The Chemical Modification to Improve Solubility of Chitosan and Its Derivatives Application, Preparation Method, Toxicity as a Nanoparticles

References

• Tiyaboonchai W. Chitosan nanoparticles: a promising system for drug delivery. Naresuan Univ J. 2003;11:51–66.
   Web of Science ®Google Scholar
• Wang W, Chen S, Zhang L, et al. Poly(lactic acid)/chitosan hybrid nanoparticles or controlled release of anticancer drug. Mater Sci Eng C. 2015;46:514–520. doi:10.1016/j.msec.2014.10.048
   PubMed Web of Science ®Google Scholar
• Saheb M, Fereydouni N, Nemati S, et al. Chitosan-based delivery systems for curcumin: a review of pharmacodynamic and pharmacokinetic aspects. J Cell Physiol. 2019’2019:1–16.
   Google Scholar
• Rashki S, Asgarpour K, Tarrahimofrad H, et al. Chitosan-based nanoparticles against bacterial infections. Carbohydr Polym. 2020;251:1–12.
   Web of Science ®Google Scholar
• Chen MC, Mi FL, Liao ZX, et al. Recent advances in chitosan-based nanoparticles for oral delivery of macromolecules. Adv Drug Deliv Rev. 2013;65:865–879. doi:10.1016/j.addr.2012.10.010
   PubMed Web of Science ®Google Scholar
• Trapani A, Garcia-Fuentes M, Alonso MJ. Novel drug nanocarriers combining hydrophilic cyclodextrins and chitosan. Nanotechnology. 2008;1:185101.
   Google Scholar
• Sogias IA, Khutoryanskiy V, Williams AC. Exploring the factors affecting the solubility of chitosan in water. Macromol Chem Phys. 2010;211(4):426–433. doi:10.1002/macp.200900385
   Web of Science ®Google Scholar
• Gyu-yoon C, Korean Intellectual Property Office., assignee. Chitosan. Chitosan ester derivatives and methods for preparing the same (Chitosan Ester derivatives and method for preparation of the same). South Korea Patent KR20110111197A; 2010.
   Google Scholar
• Suryani S, Chaerunisaa AY, Joni IM, et al. Production of low molecular weight chitosan using a combination of weak acid and ultrasonication methods. Polymers. 2022;14:1–15. doi:10.3390/polym14163417
   Web of Science ®Google Scholar
• Wang W, Meng Q, Li Q, et al. Chitosan derivatives and their application in biomedicine. Int J Mol Sci. 2020;21:1–26.
   Web of Science ®Google Scholar
• Mendoza JL, Monal WMA, Valencia FMG. Chemical Characteristics and Functional Properties of Chitosan. Cambridge Massachussets: Academic Press; 2016:3–31.
   Google Scholar
• Zhao D, Yu S, Sun B, et al. Biomedical applications of chitosan and its derivative nanoparticles. Polymers. 2018;10(4):1–10. doi:10.3390/polym10040462
   Web of Science ®Google Scholar
• Bashir S, Teo YY, Ramesh S, et al. N-succinyl chitosan preparation, characterization, properties, and biomedical applications: a state of the art review. Rev Chem Eng. 2015;31:563–597.
   Web of Science ®Google Scholar
• Sashiwa H, Kawasaki N, Nakayama A, et al. Chemical modification of Chitosan. Part 15: synthesis of novel Chitosan derivatives by substitution of hydrophilic amine using N-carboxyethylchitosan ethyl ester as an intermediate. Carbohydr Res. 2003;338:557–561. doi:10.1016/S0008-6215(02)00492-5
   PubMed Web of Science ®Google Scholar
• Hirano S, Yamaguchi Y, Kamiya M. Water-soluble N-(n-Fatty acyl)chitosans. Macromol Biosci. 2003;3:629–631. doi:10.1002/mabi.200350029
   Web of Science ®Google Scholar
• Gonzalez PA, Justo JAZ, Lopez AS, et al. Gold nanoparticles with chitosan, N-acylated chitosan, and chitosan oligosaccharide as DNA carriers. Nanoscale Res Lett. 2019;258:1–14.
   Google Scholar
• Yang Z, Peng H, Wang W, et al. Preparation, characterization, and protein loading properties of N-acyl chitosan nanoparticles. J Appl Polym Sci. 2010;16:1365–1371.
   Google Scholar
• Cho Y, Kim JT, Park HJ. Size-controlled self-aggregated N-acyl chitosan nanoparticles as a vitamin C carrier. Carbohydr Polym. 2012;88:1087–1092. doi:10.1016/j.carbpol.2012.01.074
   Web of Science ®Google Scholar
• Prajapti C, Agrawal YO, Agnihotri VV, et al. Development and biological evaluation of protective effect of kidney targeted N - Acetylated Chitosan nanoparticles containing thymoquinone or the treatment of DNA damage in cyclophosphamide- induced haemorrhagic cystitis. Int J Biol Macromol. 2022;214:391–401. doi:10.1016/j.ijbiomac.2022.06.070
   PubMed Web of Science ®Google Scholar
• Park YS, Park HJ, Lee J. Stabilization of Glabridin by chitosan nano-complex. J Korean Soc Appl Biol Chem. 2012;5:457–462.
   Google Scholar
• Naberezhnykh GA, Gorbach VI, Likhatskaya GN, et al. Interaction of N-acylated and N-alkylated chitosans included in liposomes with lipopolysaccharide of gram-negative bacteria. Biochem. 2013;78:301–308.
   PubMed Web of Science ®Google Scholar
• Chen Q, Qi Y, Jiang Y, et al. Progress in research of chitosan chemical modification technologies and their applications. Mar Drugs. 2022;20:1–36. doi:10.3390/md20080536
   Web of Science ®Google Scholar
• Pokhrel S, Yadav PN. Functionalization of Chitosan polymer and their applications. J Macromol Sci Part a Pure Appl Chem. 2019;56:450–475. doi:10.1080/10601325.2019.1581576
   Web of Science ®Google Scholar
• Ma G, Yang D, Zhou Y, et al. J preparation and characterization of water-soluble N -alkylated chitosan. Carbohydr Polym. 2008;74:121–126.
   Web of Science ®Google Scholar
• Yang TC, Chou CC, Li CF. Preparation, water solubility and rheological property of the N-alkylated mono or disaccharide chitosan derivatives. Food Res Int. 2002;35:707–713. doi:10.1016/S0963-9969(02)00064-9
   Web of Science ®Google Scholar
• Palacio DA, Urbano BF, Palencia M, et al. Preparation of alkylated chitosan-based polyelectrolyte hydrogels: the effect of monomer charge on polymerization. Eur Polym J. 2019;118:551–560. doi:10.1016/j.eurpolymj.2019.06.024
   Web of Science ®Google Scholar
• Chen H, Cui S, Zhao Y, et al. O-alkylation of chitosan for gene delivery by using ionic liquid in an in- situ reactor. Engineering. 2012;04(10):114–117. doi:10.4236/eng.2012.410B029
   Google Scholar
• Robles E, Villar E, Alatorre-Meda M, et al. Effects of the hydrophobization on chitosan-insulin nanoparticles obtained by an alkylation reaction on Chitosan. J Appl Polym Sci. 2013;129:822–834. doi:10.1002/app.38870
   Web of Science ®Google Scholar
• Liu C, Wang J, Huang S, et al. Self-assembled nanoparticles for cellular delivery of peptide nucleic acid using amphiphilic N, N, N-trimethyl-O-alkyl chitosan derivatives. J Mater Sci Mater Med. 2018;29:1–14. doi:10.1007/s10856-018-6120-y
   Web of Science ®Google Scholar
• Pinto RJB, Fernandes SCM, Freire CSR, et al. Antibacterial activity of optically transparent nanocomposite films based on chitosan or its derivatives and silver nanoparticles. Carbohydr Res. 2012;348:77–83. doi:10.1016/j.carres.2011.11.009
   PubMed Web of Science ®Google Scholar
• Jimtaisong A, Saewan N. Utilization of carboxymethyl chitosan in cosmetics. Int J Cosmet Sci. 2014;36:12–21. doi:10.1111/ics.12102
   PubMed Web of Science ®Google Scholar
• Boamah P, Huang Y, Hua M, et al. Sorption of heavy metal ions into carboxylate chitosan derivatives-a mini-review. Ecotoxicol Environ Saf. 2015;116:113–120. doi:10.1016/j.ecoenv.2015.01.012
   PubMed Web of Science ®Google Scholar
• Song Q, Zhang Z, Gao J, et al. Synthesis and property studies of N-carboxymethyl chitosan. J Appl Polym Sci. 2010;116:2658–2667.
   Google Scholar
• Mohamed NA, Mohamed RR, Seoudi RS. Synthesis and characterization of some novel antimicrobial thiosemicarbazone O-carboxymethyl chitosan derivatives. Int J Biol Macromol. 2014;63:63–69. doi:10.1016/j.ijbiomac.2013.10.044
   Web of Science ®Google Scholar
• Patale RL, Patravale VB. O, N-carboxymethyl chitosan-zinc complex: a novel chitosan complex with enhanced antimicrobial activity. Carbohydr Polym. 2011;85:105–110. doi:10.1016/j.carbpol.2011.02.001
   Web of Science ®Google Scholar
• Manimohan M, Pugalmani S, Sithique MA. Biologically active water soluble novel biopolymer/hydrazide based O-carboxymethyl chitosan Schiff bases: synthesis and characterisation. J Inorg Organomet Polym Mater. 2020;30:3658–3676. doi:10.1007/s10904-020-01487-9
   Web of Science ®Google Scholar
• Wang H, Gong X, Miao Y, et al. Preparation and characterization of multilayer films composed of chitosan, sodium alginate and carboxymethyl Chitosan-Zno nanoparticles. Food Chem. 2019;283:397–403. doi:10.1016/j.foodchem.2019.01.022
   PubMed Web of Science ®Google Scholar
• Huang YC, Kuo TH. O-carboxymethyl Chitosan/fucoidan nanoparticles increase cellular curcumin uptake. Food Hydrocoll. 2016;53:261–269. doi:10.1016/j.foodhyd.2015.02.006
   Web of Science ®Google Scholar
• Liu S, Yang S, Ho PC. Intranasal administration of carbamazepine-loaded carboxymethyl chitosan nanoparticles for drug delivery to the brain. Asian J Pharm Sci. 2018;13:72–81. doi:10.1016/j.ajps.2017.09.001
   PubMed Web of Science ®Google Scholar
• Feng C, Wang Z, Jiang C, et al. Chitosan/O-carboxymethyl chitosan nanoparticles for efficient and safe oral anticancer drug delivery: in vitro and in vivo evaluation. Int J Pharm. 2013;457:158–167. doi:10.1016/j.ijpharm.2013.07.079
   PubMed Web of Science ®Google Scholar
• Mahjub RL, Heidari ST, Radmehr M, et al. Preparation and optimization of N-trimethyl-O-carboxymethyl chitosan nanoparticles for delivery of low-molecular-weight heparin. Pharm Dev Technol. 2016;21:14–25. doi:10.3109/10837450.2014.965320
   PubMed Web of Science ®Google Scholar
• Chaiwarit T, Sommano SRP, Kantrong N, et al. Development of carboxymethyl chitosan nanoparticles prepared by ultrasound-assisted technique for a clindamycin HCl carrier. Polymers. 2022:14. doi:10.3390/polym15010014
   PubMedGoogle Scholar
• Xu C, Xing R, Liu S, et al. The immunostimulatory effects of hydroxypropyltrimethyl ammonium chloride chitosan-carboxymethyl chitosan nanoparticles. Int J Biol Macromol. 2021;181:398–409. doi:10.1016/j.ijbiomac.2021.03.148
   PubMed Web of Science ®Google Scholar
• Pedro RDO, Schmitt CC, Neumann MG. Syntheses and characterization of amphiphilic quaternary ammonium chitosan derivatives. Carbohydr Polym. 2016;147:97–103. doi:10.1016/j.carbpol.2016.03.083
   PubMed Web of Science ®Google Scholar
• Andreica B, Cheng X, Marin L. Quaternary ammonium salts of Chitosan. A critical overview of the synthesis and properties generated by quaternization. Eur Polym J. 2020;139:1–16. doi:10.1016/j.eurpolymj.2020.110016
   Web of Science ®Google Scholar
• Fan L, Yang J, Wu H, et al. Preparation and characterization of quaternary ammonium chitosan hydrogel with significant antibacterial activity. Int J Biol Macromol. 2015;79:830–836. doi:10.1016/j.ijbiomac.2015.04.013
   PubMed Web of Science ®Google Scholar
• Sajomsang W, Gonil P, Tantayanon S. Antibacterial activity of quaternary ammonium chitosan containing mono or disaccharide moieties: preparation and characterization. Int J Biol Macromol. 2009;44:419–427. doi:10.1016/j.ijbiomac.2009.03.003
   PubMed Web of Science ®Google Scholar
• Naskar S, Koutsu K, Sharma S. Chitosan-based nanoparticles s drug delivery systems: a review n two decades of research. J Drug Target. 2019;27:379–393. doi:10.1080/1061186X.2018.1512112
   PubMed Web of Science ®Google Scholar
• Mi F-L, Wu -Y-Y, Lin Y-H, et al. Oral delivery of peptide drugs using nanoparticles self-assembled by poly(Γ-glutamic acid) and A chitosan derivative functionalized by trimethylation. Bioconjug Chem. 2008;19(6):1248–1255. doi:10.1021/bc800076n
   PubMed Web of Science ®Google Scholar
• Li SD, Li PW, Yang ZM, et al. Synthesis and characterization of chitosan quaternary ammonium salt and its application as drug carrier for ribavirin. Drug Deliv. 2014;21:548–552. doi:10.3109/10717544.2013.853708
   PubMed Web of Science ®Google Scholar
• Ahmed TA, Aljaeid BM. Preparation, characterization, and potential application of chitosan, chitosan derivatives, and chitosan metal nanoparticles in pharmaceutical drug delivery. Drug Des Devel Ther. 2016;10:483–507. doi:10.2147/DDDT.S99651
   PubMed Web of Science ®Google Scholar
• Hu F, Zhou Z, Xu Q, et al. Novel pH-responsive quaternary ammonium chitosan-liposome nanoparticles for periodontal treatment. Int J Biol Macromol. 2019;129:1113–1119. doi:10.1016/j.ijbiomac.2018.09.057
   PubMed Web of Science ®Google Scholar
• Huang TW, Ho YC, Tsai TN, et al. Enhancement of the permeability and activities of epigallocatechin gallate y quaternary ammonium chitosan/fucoidan nanoparticles. Carbohydr Poly. 2020;242:1–9. doi:10.1016/j.carbpol.2020.116312
   Web of Science ®Google Scholar
• Wang J, Wang H. Preparation of soluble P-aminobenzoyl chitosan ester by schiff’s base and antibacterial activity of the derivatives. Int J Biol Macromo. 2011;48:523–529. doi:10.1016/j.ijbiomac.2011.01.016
   PubMed Web of Science ®Google Scholar
• Jayakumar R, Nwe N, Tokura S, et al. Sulfated chitin and chitosan as novel biomaterials. Int J Biol Macromol. 2007;40(3):175–181. doi:10.1016/j.ijbiomac.2006.06.021
   PubMed Web of Science ®Google Scholar
• Li Y, Chen XG, Liu N, et al. Physicochemical characterization and antibacterial property of chitosan acetates. Carbohydr Polym. 2007;67:227–232. doi:10.1016/j.carbpol.2006.05.022
   Web of Science ®Google Scholar
• Luangtana-anan M, Nunthanid J, Limmatvapirat S. Potential of different salt forming agents on the formation of chitosan nanoparticles as carriers for protein drug delivery systems. J Pharm Investi. 2019;49:37–44. doi:10.1007/s40005-017-0369-x
   Google Scholar
• Al RZ, Abulateefeh SR, Taha MO. Synthesis and characterization of chitosan-lactate – phthalate and evaluation of the corresponding zinc- and aluminum- crosslinked beads as potential controlled release matrices. Eur Polym. 2015;73:402–412. doi:10.1016/j.eurpolymj.2015.11.004
   Web of Science ®Google Scholar
• Bhattari N. Preparation of lactid acid-grafted chitosan nanoparticles as carriers for prolonged drug delivery. Int J Nanomed. 2006;1:181–187. doi:10.2147/nano.2006.1.2.181
   PubMed Web of Science ®Google Scholar
• Jadidi-Niaragh F, Atyabi F, Rastegari A, et al. CD73 specific siRNA loaded chitosan lactate nanoparticles potentiate the antitumor effect of a dendritic cell vaccine in 4T1 breast cancer bearing mice. J Control Release. 2017;246:46–59. doi:10.1016/j.jconrel.2016.12.012
   PubMed Web of Science ®Google Scholar
• Colonna C, Conti B, Perugini P, et al. Chitosan glutamate nanoparticles for protein delivery: development and effect on prolidase stability. J Microencapsul. 2007;24:553–564. doi:10.1080/02652040701449608
   PubMed Web of Science ®Google Scholar
• Sandhya M, Aparna V, Maneesha KS, et al. Amphotericin B loaded sulfonated chitosan nanoparticles for targeting macrophages to treat intracellular candida glabrata infections. Int J Biol Macromol. 2018;110:133–139. doi:10.1016/j.ijbiomac.2018.01.028
   PubMed Web of Science ®Google Scholar
• Ding N. Homogeneous etherification modification of chitosan and preparation of high-strength hydrogel. J Phys Conf Ser. 2022;2261:1–8. doi:10.1088/1742-6596/2261/1/012011
   Google Scholar
• Wang J, Zhuang S. Chitosan-based materials: preparation, modification and application. J Clean Prod. 2022;355:1–10. doi:10.1016/j.jclepro.2022.131825
   Web of Science ®Google Scholar
• Cao J, You J, Zhang L, et al. Homogeneous synthesis and characterization of chitosan ethers prepared in aqueous alkali/urea solutions. Carbohydr Polym. 2018;185:138–144. doi:10.1016/j.carbpol.2018.01.010
   PubMed Web of Science ®Google Scholar
• Putra P, Husni A, Puspita ID. Characterization and application of N, O-carboxy methyl chitosan produced at different temperature of etherification. Int J Pharm Clin Res. 2016;8:1493–1498.
   Google Scholar
• Zou X, Zhao X, Ye L. Synthesis of cationic chitosan hydrogel with long chain alkyl and its controlled glucose-responsive drug delivery behavior. RSC Adv. 2015;5:96230–96241. doi:10.1039/C5RA16328E
   Web of Science ®Google Scholar
• Yang R, Li H, Huang M, et al. A review on chitosan-based flocculants and their applications in water treatment. Water Res. 2016;95:59–89. doi:10.1016/j.watres.2016.02.068
   PubMed Web of Science ®Google Scholar
• Sun M, Wang T, Pang J, et al. Hydroxybutyl chitosan centered biocomposites for potential curative applications: a critical review. Biomacromolecules. 2020;21(4):1351–1367. doi:10.1021/acs.biomac.0c00071
   PubMed Web of Science ®Google Scholar
• Xie W. Preparation and antibacterial activity of a water-soluble chitosan derivative. Carbohydr Polym. 2002;50(1):35–40. doi:10.1016/S0144-8617(01)00370-8
   Web of Science ®Google Scholar
• Sun M, Yu X, Wang T, et al. Nasal adaptive chitosan-based nano-vehicles for anti-allergic drug delivery. Int J Biol Macromol. 2019;135:1182–1192. doi:10.1016/j.ijbiomac.2019.05.188
   PubMed Web of Science ®Google Scholar
• Lu YH, Liu ZM, Cheng DH. Preparation of hydroxypropyl chitosan nanoparticles and their application in Antheraea pernyi silk treatment. Adv Mater Res. 2013;796:380–384. doi:10.4028/www.scientific.net/AMR.796.380
   Google Scholar
• Hoang NH, Thanh TL, Sangpueak R, et al. Chitosan nanoparticles-based ionic gelation method: a promising candidate for plant disease management. Polymers. 2022;14(4):1–28. doi:10.3390/polym14040662
   Web of Science ®Google Scholar
• Algharib SA, Dawood A, Zhou K, et al. Preparation of chitosan nanoparticles by ionotropic gelation technique: effects of formulation parameters and in vitro characterization. J Mol Struct. 2022;1252:67–78. doi:10.1016/j.molstruc.2021.132129
   Web of Science ®Google Scholar
• Abrica-González P, Zamora-Justo JA, Sotelo-López A, et al. Gold nanoparticles with chitosan, N-acylated chitosan, and chitosan oligosaccharide as DNA carriers. Nanoscale Res Lett. 2019;14(1):258. doi:10.1186/s11671-019-3083-y
   PubMedGoogle Scholar
• Canepa C, Imperiale JC, Berini CA, et al. Development of drug delivery SYSTEM based on chitosan nanoparticles for oral administrations of interferon-alpha. Bio Macromolecules. 2017;18:3302–3309. doi:10.1021/acs.biomac.7b00959
   Google Scholar
• Sayın B, Somavarapu S, Li XW, et al. Mono-N-Carboxymethyl Chitosan (MCC) and N-Trimethyl Chitosan (TMC) nanoparticles for non-invasive vaccine delivery. Int j Pharm. 2008;363:139–148.
   PubMed Web of Science ®Google Scholar
• Maestrelli F, Garcia-Fuentes M, Mura P, et al. A new drug nanocarrier consisting of chitosan and hydoxypropylcyclodextrin. Eur J Pharm Biopharm. 2006;63:79–86. doi:10.1016/j.ejpb.2005.12.006
   PubMed Web of Science ®Google Scholar
• Hecq J, Siepmann F, Siepmann J, et al. Development and evaluation of chitosan and chitosan derivative nanoparticles containing insulin for oral administration. Drug Dev Indust Pharm. 2015;41(12):2037–2044. doi:10.3109/03639045.2015.1044904
   PubMed Web of Science ®Google Scholar
• Yan CY, Gu JW, Hou DP, et al. Synthesis of tat tagged and folate modified N-succinyl-chitosan self-assembly nanoparticles as a novel gene vector. Int J Bio Macromol. 2015;72:751–756. doi:10.1016/j.ijbiomac.2014.09.031
   PubMed Web of Science ®Google Scholar
• Rostami E. Progresses in targeted drug delivery system using chitosan nanoparticles in cancer therapy: mini review. J Drug Delivery Sci Technol. 2020;20:1–28.
   Google Scholar
• Shahbazi Y, Shavisi N. Current advancements in application of chitosan based nano metal oxide as food preservative materials. Nanomed Res Journal. 2019;4:122–129.
   Google Scholar
• Fako VE, Furgeson DY. Zebrafish as a corelative and predictive model for assessing biomaterial nanotoxicity. Adv. Drug Delivery Rev. 2020;61:478–486. doi:10.1016/j.addr.2009.03.008
   Google Scholar
• Dou T, Wang J, Han C, et al. Cellular uptake and transport characteristics of chitosan modified nanoparticles in Caco-2 cell monolayers. Int J Biol Macromol. 2019;138:791–799. doi:10.1016/j.ijbiomac.2019.07.168
   PubMed Web of Science ®Google Scholar
• Zoe LH, David SR, Rajabalaya R. Chitosan nanoparticles toxicity: a comprehensive literature review of in vivo and in vitro assessments for medical applications. Toxicol Rep. 2023;11:83–106. doi:10.1016/j.toxrep.2023.06.012
   PubMedGoogle Scholar
• Svirshchevskaya EV, Zubareva AA, Boyko AA, et al. Analysis of toxicity and biocompatibility of chitosan derivatives with different physico-chemical properties. Appl Biochem Microbiol. 2016;52:483–490. doi:10.1134/S000368381605015X
   Web of Science ®Google Scholar
• Hu Z, Cheng SLY, Kong S, et al. Investigation of the effect of molecular parameters on the hemostatic properties of chitosan. Molecules. 2018;23:1–14. doi:10.3390/molecules23123147
   Web of Science ®Google Scholar
• Nikapitiya C, Dananjaya SHS, Silva BCJD, et al. Chitosan nanoparticles: a positive immune response modulator as displays in zebrafish larvae against Aeromonas hydrophila infection. Fish Shellfish Immunol. 2018;76:240–246. doi:10.1016/j.fsi.2018.03.010
   PubMed Web of Science ®Google Scholar
• Chou CM, Mi FL, Horng JL, et al. Characterization and toxicology evaluation of low molecular weight chitosan on zebrafish. Carbohydr Polym. 2020;240:1–12. doi:10.1016/j.carbpol.2020.116164
   Web of Science ®Google Scholar
• Hu YL, Qi W, Han F, et al. Toxicity evaluation of biodegradable chitosan nanoparticles using a zebrafish embryo model. Int j Nanomed. 2011;6:3351–3359. doi:10.2147/IJN.S25853
   PubMed Web of Science ®Google Scholar
• Wang Y, Zhou J, Liu L, et al. Characterization and toxicology evaluation of chitosan nanoparticles on the embryonic development of zebrafish, Danio rerio. Carbohydr. Polym. 2016;141:204–210. doi:10.1016/j.carbpol.2016.01.012
   PubMed Web of Science ®Google Scholar
• Abou-Saleh H, Younes N, Rasool K, et al. Impaired liver size and compromised neurobehavioral activity are elicited by chitosan nanoparticles in the zebrafish embryo model. Nanomaterials. 2019;9(1):1–13. doi:10.3390/nano9010122
   Web of Science ®Google Scholar
• Qi L, Xu Z, Jiang X, et al. Cytotoxic activity of chitosan nanoparticles and copper loaded nanoparticles. Bioorg. Med. Chem. Lett. 2005;15:1397–1399. doi:10.1016/j.bmcl.2005.01.010
   PubMed Web of Science ®Google Scholar
• Loh JW, Yeoh G, Saunders M, et al. Uptake and cytotoxicity of chitosan nanoparticles in human liver cells. Toxicol Appl Pharmacol. 2010;249(2):148–157. doi:10.1016/j.taap.2010.08.029
   PubMed Web of Science ®Google Scholar
• Kritchenkov AS, Kurasova MN, Godzishevskaya AA, et al. High antibacterial activity and low toxicity of pyridoxal derivatives of chitosan and their nanoparticles. Mendeleev Commun. 2021;31(4):504–506. doi:10.1016/j.mencom.2021.07.022
   Web of Science ®Google Scholar
• Jafernik K, Ladniak A, Blicharska E, et al. Chitosan-based nanoparticles as effective drug delivery systems—a review. Molecules. 2023;28(4):1–17. doi:10.3390/molecules28041963
   Web of Science ®Google Scholar
• Chen L, Zheng Y, Feng L. Novel hyaluronic acid coated hydrophobically modified chitosan polyelectrolyte complex for the delivery of doxorubicin. Int J Biol Macromol. 2018;12:215.
   Google Scholar