Conjugation of hyaluronan to proteins

Carbohydrate Polymers

Volumn 92, Issue 2, 2013, Pages 2163-2170

  Mero, Anna ^a   Pasqualin, Matteo ^a   Campisi, Monica ^b   Renier, Davide ^b   Pasut, Gianfranco ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b Fidia Advanced Biopolymers   (Italy)

Author keywords

Biodegradable polymers; Haylation; Hyaluronic acid; Protein delivery

Indexed keywords

BLOOD GLUCOSE LEVEL; CARBOXYLIC GROUP; DIRECT COUPLING; HAYLATION; HYALURONAN; IMMUNOGENICITY; N-TERMINALS; PEPTIDE LOADING; PROTEIN DELIVERY; RNASE A; SITE-SELECTIVE CONJUGATION; THERAPEUTIC PROTEIN;

ALDEHYDES; BIODEGRADABLE POLYMERS; BIOSYNTHESIS; BLOOD; ENZYMES; INSULIN; LOADING; ORGANIC ACIDS; PROTEINS;

HYALURONIC ACID;

ALDEHYDE; HYALURONIC ACID; INSULIN; PANCREATIC RIBONUCLEASE; PROTEIN; TRYPSIN;

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; DRUG EFFECT; ERYTHROCYTE; MATERIALS TESTING; METABOLISM; RAT;

ALDEHYDES; ANIMALS; CATTLE; ERYTHROCYTES; HYALURONIC ACID; INSULIN; MATERIALS TESTING; PROTEINS; RATS; RIBONUCLEASE, PANCREATIC; TRYPSIN;

EID: 84871542188     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2012.11.090     Document Type: Article

References (35)

1. A. Akbarzadeh, D. Norouzian, M.R. Mehrabi, S.H. Jamshidi, A. Farhangi, and A. Allah Verdi Induction of diabetes by streptozotocin Indian Journal of Clinical Biochemistry 22 2007 60 64
2. A. Almond Hyaluronan Cellular and Molecular Life Sciences 64 2007 1591 1596
3. J.K. Armstrong, G. Hempel, S. Koling, and L.S. Chan Antibody against poly-(ethylene glycol) adversely affects PEG-asparaginase therapy in acute lymphoblastic leukemia patients Cancer 110 2007 103 111
4. E.A. Balazs, and T.C. Laurent The chemistry, biology and medical applications of hyaluronan and its derivatives T.C. Laurent, Round table discussion: New applications for hyaluronan 1998 Portland Press London 325 326
5. A. Banzato, S. Bobisse, M. Rondina, D. Renier, F. Bettella, and G. Esposito A paclitaxel-hyaluronan bioconjugate targeting ovarian cancer affords a potent in vivo therapeutic activity Clinical Cancer Research 14 2008 3598 3606
6. A. Besheer, T.C. Hertel, J. Kressler, K. Mäder, and M. Pietzsch Enzymatically catalyzed HES conjugation using microbial transglutaminase: Proof of feasibility Journal of Pharmaceutical Sciences 98 2009 4420 4428
7. D'Este, M., Pasut, G., Renier, D., & Rosato, A. (2010). Process for the synthesis of conjugates of glycosaminoglycanes (GAG) with biologically active molecules, polymeric conjugates and relative uses thereof. WO 2010/145821.
8. R. Duncan, H.R.P. Gilbert, R.J. Carbajo, and M.J. Vicent Polymer masked-unmasked protein therapy (PUMPT) 1. Bioresponsive dextrin-trypsin and -MSH conjugates designed for alpha-amylase activation Biomacromolecules 9 2008 1146 1154
9. E.L. Ferguson, and R. Duncan Dextrin-phospholipase A2: synthesis and evaluation as a novel bioresponsive anticancer conjugate Biomacromolecules 10 2009 1358 1364
10. H.F. Gaertner, and A.J. Puigserver Increased activity and stability of poly(ethylene glycol)-modified trypsin Enzyme and Microbial Technology 14 1992 150 155
11. G. Gregoriadis, S. Jain, I. Papaioannou, and P. Laing Improving the therapeutic efficacy of peptides and proteins: A role for polysialic acids International Journal of Pharmaceutics 300 2005 125 130
12. J. Hardwicke, E.L. Ferguson, R. Moseley, P. Stephens, D. Thomas, and R. Duncan Dextrin-rhEGF conjugates as bioresponsive nanomedicines for wound repair Journal of Controlled Release 130 2008 275 283
13. J.M. Harris, and R.B. Chess Effect of PEGylation on pharmaceuticals Nature Reviews Drug Discovery 2 2003 214 221
14. A. Homma, H. Sato, A. Okamachi, T. Emura, T. Ishizawa, and T. Kato Novel hyaluronic acid-methotrexate conjugates for osteoarthritis treatment Bioorganic and Medicinal Chemistry 17 2009 4647 4656
15. J. Hu, and W. Sebald N-terminal specificity of PEGylation of human bone morphogenetic protein-2 at acidic pH International Journal of Pharmaceutics 413 2011 140 146
16. B.C. Hummel A modified spectrophotometric determination of chymotrypsin, trypsin, and thrombin Canadian Journal of Biochemistry and Physiology 37 1959 1393 1399
17. A. Junod, A.E. Lambert, L. Orci, R. Pictet, A.E. Gonet, and A.E. Renold Studies of the diabetogenic action of streptozotocin Proceedings of the Society for Experimental Biology and Medicine 126 1967 201 205
18. T.C. Laurent, and J.R.E. Fraser Hyaluronan FASEB Journal 6 1992 2397 2404
19. A. Mero, Z. Fang, G. Pasut, F.M. Veronese, and T.X. Viegas Selective conjugation of poly(2-ethyl 2-oxazoline) to granulocyte colony stimulating factor Journal of Controlled Release 159 2012 353 361
20. A. Mero, G. Pasut, L. Dalla Via, M.W. Fijten, U.S. Schubert, and R. Hoogenboom Synthesis and characterization of poly(2-ethyl 2-oxazoline)- conjugates with proteins and drugs: Suitable alternatives to PEG-conjugates? Journal of Controlled Release 125 2008 87 95
21. A. Mero, and F.M. Veronese The impact of PEGylation on biological therapies BioDrugs 22 2008 315 329
22. R.A.A. Muzzarelli, F. Greco, A. Busilacchi, V. Sollazzo, and A. Gigante Chitosan, hyaluronan and chondroitin sulfate in tissue engineering for cartilage regeneration: A review Carbohydrate Polymers 89 2012 723 739
23. F.S. Palumbo, G. Pitarresi, C. Fiorica, P. Matricardi, G. Albanese, and G. Giammona In situ forming hydrogels of new amino hyaluronic acid/benzoyl-cysteine derivatives as potential scaffolds for cartilage regeneration Soft Matter 8 2012 4918 4924
24. G. Pasut, A. Mero, F. Caboi, S. Scaramuzza, L. Sollai, and F.M. Veronese A new PEG-beta-alanine active derivative for releasable protein conjugation Bioconjugate Chemistry 19 2008 2427 2431
25. G. Pasut, and F.M. Veronese Polymer-drug conjugation, recent achievements and general strategies Progress in Polymer Science 32 2007 933 961
26. G. Pasut, and F.M. Veronese State of the art in PEGylation: The great versatility achieved after forty years of research Journal of Controlled Release 161 2012 461 472
27. G. Pitarresi, F.S. Palumbo, A. Albanese, C. Fiorica, P. Picone, and G. Giammona Self assembled amphiphilic hyaluronic acid graft copolymers for targeted release of antitumoral drug Journal of Drug Targeting 18 2010 264 276
28. G. Saravanakumar, K.Y. Choi, H.Y. Yoon, K. Kim, J.H. Park, and I.C. Kwon Hydrotropic hyaluronic acid conjugates: Synthesis, characterization, and implications as a carrier of paclitaxel International Journal of Pharmaceutics 394 2010 154 161
29. M.R. Sherman, M.G. Saifer, and F. Perez-Ruiz PEGuricase in the management of treatment-resistant gout and hyperuricemia Advanced Drug Delivery Reviews 6 2008 59 68
30. P.K. Smith, R.I. Krohn, G.T. Hermanson, A.K. Mallia, F.H. Gartner, and M.D. Provenzano Measurement of protein using bicinchoninic acid Analytical Biochemistry 150 1985 76 85
31. V.P. Torchilin, A.V. Maksimenko, and A.V. Mazaev Immobilized enzymes for thrombolytic therapy Methods in Enzymology 137 1988 552 566
32. F.M. Veronese, A. Mero, F. Caboi, M. Sergi, C. Marongiu, and G. Pasut Site-specific pegylation of G-CSF by reversible denaturation Bioconjugate Chemistry 18 2007 1824 1830
33. T.X. Viegas, M.D. Bentley, J.M. Harris, Z. Fang, K. Yoon, and B. Dizman Polyoxazoline: Chemistry, properties, and applications in drug delivery Bioconjugate Chemistry 22 2011 976 986
34. J.A. Yang, K. Park, H. Jung, H. Kim, S.W. Hong, and S.K. Yoon Target specific hyaluronic acid-interferon alpha conjugate for the treatment of hepatitis C virus infection Biomaterials 32 2011 8722 8729
35. R. Zwilling, and H. Neurath Invertebrate protease Methods in Enzymology 80 1981 633 664