343
Views
24
CrossRef citations to date
0
Altmetric
Articles

Novel chitosan derivatives of 2-imidazolecarboxaldehyde and 2-thiophenecarboxaldehyde and their antibacterial activity

, &
Pages 703-710 | Received 11 Mar 2020, Accepted 24 Apr 2020, Published online: 19 May 2020

References

  • Guibal, E. Interaction of Metal Ions with Chitosan-Based Sorbents: A Review. Sep. Purif. Technol. 2004, 38, 43–74. DOI: 10.1016/j.seppur.2003.10.004.
  • Alvarenga, E. S. D. Characterization and Properties of Chitosan. In Biot. Biopolym.; Elnashar M., Ed.; InTech: Croatia, 2011; Vol. 4, pp 953–978.
  • Kubota, N.; Tatsumoto, N.; Sano, T.; Toya, K. A Simple Preparation of Half N-Acetylated Chitosan Highly Soluble in Water and Aqueous Organic Solvents. Carbohydr. Res. 2000, 324, 268–274. DOI: 10.1016/S0008-6215(99)00263-3.
  • Dutta, P. K.; Tripathi, S.; Mehrotra, G. K.; Dutta, J. Perspective for Chitosan Based Antimicrobial Films in Food Application. Food Chem. 2009, 114, 1173–1182. DOI: 10.1016/j.foodchem.2008.11.047.
  • Liu, Y.; Zhong, Z. Synthesis and Characterization of New Calixarene-Chitosan Polymers. J. Macromol. Sci. A 2017, 54, 678–683. DOI: 10.1080/10601325.2017.1321959.
  • Adhikari, H. S.; Yadav, P. N. Anticancer Activity of Chitosan, Chitosan Derivatives, and Their Mechanism of Action. Int. J. Biomater. 2018, 2018, 1–29. DOI: 10.1155/2018/2952085.
  • Pokhrel, S.; Yadav, P. N.; Adhikari, R. Applications of Chitin and Chitosan in Industry and Medical Science: A Review. Nepal J. Sci. Technol. 2016, 16, 99–104. DOI: 10.3126/njst.v16i1.14363.
  • Yaşar, A. Ö.; Kaya, İ. A Cross-Linker Containing Aldehyde Functionalized Ionic Liquid for Chitosan. J. Macromol. Sci. A 2019, 56, 860–870. DOI: 10.1080/10601325.2019.1617038.
  • Kumari, A.; Yadav, S. K.; Yadav, S. C. Biodegradable Polymeric Nanoparticles Based Drug Delivery Systems. Colloids Surf. B Biointerfaces 2010, 75, 1–18. DOI: 10.1016/j.colsurfb.2009.09.001.
  • Abdel-Monem, R. A.; Khalil, A. M.; Darwesh, O. M.; Hashim, A. I.; Rabie, S. T. Antibacterial Properties of Carboxymethyl Chitosan Schiff-Base Nanocomposites Loaded with Silver Nanoparticles. J. Macromol. Sci. A 2020, 57, 145–155. DOI: 10.1080/10601325.2019.1674666.
  • Kumar, M. N. V. A Review of Chitin and Chitosan Applications. React. Funct. Polym. 2000, 46, 1–27.
  • Pokhrel, S.; Yadav, P. N. Functionalization of Chitosan Polymer and Their Applications. J. Macromol. Sci. A 2019, 56, 450–475. DOI: 10.1080/10601325.2019.1581576.
  • Romero, D. H.; Heredia, V. E. T.; Barradas, O. G.; Lopez, M. E. M.; Pavon, E. S. Synthesis of Imidazole Derivatives and Their Biological Activities. J. Chem. Biochem. 2014, 2, 45–83.
  • Katritzsky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry; Pergamon Press: Oxford, 1984; Vol. 5, pp 469–498.
  • Kumari, S.; Sharma, P. K.; Kumar, N. Imidazole and Biological Activities: A Review. Der. Chem. Sin. 2010, 1, 36–47.
  • Meyer, V. Ueber Den Begleiter Dee Bensole im Steinkohlentheer. Ber. Dtsch. Chem. Ges. 1883, 16, 1465–1478. DOI: 10.1002/cber.188301601324.
  • Chaudhary, A.; Jha, K. K.; Kumar, S. Biological Diversity of Thiophene: A Review. J. Adv. Sci. Res. 2012, 3, 3–10.
  • Richard, H. A. Lippincott’s Pharmacology; Wolter Kluwer Pvt Ltd, 2009; Vol. 4, pp 347–502.
  • Martins, A. F.; Facchi, S. P.; Follmann, H. D. M.; Pereira, A. G. B.; Rubira, A. F.; Muniz, E. C. Antimicrobial Activity of Chitosan Derivatives Containing N-Quaternized Moieties in Its Backbone: A Review. Int. J. Mol. Sci. 2014, 15, 20800–20832. DOI: 10.3390/ijms151120800.
  • Pokhrel, S.; Lach, R.; Grellmann, W.; Wutzler, A.; Lebek, W.; Godehardt, R.; Yadav, P. N.; Adhikari, R. Synthesis of Chitosan from Prawn Shells and Characterization of Its Structural and Antimicrobial Properties. Nepal J. Sci. Technol. 2016, 17, 5–9. DOI: 10.3126/njst.v17i1.25056.
  • Saud, R.; Pokhrel, S.; Yadav, P. N. Synthesis, Characterization and Antimicrobial Activity of Maltol Functionalized Chitosan Derivatives. J. Macromol. Sci. A 2019, 56, 375–383. DOI: 10.1080/10601325.2019.1578616.
  • No, H. K.; Lee, M. Y. Isolation of Chitin from Crab Shell Waste. J. Korean Soc. Food Sci. Nutr. 1995, 24, 105–113.
  • Yuan, Y.; Chesnutt, B. M.; Haggard, W. O.; Bumgardner, J. D. Deacetylation of Chitosan: Material Characterization and In Vitro Evaluation via Albumin Adsorption and Pre-Osteoblastic Cell Cultures. Materials 2011, 4, 1399–1416. DOI: 10.3390/ma4081399.
  • Jiang, T. D. Chitosan; Chemical Industry Press: Beijing, China, 2001.
  • Black, C. A. Methods of Soil Analysis: Part I, Physical and Mineralogical Properties; Amer. Soc. Agronomy: Madison, WI, 1965; pp 671–698.
  • Abdelwahab, H. E.; Hassa, S. Y.; Yacout, G. A.; Mostafa, M. A.; El Sadek, M. M. Synthesis and Biological Evaluation of New Imine and Amine Chitosan Derivatives. Polymers 2015, 7, 2690–2700. DOI: 10.3390/polym7121532.
  • Chen, S.; Wu, G.; Zeng, H. Preparation of High Antimicrobial Activity Thiourea Chitosan-Ag Complex. Carbohydr. Polym. 2005, 60, 33–38. DOI: 10.1016/j.carbpol.2004.11.020.
  • Sashikala, S.; Shafi, S. S. Synthesis and Characterization of Chitosan Schiff Base Derivatives. Der Pharm. Lett. 2014, 6, 90–97.
  • Fernandez-Megia, E.; Novoa-Carballal, R.; Quiñoá, E.; Riguera, R. Optimal Routine Conditions for the Determination of the Degree of Acetylation of Chitosan by 1H-NMR. Carbohydr. Polym. 2005, 61, 155–161. DOI: 10.1016/j.carbpol.2005.04.006.
  • Silva, D. J. B.; Zuluaga, F.; Carlos, H. Evaluation of Biocompatibility of Chitosan Films from the Mycelium of Aspergillus niger in Connective Tissue of Rattus norvegicus. J. Med. Genet. Med. 2015, 9, 1–8.
  • Zhong, Z.; Zhong, Z.; Xing, R.; Li, P.; Mo, G. The Preparation and Antioxidant Activity of Thiosemicarbazone Chitosan. Intl. J. Biol. Macromol. 2010, 47, 93–97. DOI: 10.1016/j.ijbiomac.2010.05.016.
  • Bangyekan, C.; Aht-Ong, D.; Srikulkit, K. Preparation and Properties Evaluation Chitosan Coated Cassava Starch Film. Carbohydr. Polym. 2006, 63, 61–71. DOI: 10.1016/j.carbpol.2005.07.032.
  • Mishra, V. M. M.; Paliwal, J. S.; Singh, S. K.; Selvarajan, E.; Suganthi, V.; Subhadra Devi, C. Studies on Heavy Metal Removal Efficiency and Antibacterial Activity of Chitosan Prepared from Shrimp Shell Waste. 3 Biotech 2014, 4, 167–175.
  • Martínez, J. M. L.; Romasanta, P. N.; Chattah, A. K.; Buldain, G. Y. NMR Characterization of Hydrate and Aldehyde Forms of Imidazole-2-Carboxaldehyde and Derivatives. J. Org. Chem. 2010, 75, 3208–3213. DOI: 10.1021/jo902588s.
  • Jin, X. X.; Wang, J. T.; Bai, J. Synthesis and Antimicrobial Activity of the Schiff’s Base from Chitosan and Citral. Carbohydr. Res. 2009, 344, 825–829. DOI: 10.1016/j.carres.2009.01.022.
  • Jiao, T. F.; Zhou, J.; Zhou, J. X.; Gao, L.; Xing, Y. Y.; Li, X. H. Synthesis and Characterization of Chitosan Based Schiff Base Compounds with Aromatic Substituent Groups. Iran. Polym. J. 2011, 20, 123–136.
  • Zhang, Y.; Xue, C.; Xue, Y.; Gao, R.; Zhang, X. Determination of Degree of Deacetylation of Chitin and Chitosan by X-Ray Power Diffraction. Carbohydr. Res. 2005, 340, 1914–1917. DOI: 10.1016/j.carres.2005.05.005.
  • Lomadze, N.; Schneider, H. J. A Chitosan Based Chemomechanical Polymer Triggered by Stacking Effect with Artomatic Effectors Including Amino Acid Derivatives. Tetrahedron 2005, 61, 8694–8698. DOI: 10.1016/j.tet.2005.06.092.
  • Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991; p 241.
  • Qin, Y.; Xing, R.; Liu, S.; Li, K.; Meng, X.; Li, R.; Cui, J.; Li, B.; Li, P. Novel Thiosemicarbazone Chitosan Derivatives: Preparation, Characterization, and Antifungal Activity. Carbohydr. Polym. 2012, 87, 2664–2670. DOI: 10.1016/j.carbpol.2011.11.048.
  • Trimukhe, K. D.; Varma, A. J. Metal Complexes of Crosslinked Chitosans: Correlation between Metal Ion Complexation Values and Thermal Properties. Carbohydr. Polym. 2009, 75, 63–70. DOI: 10.1016/j.carbpol.2008.06.011.
  • Bukzem, A. L.; Signini, R.; dos Santos, D. M.; Lião, L. M.; Ascheri, D. P. R. Optimization of Carboxymethyl Chitosan Synthesis Using Surface Methodology and Desirability Function. Int. J. Biol. Macromol. 2016, 85, 615–624. DOI: 10.1016/j.ijbiomac.2016.01.017.
  • Khalid, M. N.; Agnely, F.; Yagoubi, N.; Grossiord, J. L.; Couarraze, G. Water State Characterization, Swelling Behavior, Thermal and Mechanical Properties of Chitosan Based Networks. Eur. J. Pharm. Sci. 2002, 15, 425–432. DOI: 10.1016/S0928-0987(02)00029-5.
  • de Britto, D.; Campana-Filho, S. P. A. Kinetic Study on Thermal Degradation of N,N,N-Trimethyl Chitosan. Polym. Degrad. Stab. 2004, 84, 353–361.
  • Cui, Z.; Xiang, Y.; Si, J.; Yang, M.; Zhang, Q.; Zhang, T. Ionic Interactions between Sulfuric Acid and Chitosan Membranes. Carbohydr. Polym. 2008, 73, 111–116. DOI: 10.1016/j.carbpol.2007.11.009.
  • Parparita, E.; Cheaburu, C. N.; Vasile, C. M. Thermal and Rheological Characterization of Polyvinyl Alcohol/Chitosan Blend. Cellul. Chem. Technol. 2012, 46, 571–581.
  • Chen, C. H.; Wang, F. Y.; Ou, Z. P. Deacetylation of β Chitin. I. Influence of the Deacetylation Conditions. J. Appl. Polym. Sci. 2004, 93, 2416–2422. DOI: 10.1002/app.20753.
  • Zawadzki, J.; Kaczmarek, H. Thermal Treatment of Chitosan in Various Conditions. Carbohydr. Polym. 2010, 80, 394–400. DOI: 10.1016/j.carbpol.2009.11.037.
  • Chethan, P. D.; Vishalakshi, B.; Sathish, L.; Ananda, K.; Poojary, B. Preparation of Substituted Quertinized Arylfuran Chitosan Derivative. Carbohydr. Polym. 2013, 59, 158–164. DOI: 10.1016/j.ijbiomac.2013.04.045.
  • Michael, I. Crystallinity and Hydrophility of Chitin and Chitosan. J. Chem. 2014, 3, 7–14.
  • Sudarshan, N. R.; Hoover, D. G.; Knorr, D. Antibacterial Action of Chitosan. Food Biotechnol. 1992, 6, 257–272. DOI: 10.1080/08905439209549838.
  • Liu, X. F.; Guan, Y. L.; Yang, D. G.; Li, Z.; Yao, K. D. Antibacterial Action of Chitosan and Carboxymethylated Chitosan. J. Appl. Polym. Sci. 2001, 79, 1324–1335.
  • Goy, R. C.; De Britto, D.; Assis, O. B. G. A Review of the Antimicrobial Activity of Chitosan. Polimeros 2009, 19, 241–247. DOI: 10.1590/S0104-14282009000300013.
  • Younes, I.; Sellimi, S.; Rinaudo, M.; Jellouli, K.; Nasri, M. Influence of Acetylation Degree and Molecular Weight of Homogeneous Chitosans on Antibacterial and Antifungal Activities. Int. J. Food Microbiol. 2014, 185, 57–63. DOI: 10.1016/j.ijfoodmicro.2014.04.029..
  • Sekiguchi, S.; Miura, Y.; Kaneko, H.; Nishimura, S.-I.; Nishi, N.; Iwase, M.; Tokura, S. Molecular Weight Dependency of Antimicrobial Activity by Chitosan Oligomers. In Food Hydrocolloids: Structures, Properties, and Functions; Nishinari, K., Doi, E. Eds.; Plenum Press, New York, 1994; pp 71–76.
  • Leuba, S.; Stossel, P. Chitin in Nature and Technology; Plenum Press: New York, 1985; p 217.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.