Chemical functionalization of hyaluronic acid for drug delivery applications

Materials Science and Engineering C

Volumn 38, Issue 1, 2014, Pages 177-185

  Vasi, Ana Maria ^a   Popa, Marcel Ionel ^a   Butnaru, Maria ^b   Dodi, Gianina ^a,c   Verestiuc, Liliana ^b  

^a GHEORGHE ASACHI TECHNICAL UNIVERSITY OF IASI   (Romania)

^b GRIGORE T POPA UNIVERSITY OF MEDICINE AND PHARMACY   (Romania)

^c SC CROMATEC PLUS SRL   (Romania)

Author keywords

Acrylic acid; Functionalized hyaluronic acid; Gels; Pilocarpine; Ring opening mechanism

Indexed keywords

GEL; GLUCAN; HYALURONIC ACID; PILOCARPINE; PULLULAN;

CALIBRATION; CELL DEATH; CELL LINE; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG EFFECTS; GEL; GEL CHROMATOGRAPHY; HUMAN; INFRARED SPECTROSCOPY; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROCEDURES; SCANNING ELECTRON MICROSCOPY; TEMPERATURE; THERMOGRAVIMETRY;

CALIBRATION; CELL DEATH; CELL LINE; CHROMATOGRAPHY, GEL; DRUG DELIVERY SYSTEMS; GELS; GLUCANS; HUMANS; HYALURONIC ACID; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, SCANNING; PILOCARPINE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE; THERMOGRAVIMETRY;

EID: 84894564200     PISSN: 09284931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.msec.2014.01.052     Document Type: Article

References (45)

1. T.C. Laurent Biology and Medical Applications of Hyalorunan and Its derivatives, the chemistry 1998 Portland Press London
2. C. Melander, and K. Tømmeraas The influence of sodium hyaluronate molecular weight on protein content according to Lowry and Coomassie blue assays Carbohydr. Polym. 74 2008 745 748
3. S. Park, M.G. Chung, and B. Yoo Rheological properties of octenyl succinated corn starch pastes Starch 56 2004 399 406
4. E.A. Balazs, and J.L. Denlinger Visco suplimentation: a new concept in the treatment of osteoarthritis J. Rheumatol. 20 1993 3 9
5. E.A. Balazs Sodium hyaluronate and viscosurgery D. Miller, R. Stehman, Healon (Sodium Hyaluronate), a Guide to Its USE in Ophthalmic Surgery 1983 Wiley New York
6. R. Ohry, S.K. Hahn, A.S. Hoffman, P.S. Stayton, and C.M. Giachelli Hyaluronic acid grafting mitigates calcification of glutaraldehyde fixed bovine pericardium J. Biomed. Mater. Res. 70A 2004 159 165
7. D. Jiang, J. Liang, and P. Noble Hyalorunan in tissue injury and repair Annu. Rev. Cell Dev. Biol. 23 2007 435 461
8. S.K. Hahn, S.J. Kim, M.J. Kim, and D.H. Kim Characterization and in vivo study of sustained release formulation of human growth hormone using sodium hyaluronate Pharm. Res. 21 2004 1374 1381
9. S.J. Kim, S.K. Hahn, M.J. Kim, and Y.P. Lee Development of a novel sustained release formulation of recombinant human growth hormone using sodium hyaluronate microparticles J. Control. Release 104 2005 323 335
10. W. Knudson, and R.S. Peterson The hyalorunan 388 receptor: CD44 H.G. Garg, C.A. Hales, Chemistry and Biology of Hyalorunan 2004 Elsevier Ltd. Oxford 83 124
11. X.Z. Shu, and G.D. Prestwich Therapeutic biomaterials from chemically modified hyaluronan H.G. Garg, C.A. Hales, Chemistry and Biology of Hyalorunan 2004 Elsevier Ltd Oxford 475 504
12. K.S. Girish, and K. Kemparaju The magic glue of hyaluronan and its eraser hyaluronidase: a biological overview Life Sci. 80 2007 1921 1943
13. M.J. Jedrzejas, and R. Stern Structures of vertebrate hyaluronidases and their unique enzymatic mechanism of hydrolysis Proteins 61 2005 227 238
14. Z. Lurie, T. Offer, A. Russo, A. Samuni, and D. Nitzan Do stable notroxide radicals catalyze or inhibit the degradation of hyaluronic acid? Free Radic. Biol. Med. 35 2003 169 178
15. G. Leone, M. Consumi, S. Lamponi, and A. Magnani New hyaluronan derivative with prolonged half-life for ophthalmogical formulation Carbohydr. Polym. 88 2012 799 808
16. P. Ghosh, and D. Guidolin Potential mechanism of action of intra-articular hyaluronan therapy in osteoarthritis: are the effects molecular weights dependent? Semin. Arthritis Rheum. 32 2002 10 37
17. R. Stern, A. Asari, and K. Sugaraha Hyalorynan fragments: an information-rich system Eur. J. Cell Biol. 85 2006 699 715
18. C.E. Schante, G. Zuber, C. Herlin, and T.F. Vandamme Improvement of hyaluronic acid enzymatic stability by the grafting of amino-acids Carbohydr. Polym. 87 2012 2211 2216
19. E.J. Oh, K. Park, K.S. Kim, J. Kim, J.A. Yang, J.H. Kong, M.Y. Lee, A.S. Hoffman, and S.K. Hahn Target specific and long-acting delivery of protein, peptide, and nucleotide therapeutics using hyaluronic acid derivatives J. Control. Release 141 2010 2 12
20. C. Creuzet, S. Kadi, M. Rinaudo, and R. Auzely-Velty New associative systems based on alkylated hyaluronic acid, synthesis and aqueous solution properties Polymer 47 2006 2706 2713
21. S. Pelletier, P. Hubert, F. Lapicque, E. Payan, and E. Dellacherie Amphiphilic derivatives of sodium alginate and hyaluronate: synthesis and physicochemical properties of aqueous dilute solutions Carbohydr. Polym. 43 2000 343 349
22. V. Kumar, F. Longin, K. Schwach-Abdellaoui, R.A. Gross. Methyl esters of hyaluronic acid, World Intellectual Property Organization, (2008), Pat. No. WO 2008/091915 A1.
23. K. Benesova, M. Pekar, L. Lapcik, and J. Kuceric Stability evaluation of n-alkyl hyaluronic acids derivatives by DSC and TG measurement J. Therm. Anal. Calorim. 83 2006 341 348
24. Y. Kawaguchi, K. Matsukawa, Y. Gama, and Y. Ishigami New polysaccharide surfactants from hyaluronate Chem. Express 6 1991 647 650
25. P. Mlochova, V. Hajkova, B. Steiner, S. Bystricky, M. Koos, M. Medova, and V. Velebny Preparation and characterization of biodegradable alkyl ether derivatives of hyalorunonan Carbohydr. Polym. 69 2007 344 352
26. S.C. Eenschooten, M.W. Christensen. Aryl/Alkyl vinyl sulfone hyaluronic acid derivatives, World Intellectual Property Organization, (2007), Pat No. WO 2007/098770A1.
27. K. Schwach-Abdellaoui, M. Vert, L. Pravata. Hyaluronic acid linked with a polymer of an alpha hydroxyl acid, World Intellectual Property Organization, (2006), Pat No. WO 2006/069578 A1.
28. J.R.E. Fraser, T.J. Brown, and T.C. Laurent Catabolism of hyaluronan, In The chemistry, Biology and Medical Applications of Hyaluronan and Its derivatives 1998 Portland Press London
29. P.L. Lu, J.Y. Lai, D.H. Ma, and G.H. Hsiue Carbodiimide cross-linked hyaluronic acid hydrogels as cell sheet delivery vehicles: characterization and interaction with corneal endothelial cells J. Biomater. Sci. Polym. Ed. 19 2008 1 18
30. J.Y. Lai Solvent composition is critical for carbodiimide cross-linking of hyaluronic acid as an ophthalmic biomaterial Materials 5 2012 1986 2002
31. T. Fujisawa, H. Miyai, K. Hironaka, T. Tsukamoto, K. Tahara, Y. Tozuka, M. Ito, and H. Takeuchi Liposomal diclofenac eye drop formulations targeting the retina: formulation stability improvement using surface modification of liposomes Int. J. Pharm. 436 2012 564 567
32. L. Nie, and R. Narayan Upper limit of grafting conversion and phase homogeneity: cellulose acetate/poly (styrene-co-maleic anhydride) grafting reaction, system 35 1994 4334 4342
33. D. Rutot, P. Degee, R. Narayan, and P. Dubois Aliphatic polyester-grafted starch composites by in situ ring opening polymerization Compos. Interface 7 2000 215 225
34. D. Macocinschi, D. Filip, V. Stelian, M. Butnaru, and L. Knieling Evaluation of polyurethane based on cellulose derivative-ketoprofen biosystem for implant biomedical devices Int. J. Biol. Macromol. 52 2013 32 37
35. G. Leone, M. Consumi, S. Lamponi, and A. Magnani New hyaluronan derivative with prolonged half-life for ophthalmic formulation Carbohydr. Polym. 88 2012 799 808
36. E. Carole Schante, G. Zuber, C. Herlin, and T.F. Vandamme Chemical modifications of hyaluronic acid for the synthesis of derivatives for a broad range of biomedical application Carbohydr. Polym. 85 2011 469 489
37. C. Eenschooten, F. Guillaumie, G.M. Kontogeorgis, E.H. Stenby, and K. Schwach-Abdellaoui Preparation and structural characterization of novel and versatile amphiphilic octenyl succinic anhydride-modified hyaluronic acid derivatives Carbohydr. Polym. 79 2010 597 605
38. J. Alyoussef Alkrad, Y. Mrestani, D. Stroehl, S. Wartewig, and R. Neubert Characterization of enzymatically digested hyaluronic acid using NMR, Raman, IR, and UV-Vis spectroscopies J. Pharm. Biomed. Anal. 31 2003 545 550
39. M.A. Villetti, J.S. Crespo, M.S. Soldi, A.T.N. Pires, R. Borsali, and V. Soldi Thermal degradation of natural polymers J. Therm. Anal. Calorim. 67 2002 295
40. R. Stern, G. Kogan, M. Jedrzejas, and L. Soltes The many ways to cleave hyaluronan Biotechnol. Adv. 25 2007 537 557
41. A. Maleki, A. Kjønisen, and B. Nzström Effect of pH on the behavior of hyaluronic acid in dilute and semidilute aqueous solutions Macromol. Symp. 274 2008 131 140
42. J.Y. Lai, and A.C. Hsieh A gelatin-g-poly(N-isopropylacrylamide) biodegradable in situ gelling delivery system for the intracameral administration of pilocarpine Biomaterials 33 2012 2372 2387
43. S. Li, Y. Shen, W. Li, and X. Hao A common profile for polymer-based controlled releases and its logical interpretation to general release process J. Pharm. Pharm. Sci. 9 2006 238 244
44. N.A. Peppas, P. Bures, W. Leobandung, and H. Ichikawa Hydrogels in pharmaceutical formulations Eur. J. Pharm. Biopharm. 50 2000 27 46
45. L. Wei, C. Cai, J. Lin, and T. Chen Dual-drug delivery system based on hydrogel/micelle composites Biomaterials 30 2009 2606 2613