Chitosan and its Derivatives for Ocular Delivery Formulations: Recent Advances and Developments: Comparison
Please note this is a comparison between Version 2 by Catherine Yang and Version 1 by Dimitrios Bikiaris.

 Chitosan (CS) is a hemi-synthetic cationic linear polysaccharide produced by the

deacetylation of chitin. CS is non-toxic, highly biocompatible, and biodegradable, and it has a

low immunogenicity. Additionally, CS has inherent antibacterial properties and a mucoadhesive

character and can disrupt epithelial tight junctions, thus acting as a permeability enhancer. As such,

CS and its derivatives are well-suited for the challenging field of ocular drug delivery. In the present

review article, we will discuss the properties of CS that contribute to its successful application in

ocular delivery before reviewing the latest advances in the use of CS for the development of novel

ophthalmic delivery systems. Colloidal nanocarriers (nanoparticles, micelles, liposomes) will be

presented, followed by CS gels and lenses and ocular inserts. Finally, instances of CS coatings,

aiming at conferring mucoadhesiveness to other matrixes, will be presented.

  • chitosan
  • derivatives
  • ocular drug delivery
  • ophthalmic applications
  • mucoadhesion
  • antibacterial
  • nanoparticles
  • hydrogels
  • coatings
Please wait, diff process is still running!

References

  1. Sánchez-López, E.; Espina, M.; Doktorovova, S.; Souto, E.B.; García, M.L. Lipid nanoparticles (SLN, NLC): Overcoming the anatomical and physiological barriers of the eye—Part I—Barriers and determining factors in ocular delivery. Eur. J. Pharm. Biopharm. 2017, 110, 70–75.
  2. Jumelle, C.; Gholizadeh, S.; Annabi, N.; Dana, R. Advances and limitations of drug delivery systems formulated as eye drops. J. Control. Release 2020, 321, 1–22.
  3. Souto, E.B.; Dias-Ferreira, J.; López-Machado, A.; Ettcheto, M.; Cano, A.; Espuny, A.C.; Espina, M.; Garcia, M.L.; Sánchez-López, E. Advanced formulation approaches for ocular drug delivery: State-of-the-art and recent patents. Pharmaceutics 2019, 11, 460.
  4. Urtti, A. Challenges and obstacles of ocular pharmacokinetics and drug delivery. Adv. Drug Deliv. Rev. 2006, 58, 1131–1135. [Google Scholar] [CrossRef] [PubMed]
  5. Gaudana, R.; Ananthula, H.K.; Parenky, A.; Mitra, A.K. Ocular drug delivery. AAPS J. 2010, 12, 348–360. [Google Scholar] [CrossRef]
  6. Alvarez-Lorenzo, C.; Yañez, F.; Concheiro, A. Ocular drug delivery from molecularly-imprinted contact lenses. J. Drug Deliv. Sci. Technol. 2010, 20, 237–248. [Google Scholar] [CrossRef]
  7. Patel, A.; Cholkar, K.; Agrahari, V.; Mitra, A.K. Ocular drug delivery systems: An overview. World J. Pharmacol. 2013, 2, 47–64. [Google Scholar] [CrossRef]
  8. Silva, M.M.; Calado, R.; Marto, J.; Bettencourt, A.; Almeida, J.; Gonçalves, L.M.D. Chitosan nanoparticles as a mucoadhesive drug delivery system for ocular administration. Mar. Drugs 2017, 15, 370. [Google Scholar] [CrossRef]
  9. Gaudana, R.; Jwala, J.; Boddu, S.H.S.; Mitra, A.K. Recent perspectives in ocular drug delivery. Pharm. Res. 2009, 26, 1197–1216. [Google Scholar] [CrossRef]
  10. Achouri, D.; Alhanout, K.; Piccerelle, P.; Andrieu, V. Recent advances in ocular drug delivery. Drug Dev. Ind. Pharm. 2013, 39, 1599–1617. [Google Scholar] [CrossRef]
  11. Duxfield, L.; Sultana, R.; Wang, R.; Englebretsen, V.; Deo, S.; Rupenthal, I.D.; Al-Kassas, R. Ocular delivery systems for topical application of anti-infective agents. Drug Dev. Ind. Pharm. 2016, 42, 1–11. [Google Scholar] [CrossRef]
  12. Khare, A.; Grover, K.; Pawar, P.; Singh, I. Mucoadhesive polymers for enhancing retention in ocular drug delivery: A critical review. Rev. Adhes. Adhes. 2014, 2, 467–502.
  13. White, C.J.; Tieppo, A.; Byrne, M.E. Controlled drug release from contact lenses: A comprehensive review from 1965-present. J. Drug Deliv. Sci. Technol. 2011, 21, 369–384. [Google Scholar] [CrossRef]
  14. Fulgêncio, G.; De, O.; Viana, F.A.B.; Ribeiro, R.R.; Yoshida, M.I.; Faraco, A.G.; Da Silva Cunha-Júnior, A. New mucoadhesive chitosan film for ophthalmic drug delivery of timolol maleate: In vivo evaluation. J. Ocul. Pharmacol. Ther. 2012, 28, 350–358. [Google Scholar] [CrossRef]
  15. Bachu, R.D.; Chowdhury, P.; Al-Saedi, Z.H.F.; Karla, P.K.; Boddu, S.H.S. Ocular drug delivery barriers—Role of nanocarriers in the treatment of anterior segment ocular diseases. Pharmaceutics 2018, 10, 28. [Google Scholar] [CrossRef] [PubMed]
  16. Huang, D.; Chen, Y.S.; Rupenthal, I.D. Overcoming ocular drug delivery barriers through the use of physical forces. Adv. Drug Deliv. Rev. 2018, 126, 96–112. [Google Scholar] [CrossRef] [PubMed]
  17. Gote, V.; Sikder, S.; Sicotte, J.; Pal, D. Ocular drug delivery: Present innovations and future challenges. J. Pharmacol. Exp. Ther. 2019, 370, 602–624. [Google Scholar] [CrossRef] [PubMed]
  18. Cao, Y.; Samy, K.E.; Bernards, D.A.; Desai, T.A. Recent advances in intraocular sustained—Release drug delivery devices. Drug Discov. Today 2019, 24, 1694–1700. [Google Scholar] [CrossRef] [PubMed]
  19. Agban, Y.; Thakur, S.S.; Mugisho, O.O.; Rupenthal, I.D. Depot formulations to sustain periocular drug delivery to the posterior eye segment. Drug Discov. Today 2019, 24, 1458–1469. [Google Scholar] [CrossRef]
  20. Maharjan, P.; Cho, K.H.; Maharjan, A.; Shin, M.C.; Moon, C.; Min, K.A. Pharmaceutical challenges and perspectives in developing ophthalmic drug formulations. J. Pharm. Investig. 2019, 49, 215–228. [Google Scholar] [CrossRef]
  21. Bhattacharjee, A.; Das, P.J.; Adhikari, P.; Marbaniang, D.; Pal, P.; Ray, S.; Mazumder, B. Novel drug delivery systems for ocular therapy: With special reference to liposomal ocular delivery. Eur. J. Ophthalmol. 2019, 29, 113–126. [Google Scholar] [CrossRef]
  22. Suri, R.; Beg, S.; Kohli, K. Target strategies for drug delivery bypassing ocular barriers. J. Drug Deliv. Sci. Technol. 2020, 55, 101389. [Google Scholar] [CrossRef]
  23. Ntohogian, S.; Gavriliadou, V.; Christodoulou, E.; Nanaki, S.; Lykidou, S.; Naidis, P.; Mischopoulou, L.; Barmpalexis, P.; Nikolaidis, N.; Bikiaris, D.N. Chitosan nanoparticles with encapsulated natural and Uf-purified annatto and saffron for the preparation of UV protective cosmetic emulsions. Molecules 2018, 23, 2107. [Google Scholar] [CrossRef] [PubMed]
  24. Tashakori-Sabzevar, F.; Mohajeri, S.A. Development of ocular drug delivery systems using molecularly imprinted soft contact lenses. Drug Dev. Ind. Pharm. 2015, 41, 703–713.
  25. Kumar, A.; Vimal, A.; Kumar, A. Why chitosan? From properties to perspective of mucosal drug delivery. Int. J. Biol. Macromol. 2016, 91, 615–622
  26. Li, J.; Cai, C.; Li, J.; Li, J.; Li, J.; Sun, T.; Wang, L.; Wu, H.; Yu, G. Chitosan-based nanomaterials for drug delivery. Molecules 2018, 23, 2661.
  27. Mohammed, M.A.; Syeda, J.T.M.; Wasan, K.M.; Wasan, E.K. An overview of chitosan nanoparticles and its application in non-parenteral drug delivery. Pharmaceutics 2017, 9, 53.
  28. Green, S.; Roldo, M.; Douroumis, D.; Bouropoulos, N.; Lamprou, D.; Fatouros, D.G. Chitosan derivatives alter release profiles of model compounds from calcium phosphate implants. Carbohydr. Res. 2009, 344, 901–907. [Google Scholar] [CrossRef]
  29. Kean, T.; Thanou, M. Biodegradation, biodistribution and toxicity of chitosan. Adv. Drug Deliv. Rev. 2010, 62, 3–11. [Google Scholar] [CrossRef]
  30. Mendes, A.C.; Moreno, J.S.; Hanif, M.; Douglas, T.E.L.; Chen, M.; Chronakis, I.S. Morphological, mechanical and mucoadhesive properties of electrospun chitosan/phospholipid hybrid nanofibers. Int. J. Mol. Sci. 2018, 19, 2266. [Google Scholar] [CrossRef]
  31. Hafezi, F.; Scoutaris, N.; Douroumis, D.; Boateng, J. 3D printed chitosan dressing crosslinked with genipin for potential healing of chronic wounds. Int. J. Pharm. 2019, 560, 406–415. [Google Scholar] [CrossRef]
  32. Michailidou, G.; Ainali, N.M.; Xanthopoulou, E.; Nanaki, S.; Kostoglou, M.; Koukaras, E.N.; Bikiaris, D.N. Effect of poly(vinyl alcohol) on nanoencapsulation of budesonide in chitosan nanoparticles via ionic gelation and its improved bioavailability. Polymers 2020, 12, 1101.
  33. Roy, S.; Pal, K.; Anis, A.; Pramanik, K.; Prabhakar, B. Polymers in mucoadhesive drug-delivery systems: A brief note. Des. Monomers Polym. 2009, 12, 483–495. [Google Scholar] [CrossRef]
  34. Shaikh, R.; Raj Singh, T.; Garland, M.; Woolfson, A.; Donnelly, R. Mucoadhesive drug delivery systems. J. Pharm. Bioallied Sci. 2011, 3, 89–100. [Google Scholar]
  35. Ensign, L.M.; Cone, R.; Hanes, J. Oral drug delivery with polymeric nanoparticles: The gastrointestinal mucus barriers. Adv. Drug Deliv. Rev. 2012, 64, 557–570.
  36. Boegh, M.; Nielsen, H.M. Mucus as a barrier to drug delivery—Understanding and mimicking the barrier properties. Basic Clin. Pharmacol. Toxicol. 2015, 116, 179–186.
  37. Peppas, N.A.; Buri, P.A. Surface, interfacial and molecular aspects of polymer bioadhesion on soft tissues. J. Control. Release 1985, 2, 257–275. [Google Scholar] [CrossRef]
  38. Mikos, A.G.; Peppas, N.A. Scaling concepts and molecular theories of adhesion of synthetic polymers to glycoproteinic networks. In Bioadhesive Drug Delivery Systems; Lenaerts, V.M., Gurny, R., Eds.; CRC Press: Boca Raton, FL, USA, 1990; pp. 25–42. [Google Scholar]
  39. Khutoryanskiy, V.V. Advances in mucoadhesion and mucoadhesive polymers. Macromol. Biosci. 2011, 11, 748–764. [Google Scholar] [CrossRef]
  40. Bassi Da Silva, J.; Ferreira, S.B. de S.; de Freitas, O.; Bruschi, M.L. A critical review about methodologies for the analysis of mucoadhesive properties of drug delivery systems. Drug Dev. Ind. Pharm. 2017, 43, 1053–1070.
  41. Grabovac, V.; Guggi, D.; Bernkop-Schnürch, A. Comparison of the mucoadhesive properties of various polymers. Adv. Drug Deliv. Rev. 2005, 57, 1713–1723. [Google Scholar] [CrossRef]
  42. Andrews, G.P.; Laverty, T.P.; Jones, D.S. Mucoadhesive polymeric platforms for controlled drug delivery. Eur. J. Pharm. Biopharm. 2009, 71, 505–518. [Google Scholar] [CrossRef] [PubMed]
  43. Bagan, J.; Paderni, C.; Termine, N.; Campisi, G.; Russo, L.L.; Compilato, D.; Di Fede, O. Mucoadhesive polymers for oral transmucosal drug delivery: A review. Curr. Pharm. Des. 2012, 18, 5497–5514.
  44. Kellaway, I.W. In vitro test methods for the measurement of mucoadhesion. In Bioadhesion Possibilities and Future Trends (APV, Band 25); Gurny, R., Junginger, H.E., Eds.; Wissenschaftliche Verlagsgesellschaft mbH: Stuttgart, Germany, 1990; pp. 86–92. [Google Scholar]
  45. Peppas, N.A.; Sahlin, J.J. Hydrogels as mucoadhesive and bioadhesive materials: A review. Biomaterials 1996, 17, 1553–1561. [Google Scholar] [CrossRef]
  46. Eliyahu, S.; Aharon, A.; Bianco-Peled, H. Acrylated chitosan nanoparticles with enhanced mucoadhesion. Polymers 2018, 10, 106.
  47. Van Der Lubben, I.M.; Verhoef, J.C.; Van Aelst, A.C.; Borchard, G.; Junginger, H.E. Chitosan microparticles for oral vaccination: Preparation, characterization and preliminary in vivo uptake studies in murine Peyer’s patches. Biomaterials 2001, 22, 687–694. [Google Scholar] [CrossRef]
  48. Mahmood, A.; Lanthaler, M.; Laffleur, F.; Huck, C.W.; Bernkop-Schnürch, A. Thiolated chitosan micelles: Highly mucoadhesive drug carriers. Carbohydr. Polym. 2017, 167, 250–258. [Google Scholar] [CrossRef]
  49. Pontillo, A.R.N.; Detsi, A. Nanoparticles for ocular drug delivery: Modified and non-modified chitosan as a promising biocompatible carrier. Nanomedicine 2019, 14, 1889–1909.
  50. Collado-González, M.; González Espinosa, Y.; Goycoolea, F.M. Interaction between chitosan and mucin: Fundamentals and applications. Biomimetics 2019, 4, 32.
  51. Lohani, A.; Chaudhary, G. Mucoadhesive microspheres: A novel approach to increase gastroretention. Chronicles Young Sci. 2012, 3, 121.
  52. Barbu, E.; Verestiuc, L.; Nevell, T.G.; Tsibouklis, J. Polymeric materials for ophthalmic drug delivery: Trends and perspectives. J. Mater. Chem. 2006, 16, 3439–3443.
  53. Meng-Lund, E.; Muff-Westergaard, C.; Sander, C.; Madelung, P.; Jacobsen, J. A mechanistic based approach for enhancing buccal mucoadhesion of chitosan. Int. J. Pharm. 2014, 461, 280–285.
  54. Sogias, I.A.; Williams, A.C.; Khutoryanskiy, V.V. Why is chitosan mucoadhesive? Biomacromolecules 2008, 9, 1837–1842. [Google Scholar] [CrossRef] [PubMed]
  55. Sogias, I.A.; Williams, A.C.; Khutoryanskiy, V.V. Chitosan-based mucoadhesive tablets for oral delivery of ibuprofen. Int. J. Pharm. 2012, 436, 602–610.
  56. Nafee, N.A.; Boraie, N.A.; Ismail, F.A.; Mortada, L.M. Design and characterization of mucoadhesive buccal patches containing cetylpyridinium chloride. Acta Pharm. 2003, 53, 199–212.
  57. Karavas, E.; Georgarakis, E.; Bikiaris, D. Application of PVP/HPMC miscible blends with enhanced mucoadhesive properties for adjusting drug release in predictable pulsatile chronotherapeutics. Eur. J. Pharm. Biopharm. 2006, 64, 115–126.
  58. Lehr, C.M.; Bouwstra, J.A.; Schacht, E.H.; Junginger, H.E. In vitro evaluation of mucoadhesive properties of chitosan and some other natural polymers. Int. J. Pharm. 1992, 78, 43–48.
  59. Shojaei, A.H.; Paulson, J.; Honary, S. Evaluation of poly(acrylic acid-co-ethylhexyl acrylate) films for mucoadhesive transbuccal drug delivery: Factors affecting the force of mucoadhesion. J. Control. Release 2000, 67, 223–232.
  60. De Sá, L.L.F.; Nogueira, N.C.; Filho, E.C.D.S.; Figueiras, A.; Veiga, F.; Nunes, L.C.C.; Soares-Sobrinho, J.L. Design of buccal mucoadhesive tablets: Understanding and development. J. Appl. Pharm. Sci. 2018, 8, 150–163.
  61. Bartkowiak, A.; Rojewska, M.; Hyla, K.; Zembrzuska, J.; Prochaska, K. Surface and swelling properties of mucoadhesive blends and their ability to release fluconazole in a mucin environment. Colloids Surf. B 2018, 172, 586–593.
  62. Nafee, N.A.; Ismail, F.A.; Boraie, N.A.; Mortada, L.M. Mucoadhesive delivery systems. I. Evaluation of mucoadhesive polymers for buccal tablet formulation. Drug Dev. Ind. Pharm. 2004, 30, 985–993.
  63. Abu-Huwaij, R.; Obaidat, R.M.; Sweidan, K.; Al-Hiari, Y. Formulation and in vitro evaluation of xanthan gum or carbopol 934-based mucoadhesive patches, loaded with nicotine. AAPS PharmSciTech 2011, 12, 21–27.
  64. Chopra, S.; Mahdi, S.; Kaur, J.; Iqbal, Z.; Talegaonkar, S.; Ahmad, F.J. Advances and potential applications of chitosan derivatives as mucoadhesive biomaterials in modern drug delivery. J. Pharm. Pharmacol. 2006, 58, 1021–1032. [Google Scholar] [CrossRef] [PubMed]
  65. Bhavsar, C.; Momin, M.; Gharat, S.; Omri, A. Functionalized and graft copolymers of chitosan and its pharmaceutical applications. Expert Opin. Drug Deliv. 2017, 14, 1189–1204. [Google Scholar] [CrossRef] [PubMed]
  66. Ways, T.M.M.; Lau, W.M.; Khutoryanskiy, V.V. Chitosan and its derivatives for application in mucoadhesive drug delivery systems. Polymers 2018, 10, 267.
  67. Greaves, J.L.; Wilson, C.G. Treatment of diseases of the eye with mucoadhesive delivery systems. Adv. Drug Deliv. Rev. 1993, 11, 349–383.
  68. Muzzarelli, R.A.A.; Tanfani, F. The N-permethylation of chitosan and the preparation of N-trimethyl chitosan iodide. Carbohydr. Polym. 1985, 5, 297–307.
  69. Karavasili, C.; Katsamenis, O.L.; Bouropoulos, N.; Nazar, H.; Thurner, P.J.; van der Merwe, S.M.; Fatouros, D.G. Preparation and characterization of bioadhesive microparticles comprised of low degree of quaternization trimethylated chitosan for nasal administration: Effect of concentration and molecular weight. Langmuir 2014, 30, 12337–12344.
  70. Jayakumar, R.; Prabaharan, M.; Nair, S.V.; Tokura, S.; Tamura, H.; Selvamurugan, N. Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications. Prog. Mater. Sci. 2010, 55, 675–709. [Google Scholar] [CrossRef]
  71. Upadhyaya, L.; Singh, J.; Agarwal, V.; Tewari, R.P. The implications of recent advances in carboxymethyl chitosan based targeted drug delivery and tissue engineering applications. J. Control. Release 2014, 186, 54–87.
  72. Aggarwal, S.; Agarwal, S. Mucoadhesive polymeric platform for drug delivery: A comprehensive review. Curr. Drug Deliv. 2015, 12, 139–156
  73. Hunt, G.; Kearney, P.; Kellaway, I.W. Mucoadhesive polymers in drug delivery systems. In Drug Delivery Systems: Fundamentals and Techniques; Johnson, P., Lloyd Jones, J., Ellis, H., Eds.; Ellis Horwood: Chichester, UK, 1987; pp. 180–199. [Google Scholar]
  74. Bernkop-Schnürch, A.; Steininger, S. Synthesis and characterisation of mucoadhesive thiolated polymers. Int. J. Pharm. 2000, 194, 239–247. [Google Scholar] [CrossRef]
  75. Bernkop-Schnürch, A.; Scholler, S.; Biebel, R.G. Development of controlled drug release systems based on thiolated polymers. J. Control. Release 2000, 66, 39–48. [Google Scholar] [CrossRef]
  76. Bernkop-Schnürch, A.; Hornof, M.; Guggi, D. Thiolated chitosans. Eur. J. Pharm. Biopharm. 2004, 57, 9–17. [Google Scholar] [CrossRef]
  77. Langoth, N.; Kahlbacher, H.; Schöffmann, G.; Schmerold, I.; Schuh, M.; Franz, S.; Kurka, P.; Bernkop-Schnürch, A. Thiolated chitosans: Design and in vivo evaluation of a mucoadhesive buccal peptide drug delivery system. Pharm. Res. 2006, 23, 573–579. [Google Scholar] [CrossRef] [PubMed]
  78. Kongsong, M.; Songsurang, K.; Sangvanich, P.; Siralertmukul, K.; Muangsin, N. Design, synthesis, fabrication and in vitro evalution of mucoadhesive 5-amino-2-mercaptobenzimidazole chitosan as low water soluble drug carriers. Eur. J. Pharm. Biopharm. 2014, 88, 986–997. [Google Scholar] [CrossRef]
  79. Cho, I.S.; Oh, H.M.; Cho, M.O.; Jang, B.S.; Cho, J.-K.; Park, K.H.; Kang, S.-W.; Huh, K.M. Synthesis and characterization of thiolated hexanoyl glycol chitosan as a mucoadhesive thermogelling polymer. Biomater. Res. 2018, 22, 1–10. [Google Scholar] [CrossRef] [PubMed]
  80. Nanaki, S.; Tseklima, M.; Christodoulou, E.; Triantafyllidis, K.; Kostoglou, M.; Bikiaris, D.N. Thiolated chitosan masked polymeric microspheres with incorporated mesocellular silica foam (MCF) for intranasal delivery of paliperidone. Polymers 2017, 9, 617.
  81. Bernkop-Schnürch, A. Thiomers: A new generation of mucoadhesive polymers. Adv. Drug Deliv. Rev. 2005, 57, 1569–1582.
  82. Menzel, C.; Hauser, M.; Frey, A.; Jelkmann, M.; Laffleur, F.; Götzfried, S.K.; Gust, R.; Bernkop-Schnürch, A. Covalently binding mucoadhesive polymers: N-hydroxysuccinimide grafted polyacrylates. Eur. J. Pharm. Biopharm. 2019, 139, 161–167.
  83. Eshel-Green, T.; Bianco-Peled, H. Mucoadhesive acrylated block copolymers micelles for the delivery of hydrophobic drugs. Colloids Surf. B 2016, 139, 42–51.
  84. Shitrit, Y.; Bianco-Peled, H. Acrylated chitosan for mucoadhesive drug delivery systems. Int. J. Pharm. 2017, 517, 247–255.
  85. Ryu, J.H.; Choi, J.S.; Park, E.; Eom, M.R.; Jo, S.; Lee, M.S.; Kwon, S.K.; Lee, H. Chitosan oral patches inspired by mussel adhesion. J. Control. Release 2020, 317, 57–66.
  86. Kolawole, O.M.; Lau, W.M.; Khutoryanskiy, V.V. Methacrylated chitosan as a polymer with enhanced mucoadhesive properties for transmucosal drug delivery. Int. J. Pharm. 2018, 550, 123–129.
  87. Bernkop-Schnürch, A. Mucoadhesive systems in oral drug delivery. Drug Discov. Today Technol. 2005, 2, 83–87.
  88. Sigurdsson, H.H.; Kirch, J.; Lehr, C.M. Mucus as a barrier to lipophilic drugs. Int. J. Pharm. 2013, 453, 56–64.
  89. Lehr, C.M.; Poelma, F.G.J.; Junginger, H.E.; Tukker, J.J. An estimate of turnover time of intestinal mucus gel layer in the rat in situ loop. Int. J. Pharm. 1991, 70, 235–240. [Google Scholar] [CrossRef]
  90. Lai, S.K.; Wang, Y.Y.; Hanes, J. Mucus-penetrating nanoparticles for drug and gene delivery to mucosal tissues. Adv. Drug Deliv. Rev. 2009, 61, 158–171.
  91. Ponchel, G.; Montisci, M.-J.; Dembri, A.; Durrer, C.; Duchêne, D. Mucoadhesion of colloidal particulate systems in the gastro-intestinal tract. Eur. J. Pharm. Biopharm. 1997, 44, 25–31.
  92. Zhang, X.; Cheng, H.; Dong, W.; Zhang, M.; Liu, Q.; Wang, X.; Guan, J.; Wu, H.; Mao, S. Design and intestinal mucus penetration mechanism of core-shell nanocomplex. J. Control. Release 2018, 272, 29–38.
  93. Rabea, E.I.; Badawy, M.E.T.; Stevens, C.V.; Smagghe, G.; Steurbaut, W. Chitosan as antimicrobial agent: Applications and mode of action. Biomacromolecules 2003, 4, 1457–1465. [Google Scholar] [CrossRef]
  94. Tang, H.; Zhang, P.; Kieft, T.L.; Ryan, S.J.; Baker, S.M.; Wiesmann, W.P.; Rogelj, S. Antibacterial action of a novel functionalized chitosan-arginine against Gram-negative bacteria. Acta Biomater. 2010, 6, 2562–2571. [Google Scholar] [CrossRef] [PubMed]
  95. Matica, M.A.; Aachmann, F.L.; Tøndervik, A.; Sletta, H.; Ostafe, V. Chitosan as a wound dressing starting material: Antimicrobial properties and mode of action. Int. J. Mol. Sci. 2019, 20, 5889. [Google Scholar] [CrossRef] [PubMed]
  96. Michailidou, G.; Christodoulou, E.; Nanaki, S.; Barmpalexis, P.; Karavas, E.; Vergkizi-Nikolakaki, S.; Bikiaris, D.N. Super-hydrophilic and high strength polymeric foam dressings of modified chitosan blends for topical wound delivery of chloramphenicol. Carbohydr. Polym. 2019, 208, 1–13. [Google Scholar] [CrossRef] [PubMed]
  97. Kong, M.; Chen, X.G.; Xing, K.; Park, H.J. Antimicrobial properties of chitosan and mode of action: A state of the art review. Int. J. Food Microbiol. 2010, 144, 51–63.
  98. Kandimalla, K.K.; Borden, E.; Omtri, R.S.; Boyapati, S.P.; Smith, M.; Lebby, K.; Mulpuru, M.; Gadde, M. Ability of chitosan gels to disrupt bacterial biofilms and their applications in the treatment of bacterial vaginosis. J. Pharm. Sci. 2013, 102, 2096–2101.
  99. Shariatinia, Z. Carboxymethyl chitosan: Properties and biomedical applications. Int. J. Biol. Macromol. 2018, 120, 1406–1419.
  100. Rúnarsson, Ö.V.; Holappa, J.; Nevalainen, T.; Hjálmarsdóttir, M.; Järvinen, T.; Loftsson, T.; Einarsson, J.M.; Jónsdóttir, S.; Valdimarsdóttir, M.; Másson, M. Antibacterial activity of methylated chitosan and chitooligomer derivatives: Synthesis and structure activity relationships. Eur. Polym. J. 2007, 43, 2660–2671. [Google Scholar] [CrossRef]
  101. Sadeghi, A.M.M.; Amini, M.; Avadi, M.R.; Siedi, F.; Rafiee-Tehrani, M.; Junginger, H.E. Synthesis, characterization, and antibacterial effects of trimethylated and triethylated 6-NH2-6-deoxy chitosan. J. Bioact. Compat. Polym. 2008, 23, 262–275. [Google Scholar] [CrossRef]
  102. De Britto, D.; Celi Goy, R.; Campana Filho, S.P.; Assis, O.B.G. Quaternary salts of chitosan: History, antimicrobial features, and prospects. Int. J. Carbohydr. Chem. 2011, 2011, 1–12. [Google Scholar] [CrossRef]
  103. Zhang, J.; Tan, W.; Luan, F.; Yin, X.; Dong, F.; Li, Q.; Guo, Z. Synthesis of quaternary ammonium salts of chitosan bearing halogenated acetate for antifungal and antibacterial activities. Polymers 2018, 10, 530.
  104. Sadeghi, A.M.M.; Dorkoosh, F.A.; Avadi, M.R.; Saadat, P.; Rafiee-Tehrani, M.; Junginger, H.E. Preparation, characterization and antibacterial activities of chitosan, N-trimethyl chitosan (TMC) and N-diethylmethyl chitosan (DEMC) nanoparticles loaded with insulin using both the ionotropic gelation and polyelectrolyte complexation methods. Int. J. Pharm. 2008, 355, 299–306.
  105. Liu, P.; Meng, W.; Wang, S.; Sun, Y.; Aqeel Ashraf, M. Quaternary ammonium salt of chitosan: Preparation and antimicrobial property for paper. Open Med. 2015, 10, 473–478.
  106. Xu, T.; Xin, M.; Li, M.; Huang, H.; Zhou, S.; Liu, J. Synthesis, characterization, and antibacterial activity of N,O-quaternary ammonium chitosan. Carbohydr. Res. 2011, 346, 2445–2450.
  107. Jadhav, R.L.; Yadav, A.V.; Patil, M.V. Poly Sulfoxyamine grafted chitosan as bactericidal dressing for wound healing. Asian J. Chem. 2020, 32, 127–132.
  108. De la Fuente, M.; Raviña, M.; Paolicelli, P.; Sanchez, A.; Seijo, B.; Alonso, M.J. Chitosan-based nanostructures: A delivery platform for ocular therapeutics. Adv. Drug Deliv. Rev. 2010, 62, 100–117.
  109. Eljarrat-Binstock, E.; Orucov, F.; Aldouby, Y.; Frucht-Pery, J.; Domb, A.J. Charged nanoparticles delivery to the eye using hydrogel iontophoresis. J. Control. Release 2008, 126, 156–161. [Google Scholar] [CrossRef] [PubMed]
  110. Nagarwal, R.C.; Kant, S.; Singh, P.N.; Maiti, P.; Pandit, J.K. Polymeric nanoparticulate system: A potential approach for ocular drug delivery. J. Control. Release 2009, 136, 2–13.
  111. De Campos, A.M.; Sánchez, A.; Alonso, M.J. Chitosan nanoparticles: A new vehicle for the improvement of the delivery of drugs to the ocular surface. Application to cyclosporin A. Int. J. Pharm. 2001, 224, 159–168. [Google Scholar] [CrossRef]
  112. Motwani, S.K.; Chopra, S.; Talegaonkar, S.; Kohli, K.; Ahmad, F.J.; Khar, R.K. Chitosan-sodium alginate nanoparticles as submicroscopic reservoirs for ocular delivery: Formulation, optimisation and in vitro characterisation. Eur. J. Pharm. Biopharm. 2008, 68, 513–525. [Google Scholar] [CrossRef]
  113. Mahmoud, A.A.; El-Feky, G.S.; Kamel, R.; Awad, G.E.A. Chitosan/sulfobutylether-β-cyclodextrin nanoparticles as a potential approach for ocular drug delivery. Int. J. Pharm. 2011, 413, 229–236.
  114. Sadeghi, A.M.M.; Dorkoosh, F.A.; Avadi, M.R.; Weinhold, M.; Bayat, A.; Delie, F.; Gurny, R.; Larijani, B.; Rafiee-Tehrani, M.; Junginger, H.E. Permeation enhancer effect of chitosan and chitosan derivatives: Comparison of formulations as soluble polymers and nanoparticulate systems on insulin absorption in Caco-2 cells. Eur. J. Pharm. Biopharm. 2008, 70, 270–278.
  115. Mei, D.; Mao, S.; Sun, W.; Wang, Y.; Kissel, T. Effect of chitosan structure properties and molecular weight on the intranasal absorption of tetramethylpyrazine phosphate in rats. Eur. J. Pharm. Biopharm. 2008, 70, 874–881.
  116. Li, J.; Cheng, T.; Tian, Q.; Cheng, Y.; Zhao, L.; Zhang, X.; Qu, Y. A more efficient ocular delivery system of triamcinolone acetonide as eye drop to the posterior segment of the eye. Drug Deliv. 2019, 26, 188–198.
  117. Cheng, T.; Li, J.; Cheng, Y.; Zhang, X.; Qu, Y. Triamcinolone acetonide-chitosan coated liposomes efficiently treated retinal edema as eye drops. Exp. Eye Res. 2019, 188, 107805.
  118. Tan, G.; Yu, S.; Pan, H.; Li, J.; Liu, D.; Yuan, K.; Yang, X.; Pan, W. Bioadhesive chitosan-loaded liposomes: A more efficient and higher permeable ocular delivery platform for timolol maleate. Int. J. Biol. Macromol. 2017, 94, 355–363.
  119. Khalil, M.; Hashmi, U.; Riaz, R.; Rukh Abbas, S. Chitosan coated liposomes (CCL) containing triamcinolone acetonide for sustained delivery: A potential topical treatment for posterior segment diseases. Int. J. Biol. Macromol. 2020, 143, 483–491.
  120. Chen, H.; Pan, H.; Li, P.; Wang, H.; Wang, X.; Pan, W.; Yuan, Y. The potential use of novel chitosan-coated deformable liposomes in an ocular drug delivery system. Colloids Surf. B 2016, 143, 455–462.
  121. Sun, C.C.; Chou, S.F.; Lai, J.Y.; Cho, C.H.; Lee, C.H. Dependence of corneal keratocyte adhesion, spreading, and integrin β1 expression on deacetylated chitosan coating. Mater. Sci. Eng. C 2016, 63, 222–230.
  122. Eid, H.M.; Elkomy, M.H.; El Menshawe, S.F.; Salem, H.F. Development, optimization, and in vitro/in vivo characterization of enhanced lipid nanoparticles for ocular delivery of ofloxacin: The influence of pegylation and chitosan coating. AAPS PharmSciTech 2019, 20, 1–14.
  123. Ban, J.; Zhang, Y.; Huang, X.; Deng, G.; Hou, D.; Chen, Y.; Lu, Z. Corneal permeation properties of a charged lipid nanoparticle carrier containing dexamethasone. Int. J. Nanomed. 2017, 2017, 1329–1339.
  124. Gelfuso, G.M.; Ferreira-Nunes, R.; Dalmolin, L.F.; Ana, A.C.; Dos Santos, G.A.; De Sá, F.A.P.; Cunha-Filho, M.; Alonso, A.; Neto, S.A.M.; Anjos, J.L.V.; et al. Iontophoresis enhances voriconazole antifungal potency and corneal penetration. Int. J. Pharm. 2020, 576, 118991.
  125. Seyfoddin, A.; Sherwin, T.; Patel, D.V.; McGhee, C.N.; Rupenthal, I.D.; Taylor, J.A.; Al-Kassas, R. Ex vivo and in vivo evaluation of chitosan coated nanostructured lipid carriers for ocular delivery of acyclovir. Curr. Drug Deliv. 2016, 13, 923–934.
  126. Wang, F.; Zhang, M.; Zhang, D.; Huang, Y.; Chen, L.; Jiang, S.; Shi, K.; Li, R. Preparation, optimization, and characterization of chitosan-coated solid lipid nanoparticles for ocular drug delivery. J. Biomed. Res. 2018, 32, 411–423.
  127. Jurišić Dukovski, B.; Juretić, M.; Bračko, D.; Randjelović, D.; Savić, S.; Crespo Moral, M.; Diebold, Y.; Filipović-Grčić, J.; Pepić, I.; Lovrić, J. Functional ibuprofen-loaded cationic nanoemulsion: Development and optimization for dry eye disease treatment. Int. J. Pharm. 2020, 576, 118979.
  128. Zhang, J.; Liang, X.; Li, X.; Guan, Z.; Liao, Z.; Luo, Y.; Luo, Y. Ocular delivery of cyanidin-3-glycoside in liposomes and its prevention of selenite-induced oxidative stress. Drug Dev. Ind. Pharm. 2016, 42, 546–553.
  129. Huang, C.; Li, C.; Muhemaitia, P. Impediment of selenite-induced cataract in rats by combinatorial drug laden liposomal preparation. Libyan J. Med. 2019, 14, 1548252.
  130. Pai, R.V.; Vavia, P.R. Chitosan oligosaccharide enhances binding of nanostructured lipid carriers to ocular mucins: Effect on ocular disposition. Int. J. Pharm. 2020, 577, 119095.
  131. Liu, D.; Li, J.; Pan, H.; He, F.; Liu, Z.; Wu, Q.; Bai, C.; Yu, S.; Yang, X. Potential advantages of a novel chitosan-N-acetylcysteine surface modified nanostructured lipid carrier on the performance of ophthalmic delivery of curcumin. Sci. Rep. 2016, 6, 1–14.
  132. Li, J.; Tan, G.; Cheng, B.; Liu, D.; Pan, W. Transport mechanism of chitosan-N-acetylcysteine, chitosan oligosaccharides or carboxymethyl chitosan decorated coumarin-6 loaded nanostructured lipid carriers across the rabbit ocular. Eur. J. Pharm. Biopharm. 2017, 120, 89–97. [Google Scholar] [CrossRef]
  133. Liu, D.; Li, J.; Cheng, B.; Wu, Q.; Pan, H. Ex vivo and in vivo evaluation of the effect of coating a coumarin-6-labeled nanostructured lipid carrier with chitosan-n-acetylcysteine on rabbit ocular distribution. Mol. Pharm. 2017, 14, 2639–2648.
  134. Salama, A.H.; Mahmoud, A.A.; Kamel, R. A novel method for preparing surface-modified fluocinolone acetonide loaded plga nanoparticles for ocular use: In vitro and in vivo evaluations. AAPS PharmSciTech 2016, 17, 1159–1172.
  135. Pandit, J.; Sultana, Y.; Aqil, M. Chitosan-coated PLGA nanoparticles of bevacizumab as novel drug delivery to target retina: Optimization, characterization, and in vitro toxicity evaluation. Artif. Cells Nanomed. Biotechnol. 2017, 45, 1397–1407.
  136. Khan, N.; Ameeduzzafar; Khanna, K.; Bhatnagar, A.; Ahmad, F.J.; Ali, A. Chitosan coated PLGA nanoparticles amplify the ocular hypotensive effect of forskolin: Statistical design, characterization and in vivo studies. Int. J. Biol. Macromol. 2018, 116, 648–663
  137. Dyawanapelly, S.; Koli, U.; Dharamdasani, V.; Jain, R.; Dandekar, P. Improved mucoadhesion and cell uptake of chitosan and chitosan oligosaccharide surface-modified polymer nanoparticles for mucosal delivery of proteins. Drug Deliv. Transl. Res. 2016, 6, 365–379.
  138. Mahaling, B.; Katti, D.S. Physicochemical properties of core-shell type nanoparticles govern their spatiotemporal biodistribution in the eye. Nanomed. Nanotechnol. Biol. Med. 2016, 12, 2149–2160. [Google Scholar] [CrossRef] [PubMed]
  139. Mahaling, B.; Katti, D.S. Understanding the influence of surface properties of nanoparticles and penetration enhancers for improving bioavailability in eye tissues in vivo. Int. J. Pharm. 2016, 501, 1–9.
  140. Nasr, F.H.; Khoee, S. Design, characterization and in vitro evaluation of novel shell crosslinked poly(butylene adipate)-co-N-succinyl chitosan nanogels containing loteprednol etabonate: A new system for therapeutic effect enhancement via controlled drug delivery. Eur. J. Med. Chem. 2015, 102, 132–142.
More
ScholarVision Creations