Hemocompatibility and Antibacterial Properties |
| title_sort | new n methylimidazole functionalized chitosan derivatives hemocompatibility and antibacterial properties |
| topic | chitosan chitosan derivatives click chemistry hemocompatibility |
| url | https://www.mdpi.com/2313-7673/8/3/302 |
| work_keys_str_mv | AT nataliadrozd newnmethylimidazolefunctionalizedchitosanderivativeshemocompatibilityandantibacterialproperties AT alexeylunkov newnmethylimidazolefunctionalizedchitosanderivativeshemocompatibilityandantibacterialproperties AT balzhimashagdarova newnmethylimidazolefunctionalizedchitosanderivativeshemocompatibilityandantibacterialproperties AT allailina newnmethylimidazolefunctionalizedchitosanderivativeshemocompatibilityandantibacterialproperties AT valeryvarlamov newnmethylimidazolefunctionalizedchitosanderivativeshemocompatibilityandantibacterialproperties |