Water-Soluble Quaternary and Protonable Basic Chitotriazolans: Synthesis by Click Chemistry Conversion of Chitosan Azides and Investigation of Antibacterial Activity
Source abstract
Abstract
The azide transfer reaction and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) can be used to convert the amino groups in chitosan to triazole 1,2,3-moieties. The resulting polymer has been named chitotriazolan. This synthesis was performed with six different quaternary ammonium alkynes and three amine alkynes to obtain a series of nine water-soluble chitotriazolan derivatives. The structure and complete conversion of the azide were confirmed by FT-IR and proton NMR spectroscopy. The derivatives were investigated for antibacterial activity against S. aureus, E. faecalis, E. coli, and P. aeruginosa. The activity of the quaternized chitotriazolan derivatives varied depending on the structure of the quaternary moiety and the species of bacteria. The basic protonable derivatives were less active or inactive against the bacteria.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Click Chemistry and Applications · RNA Interference and Gene Delivery · Peptidase Inhibition and Analysis
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Hofsvallagata 53, IS-107 Reykjavík, Iceland
Department of Biomedical Science, Faculty of Medicine, School of Health Sciences, University of Iceland, Hringbraut 31, IS-101 Reykjavík, Iceland
Funding
Icelandic Research Fund · University of Iceland research fund · Erasmus+ grant
References (67)
Show source-provided references
1. Phillips, G.O., and Williams, P.A. (2021). Handbook of Hydrocolloids, Woodhead Publishing. [3rd ed.].
2. Chitin and chitosan: Properties and applications10.1016/j.progpolymsci.2006.06.001 ↗
3. A review of chitin and chitosan applications10.1016/S1381-5148(00)00038-9 ↗
4. Rathinam, S. (2022). N-alkyl, N-acyl, and Triazolyl Derivatives of Chitosan: Synthesis and Antibacterial Properties. [Ph.D. Thesis, University of Iceland].
5. Synthesis and characterization of schiff bases from chitosan and salicylaldehyde derivatives10.1016/j.carbpol.2004.12.008 ↗
6. Synthesis of pyrazole-based schiff bases of chitosan: Evaluation of antimicrobial activity10.1016/j.ijbiomac.2018.07.129 ↗
7. Synthesis of schiff bases based on chitosan and heterocyclic moiety: Evaluation of antimicrobial activity10.1021/acsomega.3c08446 ↗
8. Piegat, A., Goszczyńska, A., Idzik, T., and Niemczyk, A. (2019). The importance of reaction conditions on the chemical structure of n,o-acylated chitosan derivatives. Molecules, 24.10.3390/molecules24173047 ↗
9. Reis, B., Gerlach, N., Steinbach, C., Haro Carrasco, K., Oelmann, M., Schwarz, S., Müller, M., and Schwarz, D. (2021). A complementary and revised view on the n-acylation of chitosan with hexanoyl chloride. Mar. Drugs, 19.10.3390/md19070385 ↗
10. Selective synthesis of n,n,n-trimethylated chitosan derivatives at different degree of substitution and investigation of structure-activity relationship for activity against p. Aeruginosa and mrsa10.1016/j.ijbiomac.2020.05.109 ↗
11. The antibacterial structure-activity relationship for common chitosan derivatives10.1016/j.ijbiomac.2020.09.200 ↗
12. Advances in alkylated chitosan and its applications for hemostasis10.3390/macromol2030022 ↗
13. Chelation capability of chitosan and chitosan derivatives: Recent developments in sustainable corrosion inhibition and metal decontamination applications10.1016/j.crgsc.2021.100184 ↗
14. Sharef, H.Y., and Fakhre, N.A. (2022). Rapid adsorption of some heavy metals using extracted chitosan anchored with new aldehyde to form a schiff base. PLoS ONE, 17.10.1371/journal.pone.0274123 ↗
15. Luan, F., Wei, L., Zhang, J., Mi, Y., Dong, F., Li, Q., and Guo, Z. (2018). Antioxidant activity and antifungal activity of chitosan derivatives with propane sulfonate groups. Polymers, 10.10.3390/polym10040395 ↗
16. Synthesis, characterization, and antimicrobial activities of sulfonated chitosan10.1016/j.carbpol.2016.08.069 ↗
17. An improved method for synthesizing n,n′-dicarboxymethylchitosan10.1016/j.carbpol.2007.11.025 ↗
18. An overview of carboxymethyl derivatives of chitosan: Their use as biomaterials and drug delivery systems10.1016/j.msec.2017.03.198 ↗
19. Carboxymethyl chitin and chitosan derivatives: Synthesis, characterization and antibacterial activity
20. Quercetin-grafted chitosan prepared by free radical grafting: Characterization and evaluation of antioxidant and antibacterial properties10.1007/s13197-020-04263-2 ↗
21. Stability of chitosan-a challenge for pharmaceutical and biomedical applications10.3390/md13041819 ↗
22. Click chemistry: Diverse chemical function from a few good reactions10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 ↗
23. A stepwise huisgen cycloaddition process: Copper(i)-catalyzed regioselective “ligation” of azides and terminal alkynes10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 ↗
24. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides10.1021/jo011148j ↗
25. Synthesis of glycoconjugate mimics by ‘click chemistry’10.1016/j.carres.2019.107775 ↗
26. Click chemistry and material selection for in situ fabrication of hydrogels in tissue engineering applications10.1021/acsbiomaterials.8b00230 ↗
27. ‘Click’ chemistry in polymer and material science: An update10.1002/marc.200800089 ↗
28. Nanoparticle assembling through click chemistry directed by mixed sams for magnetic applications10.1021/acsanm.8b02152 ↗
29. Yi, G., Son, J., Yoo, J., Park, C., and Koo, H. (2018). Application of click chemistry in nanoparticle modification and its targeted delivery. Biomater. Res., 22.10.1186/s40824-018-0123-0 ↗
30. Click triazoles for bioconjugation10.1007/7081_2011_72 ↗
31. Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand diels−alder reactivity10.1021/ja8053805 ↗
32. Synthesis of 6-n,n,n-trimethyltriazole chitosan via “click chemistry” and evaluation for gene delivery10.1021/bm900341d ↗
33. Sarwar, A., Katas, H., Samsudin, S.N., and Zin, N.M. (2015). Regioselective sequential modification of chitosan via azide-alkyne click reaction: Synthesis, characterization, and antimicrobial activity of chitosan derivatives and nanoparticles. PLoS ONE, 10.10.1371/journal.pone.0123084 ↗
34. Tethering antimicrobial peptides onto chitosan: Optimization of azide-alkyne “click” reaction conditions10.1016/j.carbpol.2017.02.050 ↗
35. Antimicrobial peptide shows enhanced activity and reduced toxicity upon grafting to chitosan polymers10.1039/C5CC04010H ↗
36. 2-azido-2-deoxycellulose: Synthesis and 1,3-dipolar cycloaddition10.1002/hlca.200890064 ↗
37. Chitotriazolan (poly(β(1–4)-2-(1h-1,2,3-triazol-1-yl)-2-deoxy-d-glucose)) derivatives: Synthesis, characterization, and evaluation of antibacterial activity10.1016/j.carbpol.2021.118162 ↗
38. N-peg’ylation of chitosan via “click chemistry” reactions10.1016/j.reactfunctpolym.2009.06.010 ↗
39. Simple method for ultrasound assisted «click» modification of azido-chitosan derivatives by cuaac10.1016/j.carbpol.2022.119109 ↗
40. Ultrasound-assisted cu(i)-catalyzed azide-alkyne click cycloaddition as polymer-analogous transformation in chitosan chemistry. High antibacterial and transfection activity of novel triazol betaine chitosan derivatives and their nanoparticles10.1016/j.ijbiomac.2019.06.190 ↗
41. Luan, F., Wei, L., Zhang, J., Tan, W., Chen, Y., Dong, F., Li, Q., and Guo, Z. (2018). Preparation and characterization of quaternized chitosan derivatives and assessment of their antioxidant activity. Molecules, 23.10.3390/molecules23030516 ↗
42. Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and n-methylation10.1016/j.carbpol.2018.07.056 ↗
43. Synthesis of water soluble chitosan derivatives with halogeno-1,2,3-triazole and their antifungal activity10.1016/j.ijbiomac.2016.06.006 ↗
44. A short synthesis of highly soluble chemoselective chitosan derivatives via “click chemistry”10.1016/j.carbpol.2012.06.074 ↗
45. Novel triazolyl-functionalized chitosan derivatives with different chain lengths of aliphatic alcohol substituent: Design, synthesis, and antifungal activity10.1016/j.carres.2015.10.005 ↗
46. Preparation of highly regioselective amphiprotic chitosan derivative via “click chemistry”10.1016/j.ijbiomac.2012.08.012 ↗
47. Preparation of highly regioselective chitosan derivatives via “click chemistry”10.1016/j.carbpol.2011.03.030 ↗
48. Li, Q., Sun, X., Gu, G., and Guo, Z. (2018). Novel water soluble chitosan derivatives with 1,2,3-triazolium and their free radical-scavenging activity. Mar. Drugs, 16.10.3390/md16040107 ↗
49. Novel cationic chitosan derivative bearing 1,2,3-triazolium and pyridinium: Synthesis, characterization, and antifungal property10.1016/j.carbpol.2017.11.023 ↗
50. Synthesis, characterization, and evaluation of antifungal and antioxidant properties of cationic chitosan derivative via azide-alkyne click reaction10.1016/j.ijbiomac.2018.08.111 ↗
51. Water-soluble chitotriazolans derived from cationic, neutral, and anionic common chitosan derivatives: Synthesis, characterization, and antibacterial activity10.1016/j.eurpolymj.2023.112311 ↗
52. A novel approach to 1,2,3-triazole grafted chitosans via modified wolff’s cyclocondensation10.1016/j.eurpolymj.2017.11.047 ↗
53. ‘Click’ synthesized non-substituted triazole modified chitosan from cac2 as a novel antibacterial and antioxidant polymer10.1007/s10965-022-03032-3 ↗
54. Ionic liquids with thioether motifs as synthetic cationic lipids for gene delivery10.1039/C7CC03235H ↗
55. Spectroscopic study of reaction of propargyl bromide with pyridine10.1023/A:1019572605480 ↗
56. Trisubstitution of pyridine through sequential and regioselective palladium cross-coupling reactions affording analogs of known gpr54 antagonists10.1039/c3ra41985a ↗
57. Structure aided design of chimeric antibiotics10.1016/j.bmcl.2012.02.019 ↗
58. (2009). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically (Standard No. CLSI standard M07).
59. Synthesis of novel quaternary chitosan derivatives via n-chloroacyl-6-o-triphenylmethylchitosans10.1021/bm050707j ↗
60. Synthesis and characterization of chitosan n-betainates having various degrees of substitution10.1021/ma0358780 ↗
61. Antibacterial activity of n-quaternary chitosan derivatives: Synthesis, characterization and structure activity relationship (sar) investigations10.1016/j.eurpolymj.2010.03.001 ↗
62. Chitosan-hydroxycinnamic acid conjugates: Optimization of the synthesis and investigation of the structure activity relationship10.1016/j.carbpol.2021.118896 ↗
63. Novel water-soluble quaternary piperazine derivatives of chitosan: Synthesis and characterization10.1002/mabi.200500202 ↗
64. Antimicrobial effect of a novel chitosan derivative and its synergistic effect with antibiotics10.1021/acsami.0c20881 ↗
65. Chitosan derivatives active against multidrug-resistant bacteria and pathogenic fungi: In vivo evaluation as topical antimicrobials10.1021/acs.molpharmaceut.6b00764 ↗
66. Chitosan as antimicrobial agent: Applications and mode of action10.1021/bm034130m ↗
67. Jayakumar, R., and Prabaharan, M. (2021). Chitosan for Biomaterials iii: Structure-Property Relationships, Springer International Publishing.10.1007/978-3-030-83807-2 ↗