Polymeric micelles in mucosal drug delivery: Challenges towards clinical translation

Biotechnology Advances

Volumn 33, Issue 6, 2015, Pages 1380-1392

  Sosnik, Alejandro ^a   Menaker Raskin, Maya ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Clinical translation; Modified polymeric amphiphiles; Mucoadhesion; Mucoadhesive polymeric micelles; Non parenteral drug delivery; Polysaccharide graft copolymers

Indexed keywords

AMPHIPHILES; CONTROLLED DRUG DELIVERY; MEDICAL APPLICATIONS; MICELLES; TARGETED DRUG DELIVERY;

CLINICAL APPLICATION; CLINICAL TRANSLATION; CRITICAL MICELLAR CONCENTRATIONS; MUCOADHESION; POLYMERIC AMPHIPHILES; POLYMERIC MICELLE; THERAPEUTIC AGENTS; THERAPEUTIC POTENTIALS;

POLYMERS;

ADHESION; CANCER; DRUG; FATTY ACID; MOLECULAR ANALYSIS; NANOTECHNOLOGY; POLYMER; POLYSACCHARIDE;

ACRYLIC ACID RESIN; CARBOPOL 940; CHITOSAN; MICELLE; POLYMER; POLYMETHACRYLIC ACID DERIVATIVE; POLYSACCHARIDE;

CHEMISTRY; DRUG DELIVERY SYSTEM; MICELLE; MUCOSA; NANOTECHNOLOGY; PHARMACEUTICS; PROCEDURES; TRANSLATIONAL RESEARCH; TRENDS;

ACRYLIC RESINS; CHITOSAN; DRUG DELIVERY SYSTEMS; MICELLES; MUCOUS MEMBRANE; NANOTECHNOLOGY; POLYMERS; POLYMETHACRYLIC ACIDS; POLYSACCHARIDES; TECHNOLOGY, PHARMACEUTICAL; TRANSLATIONAL MEDICAL RESEARCH;

EID: 84955185068     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biotechadv.2015.01.003     Document Type: Review

References (200)

1. Abdelbary G.A., Tadros M.I. Brain targeting of olanzapine via intranasal delivery of core-shell difunctional block copolymer mixed nanomicellar carriers: in vitro characterization, ex vivo estimation of nasal toxicity and in vivo biodistribution studies. Int J Pharm 2013, 452:300-310.
2. Ahmed F., Discher D.E. Self-porating polymersomes of PEG-PLA and PEG-PCL: hydrolysis-triggered controlled release vesicles. J Control Release 2004, 96:37-53.
3. Alonso M.J., Sanchez A. The potential of chitosan in coular drug delivery. J Pharm Pharmacol 2003, 55:1451-1463.
4. Alvarez-Lorenzo C., Rey-Rico A., Brea J., Loza M.I., Concheiro A., Sosnik A. Inhibition of P-glycoprotein pumps by PEO-PPO amphiphiles: branched versus linear derivatives. Nanomedicine (Lond) 2010, 5:1371-1383.
5. Alvarez-Lorenzo C., Sosnik A., Concheiro A. PEO-PPO block copolymers for passive micellar targeting and overcoming multidrug resistance in cancer therapy. Curr Drug Targets 2011, 12:1112-1130.
6. Andrade F., Goycoolea F., Chiappetta D.A., das Neves J., Sosnik A., Sarmento B. Chitosan-grafted copolymers and chitosan-ligand conjugates as matrices for pulmonary drug delivery. Int J Carbohydr Chem 2011, 2011. [Art. 865704].
7. Andrade F., Videira M., Ferreira D., Sarmento B. Micelle-based systems for pulmonary drug delivery and targeting. Drug Deliv Lett 2011, 1:171-185.
8. Andrade F., das Neves J., Ferreira D., Sosnik A., Sarmento B. Nanotechnology pulmonary delivery to overcome resistance in infectious diseases. Adv Drug Deliv Rev 2013, 65:1816-1827.
9. Atuma C., Strugala V., Allen A., Holm L. The adherent gastrointestinal mucus gel layer: thickness and physical state in vivo. Am J Physiol Gastrointest Liver Physiol 2001, 280:G922-G929.
10. Augst A.D., Kong H.J., Mooney D.J. Alginate hydrogels as biomaterials. Macromol Biosci 2006, 6:623-633.
11. Aungst B.J. P-glycoprotein, secretory transport, and other barriers to the oral delivery of anti-HIV drugs. Adv Drug Deliv Rev 1999, 39:105-116.
12. Bansil R., Stanley E., LaMont J.T. Mucin biophysics. Annu Rev Physiol 1995, 57:635-657.
13. Barreiro Iglesias R., Bromberg L., Temchenko M., Hatton T.A., Concheiro A., Alvarez-Lorenzo C. Solubilization and stabilization of camptothecin in micellar solution of pluronic-g-poly (acrylic acid) copolymers. J Control Release 2004, 97:537-549.
14. Basalo I.M., Chahine N.O., Kaplun M., Chen F.H., Hung C.T., Ateshian G.A. Chondroitin sulfate reduces the friction coefficient of articular cartilage. J Biomech 2007, 40:1847-1854.
15. Batrakova E., Li S., Vinogradov S., Alakhov V.Yu., Miller D.W., Kabanov A.V. Mechanism of pluronic effect on P-glycoprotein efflux system in blood-brain barrier: contributions of energy depletion and membrane fluidization. J Pharmacol Exp Ther 2001, 299:483-493.
16. Batrakova E.V., Li S., Brynskikh A.M., Sharma A.K., Li Y., Boska M., et al. Effects of pluronic and doxorubicin on drug uptake, cellular metabolism, apoptosis and tumor inhibition in animal models of MDR cancer. J Control Release 2010, 143:290-301.
17. Bei Y.-Y., Yuan Z.-Q., Zhang L., Zhou X.-F., Chen W.-L., et al. Novel self-assembled micelles based on palmitoyl-trimethyl-chitosan for efficient delivery of harmine to liver cancer. Expert Opin Drug Deliv 2014, 11:843-854.
18. Benykhlef S., Dulong V., Bengharez Z., Picton L., Guemra K., Le Cerf D. Alginate grafted with poly(ε-caprolactone): effect of enzymatic degradation on physicochemical properties. Polym Int 2012, 61:1456-1461.
19. Bernkop-Schnürch A. Thiomers: a new generation of mucoadhesive polymers. Adv Drug Deliv Rev 2005, 57:1569-1582.
20. Bernkop-Schnürch A., Dünnhaupt S. Chitosan-based drug delivery systems. Eur J Pharm Biopharm 2012, 81:463-469.
21. Bernkop-Schnürch A., Hornof M.D., Kast C.E., Langoth N. Thiolated polymers: stability of thiol moieties under different storage conditions. Sci Pharm 2002, 70:331-339.
22. Bian F., Jia L., Yu W., Liu M. Self-assembled micelles of N-phthaloylchitosan-g-polyvinylpyrrolidone for drug delivery. Carbohydr Polym 2009, 76:454-459.
23. Bonferoni M.C., Sandri G., Ferrari F., Rossi S., Larghi V., Zambito Y. Comparison of different in vitro and ex vivo methods to evaluate mucoadhesion of glycol-palmitoyl chitosan micelles. J Drug Deliv Sci Technol 2010, 20:419-444.
24. Bonferoni M.C., Sandri G., Dellera E., Rossi S., Ferrari F., Mori M., et al. Ionic polymeric micelles based on chitosan and fatty acids and intended for wound healing. Comparison of linoleic and oleic acid. Eur J Pharm Biopharm 2014, 87:101-106.
25. Booth C., Attwood D., Price C. Self-association of block copoly(oxyalkylene)s in aqueous solution. Effects of composition, block length and block architecture. Phys Chem Chem Phys 2006, 8:3612-3622.
26. 2+-induced gelation in alginates and pectins: the Egg-Box model revisited. Biomacromolecules 2001, 2:1089-1096.
27. Bravo-Osuna I., Vauthier C., Farabollini C., Palmieri G.F., Ponchel G. Mucoadhesion mechanism of chitosan and thiolated chitosan-poly(isobutyl cyanoacrylate) core-shell nanoparticles. Biomaterials 2007, 28:2233-2243.
28. Breitenkamp K., Sill K.N., Skaff H., Breitenkamp R. Polymeric micelles for, drug delivery 2006, [US20060240092].
29. Bromberg L. Properties of aqueous solutions and gels of poly(ethylene oxide)-b-poly(propylene oxide)-b-poly(ethylene oxide)-g-poly(acrylic acid). J Phys Chem B 1998, 102:10736-10744.
30. Bromberg L. Polymeric micelles in oral chemotherapy. J Control Release 2008, 128:99-112.
31. Cabral H., Kataoka K. Progress of drug-loaded polymeric micelles into clinical studies. J Control Release 2014, 190:465-476.
32. Cao M., Yu L., Zhang P., Xiong H., Jin Y., Lu L., et al. Soft-binding ligand-capped fluorescent CdSe/ZnS quantum dots for the facile labeling of polysaccharide-based self-assemblies. Colloids Surf B Biointerfaces 2013, 109:154-160.
33. Carreira A.S., Gonçalves F.A.M.M., Mendonça P.V., Gil M.H., Coelho J.F.J. Temperature and pH responsive polymers based on chitosan: applications and new graft copolymerization strategies based on living radical polymerization. Carbohydr Polym 2010, 80:618-630.
34. Cellesi F., Tirelli N., Hubbell J.A. Towards a fully-synthetic substitute of alginate: development of a new process using thermal gelation and chemical cross-linking. Biomaterials 2004, 25:5115-5124.
35. Cellesi F., Weber W., Fussenegger M., Hubbell J.A., Tirelli N. Towards a fully synthetic substitute of alginate: optimization of a thermal gelation/chemical cross-linking scheme ("tandem" gelation) for the production of beads and liquid-core capsules. Biotechnol Bioeng 2004, 88:740-749.
36. Chayed S., Winnik F.M. In vitro evaluation of the mucoadhesive properties of polysaccharide-based nanoparticulate oral drug delivery systems. Eur J Pharm Biopharm 2007, 65:363-370.
37. Chen X., Ding S., Qu G., Zhang C. Synthesis of novel chitosan derivatives for micellar solubilization of cyclosporine A. J Bioact Compat Polym 2008, 23:563-578.
38. Chen M.-C., Mi F.-L., Liao Z.-X., Hsiao C.-W., Sonaje K., Chung M.-F., et al. Recent advances in chitosan-based nanoparticles for oral delivery of macromolecules. Adv Drug Deliv Rev 2013, 65:865-879.
39. Chiappetta D.A., Sosnik A. Poly(ethylene oxide)-poly(propylene oxide) block copolymer micelles as drug delivery agents: improved hydrosolubility, stability and bioavailability of drugs. Eur J Pharm Biopharm 2007, 66:303-317.
40. Chiappetta D.A., Degrossi J., Teves S., D'Aquino M., Bregni C., Sosnik A. Triclosan-loaded poloxamine micelles for enhanced antibacterial activity against biofilm. Eur J Pharm Biopharm 2008, 69:535-545.
41. Chiappetta D.A., Hocht C., Sosnik A. A highly concentrated and taste-improved aqueous formulation of efavirenz for a more appropriate paediatric management of the anti-HIV therapy. Curr HIV Res 2010, 8:23-31.
42. Chiappetta D.A., Hocht C., Taira C., Sosnik A. Efavirenz-loaded polymeric micelles for pediatric anti-HIV pharmacotherapy with significantly higher oral bioavailaibility. Nanomedicine (Lond) 2010, 5:11-23.
43. Chiappetta D.A., Facorro G., Rubin de Celis E., Sosnik A. Synergistic encapsulation of the anti-HIV agent efavirenz within poly(ethylene oxide)-poly(propylene oxide) mixed polymeric micelles. Nanomed: Nanotechnol Biol Med 2011, 7:624-637.
44. Chiappetta D.A., Hocht C., Taira C., Sosnik A. Oral pharmacokinetics of efavirenz-loaded polymeric micelles. Biomaterials 2011, 32:2379-2387.
45. Chiappetta D.A., Hocht C., Opezzo J.A.W., Sosnik A. Intranasal administration of antiretroviral-loaded micelles for anatomical targeting to the brain in HIV. Nanomedicine (Lond) 2013, 8:223-237.
46. Chuang C.-Y., Don T.-M., Chiu W.-Y. Synthesis of chitosan-based thermo- and pH-responsive porous nanoparticles by temperature-dependent self-assembly method and their application in drug release. J Polym Sci Part A: Polym Chem 2009, 47:5126-5136.
47. Chuang C.-Y., Don T.-M., Chiu W.-Y. Synthesis and characterization of stimuli-responsive porous/hollow nanoparticles by self-assembly of chitosan-based graft copolymers and application in drug release. J Polym Sci Part A: Polym Chem 2010, 48:2377-2387.
48. Chuang C.-Y., Don T.-M., Chiu W.-Y. Preparation of environmental-responsive chitosan-based nanoparticles by self-assembly method. Carbohydr Polym 2011, 84:765-769.
49. Chung H.J., Bae J.W., Park H.D., Lee J.W., Park K.D. Thermosensitive chitosans as novel injectable biomaterials. Macromol Symp 2005, 224:275-286.
50. Cohn D., Sosnik A. Novel reverse thermo-responsive injectable poly(ether carbonate)s. J Mat Sci Mater Med 2003, 14:175-180.
51. Cohn D., Sosnik A., Levy A. Improved reverse thermo-responsive polymeric systems. Biomaterials 2003, 24:3707-3714.
52. Collnot E.-M., Ali H., Lehr C.-M. Nano- and microparticulate drug carriers for targeting of the inflamed intestinal mucosa. J Control Release 2012, 161:235-246.
53. Cone R.A. Mucus. Mucosal Immunol 2005, 49-72. Academic Press, San Diego, CA, USA. 3rd ed. J. Mestecky, M.E. Lamm, W. Strober, J. Bienenstock, J.R. McGhee, L. Mayer (Eds.).
54. Cuestas M.L., Sosnik A., Mathet V.L. Poloxamines display a multiple inhibitory activity of ATP-Binding Cassette (ABC) transporters in cancer cell lines. Mol Pharm 2011, 8:1152-1164.
55. Cuestas M.L., Castillo A., Sosnik A., Mathet V.L. Downregulation of mdr1 and abcg2 genes is a mechanism of inhibition of efflux pumps mediated by polymeric amphiphiles. Bioorg Med Chem Lett 2012, 22:6577-6579.
56. Cumpstey I. Chemical modification of polysaccharides. ISRN Org Chem 2013, 2013. [Art. 417672].
57. das Neves J., Bahia M.F., Amiji M.M., Sarmento B. Mucoadhesive nanomedicines: characterization and modulation of mucoadhesion at the nanoscale. Expert Opin Drug Deliv 2011, 8:1085-1104.
58. de la Fuente M., Ravina 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.
59. de Medeiros Modolon S., Otsuka I., Fort S., Minatti E., Borsali R., Halila S. Sweet block copolymer nanoparticles: preparation and self-assembly of fully oligosaccharide-based amphiphile. Biomacromolecules 2012, 13:1129-1135.
60. Dekker J., Rossen J.W., Buller H.A., Einerhand A.W. The MUC family: an obituary. Trends Biochem Sci 2002, 27:126-131.
61. Deshpande P.P., Biswas S., Torchilin V.P. Current trends in the use of liposomes for tumor targeting. Nanomedicine (Lond) 2013, 8:1509-1528.
62. Dietrich C.G., Geier A., Oude Elferink R.P. ABC of oral bioavailability: transporters as gatekeepers in the gut. Gut 2003, 52:1788-1795.
63. Discher B.M., Won Y.-Y., Ege D.S., Lee J.C.-M., Bates F.S., Discher D.E., et al. Polymersomes: tough vesicles made from diblock copolymers. Science 1999, 284:1143-1145.
64. Du Y.-Z., Wang L., Yuan H., Wei X.-H., Hu F.-Q. Preparation and characteristics of linoleic acid-grafted chitosan oligosaccharide micelles as a carrier for doxorubicin. Colloids Surf B Biointerfaces 2009, 69:257-263.
65. Duan K., Chen H., Huang J., Yu J., Liu S., Wang D., et al. One-step synthesis of amino-reserved chitosan-graft-polycaprolactone as a promising substance of biomaterial. Carbohydr Polym 2010, 80:498-503.
66. Duan K., Zhanga X., Tang X., Yu J., Liu S., Wang S., et al. Fabrication of cationic nanomicelle from chitosan-graft-polycaprolactone as the carrier of 7-ethyl-10-hydroxy-camptothecin. Colloids Surf B Biointerfaces 2010, 76:475-482.
67. Dufresne M.-H., Gauthier M.A., Leroux J.-C. Thiol-functionalized polymeric micelles: from molecular recognition to improved mucoadhesion. Bioconjug Chem 2005, 16:1027-1033.
68. Eenschooten C., Guillaumie F., Kontogeorgis G.M., Stenby E.H., Schwach-Abdellaoui K. Preparation and structural characterisation of novel and versatile amphiphilic octenyl succinic anhydride-modified hyaluronic acid derivatives. Carbohydr Polym 2010, 79:597-605.
69. 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.
70. Fajardo A.R., Guerry A., Britta E.A., Nakamura C.V., Muniz E.C., Borsali R., et al. Sulfated glycosaminoglycan-based block copolymer: preparation of biocompatible chondroitin sulfate-b-poly(lactic acid) micelles. Biomacromolecules 2014, 15:2691-2700.
71. Falamarzian A., Xiong X.-B., Uludag H., Lavasanifar A. Polymeric micelles for siRNA delivery. J Drug Deliv Sci Technol 2012, 22:43-54.
72. Felber A.E., Dufresne M.-H., Leroux J.-C. pH-sensitive vesicles, polymeric micelles, and nanospheres prepared with polycarboxylates. Adv Drug Deliv Rev 2012, 64:979-992.
73. Francis M.F., Lavoie L., Winnik F.M., Leroux J.-C. Solubilization of cyclosporine A in dextran-g-polyethyleneglycolalkyl ether polymeric micelles. Eur J Pharm Biopharm 2003, 56:337-346.
74. Francis M.F., Piredda M., Winnik F.M. Solubilization of poorly water soluble drugs in micelles of hydrophobically modified hydroxypropylcellulose copolymers. J Control Release 2003, 93:59-68.
75. Francis M.F., Cristea M., Yang Y., Winnik F.M. Engineering polysaccharide-based polymeric micelles to enhance permeability of cyclosporin A across Caco-2 cells. Pharm Res 2005, 22:209-219.
76. Fray M.E., Niemczyk A., Pabin-Szafko B. Chemical modification of chitosan with fatty acids. Prog Chem Appl Chitin Deriv 2012, 17:29-36.
77. Garcia Vior C., Marino J., Roguin L.P., Sosnik A., Awruch J. Photodynamic effects of zinc(II) phthalocyanine-loaded polymeric micelles in human nasopharynx KB carcinoma cells. Photochem Photobiol 2013, 89:492-500.
78. Gaucher G., Dufresne M.-H., Sant V.P., Kang N., Maysinger D., Leroux J.-C. Block copolymer micelles: preparation, characterization and application in drug delivery. J Control Release 2005, 109:169-188.
79. Gaucher G., Satturwar P., Jones M.-C., Furtos A., Leroux J.-C. Polymeric micelles for oral drug delivery. Eur J Pharm Biopharm 2010, 76:147-158.
80. Glover A.L., Nikles S.M., Nikles J.A., Brazel C.S., Nikles D.E. Polymer micelles with crystalline cores for thermally triggered release. Langmuir 2012, 28:10653-10660.
81. Gonzalez-Lopez J., Alvarez-Lorenzo C., Taboada P., Sosnik A., Sandez-Macho I., Concheiro A. Self-associative behavior and drug solubilizing ability of poloxamine (Tetronic®) block copolymers. Langmuir 2008, 24:10688-10697.
82. Gotelli G., Bonelli P., Abraham G., Sosnik Fast and efficient synthesis of high molecular weight poly(epsilon-caprolactone) diols by Microwave-Assisted Polymer Synthesis (MAPS). J Appl Polym Sci 2011, 121:1321-1329.
83. Gu J.M., Robinson J.R., Leung S.H. Binding of acrylic polymers to mucin/epithelial surfaces: structure-property relationships. Crit Rev Ther Drug Carrier Syst 1988, 5:21-67.
84. Gua C., Le V., Lang M., Liu J. Preparation of polysaccharide derivates chitosan-graft-poly(ε-caprolactone) amphiphilic copolymer micelles for 5-fluorouracil drug delivery. Colloids Surf B Biointerfaces 2014, 116:745-750.
85. Harding S.E. Mucoadhesive interactions. Biochem Soc Trans 2003, 31:1036-1041.
86. He Z., Lian H., Sun J., Yu Y.P., Liu Y.H., Cao W., et al. Supramolecular micellar nanoaggregates based on a novel chitosan/vitamin E succinate copolymer for paclitaxel selective delivery. Int J Nanomedicine 2011, 6:3323-3334.
87. Hong S., Leroueil P.R., Janus E.K., Peters J.L., Kober M.-M., Islam M.T., et al. Interaction of polycationic polymers with supported lipid bilayers and cells: Nanoscale hole formation and enhanced membrane permeability. Bioconjug Chem 2006, 17:728-734.
88. Hornof H. In vitro and in vivo evaluation of novel polymeric excipients in the ophthalmic field 2003, University of Vienna, [Thesis].
89. Hu F.Q., Ren G.-F., Yuan H., Du Y.-Z., Zeng S. Shell cross-linked stearic acid grafted chitosan oligosaccharide self-aggregated micelles for controlled release of paclitaxel. Colloids Surf B Biointerfaces 2006, 50:97-103.
90. Huang C.-H., Wang C.-F., Don T.-M., Chiu W.-Y. Preparation of pH- and thermo-sensitive chitosan-PNIPAAm core-shell nanoparticles and evaluation as drug carriers. Cellulose 2013, 20:1791-1805.
91. Huang J., Zhang H., Yu Y., Chen Y., Wang D., Zhang G. Biodegradable self-assembled nanoparticles of poly (d, l-lactide-co-glycolide)/hyaluronic acid block copolymers for target delivery of docetaxel to breast cancer. Biomaterials 2014, 35:550-566.
92. Hyde S.V., Emsley P., Hartshorn M.J., Mimmack M.M., Gileadi U., Pearce S.R., et al. Structural model of ATP-binding protein associated with cystic fibrosis, multidrug resistance and bacterial transport. Nature 1990, 346:362-365.
93. Illum L., Jabbal-Gill I., Hinchcliffe M., Fisher A.N., Davis S.S. Chitosan as a novel nasal delivery system for vaccines. Adv Drug Deliv Rev 2001, 51:81-96.
94. Imperiale J.C., Nejamkin P., Del Sole M.J., Lanusse C., Sosnik A. Novel protease inhibitor Nanoparticle-in-Microparticle Delivery System leads to a dramatic improvement of the oral pharmacokinetics in dogs. Biomaterials 2015, 37:383-394.
95. Isiklan N., Kucukbalci G. Microwave-induced synthesis of alginate-graft-poly(N-isopropylacrylamide) and drug release properties of dual pH- and temperature-responsive beads. Eur J Pharm Biopharm 2012, 82:316-331.
96. Izumi Y., Kikuta N., Sakai K., Takezawa H. Phase diagrams and molecular structures of sodium-salt-type gellan gum. Carbohydr Polym 1996, 30:121-127.
97. Jhaveri A.M., Torchilin V.P. Multifunctional polymeric micelles for delivery of drugs and siRNA. Front Pharmacol 2014, 5. [Art. 77].
98. Jiang G.-B., Quan D., Liao K., Wang H. Novel polymer micelles prepared from chitosan grafted hydrophobic palmitoyl groups for drug delivery. Mol Pharm 2006, 3:152-160.
99. Jiang G.-B., Quan D., Liao K., Wang H. Preparation of polymeric micelles based on chitosan bearing a small amount of highly hydrophobic groups. Carbohydr Polym 2006, 66:514-520.
100. Jones M.C., Ranger M., Leroux J.-C. pH-sensitive unimolecular polymeric micelles: synthesis of a novel drug carrier. Bioconjug Chem 2003, 14:774-781.
101. Kabanov A.K., Alakhov V.Yu. Pluronic block copolymers in drug delivery: from micellar nanocontainers to biological response modifiers. Crit Rev Ther Drug Carrier Syst 2002, 19:1-72.
102. Polysaccharide based graft copolymers 2013, Springer, Verlag Berlin Heidelberg. S. Kalia, M.W. Sabaa (Eds.).
103. Kang H.-A., Shin M.-S., Yang J.-W. Preparation and characterization of hydrophobically modified alginate. Polym Bull 2002, 47:429-435.
104. Kataoka K., Harada A., Nagasaki Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv Drug Deliv Rev 2001, 47:113-131.
105. Keana T., Thanou M. Biodegradation, biodistribution and toxicity of chitosan. Adv Drug Deliv Rev 2010, 62:3-11.
106. Kim J.H., Lee S.B., Kim S.J., Lee Y.M. Rapid temperature/pH response of porous alginate-g-poly(nisopropylacrylamide) hydrogels. Polymer 2002, 43:7549-7558.
107. Kim S., Shi Y., Kim J.Y., Park K., Cheng J.-X. Overcoming the barriers in micellar drug delivery: loading efficiency, in vivo stability, and micelle-cell interaction. Expert Opin Drug Deliv 2010, 7:49-62.
108. Krylova O.O., Pohl P. Ionophoric activity of pluronic block copolymers. Biochemistry 2004, 43:3696-3703.
109. 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.
110. Lai S.K., Wang Y.Y., Wirtz D., Hanes J. Micro- and macrorheology of mucus. Adv Drug Deliv Rev 2009, 61:86-100.
111. Lai S.K., Wang Y.Y., Hida K., Cone R., Hanes J. Nanoparticles reveal that human cervicovaginal mucus is riddled with pores larger than viruses. Proc Natl Acad Sci U S A 2010, 107:598-603.
112. Lee K.Y., Mooney D.J. Alginate: properties and biomedical applications. Prog Polym Sci 2012, 37:106-126.
113. Lee K.Y., Jo W.H., Kwon I.C., Kim Y.H., Jeong S.H. Physicochemical characteristics of self-aggregates of hydrophobically modified chitosan. Langmuir 1998, 14:2329-2332.
114. Lee K.Y., Jo W.H., Kwon I.C., Kim Y.H., Jeong S.H. Structural determination and interior polarity of self-aggregates prepared from deoxycholic acid-modified chitosan in water. Macromolecules 1998, 31:378-383.
115. Lee S., Muller M., Rezwan K., Spencer N.D. Porcine gastric mucin (PGM) at the water/poly(dimethylsiloxane) (PDMS) interface: influence of pH and ionic strength on its conformation, adsorption, and aqueous lubrication properties. Langmuir 2005, 21:8344-8353.
116. Lee E.S., Oh K.T., Kim D., Youn Y.S., Bae Y.H. Tumor pH-responsive flower-like micelles of poly(l-lactic acid)-b-poly(ethylene glycol)-b-poly(l-histidine). J Control Release 2007, 123:19-26.
117. Lee H., Ahn C.-H., Park T.G. Poly[lactic-co-(glycolic acid)]-grafted hyaluronic acid copolymer micelle nanoparticles for target-specific delivery of doxorubicin. Macromol Biosci 2009, 9:336-342.
118. Lee H., Soo P.L., Liu J., Butler M., Allen C. Polymeric micelles for formulation of anti-cancer drugs. Nanotechnology for cancer therapy 2007, 318-355. CRC Press, Boca Raton:FL. M.M. Amiji (Ed.).
119. Leitner V.M., Walker G.F., Bernkop-Schnürch A. Thiolated polymers: evidence for the formation of disulphide bonds with mucus proteins. Eur J Pharm Biopharm 2003, 56:207-214.
120. Li G., Guo L., Meng Y., Zhang T. Self-assembled nanoparticles from thermo-sensitive polyion complex micelles for controlled drug release. Chem Eng J 2011, 174:199-205.
121. Lian H., Zhang T., Sun J., Liu X., Ren G., Kou L., et al. Enhanced oral delivery of paclitaxel using acetylcysteine functionalized chitosan-vitamin E succinate nanomicelles based on a mucus bioadhesion and penetration mechanism. Mol Pharm 2013, 10:3447-3458.
122. Lin T.-C., Chen J.H., Chen Y.-H., Teng T.M., Suc C.-H., Hsu S.-H. Biodegradable micelles from a hyaluronan-poly(ε-caprolactone) graft copolymer as nanocarriers for fibroblast growth factor 1. J Mater Chem B 2013, 1:5977-5987.
123. Litt M. Comparative studies of mucus and mucin physicochemistry. Ciba Found Symp 1984, 109:196-211.
124. Liu C.G., Desai K.G.H., Chen X.-G., Park H.-J. Linoleic acid-modified chitosan for formation of self-assembled nanoparticles. J Agric Food Chem 2005, 53:437-441.
125. Liu G.-Y., Zhai Y.-L., Wanga X.-L., Wang W.-T., Pan Y.-B., Dong X.-T., et al. Preparation, characterization, and in vitro drug release behavior of biodegradable chitosan-graft-poly(1, 4-dioxan-2-one) copolymer. Carbohydr Polym 2008, 74:862-867.
126. Liu L., Shi A., Guo S., Fang Y., Chen S., Li S. Preparation of chitosan-g-polylactide graft copolymers via self-catalysis of phthaloylchitosan and their complexation with DNA. React Funct Polym 2010, 70:301-305.
127. Liu L., Liu Y., Li J., Du G., Chen J. Microbial production of hyaluronic acid: current state, challenges, and perspectives. Microb Cell Fact 2011, 10:99.
128. Liu D.L., Zhu X.B., Xu K.L., Fang D.M. Synthesis and characterization of an amphiphilic nanoparticles based on chitosan oligosaccharide-grafted-polycaprolactone. Appl Mech Mater 2014, 86:513-517.
129. Lu H.W., He H., Zhang B., Liu G.-Q., Li M.-Y., Nie Q.-L. Facile synthesis of amphiphilic chitosan-g-poly(lactic acid) derivatives and the study of their controlled drug release. J Appl Polym Sci 2011, 130:908-915.
130. Lu J., Owen S.C., Shoichet M.S. Stability of self-assembled polymeric micelles in serum. Macromolecules 2011, 44:6002-6008.
131. Luo Y., Wang Q. Recent development of chitosan-based polyelectrolyte complexes with natural polysaccharides for drug delivery. Int J Biol Macromol 2014, 64:353-367.
132. Maiti S., Chakravorty A., Chowdhury M. Gellan co-polysaccharide micellar solution of budesonide for allergic anti-rhinitis: an in vitro appraisal. Int J Biol Macromol 2014, 68:241-246.
133. Mayol L., Biondi M., Russo L., Malle B.M., Schwach-Abdellaoui K., Borzacchiello A. Amphiphilic hyaluronic acid derivatives toward the design of micelles for the sustained delivery of hydrophobic drugs. Carbohydr Polym 2014, 102:110-116.
134. Mirosevich J., Cardoen G., Sill K., Skaff H. Polymeric micelles for polynucleotide encapsulation 2013, [US20130266617].
135. Mitra A., Gupta A.K., Majumdar D., Madan S. Sustained release and long residing ophthalmic formulation and the process of preparing the same 2002, [US20020064513].
136. Mitra A.K., Velagaleti P., Subramanian N. Ophthalmic compositions comprising calcineurin inhibitors or motor inhibitors 2009, [US20090092665].
137. Mitra A.K., Velagaleti P., Grau U.M. Topical drug delivery systems for ophthalmic use 2010, [WO2010144194].
138. Moretton M.A., Glisoni R.J., Chiappetta D.A., Sosnik A. Molecular implications in the nanoencapsulation of the antituberculosis drug rifampicin within flower-like polymeric micelles. Colloids Surf B Biointerfaces 2010, 79:467-479.
139. Moretton M.A., Chiappetta D.A., Sosnik A. Cryoprotection-lyophilisation and physical stabilization of rifampicin-loaded flower-like polymeric micelles. J R Soc Interface 2012, 9:487-502.
140. Moretton M.A., Chiappetta D.A., Andrade F., das Neves J., Ferreira D., Sarmento B., et al. Hydrolyzed galactomannan-modified nanoparticles and flower-like polymeric micelles for the active targeting of rifampicin to macrophages. J Biomed Nanotechnol 2013, 9:1076-1087.
141. Moretton M.A., Hotch C., Taira C., Sosnik A. Encapsulation of rifampicin within flower-like polymeric micelles enhances the oral bioavailability in a pediatric fixed dose combination with isoniazid. Nanomedicine (Lond) 2014, 9:1635-1650.
142. Mourya V.K., Inamdar N.N. Trimethyl chitosan and its applications in drug delivery. J Mater Sci Mater Med 2009, 20:1057-1079.
143. Muzzarelli R.A.A., Muzzarelli C. Chitosan chemistry: relevance to the biomedical sciences. Adv Polym Sci 2005, 186:151-209.
144. 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.
145. Nam J.-P., Park S.-C., Kim T.-H., Jang J.-Y., Choi C., Jang M.-K., Nah J.-W. Encapsulation of paclitaxel into lauric acid-O-carboxymethyl chitosan-transferrin micelles for hydrophobic drug delivery and site-specific targeted delivery. Int J Pharm 2013, 457:124-135.
146. Nayaka A.K., Pal D. Trigonella foenum-graecum L. seed mucilage-gellan mucoadhesive beads for controlled release of metformin HCl. Carbohydr Polym 2014, 107:31-40.
147. Newkome G.R., Moorefield C.N., Baker G.R., Saunders M.J., Grossman S.H. Unimolecular micelles. Angew Chem Int Ed Engl 1991, 30:1178-1180.
148. Oh K.T., Oh Y.T., Oh N.-M., Kim K., Lee D.H., Lee E.S. A smart flower-like polymeric micelle for pH-triggered anticancer drug release. Int J Pharm 2009, 375:163-169.
149. Olmsted S.S., Padgett J.L., Yudin A.I., Whaley K.J., Moench T.R., Cone R.A. Diffusion of macromolecules and virus-like particles in human cervical mucus. Biophys J 2001, 81:1930-1937.
150. Otsuka I., Fuchise K., Halila S., Fort S., Aissou K., Pignot-Paintrand, et al. Thermoresponsive vesicular morphologies obtained by self-assemblies of hybrid oligosaccharides-block-poly(N-isopropylacrylamide) copolymer systems. Langmuir 2010, 26:2325-2332.
151. Owen S.C., Chan D.P.Y., Shoichet M.S. Polymeric micelle stability. Nano Today 2012, 7:53-65.
152. Park S., Son Y.J., Leong K.W., Yoo H.S. Therapeutic nanorods with metallic multi-segments: thermally inducible encapsulation of doxorubicin for anti-cancer therapy. Nano Today 2012, 7:76-84.
153. Pawar S.N., Edgar K.J. Alginate derivatization: a review of chemistry, properties and applications. Biomaterials 2012, 33:3279-3305.
154. Pepic I., Lovric J., Filipovic-Grcic J. How do polymeric micelles cross epithelial barriers?. Eur J Pharm Sci 2013, 50:42-55.
155. Quintana S., Glisoni R.J., Molina Soler M.A., Moglioni A., Calderón M., Sosnik A. Chitosan-g-oligo(epsilon-caprolactone) polymeric micelles: synthesis, physicochemical and cytocompatibility characterization and rifampicin encapsulation. 2014 IUPAC world polymer congress-MACRO 2014 2014, Chiang Mai, Thailand.
156. Ribeiro A., Sosnik A., Chiappetta D.A., Veiga F., Concheiro A., Alvarez-Lorenzo C. Single and mixed poloxamine micelles as suitable nanocarriers for solubilization and sustained release of ethoxzolamide for topical glaucoma therapy. J R Soc Interface 2012, 9:2059-2069.
157. Sakuma S., Hayashi M., Akashi M. Design of nanoparticles composed of graft copolymers for oral peptide delivery. Adv Drug Deliv Rev 2001, 47:21-37.
158. Sashiwa H., Shigemasa Y., Roy R. Dissolution of chitosan in dimethyl sulfoxide by salt formation. Chem Lett 2000, 29:596-597.
159. Schiller J., Volpi N., Hrabárová E., Šoltés L. Hyaluronic acid: a natural biopolymer. Biopolymers: biomedical and environmental applications 2011, 3-34. John Wiley & Sons Inc., Hoboken, NJ. S. Kalia, L. Avérous (Eds.).
160. Schmidt N., Mishra A., Lai G.H., Wong G.C.L. Arginine-rich cell-penetrating peptides. FEBS Lett 2010, 584:1806-1813.
161. Schrager J. The chemical composition and function of gastrointestinal mucus. Gut 1970, 11:450-456.
162. Shan M., Gentile M., Yeiser J.R., Walland A.C., Bornstein V.U., Chen K., et al. Mucus enhances gut homeostasis and oral tolerance by delivering immunoregulatory signals. Science 2013, 342:447-453.
163. Singh D., Dubey P., Pradhan M., Singh M.R. Ceramic nanocarriers: versatile nanosystem for protein and peptide delivery. Expert Opin Drug Deliv 2013, 10:241-259.
164. Sogias I.A., Williams A.C., Khutoryanskiy V.V. Why is chitosan mucoadhesive?. Biomacromolecules 2008, 9:1837-1842.
165. Sosnik A. Reversal of multidrug resistance by the inhibition of ATP-binding cassette pumps with Generally Regarded As Safe (GRAS) nanopharmaceuticals. Adv Drug Deliv Rev 2013, 65:1828-1851.
166. Sosnik A. Temperature- and pH-sensitive polymeric micelles for drug encapsulation, release and targeting. Smart materials for drug delivery 2013, 115-147. Royal Society of Chemistry, London, UK. C. Alvarez-Lorenzo, A. Concheiro (Eds.).
167. Sosnik A. Alginate particles for oral drug delivery applications: state-of-the-art. ISRN Pharm 2014, 2014. [Art. 926157].
168. Sosnik A., Cohn D. Reverse thermo-responsive poly(ethylene oxide) and poly(propylene oxide) multiblock copolymers. Biomaterials 2005, 26:349-357.
169. Sosnik A., Carcaboso A., Chiappetta D.A. Polymeric nanocarriers: new endeavors for the optimization of the technological aspects of drugs. Recent Pat Biomed Eng 2008, 1:43-59.
170. Sosnik A., Gotelli G., Abraham G.A. Microwave-assisted polymer synthesis (MAPS) as a tool in biomaterials science: how new and how powerful. Prog Polym Sci 2011, 36:1050-1078.
171. Sosnik A., das Neves J., Sarmento B. Mucoadhesive polymers in the design of nano-drug delivery systems for administration by non-parenteral routes: a review. Prog Polym Sci 2014, 39:2030-2075.
172. Sosnik A., Seremeta K.P., Imperiale J.C., Chiappetta D.A. Novel formulation and drug delivery strategies for the treatment of pediatric poverty related diseases (PRDs). Expert Opin Drug Del 2012, 9:303-323.
173. Sosnik A., Vázquez-González B., Imperiale J.C., Muñoz-Muñoz F., Burillo G., Cedillo G., et al. Muco-adhesive chitosan-g-poly(NIPAAm) polymeric micelles by gamma radiation: synthesis and chemical and self-assembly characterization 2014, Chiang Mai, Thailand, [July].
174. Stegemann S., Leveiller F., Franchi D., de Jong H., Linden H. When poor solubility becomes an issue: from early stage to proof of concept. Eur J Pharm Sci 2007, 31:249-261.
175. Talelli M., Rijcken C.J.F., van Nostrum C.F., Storm G., Hennink W.E. Micelles based on HPMA copolymers. Adv Drug Deliv Rev 2010, 62:231-239.
176. Thanou M., Verhoef J.C., Junginger H.E. Oral drug absorption enhancement by chitosan and its derivatives. Adv Drug Deliv Rev 2001, 52:117-126.
177. Tian Y., Ravi P., Bromberg L., Hatton T.A., Tam K.C. Synthesis and aggregation behavior of Pluronic F87/poly(acrylic acid) block copolymer in the presence of doxorubicin. Langmuir 2007, 23:2638-2646.
178. Tiwaria A., Prabaharan M. An amphiphilic nanocarrier based on guar gum-graft-poly(ε-caprolactone) for potential drug-delivery applications. J Biomater Sci Polym Ed 2010, 21:937-949.
179. Tong Y.-C., Yu T.-Y., Chang S.-F., Liaw J. Nanopolymeric micelle effect on the transdermal permeability, the bioavailability and gene expression of plasmid. Mol Pharm 2012, 9:111-120.
180. Tønnesen H.H., Karlsen J. Alginate in drug delivery systems. Drug Dev Ind Pharm 2002, 28:621-630.
181. Toole B.P. Hyaluronan-CD44 interactions in cancer: paradoxes and possibilities. Clin Cancer Res 2009, 15:7462-7468.
182. Tu Y., Graham M.J., Van Horn R.M., Chen E., Fan X., Chen X., et al. Controlled organization of self-assembled rod-coil block copolymer micelles. Polymer 2009, 50:5170-5174.
183. Ueno H., Mori T., Fujinaga T. Topical formulations and wound healing applications of chitosan. Adv Drug Deliv Rev 2001, 52:105-115.
184. Valle J.W., Armstrong A., Newman C., Alakhov V., Pietrzynski G., Brewer J., et al. A phase 2 study of SP1049C, doxorubicin in P-glycoprotein-targeting pluronics, in patients with advanced adenocarcinoma of the esophagus and gastroesophageal junction. Invest New Drugs 2011, 29:1029-1037.
185. van Nostrum C.F. Covalently cross-linked amphiphilic block copolymer micelles. Soft Matter 2011, 7:3246-3259.
186. Venkataraman S., Hedrick J.L., Ong Z.Y., Yang C., Ee P.L.R., Hammond P.T., et al. The effects of polymeric nanostructure shape on drug delivery. Adv Drug Deliv Rev 2011, 63:1228-1246.
187. Wang C., Li G., Tao S., Guo R., Yan Z. Crystalline and micellar properties of amphiphilic biodegradable chitooligosaccharide-graft-poly(ε-caprolactone) copolymers. Carbohydr Polym 2006, 64:466-472.
188. Wu T., Zivanovic S., Hayes D.G., Weiss J. Efficient reduction of chitosan molecular weight by high-intensity ultrasound: underlying mechanism and effect of process parameters. J Agric Food Chem 2008, 56:5112-5119.
189. Xiao Y., Li P., Cheng Y., Zhang X., Sheng J., Wang D., et al. Enhancing the intestinal absorption of low molecular weight chondroitin sulfate by conjugation with a-linolenic acid and the transport mechanism of the conjugates. Int J Pharm 2014, 465:143-158.
190. Yang J.M., Lin H.T. Properties of chitosan containing PP-g-AA-g-NIPAAm bigraft nonwoven fabric for wound dressing. J Membr Sci 2004, 243:1-7.
191. Yang J., Yan J., Zhou Z., Amsden B.G. Dithiol-PEG-PDLLA micelles: preparation and evaluation as potential topical ocular delivery vehicle. Biomacromolecules 2014, 15:1346-1354.
192. Yasugi K., Nagasaki Y., Kato M., Kataoka K. Preparation and characterization of polymer micelles from poly(ethylene glycol)-poly(d, l-lactide) block copolymers as potential drug carrier. J Control Release 1999, 62:89-100.
193. Yoon S.J., Chu D.C., Raj Juneja L. Chemical and physical properties, safety and application of partially hydrolized guar gum as dietary fiber. J Clin Biochem Nutr 2008, 42:1-7.
194. You J., Hu F.-Q., Du Y.-Z., Yuan H. Improved cytotoxicity of doxorubicin by enhancing its nuclear delivery mediated via nanosized micelles. Nanotechnology 2008, 19. [Art. 255103].
195. Zhang J., Li S., Li X. Polymeric nano-assemblies as emerging delivery carriers for therapeutic applications: a review of recent patents. Recent Pat Nanotechnol 2009, 3:225-231.
196. Zhang L., He Y., Ma G., Song C., Sun H. Paclitaxel-loaded polymeric micelles based on poly(ε-caprolactone)-poly(ethylene glycol)-poly(ε-caprolactone) triblock copolymers: in vitro and in vivo evaluation. Nanomed: Nanotechnol Biol Med 2012, 8:925-934.
197. Zhang N., Wardell P.R., Badder R.A. Polysaccharide-based micelles for drug delivery. Pharmaceutics 2013, 5:329-352.
198. Zhang Z.-H., Abbad S., Pan R.-R., Waddad A.Y., Hou L.-L., Lv H.-X., et al. N-Octyl-N-arginine chitosan micelles as an oral delivery system of insulin. J Biomed Nanotechnol 2013, 9:601-609.
199. Zhao D., Xu J.F., Wang L., Du J.J., Dong K.D., Wang C.F., et al. Study of two chitosan derivatives phosphorylated at hydroxyl or amino groups for application as flocculants. J Appl Polym Sci 2012, 125:E299-E305.
200. Zhou Y.Y., Du Y.Z., Wang L., Yuan H., Zhou J.P., Hu F.Q. Preparation and pharmacodynamics of stearic acid and poly (lactic-co-glycolic acid) grafted chitosan oligosaccharide micelles for 10-hydroxycamptothecin. Int J Pharm 2010, 393:143-151.