Target specific and long-acting delivery of protein, peptide, and nucleotide therapeutics using hyaluronic acid derivatives

Journal of Controlled Release

Volumn 141, Issue 1, 2010, Pages 2-12

  Oh, Eun Ju ^a   Park, Kitae ^a   Kim, Ki Su ^a   Kim, Jiseok ^a   Yang, Jeong A ^a   Kong, Ji Hyun ^a   Lee, Min Young ^a   Hoffman, Allan S ^b   Hahn, Sei Kwang ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b University of Washington   (United States)

Author keywords

Bio imaging; Conjugation; Drug delivery; Hyaluronic acid; Hydrogel

Indexed keywords

BIO-IMAGING; BIOPHARMACEUTICALS; CHEMICALLY CROSS-LINKED HYDROGEL; CLINICAL DEVELOPMENT; DRUG DELIVERY SYSTEM; EFFECT OF CHEMICALS; HIGH SPECIFICITY; HYALURONIC ACID HYDROGELS; HYALURONIC ACIDS; INTRACELLULAR DELIVERY; PROTEIN DRUG DELIVERY; PROTEIN THERAPEUTICS; QUANTUM DOT;

AMINES; BINDING ENERGY; BINDING SITES; CHEMICAL MODIFICATION; CROSSLINKING; DRUG DELIVERY; HYDROGELS; HYDROXYLATION; LIGANDS; LIVER; MEDICAL APPLICATIONS; NUCLEOTIDES; ORGANIC ACIDS; PEPTIDES; SEMICONDUCTOR QUANTUM DOTS; TARGETS;

BIOLOGICAL MATERIALS;

CHITOSAN; CHONDROITIN; DECLAGE; ERYTHROPOIETIN; GLUCAGON LIKE PEPTIDE 1; HEPARIN; HUMAN GROWTH HORMONE; HYALURONIC ACID; HYALURONIC ACID DERIVATIVE; HYDROXYPROPYLCELLULOSE; LIPOSOME; MACROGOL; PEGINTERFERON ALPHA2A; PEGVISOMANT; PLASMID DNA; POLOXAMER; POLY(N ISOPROPYLACRYLAMIDE); POLYETHYLENEIMINE; POLYGLACTIN; POLYLYSINE; QUANTUM DOT; RECOMBINANT GRANULOCYTE COLONY STIMULATING FACTOR; RECOMBINANT HUMAN INSULIN; SMALL INTERFERING RNA; UNCLASSIFIED DRUG;

AREA UNDER THE CURVE; BIOCOMPATIBILITY; BIODEGRADABILITY; CANCER INHIBITION; CHEMICAL MODIFICATION; CLINICAL TRIAL; CONJUGATION; CONTROLLED RELEASE FORMULATION; CROSS LINKING; DOSE RESPONSE; DRUG ABSORPTION; DRUG ACCUMULATION; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM COMPARISON; DRUG EFFICACY; DRUG HALF LIFE; DRUG RELEASE; DRY POWDER; HUMAN; HYDROGEL; LIPOSOMAL GENE DELIVERY SYSTEM; MEAN RESIDENCE TIME; NONHUMAN; NONVIRAL GENE DELIVERY SYSTEM; PAIN; PRIORITY JOURNAL; REVIEW; SUSTAINED RELEASE FORMULATION; TIME TO MAXIMUM PLASMA CONCENTRATION;

ANIMALS; ANTIGENS, CD44; BINDING SITES; BIOCOMPATIBLE MATERIALS; BIOPHARMACEUTICS; DRUG CARRIERS; HUMANS; HYALURONIC ACID; MOLECULAR STRUCTURE; NUCLEOTIDES; PEPTIDES; PHARMACEUTICAL PREPARATIONS; PROTEINS; QUANTUM DOTS; TIME FACTORS; TISSUE DISTRIBUTION;

EID: 70849114663     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2009.09.010     Document Type: Review

References (110)

1. Laurent T.C. The Chemistry (1998), Portland Press, London, Biology and Medical Applications of Hyaluronan and Its Derivatives
2. Kuo J.W. Practical Aspects of Hyaluronan-Based Medical Products (2006), CRC Press, New York
3. Boas N.F. Isolation of hyaluronic acid from the cock's comb. J. Biol. Chem. 181 (1949) 573-575
4. Kendall F.E., Heidelberger M., and Dawson M.H. A serologically inactive polysaccharide elaborated by mucoid strains of group A hemolytic Streptococcus. J. Biol. Chem. 118 (1937) 61-69
5. Laurant T.C. In: Balazs E.A. (Ed). Chemistry and Molecular Biology of the Intercellular Matrix (1970), Academic Press, London
6. Laurent T.C., and Fraser J.R.E. Hyaluronan. FASEB J. 6 (1992) 2397-2404
7. Comper W.D., and Laurent T.C. Physiological function of connective tissue polysaccharides. Physiol. Rev. 58 (1978) 255-315
8. Toole B.P. Hyaluronan-cell interactions in morphogenesis. In: Laurent T.C. (Ed). The Chemistry, Biology, and Medical Applications of Hyaluronan and its Derivatives (1998), Portland Press, London
9. Brecht M., Mayer U., Schlosser E., and Prehm P. Increased hyaluronate synthesis is required for fibroblast detachment and mitosis. Biochem. J. 239 (1986) 445-450
10. Toole B.P. In: Hay E.D. (Ed). Cell Biology of Extracellular Matrix (1991), Plenum, New York
11. Goldberg R.L., and Toole B.P. Hyaluronate inhibition of cell proliferation. Arthritis Rheum. 30 (1987) 769-778
12. Stern R. Hyaluronan catabolism: a new metabolic pathway. Eur. J. Cell Biol. 83 (2004) 317-325
13. Prevo R., Banerji S., Ferguson D.J.P., Clasper S., and Jackson D.G. Mouse LYVE-1 is an endocytic receptor for hyaluronan in lymphatic endothelium. J. Biol. Chem. 276 (2001) 19420-19430
14. Stern R., Asari A.A., and Sugahara K.N. Hyaluronan fragments: an information-rich system. Eur. J. Cell Biol. 85 (2006) 699-715
15. Aruffo A., Stamenkovic I., Melnick M., Underhill C.B., and Seed B. CD44 is the principal cell surface receptor for hyaluronate. Cell 61 (1990) 1303-1313
16. Entwistle J., Hall C.L., and Turley E.A. HA receptors: regulators of signaling to the cytoskeleton. J. Cell. Biochem. 61 (1996) 569-577
17. Asayama S., Nogawa M., Takei Y., Akaike T., and Maruyama A. Synthesis of novel polyampholyte comb-type copolymers consisting of a poly(l-lysine) backbone and hyaluronic acid side chains for a DNA carrier. Bioconj. Chem. 9 (1998) 476-481
18. Takei Y., Maruyama A., Ferdous A., Nishimura Y., Kawano S., Ikejima K., Okumura S., Asayama S., Nogawa M., Hashimot M., Makino Y., Kinoshita M., Watanabe S., Akaike T., Lemasters J.J., and Sato N. Targeted gene delivery to sinusoidal endothelial cells: DNA nanoassociate bearing hyaluronan-glycocalyx. FASEB J. 18 (2004) 699-701
19. + macrophages in malignant tumors and wound healing tissue in vivo and in bone marrow cultures in vitro: implications for the assessment of lymphangiogenesis. J. Pathol. 209 (2006) 67-77
20. Laurent T.C., Dahl I.M.S., Dahl L.B., Engstrom-Laurent A., Eriksson S., Fraser J.R.E., Granath K.A., Laurent C., Laurent U.G.B., Lilja K., Pertoft H., Smedsrod B., Tengblad A., and Wik O. The catabolic fate of hyaluronic acid. Connect. Tissue Res. 15 (1986) 33-41
21. Fraser J.R.E., Kimpton W.G., Laurent T.C., Cahill R.N., and Vakakis N. Uptake and degradation of hyaluronan in lymphatic tissue. Biochem. J. 256 (1988) 153-158
22. Smedsrod B. Cellular events in the uptake and degradation of hyaluronan. Adv. Drug Del. Rev. 7 (1991) 265-278
23. Fraser J.R.E., Laurent T.C., Engstrom-Laurent A., and Laurent U.G.B. Elimination of hyaluronic acid from the blood stream in the human. Clin. Exp. Pharmacol. Physiol. 11 (1984) 17-25
24. Toole B.P. Hyaluronan: from extracellular glue to pericellular cue. Nat. Rev. Cancer 4 (2004) 528-539
25. Balazs E.A., and Denlinger J.L. Viscosupplementation: a new concept in the treatment of osteoarthritis. J. Rheumatol. 20 (1993) 3-9
26. Balazs E.A. Sodium hyaluronate and viscosurgery. In: Miller D., and Stegmann R. (Eds). Healon (Sodium Hyaluronate). A Guide to its Use in Ophthalmic Surgery (1983), Wiley, New York
27. Hahn S.K., Kim S.J., Kim M.J., and Kim D.H. Characterization and in vivo study of sustained release formulation of human growth hormone using sodium hyaluronate. Pharm. Res. 21 (2004) 1374-1381
28. Kim S.J., Hahn S.K., Kim M.J., Kim D.H., and Lee Y.P. Development of a novel sustained release formulation of recombinant human growth hormone using sodium hyaluronate microparticles. J. Control. Rel. 104 (2005) 323-335
29. Ohri R., Hahn S.K., Hoffman A.S., Stayton P.S., and Giachelli C.M. Hyaluronic acid grafting mitigates calcification of glutaraldhydefixed bovine pericardium. J. Biomed. Mater. Res. 70A (2004) 159-165
30. Luo Y., Ziebell M.R., and Prestwich G.D. A hyaluronic acid-taxol antitumor bioconjugate targeted to cancer cells. Biomacromolecules 1 (2000) 208-218
31. Luo Y., Bernshaw N.J., Lu Z.R., Kopecek J., and Prestwich G.D. Targeted delivery of doxorubicin by HPMA copolymer-hyaluronan bioconjugates. Pharm. Res. 19 (2002) 396-402
32. Oh E.J., Kim J.W., Kong J.H., Ryu S.H., and Hahn S.K. Signal transduction of hyaluronic acid-peptide conjugate for FPRL1 receptor. Bioconj. Chem. 19 (2008) 2401-2408
33. Motokawa K., Hahn S.K., Nakamura T., Miyamoto H., and Shimoboji T. Selectively crosslinked hyaluronic acid hydrogels for sustained release formulation of erythropoietin. J. Biomed. Mater. Res. 78A (2006) 459-465
34. Campoccia D., Doherty P., Radice M., Brun P., Abatangelo G., and Williams D.F. Semisynthetic resorbable materials from hyaluronan esterification. Biomaterials 19 (1998) 2101-2127
35. Kuo J.W., Swann D.A., and Prestwich G.D. Chemical modification of hyaluronic acid by carbodiimides. Bioconj. Chem. 2 (1991) 232-241
36. Hahn S.K., Jelacic S., Maier R.V., Stayton P.S., and Hoffman A.S. Anti-inflammatory drug delivery from hyaluronic acid hydrogels. J. Biomat. Sci. Polym. Ed. 15 (2004) 1111-1119
37. E.A. Balazs, A. Leshchiner, A. Leshchiner, P. Band, Chemically modified hyaluronic acid preparation and method of recovery thereof from animal tissues, US Patent 4, 713, 448 (1987).
38. Luo Y., Kirker K.R., and Prestwich G.D. Cross-linked hyaluronic acid hydrogel films: new biomaterials for drug delivery. J. Control. Rel. 69 (2000) 169-184
39. Rehakova M., Bakos D., Soldan M., and Vizarova K. Depolymerization reactions of hyaluronic acid in solution. Int. J. Biol. Macromol. 16 (1994) 121-124
40. Tranchepain F., Deschrevel B., Courel M.N., Levasseur N., Le Cerf D., Loutelier-Bourhis C., and Vincent J.C. A complete set of hyaluronan fragments obtained from hydrolysis catalyzed by hyaluronidase: application to studies of hyaluronan mass distribution by simple HPLC devices. Anal. Biochem. 348 (2006) 232-242
41. Prieto J.G., Pulido M.M., Zapico J., Molina A.J., Gimeno M., Coronel P., and Alvarez A.I. Comparative study of hyaluronic derivatives: rheological behaviour, mechanical and chemical degradation. Int. J. Biol. Macromol. 35 (2005) 63-69
42. Lee H., Ahn C.H., and Park T.G. Poly[lactic-co-(glycolic acid)]-grafted hyaluronic acid copolymer micelle nanoparticles for target-specific delivery of doxorubicin. Macromol. Biosci. 9 (2009) 336-342
43. Banerji S., Wright A.J., Nobel M., Mahoney D.J., Campbell I.D., Day A.J., and Jackson D.G. Structures of the Cd44- hyaluronan complex provide insight into a fundamental carbohydrate-protein interaction. Nat. Struct. Mol. Biol. 14 (2007) 234-239
44. Zhong S.P., Campoccia D., Doherty P.J., Williams R.L., Benedetti L., and Williams D.F. Biodegradation of hyaluronic acid derivatives by hyaluronidase. Biomaterials 15 (1994) 359-365
45. Oh E.J., Kang S.W., Kim B.S., Jiang G., Cho I.H., and Hahn S.K. Control of the molecular degradation of hyaluronic acid hydrogels for tissue augmentation. J. Biomed. Mater. Res. 86A (2008) 685-693
46. Kim J., Kim K.S., Jiang G., Kang H., Kim S., Kim B.S., Park M.H., and Hahn S.K. In Vivo real-time bio-imaging of hyaluronic acid derivatives using quantum dots. Biopolymers 89 (2008) 1144-1153
47. Hyung W., Ko H., Park J., Lim E., Park S.B., Park Y.J., Yoon H.G., Suh J.S., Haam S., and Huh Y.M. Novel hyaluronic acid (HA) coated drug carriers (HCDCs) for human breast cancer treatment. Biotech. Bioeng. 99 (2008) 442-454
48. Yeo Y., Highley C.B., Bellas E., Ito T., Marini R., Langer R., and Kohane D.S. In situ cross-linkable hyaluronic acid hydrogels prevent post-operative abdominal adhesions in a rabbit model. Biomaterials 27 (2006) 4698-4705
49. Hahn S.K., Park J.K., Tomimatsu T., and Shimoboji T. Synthesis and degradation test of hyaluronic acid hydrogels. Intern. J. Biol. Macromol. 40 (2007) 374-380
50. Hermanson G.T. Bioconjugate Techniques (2008), Academic Press, San Diego
51. Serban M.A., and Prestwich G.D. Synthesis of hyaluronan haloacetates and biology of novel cross-linker-free synthetic extracellular matrix hydrogels. Biomacromolecules 8 (2007) 2821-2828
52. Lee F., Chung J.E., and Kurisawa M. An injectable hyaluronic acid-tyramine hydrogel system for protein delivery. J. Control. Rel. 134 (2009) 186-193
53. Lee Y., Lee H., Kim Y.B., Kim J., Hyeon T., Park H.W., Messersmith P.B., and Park T.G. Bioinspired surface immobilization of hyaluronic acid on monodisperse magnetite nanocrystals for targeted cancer imaging. Adv. Mater. 20 (2008) 4154-4157
54. Hiemstra C., van der Aa L.J., Zhong Z., Dijkstra P.J., and Feijen J. Novel in situ forming, degradable dextran hydrogels by Michael addition chemistry: synthesis, rheology, and degradation. Macromolecules 40 (2007) 1165-1173
55. Friedman M., Cavins J.F., and Wall J.S. Relative nucleophilic reactivities of amino groups and mercaptide ions in addition reactions with α, β unsaturated compounds. J. Am. Chem. Soc. 87 (1965) 3672-3682
56. Lutolf M.P., Tirelli N., Cerritelli S., Cavalli L., and Hubbell J.A. Systematic modulation of Michael-type reactivity of thiols through the use of charged amino acids. Bioconj. Chem. 12 (2001) 1051-1056
57. Gao X., Cui Y., Levenson R.M., Chung L.W.K., and Nie S. In vivo cancer targeting and imaging with semiconductor quantum dots. Nat. Biotech. 22 (2004) 969-976
58. Michalet X., Pinaud F.F., Bentolila L.A., Tsay J.M., Doose S., Li J.J., Sundaresan G., Wu A.M., Gambhir S.S., and Weiss S. Quantum dots for live cells, in vivo imaging, and diagnostics. Science 307 (2005) 538-544
59. Medintz I.L., Uyeda H.T., Goldman E.R., and Mattoussi H. Quantum dot bioconjugates for imaging, labelling and sensing. Nat. Mater. 4 (2005) 435-446
60. Chan W.C.W., and Nie S. Quantum dot bioconjugates for ultrasensitive nonisotopic detection. Science 281 (1998) 2016-2018
61. Jaiswal J.K., Mattoussi H., Mauro J.M., and Simon S.M. Long-term multiple color imaging of live cells using quantum dot bioconjugates. Nat. Biotech. 21 (2002) 47-51
62. Al-Jamal W.T., Al-Jamal K.T., Tian B., Lacerda L., Bomans P.H., Frederik P.M., and Kostarelos K. Lipid quantum dot bilayer vesicles enhance tumor cell uptake and retention in vitro and in vivo. ACS Nano 2 (2008) 408-418
63. Mei B.C., Susumu K., Medintz I.L., and Mattoussi H. Polyethylene glycol-based bidentate ligands to enhance quantum dot and gold nanoparticle stability in biological media. Nat. Proto. 4 (2009) 412-423
64. Kim J., Park K., and Hahn S.K. Effect of hyaluronic acid (HA) molecular weight on the morphology of quantum dot-HA conjugates. Intern. J. Biol. Macromol. 42 (2008) 41-45
65. Jiang G., Park K., Kim J., Kim K.S., and Hahn S.K. Target specific intracellular delivery of siRNA/PEI-HA complex by receptor-mediated endocytosis. Mol. Pharm. 6 (2009) 727-737
66. Bhang S.H., Won N., Lee T.J., Jin H., Nam J., Park J., Chung H., Park H.S., Sung Y.E., Hahn S.K., Kim B.S., and Kim S. Hyaluronic acid-quantum dot conjugates for in vivo lymphatic vessel imaging. ACS Nano 3 (2009) 1389-1398
67. Nishikawa M., and Huang L. Nonviral vectors in the new millennium: delivery barriers in gene transfer. Hum. Gene Ther. 12 (2001) 861-870
68. Schiffelers R.M., Ansari A., Xu J., Zhou Q., Tang Q., Strom G., Molema G., Lu P.Y., Scaria P.V., and Woodle M.C. Cancer siRNA therapy by tumor selective delivery with ligand-targeted sterically stabilized nanoparticle. Nucleic Acids Res. 32 (2004) e149
69. Oishi M., Nagsaki Y., Itaka K., Nishiyama N., and Kataoka K. Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile β-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells. J. Amer. Chem. Soc. 127 (2005) 1624-1625
70. Wilson A., Zhou W., Champion H.C., Alber S., Tang Z.L., Kennel S., Watkins S., Huang L., Pitt B., and Li S. Targeted delivery of oligodeoxynucleotides to mouse lung endothelial cells in vitro and in vivo. Mol. Therapy 12 (2005) 510-518
71. Goldman C.K., Soroceanu L., Smith N., Gillespie G.Y., Shaw W., Burgess S., Bilbao G., and Curiel D.T. In vitro and in vivo gene delivery mediated by a synthetic polycationic amino polymer. Nat. Biotech. 15 (1997) 462-466
72. Fischer D., Li Y., Ahlemeyer B., Krieglstein J., and Kissel T. In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis. Biomaterials 24 (2003) 1121-1131
73. Ruponen M., Yla-Herttuala S., and Urtti A. Interactions of polymeric and liposomal gene delivery systems with extracellular glycosaminoglycans: physicochemical and transfection studies. Biochimica et Biophysica Acta (BBA) -Biomembranes 1415 (1999) 331-341
74. Ruponen M., Ronkko S., Honkakoski P., Pelkonen J., Tammi M., and Urtti A. Extracellular glycosaminoglycans modify cellular trafficking of lipoplexes and polyplexes. J. Biol. Chem. 276 (2001) 33875-33880
75. Ruponen M., Honkakoski P., Tammi M., and Urtti A. Cell-surface glycosaminoglycans inhibit cation-mediated gene transfer. J. Gene Med. 6 (2004) 405-414
76. Danielsen S., Strand S., de Lange Davies C., and Stokke B.T. Glycosaminoglycan destabilization of DNA-chitosan polyplexes for gene delivery depends on chitosan chain length and GAG properties. Biochimica et Biophysica Acta (BBA) - General Subjects 1721 (2005) 44-54
77. Kim A., Checkla D.M., Dehazya P., and Chen W. Characterization of DNA-hyaluronan matrix for sustained gene transfer. J. Control. Rel. 90 (2003) 81-95
78. Yun Y.H., Goetz D.J., Yellen P., and Chen W. Hyaluronan microspheres for sustained gene delivery and site-specific targeting. Biomaterials 25 (2004) 147-157
79. Chun K.W., Lee J.B., Kim S.H., and Park T.G. Controlled release of plasmid DNA from photo-cross-linked pluronic hydrogels. Biomaterials 26 (2005) 3319-3326
80. Kim A., Yellen P., Yun Y.H., Azeloglu E., and Chen W. Delivery of a vector encoding mouse hyaluronan synthase 2 via a crosslinked hyaluronan film. Biomaterials 26 (2005) 1585-1593
81. De La Fuente M., Seijo B., and Alonso M.J. Design of novel polysaccharidic nanostructures for gene delivery. Nanotechnology 19 (2008) 075105 (9 pp)
82. Han S.E., Kang H., Shim G.Y., Kim S.J., Choi H.G., Kim J., Hahn S.K., and Oh Y.K. Cationic derivatives of biocompatible hyaluronic acids for delivery of siRNA and antisense oligonucleotides. J. Drug Target. 17 (2009) 123-132
83. Chono S., Li S.D., Conwell C.C., and Huang L. An efficient and low immunostimulatory nanoparticle formulation for systemic siRNA delivery to the tumor. J. Control. Rel. 131 (2008) 64-69
84. Ito T., Iida-Tanaka N., Niidome T., Kawano T., Kubo K., Yoshikawa K., Sato T., Yang Z., and Koyama Y. Hyaluronic acid and its derivative as a multi-functional gene expression enhancer: protection from non-specific interactions, adhesion to targeted cells, and transcriptional activation. J. Control. Rel. 112 (2006) 382-388
85. Jiang G., Park K., Kim J., Kim K.S., Oh E.J., Kang H., Han S.E., Oh Y.K., Park T.G., and Hahn S.K. Hyaluronic acid-polyethyleneimine conjugate for target specific intracellular delivery of siRNA. Biopolymers 89 (2008) 635-642
86. Lee H., Mok H., Lee S., Oh Y.K., and Park T.G. Target-specific intracellular delivery of siRNA using degradable hyaluronic acid nanogels. J. Control. Rel. 119 (2007) 245-252
87. Healy J.M., Lewis S.D., Kurz M., Boomer R.M., Thompson K.M., Wilson C., and McCauley T.G. Pharmacokinetics and biodistribution of novel aptamer compositions. Pharm. Res. 21 (2004) 2234-2246
88. Bailon P., and Won C.Y. PEG-modified biopharmaceuticals. Expert Opin. Drug Del. 6 (2009) 1-16
89. Ryan S.M., Mantovani G., Wang X., Haddleton D.M., and Brayden D.J. Advances in PEGylation of important biotech molecules: delivery aspects. Expert Opin. Drug Del. 5 (2008) 371-383
90. Ishida T., Maeda R., Ichihara M., Irimura K., and Kiwada H. Accelerated clearance of PEGylated liposomes in rats after repeated injections. J. Control. Rel. 88 (2003) 35-42
91. Pan C.Q., Buxton J.M., Yung S.L., Tom I., Yang L., Chen H., MacDougall M., Bell A., Claus T.H., Clairmont K.B., and Whelan J.P. Design of a long acting peptide functioning as both a glucagon-like peptide-1 receptor agonist and a glucagon receptor antagonist. J. Biol. Chem. 281 (2006) 12506-12515
92. Nakamura T., Kato T., Togawa H., Yasugi K., Konishi H., Sekimori Y., and Shimoboji T. Conjugate of Water-soluble Modified Hyaluronic Acid and GLP-1 Analogue, WO2006/095775 (2006)
93. Luo Y., and Prestwich G.D. Hyaluronic acid-N-hydroxysuccinimide: a useful intermediate for bioconjugation. Bioconj. Chem. 12 (2001) 1085-1088
94. Luo Y., and Prestwich G.D. Synthesis and selective cytotoxicity of a hyaluronic acid-antitumor bioconjugate. Bioconj. Chem. 10 (1999) 755-763
95. Zhang M., and James S.P. Silylation of hyaluronan to improve hydrophobicity and reactivity for improved processing and derivatization. Polymer 46 (2005) 3639-3648
96. Lee H., Lee K., and Park T.G. Hyaluronic acid-paclitaxel conjugate micelles: synthesis, characterization, and antitumor activity. Bioconj. Chem. 19 (2008) 1319-1325
97. Oh E.J., Park K., Choi J.S., Joo C.K., and Hahn S.K. Synthesis, characterization, and applications of anti-Flt1 peptide-hyaluronate conjugate for the treatment of corneal neovascularization. Biomaterials 30 (2009) 6026-6034
98. Fang J.Y., Chen J.P., Leu Y.L., and Hu J.W. Temperature-sensitive hydrogels composed of chitosan and hyaluronic acid as injectable carriers for drug delivery. Eur. J. Pharm. Biopharm. 68 (2008) 626-636
99. Fraser J.R.E., Laurent T.C., and Laurent U.B.G. Hyaluronan: its nature, distribution, functions and turnover. J. Intern. Med. 242 (1997) 27-33
100. Lim S.T., Forbes B., Berry D.J., Martin G.P., and Brown M.B. In vivo evaluation of novel hyaluronan/chitosan microparticulate delivery systems for the nasal delivery of gentamicin in rabbits. Int. J. Pharm. 231 (2002) 73-82
101. Prestwich G.D., and Vercruysse K.P. Profiles therapeutic applications of hyaluronic acid and hyaluronan derivatives. Pharm. Sci. Tech. Today 1 (1998) 42-43
102. Na K., Kim S., Woo D.G., Sun B.K., Yang H.N., Chung H.M., and Park K.H. Combination material delivery of dexamethasone and growth factor in hydrogel blended with hyaluronic acid constructs for neocartilage formation. J. Biomed. Mat. Res. 83A (2007) 779-786
103. Lim S.T., Martin G.P., Berry D.J., and Brown M.B. Preparation and evaluation of the in vitro drug release properties and mucoadhesion of novel microspheres of hyaluronic acid and chitosan. J. Control. Rel. 66 (2000) 281-292
104. Ahsan F., Rivas I.P., Khan M.A., and Torres Suarez A.I. Targeting to macrophages: role of physicochemical properties of particulate carriers-liposomes and microspheres- on the phagocytosis by macrophages. J. Control. Rel. 79 (2002) 29-40
105. Takeuchi H., Yamamoto H., and Kawashima Y. Mucoadhesive nanoparticulate systems for peptide drug delivery. Advan. Drug Del. Rev. 47 (2001) 39-54
106. Surendrakumar K., Martyn G.P., Hodgers E.C.M., Jansen M., and Blair J.A. Sustained release of insulin from sodium hyaluronate based dry powder formulations after pulmonary delivery to beagle dogs. J. Control. Rel. 91 (2003) 385-394
107. Ohya S., Sonoda H., Nakayama Y., and Matsuda T. The potential of poly(N-isopropylacrylamide) (PNIPAM)-grafted hyaluronan and PNIPAM-grafted gelatin in the control of post-surgical tissue adhesions. Biomaterials 26 (2005) 655-659
108. Chung H.J., Lee Y., and Park T.G. Thermo-sensitive and biodegradable hydrogels based on stereocomplexed Pluronic multi-block copolymers for controlled protein delivery. J. Control. Rel. 127 (2008) 22-30
109. Hahn S.K., Oh E.J., Miyamoto H., and Shimobouji T. Sustained release formulation of erythropoietin using hyaluronic acid hydrogels crosslinked by Michael addition. Intern. J. Pharm. 322 (2006) 44-51
110. Hahn S.K., Kim J.S., and Shimobouji T. Injectable hyaluronic acid microhydrogels for controlled release formulation of erythropoietin. J. Biomed. Mater. Res. 80A (2007) 916-924