Carboxymethylated-β-cyclodextrin/chitosan particles: bulk solids and aqueous dispersions

References

• Jansook, P.; Loftsson, T. CDs as Solubilizers: Effects of Excipients and Competing Drugs. Int. J. Pharm. 2009, 379, 32–40. DOI:10.1016/j.ijpharm.2009.06.005.
   PubMed Web of Science ®Google Scholar
• Connors, K. A. The Stability of Cyclodextrin Complexes in Solution. Chem. Rev. 1997, 97, 1325–1358. DOI:10.1021/cr960371r.
   PubMed Web of Science ®Google Scholar
• Brewster, M. E.; Loftsson, T. Cyclodextrins as Pharmaceutical Solubilizers. Adv. Drug Deliv. Rev. 2007, 59, 645–666. DOI:10.1016/j.addr.2007.05.012.
   PubMed Web of Science ®Google Scholar
• Mavridis, I. M.; Yannakopoulou, K. Anionic Cyclodextrins as Versatile Hosts for Pharmaceutical Nanotechnology: Synthesis, Drug Delivery, Enantioselectivity, Contrast Agents for MRI. Int. J. Pharm. 2015, 492, 275–290. DOI:10.1016/j.ijpharm.2015.06.004.
   PubMed Web of Science ®Google Scholar
• Loftsson, T.; Duchêne, D. Cyclodextrins and Their Pharmaceutical Applications. Int. J. Pharm. 2007, 329, 1–11. DOI:10.1016/j.ijpharm.2006.10.044.
   PubMed Web of Science ®Google Scholar
• Szejtli, J. Past, Present, and Future of Cyclodextrin Research. Pure Appl. Chem. 2004, 76, 1825–1845. DOI:10.1351/pac200476101825.
   Web of Science ®Google Scholar
• Loftsson, T.; Brewster, M. E. Pharmaceutical Applications of Cyclodextrins: Basic Science and Product Development. J. Pharm. Pharmacol. 2010, 62, 1607–1621. DOI:10.1111/j.2042-7158.2010.01030.x.
   PubMed Web of Science ®Google Scholar
• Mosivand, S.; Kazeminezhad, I. Structural and Magnetic Characterization of Electro-Crystallized Magnetite Nanoparticles under Constant Current. Mater. Res. Bull. 2015, 70, 328–335. DOI:10.1016/j.materresbull.2015.04.053.
   Web of Science ®Google Scholar
• Mosivand, S.; Monzon, L. M. A.; Ackland, K.; Kazeminezhad, I.; Coey, J. M. D. Structural and Magnetic Properties of Sonoelectrocrystallized Magnetite Nanoparticles. J. Phys. D: Appl. Phys. 2014, 47, 1–13, DOI:10.1088/0022-3727/47/5/055001.
   Web of Science ®Google Scholar
• Ran, X.; Yang, L.; Zhang, J.; Deng, G.; Li, Y.; Xie, X.; Zhao, H.; Li, C.-P. Highly Sensitive Electrochemical Sensor Based on Beta-Cyclodextrine-Gold@3, 4, 9, 10-Perylene Tetracarboxylic Acid Functionalized Single-Walled Carbon Nanohorns for Simultaneous Determination of Myricetin and Rutin. Anal. Chim. Acta 2015, 892, 85–94. DOI:10.1016/j.aca.2015.08.046.
   PubMed Web of Science ®Google Scholar
• Simoncic, B.; Tomsic, B. Structures of Novel Antimicrobial Agents for Textiles - A Review. Text. Res. J. 2010, 80, 1721–1737. DOI:10.1177/0040517510363193.
   Web of Science ®Google Scholar
• Lyklema, J. Fundamentals of Interface and Colloid Science: Soft Colloids; Elsevier: Amsterdam, 2005; Vol. 5.
   Google Scholar
• Dautzenberg, H. Polyelectrolyte Complex Formation in Highly Aggregating Systems: Methodical Aspects and General Tendencies, In: Physical Chemistry of Polylelctrolytes: Surfactant Science Series; T. Radeva, Ed.; Marcel Dekker: New York, USA, 2001.
   Google Scholar
• Ramasamy, T.; Tran, T. H.; Cho, H. J.; Kim, J. H.; Kim, Y.; Il, Jeon, J. Y.; Choi, H. G.; Yong, C. S.; Kim, J. O. Chitosan-Based Polyelectrolyte Complexes as Potential Nanoparticulate Carriers: Physicochemical and Biological Characterization. Pharm. Res. 2014, 31, 1302–1314. DOI:10.1007/s11095-013-1251-9.
   PubMed Web of Science ®Google Scholar
• Szymanska, E.; Winnicka, K. Stability of Chitosan-A Challenge for Pharmaceutical and Biomedical Applications. Mar. Drugs 2015, 13, 1819–1846. DOI:10.3390/md13041819.
   PubMed Web of Science ®Google Scholar
• Islam, S.; Bhuiyan, M. A. R.; Islam, M. N. Chitin and Chitosan: Structure, Properties and Applications in Biomedical Engineering. J. Polym. Environ. 2017, 25, 854–866. DOI:10.1007/s10924-016-0865-5.
   Web of Science ®Google Scholar
• Garcia-Fuentes, M.; Alonso, M. J. Chitosan-Based Drug Nanocarriers: Where Do We Stand? J. Control. Release 2012, 161, 496–504. DOI:10.1016/j.jconrel.2012.03.017.
   PubMed Web of Science ®Google Scholar
• 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. DOI:10.1016/0378-5173(92)90353-4.
   Web of Science ®Google Scholar
• Kim, M. G.; Jo, S. D.; Jeong, J. H.; Kim, S. H. Nanoscale Polyelectrolyte Complexes Encapsulating MRNA and Long-Chained SiRNA for Combinatorial Cancer Gene Therapy. J. Ind. Eng. Chem. 2018, 64, 430–437. DOI:10.1016/j.jiec.2018.04.005.
   Web of Science ®Google Scholar
• Rinaudo, M. Chitin and Chitosan: Properties and Applications. Prog. Polym. Sci. 2006, 31, 603–632. DOI:10.1016/j.progpolymsci.2006.06.001.
   Web of Science ®Google Scholar
• de Morais, W. A.; Silva, G. T. M.; Nunes, J. S.; Wanderley Neto, A. O.; Pereira, M. R.; Fonseca, J. L. C. Interpolyelectrolyte Complex Formation: From Lyophilic to Lyophobic Colloids. Colloids Surf. A Physicochem. Eng. Asp. 2016, 498, 112–120. DOI:10.1016/j.colsurfa.2016.03.052.
   Web of Science ®Google Scholar
• Tavares, I. S.; Caroni, A. L. P. F.; Neto, A. A. D.; Pereira, M. R.; Fonseca, J. L. C. Surface Charging and Dimensions of Chitosan Coacervated Nanoparticles. Colloids Surf. B Biointerfaces 2012, 90, 254–258. DOI:10.1016/j.colsurfb.2011.10.025.
   PubMed Web of Science ®Google Scholar
• de Vasconcelos, C. L.; Bezerril, P. M.; dos Santos, D. E. S.; Dantas, T. N. C.; Pereira, M. R.; Fonseca, J. L. C. Effect of Molecular Weight and Ionic Strength on the Formation of Polyelectrolyte Complexes Based on Poly(Methacrylic Acid) and Chitosan. Biomacromolecules 2006, 7, 1245–1252. DOI:10.1021/bm050963w.
   PubMed Web of Science ®Google Scholar
• Fernandes, A. L. P.; Morais, W. A.; Santos, A. I. B.; de Araújo, A. M. L.; dos Santos, D. E. S.; dos Santos, D. S.; Pavinatto, F. J.; Oliveira, O. N.; Jr., Dantas, T. N. C.; Pereira, M. R.; et al. The Influence of Oxidative Degradation on the Preparation of Chitosan Nanoparticles. Colloid Polym. Sci. 2005, 284, 1–9. DOI:10.1007/s00396-005-1319-0.
   Web of Science ®Google Scholar
• Stopilha, R. T.; de Lima, C. R. M.; Pereira, M. R.; Fonseca, J. L. C. Preparation of PEC’s Based on Chitosan and NaPMA. Colloids Surf. A Physicochem. Eng. Asp 2016, 489, 27–35. DOI:10.1016/j.colsurfa.2015.08.040.
   Web of Science ®Google Scholar
• de Lima, C. R. M.; de Morais, W. A.; Silva, G. T. M.; Nunes, J. S.; Wanderley Neto, A. O.; Pereira, M. R.; Fonseca, J. L. C. Preparation and Characterization of Dispersions Based on Chitosan and Poly(Styrene Sulfonate). Colloid Polym. Sci. 2017, 295, 1071–1078. DOI:10.1007/s00396-017-4099-4.
   Web of Science ®Google Scholar
• de Lima, C. R. M.; de Souza, P. R. S.; Stopilha, R. T.; de Morais, W. A.; Silva, G. T. M.; Nunes, J. S.; Wanderley Neto, A. O.; Pereira, M. R.; Fonseca, J. L. C. Formation and Structure of Chitosan–Poly(Sodium Methacrylate) Complex Nanoparticles. J. Dispers. Sci. Technol. 2017, 39, 1–9. DOI:10.1080/01932691.2017.1296772.
   Web of Science ®Google Scholar
• Maestrelli, F.; Garcia-Fuentes, M.; Mura, P.; Alonso, M. J. 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
• Krauland, A. H.; Alonso, M. J. Chitosan/Cyclodextrin Nanoparticles as Macromolecular Drug Delivery System. Int. J. Pharm. 2007, 340, 134–142. DOI:10.1016/j.ijpharm.2007.03.005.
   PubMed Web of Science ®Google Scholar
• Wang, J.; Guo, Z.; Xiong, J.; Wu, D.; Li, S.; Tao, Y.; Qin, Y.; Kong, Y. Facile Synthesis of Chitosan-Grafted Beta-Cyclodextrin for Stimuli-Responsive Drug Delivery. Int. J. Biol. Macromol. 2019, 125, 941–947. DOI:10.1016/j.ijbiomac.2018.12.150.
   PubMed Web of Science ®Google Scholar
• Caroni, A. L. P. F.; de Lima, C. R. M.; Pereira, M. R.; Fonseca, J. L. C. The Kinetics of Adsorption of Tetracycline on Chitosan Particles. J. Colloid Interface Sci. 2009, 340, 182–191. DOI:10.1016/j.jcis.2009.08.016.
   PubMed Web of Science ®Google Scholar
• dos Santos, Z. M.; Caroni, A. L. P. F.; Pereira, M. R.; da Silva, D. R.; Fonseca, J. L. C. Determination of Deacetylation Degree of Chitosan: A Comparison between Conductometric Titration and CHN Elemental Analysis. Carbohydr. Res. 2009, 344, 2591–2595. DOI:10.1016/j.carres.2009.08.030.
   PubMed Web of Science ®Google Scholar
• Morais, W. A.; de Almeida, A. L. P.; Pereira, M. R.; Fonseca, J. L. C. Equilibrium and Kinetic Analysis of Methyl Orange Sorption on Chitosan Spheres. Carbohydr. Res. 2008, 343, 2489–2493. DOI:10.1016/j.carres.2008.06.024.
   PubMed Web of Science ®Google Scholar
• Wang, Y.; Qin, F.; Tan, H.; Zhang, Y.; Jiang, M.; Lu, M.; Yao, X. PH-Responsive Glycol Chitosan-Cross-Linked Carboxymethyl-β-Cyclodextrin Nanoparticles for Controlled Release of Anticancer Drugs. Int. J. Nanomed. 2015, 10, 7359–7370. DOI:10.2147/IJN.S91906.
   PubMed Web of Science ®Google Scholar
• Mahmud, S. T.; Wilson, L. D. Synthesis and Characterization of Surface-Modified Mesoporous Silica Materials with β-Cyclodextrin. Cogent Chem. 2016, 2. DOI:10.1080/23312009.2015.1132984.
   PubMed Web of Science ®Google Scholar
• de Vasconcelos, C. L.; Pereira, M. R.; Fonseca, J. L. C. Polyelectrolytes in Solution and the Stabilization of Colloids. J. Dispers. Sci. Technol. 2005, 26, 59–70. DOI:10.1081/DIS-200040170.
   Web of Science ®Google Scholar
• Mrozek, M. F.; Weaver, M. J. Detection and Identification of Aqueous Saccharides by Using Surface-Enhanced Raman Spectroscopy. Anal. Chem. 2002, 74, 4069–4075. DOI:10.1021/ac020115g.
   PubMed Web of Science ®Google Scholar
• Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds, 7th ed.; John Wiley & Sons: Hoboken, 2005.
   Google Scholar
• Trotta, F.; Zanetti, M.; Camino, G. Thermal Degradation of Cyclodextrins. Polym. Degrad. Stab. 2000, 69, 373–379. DOI:10.1016/S0141-3910(00)00084-7.
   Web of Science ®Google Scholar
• Ammar, H. O.; El-Nahhas, S. A.; Ghorab, M. M.; Salama, A. H. Chitosan/Cyclodextrin Nanoparticles as Drug Delivery System. J. Incl. Phenom. Macrocycl. Chem. 2012, 72, 127–136. DOI:10.1007/s10847-011-9950-5.
   Web of Science ®Google Scholar
• Han, J.; Zhou, Z.; Ruixue, Y.; Dongzhi, N.; Jun, Y. Alginate-Chitosan/Hydroxyapatite Polyelectrolyte Complex Porous Scaffolds: Preparation and Characterization. Int. J. Biol. Macromol. 2010, 46, 199–205. DOI:10.1016/j.ijbiomac.2009.11.004.
   PubMed Web of Science ®Google Scholar
• Jiang, C.; Wang, Z.; Zhang, X.; Zhu, X.; Nie, J.; Ma, G. Crosslinked Polyelectrolyte Complex Fiber Membrane Based on Chitosan - Sodium Alginate by Freeze-Drying. R. Soc. Chem. Adv. 2014, 4, 41551–41560. DOI:10.1039/C4RA04208E.
   Web of Science ®Google Scholar
• Neto, C. G. T.; Giacometti, J. A.; Job, A. E.; Ferreira, F. C.; Fonseca, J. L. C.; Pereira, M. R. Thermal Analysis of Chitosan Based Networks. Carbohydr. Polym. 2005, 62, 97–103. DOI:10.1016/j.carbpol.2005.02.022.
   Web of Science ®Google Scholar
• Cabuk, M.; Yavuz, M.; Unal, H. I. Electrokinetic, Electrorheological and Viscoelastic Properties of Polythiophene-Graft-Chitosan Copolymer Particles. Colloids Surf. A Physicochem. Eng. Asp. 2016, 510, 231–238. DOI:10.1016/j.colsurfa.2016.06.014.
   Web of Science ®Google Scholar
• Cabuk, M.; Yavuz, M.; Unal, H. I. Electrokinetic Properties of Biodegradable Conducting Polyaniline-Graft-Chitosan Copolymer in Aqueous and Non-Aqueous Media. Colloids Surf. A Physicochem. Eng. Asp 2014, 460, 494–501. DOI:10.1016/j.colsurfa.2014.02.053.
   Web of Science ®Google Scholar