مروری بر معرفی کیتوزان و روش‌های مختلف کواترنایزاسیون آن

نوع مقاله : مقاله کامل علمی - پژوهشی

نویسندگان

1 دانشجوی کارشناسی‌ارشد فرآوری محصولات شیلاتی، گروه شیلات، دانشکده منابع طبیعی، دانشگاه تهران، کرج، ایران.

2 کارشناسی‌ارشد شیمی آلی، کارشناس آزمایشگاه، گروه محیط زیست، دانشکده منابع طبیعی، دانشگاه تهران، کرج، ایران.

3 نویسنده مسئول، دانشیار گروه شیلات، دانشکده منابع طبیعی، دانشگاه تهران، کرج، ایران.

چکیده

کیتین از فراوان‌ترین بیوپلیمر بعد از سلولز می‌باشد که در دیواره سلولی قارچ، کوتیکول حشرات و در اسکلت بیرونی سخت پوستانی از جمله خرچنگ و میگو وجود دارد. از د‌استیله کردن کیتین، کیتوزان حاصل می‌شود که ویژگی‌های آن به شدت به درجه استیل‌زدایی و وزن مولکولی آن بستگی دارد. در واقع می‌توان گفت کیتوزان به عنوان فراوان‌ترین آمینو پلی‌ساکارید در طبیعت است که بعنوان ترکیبی غیر‌سمی نیز شناخته می‌شود. کیتوزان به دلیل خواص منحصر به فردش از جمله زیست سازگاری، زیست تخریب‌پذیری، فعالیت ضدباکتریایی و غیره بسیار مورد توجه قرار گرفته است. اما بدلیل پایین بودن میزان حلالیت آن درpH های فیزیولوژیک امکان بهره‌مندی از بسیاری از خواص آن وجود ندارد. از همین‌رو تلاش‌های بسیاری برای تولید مشتقاتی از آن که قابلیت حلالیت در چنین شرایطی را داشته باشند، صورت گرفته است. یکی از مهم‌ترین روش‌های افزایش حلالیت کیتوزان، اصلاح شیمیایی آن است که با تکنیک موسوم به کواترنایز کردن انجام می‌شود. در این روش یک عامل اصلاحگر با برقراری یک پیوند کووالانسی با کربن شمارة دو کیتوزان (C2) باعث افزایش قابلیت انحلال‌پذیری آن در آب و درpH های فیزیولوژیک می‌شود. در این مقاله، ضمن معرفی مجدد ویژگی‌های منحصر به فرد کیتوزان، روش‌های مختلف تهیه کیتوزان کواترنایز شده با استفاده از برخی از ترکیبات شیمیایی رایج نظیرGTMAC، EPTMAC،CH3I ،DMS مورد بررسی قرار گرفته و خصوصیات و کاربردهای کیتوزان کواترنایز شدة تولیدی تشریح خواهد شد.

کلیدواژه‌ها

موضوعات

عنوان مقاله [English]

An overview of the introduction of chitosan and its different quaternization methods

نویسندگان [English]

  • Seyedeh Zahra Mirhosseini Roudbaraki 1
  • Elaheh Aghaei Meybodi 2
  • Seyed Vali Hosseini 3
1 M.Sc. Student of Fishery Products Processing, Dept. of Fisheries, Faculty of Natural Resources, University of Tehran, Karaj, Iran.
2 M.Sc. in Organic Chemistry, Laboratory Expert, Dept. of Environment, Faculty of Natural Resources, University of Tehran, Karaj, Iran.
3 Corresponding Author, Associate Prof., Dept. of Fisheries, Faculty of Natural Resources, University of Tehran, Karaj, Iran.
چکیده [English]

Chitin is one of the most abundant biopolymers after cellulose, which is present in the cell wall of fungi, the cuticle of insects, and in the exoskeleton of crustaceans such as crabs and shrimps. From the deacetylation of chitin, chitosan is obtained, whose characteristics strongly depend on the degree of deacetylation and its molecular weight. In fact, it can be said that chitosan is the most abundant amino polysaccharide in nature, which is also known as a non-toxic compound. Chitosan has received much attention due to its unique properties such as biocompatibility, biodegradability, antibacterial activity, etc. But due to its low solubility in physiological pH, it is not possible to benefit from many of its properties. Therefore, many attempts have been made to produce its derivatives that have the ability to dissolve in such a condition. One of the most important methods of increasing the solubility of chitosan is its chemical modification, which is done with the so-called quaternization technique. In this method, a modifying agent by establishing a covalent bond with carbon number two of chitosan (C2) increases its solubility in water and at physiological pH. In this article, while re-introducing the unique features of chitosan, various methods of preparing quaternized chitosan using some common chemical compounds such as GTMAC, EPTMAC, CH3I, DMS will be investigated and the characteristics and applications of the produced quaternized chitosan will be described.

کلیدواژه‌ها [English]

  • Chemical modification
  • Chitin
  • Chitosan
  • Crustacean skeleton
  • Quaternization

مراجع

1.Patrulea, V., Ostafe, V., Borchard, G., & Jordan, O. (2015). Chitosan as a starting material for wound healing applications. European Journal of Pharmaceutics and Biopharmaceutics, 97, 417-426.[1]2.Ramya, R., Sudha, P. N., & Mahalakshmi, J. (2012). Preparation and characterization of chitosan binary blend. Int. J. Sci. Res. Publ. 2 (10), 1-9.3.Chillo, S., Suriano, N., Lamacchia, C., & Del Nobile, M. A. (2009). Effects of additives on the rheological and mechanical properties of non-conventional fresh handmade tagliatelle. Journal of Cereal Science, 49 (2), 163-170.4.Yamada, M., & Honma, I. (2004). A Biopolymer Composite Material as an Anhydrous Proton‐Conducting Membrane. Angewandte Chemie International Edition, 43 (28), 3688-3691.5.Du, W. L., Xu, Z. R., Han, X. Y., Xu, Y. L., & Miao, Z. G. (2008). Preparation, characterization and adsorption properties of chitosan nanoparticles for eosin Y as a model anionic dye. Journal of Hazardous Materials, 153 (1-2), 152-156.6.Dehghani, S., Hosseini, S. V., & Regenstein, J. M. (2018). Edible films and coatings in seafood preservation: A review. Food Chemistry, 240, 505-513.7.Saxena, A., Kumar, A., & Shahi, V. K. (2006). Preparation and characterization of N-methylene phosphonic and quaternized chitosan composite membranes for electrolyte separations. Journal of Colloid and Interface Science, 303 (2), 484-493.8.Avadi, M. R., Sadeghi, A. M. M., Tahzibi, A., Bayati, K. H., Pouladzadeh, M., Zohuriaan-Mehr, M. J., & Rafiee-Tehrani, M. (2004). Diethylmethyl chitosan as an antimicrobial agent: Synthesis, characterization and antibacterial effects. European Polymer Journal, 40 (7), 1355-1361.9.Rinaudo, M. (2010). New way to crosslink chitosan in aqueous solution. European Polymer Journal, 46 (7), 1537-1544.10.Spinelli, V. A., Laranjeira, M. C., & Fávere, V. T. (2004). Preparation and characterization of quaternary chitosan salt: adsorption equilibrium of chromium (VI) ion. Reactive and Functional Polymers, 61 (3), 347-352.11.Ruihua, H., Bingchao, Y., Zheng, D., & Wang, B. (2012). Preparation and characterization of a quaternized chitosan. Journal of Materials Science, 47, 845-851.12.Qin, C., Xiao, Q., Li, H., Fang, M., Liu, Y., Chen, X., & Li, Q. (2004). Calorimetric studies of the action of chitosan-N-2-hydroxypropyl trimethyl ammonium chloride on the growth of microorganisms. International Journal of Biological Macromolecules, 34 (1-2), 121-126.13.Lim, S. H., & Hudson, S. M. (2004). Application of a fiber-reactive chitosan derivative to cotton fabric as an antimicrobial textile finish. Carbohydrate Polymers, 56 (2), 227-234.14.Wu, J., Su, Z. G., & Ma, G. H. (2006). A thermo-and pH-sensitive hydrogel composed of quaternized chitosan/ glycerophosphate. International Journal of Pharmaceutics, 315 (1-2), 1-11.15.Peng, Z. X., Wang, L., Du, L., Guo, S. R., Wang, X. Q., & Tang, T. T. (2010). Adjustment of the antibacterial activity and biocompatibility of hydroxypropyltrimethyl ammonium chloride chitosan by varying the degree of substitution of quaternary ammonium. Carbohydrate Polymers, 81 (2), 275-283.16.Pakzad, Y., Fathi, M., Omidi, Y., Mozafari, M., & Zamanian, A. (2020). Synthesis and characterization of timolol maleate-loaded quaternized chitosan-based thermosensitive hydrogel: A transparent topical ocular delivery system for the treatment of glaucoma. International Journal of Biological Macromolecules, 159, 117-128.17.Beil, S., Schamberger, A., Naumann, W., Machill, S., & van Pée, K. H. (2012). Determination of the degree of N-acetylation (DA) of chitin and chitosan in the presence of water by first derivative ATR FTIR spectroscopy. Carbohydrate Polymers, 87 (1), 117-122.18.Luo, J., Wang, X., Xia, B., & Wu, J. (2010). Preparation and characterization of quaternized chitosan under microwave irradiation. Journal of Macromolecular Science, Part A: Pure and Applied Chemistry, 47 (9), 952-956.19.Ge, H. C., & Luo, D. K. (2005). Preparation of carboxymethyl chitosan in aqueous solution under microwave irradiation. Carbohydrate Research,
340 (7), 1351-1356.20.Li, H., Du, Y., Wu, X., & Zhan, H. (2004). Effect of molecular weight and degree of substitution of quaternary chitosan on its adsorption and flocculation properties for potential retention-aids in alkaline papermaking. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 242 (1-3), 1-8.21.Shi, X. W., Du, Y. M., Li, J., Su, X. L., & Yang, J. H. (2006). Release characteristics of brilliant blue from calcium-alginate beads coated with quaternized chitosan. Journal of Microencapsulation, 23 (4), 405-415.22.Li, T., Shi, X. W., Du, Y. M., &
Tang, Y. F. (2007). Quaternized chitosan/alginate nanoparticles for protein delivery. Journal of Biomedical Materials Research Part A: An Official Journal of The Society for Biomaterials, The Japanese Society for Biomaterials, and The Australian Society for Biomaterials and the Korean Society for Biomaterials, 83 (2), 383-390.23.Xiong, Y., Liu, Q. L., Zhang, Q. G., & Zhu, A. M. (2008). Synthesis and characterization of cross-linked quaternized poly (vinyl alcohol)/ chitosan composite anion exchange membranes for fuel cells. Journal of Power Sources, 183 (2), 447-453.
24.Wang, X., Pei, X., Du, Y., & Li, Y. (2008). Quaternized chitosan/rectorite intercalative materials for a gene delivery system. Nanotechnology,19 (37), 375102.25.Wang, X., Liu, B., Ren, J., Liu, C., Wang, X., Wu, J., & Sun, R. (2010). Preparation and characterization of new quaternized carboxymethyl chitosan/ rectorite nanocomposite. Composites Science and Technology, 70 (7), 1161-167.26.Wang, J., & He, R. (2015). Formation and evaluation of interpenetrating networks of anion exchange membranes based on quaternized chitosan and copolymer poly (acrylamide)/ polystyrene. Solid State Ionics, 278, 49-57.27.Liu, Y., Li, M., Qiao, M., Ren, X., Huang, T. S., & Buschle‐Diller, G. (2017). Antibacterial membranes based on chitosan and quaternary ammonium salts modified nanocrystalline cellulose. Polymers for Advanced Technologies, 28 (12), 1629-1635.28.Zeng, X., Wang, L., Wang, J., & Qu, Z. (2021). Construction of ordered OH− migration channels in anion exchange membrane by synergizes of cationic metal‐organic framework and quaternary ammonium groups. International Journal of Energy Research, 45 (7), 10895-10911.29.Loubaki, E., Ourevitch, M., & Sicsic, S. (1991). Chemical modification of chitosan by glycidyl trimethylammonium chloride. Characterization of modified chitosan by 13C-and 1H-NMR spectroscopy. European Polymer Journal, 27 (3), 311-317.30.Chang, C., Chen, S., & Zhang, L. (2011). Novel hydrogels prepared via direct dissolution of chitin at low temperature: structure and biocompatibility. Journal of Materials Chemistry,21 (11), 3865-3871.31.Muzzarelli, R. A., & Tanfani, F. (1985). The N-permethylation of chitosan and the preparation of N-trimethyl chitosan iodide. Carbohydrate Polymers, 5 (4), 297-307.32.Domard, A., Rinaudo, M., & Terrassin, C. (1986). New method for the quaternization of chitosan. International Journal of Biological Macromolecules, 8 (2), 105-107.33.Hamman, J. H., Stander, M., & Kotze, A. F. (2002). Effect of the degree of quaternisation of N-trimethyl chitosan chloride on absorption enhancement: in vivo evaluation in rat nasal epithelia. International Journal of Pharmaceutics, 232 (1-2), 235-242.34.Snyman, D., Hamman, J. H., Kotze, J. S., Rollings, J. E., & Kotze, A. F. (2002). The relationship between the absolute molecular weight and the degree of quaternisation of N-trimethyl chitosan chloride. Carbohydrate Polymers, 50 (2), 145-150.35.Curti, E., de Britto, D., &
Campana‐Filho, S. P. (2003). Methylation of chitosan with iodomethane: effect of reaction conditions on chemoselectivity and degree of substitution. Macromolecular Bioscience, 3 (10), 571-576.36.de Britto, D., & de Assis, O. B. (2007). Synthesis and mechanical properties of quaternary salts of chitosan-based films for food application. International Journal of Biological Macromolecules, 41 (2), 198-203.37.Xu, T., Xin, M., Li, M., Huang, H., & Zhou, S. (2010). Synthesis, characteristic and antibacterial activity of N, N, N-trimethyl chitosan and its carboxymethyl derivatives. Carbohydrate Polymers,81 (4), 931-936.38.Wu, M., Long, Z., Xiao, H., & Dong, C. (2016). Recent research progress on preparation and application of N, N,
N-trimethyl chitosan. Carbohydrate Research, 434, 27-32.39.Verheul, R. J., Amidi, M., van der Wal, S., van Riet, E., Jiskoot, W., & Hennink, W. E. (2008). Synthesis, characterization and in vitro biological properties of O-methyl free N, N, N-trimethylated chitosan. Biomaterials, 29 (27), 3642-3649.40.Jintapattanakit, A., Mao, S., Kissel, T., & Junyaprasert, V. B. (2008). Physicochemical properties and biocompatibility of N-trimethyl chitosan: effect of quaternization and dimethylation. European Journal of Pharmaceutics and Biopharmaceutics, 70 (2), 563-571.41.Je, J. Y., & Kim, S. K. (2006). Chitosan derivatives killed bacteria by disrupting the outer and inner membrane. Journal of Agricultural and Food Chemistry,54 (18), 6629-6633.42.Holme, H. K., Foros, H., Pettersen, H., Dornish, M., & Smidsrød, O. (2001). Thermal depolymerization of chitosan chloride. Carbohydrate Polymers,46 (3), 287-294.43.Hu, X. J., Liu, Y., Zhou, X. F., Zhu,
Q. L., Bei, Y. Y., You, B. G., ... & Fan, Y. J. (2013). Synthesis and characterization of low-toxicity N-caprinoyl-N-trimethyl chitosan as self-assembled micelles carriers for osthole. International Journal of Nanomedicine, 3543-3558.44.de Britto, D., & Assis, O. B. (2007). A novel method for obtaining a quaternary salt of chitosan. Carbohydrate Polymers, 69 (2), 305-310.45.Abashzadeh, S., Hajimiri, M. H., Atyabi, F., Amini, M., & Dinarvand, R. (2011). Novel physical hydrogels composed of opened‐ring poly (vinyl pyrrolidone) and chitosan derivatives: Preparation and characterization. Journal of Applied Polymer Science, 121 (5), 2761-2771.46.Jia, Z., & Xu, W. (2001). Synthesis and antibacterial activities of quaternary ammonium salt of chitosan. Carbohydrate Research, 333 (1), 1-6.47.Kotzé, A. F., Lueßen, H. L., de Leeuw, B. J., Verhoef, J. C., & Junginger, H. E. (1998). Comparison of the effect of different chitosan salts and N-trimethyl chitosan chloride on the permeability of intestinal epithelial cells (Caco-2). Journal of Controlled Release, 51 (1), 35-46.48.de Britto, D., & Campana-Filho, S. P. (2004). A kinetic study on
the thermal degradation of N, N, N-trimethylchitosan. Polymer Degradation and Stability, 84 (2), 353-361.49.Duarte, M. L., Ferreira, M. C., Marvao, M. R., & Rocha, J. (2001). Determination of the degree of acetylation of chitin materials by 13C CP/MAS NMR spectroscopy. International Journal of Biological Macromolecules, 28 (5), 359-363.50.Holappa, J., Nevalainen, T., Savolainen, J., Soininen, P., Elomaa, M., Safin, R., ... & Järvinen, T. (2004). Synthesis and characterization of chitosan N-betainates having various degrees of substitution. Macromolecules, 37 (8), 2784-2789.
مجله بهره برداری و پرورش آبزیان
دوره 13، شماره 2
تیر 1403
صفحه 121-142

فایل ها

هم رسانی

ارجاع به این مقاله

آمار