A systematic analysis of DMTMM vs EDC/NHS for ligation of amines to Hyaluronan in water

Carbohydrate Polymers

Volumn 108, Issue 1, 2014, Pages 239-246

  D'Este, Matteo ^a,b   Eglin, David ^a,b   Alini, Mauro ^a,b  

^a AO RESEARCH INSTITUTE   (Switzerland)

^b AO FOUNDATION   (Switzerland)

Author keywords

Amide formation; Bioconjugates; DMTMM; EDC NHS; Hyaluronan modification

Indexed keywords

AMIDES; AMINES; CHLORINE COMPOUNDS;

AMIDE FORMATION; BIOCONJUGATES; DMTMM; EDC/NHS; HYALURONAN;

HYALURONIC ACID;

EID: 84899443533     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2014.02.070     Document Type: Article

References (42)

1. Clinical trials alchemia 2013 http://www.alchemia.com.au/ ProductsandPipeline.aspx
2. EDC/NHS Piercenet instruction 2013 http://www.piercenet.com/instructions/ 2160475.pdf
3. P.F. Bassi, A. Volpe, D. D'Agostino, G. Palermo, D. Renier, and S. Franchini et al. Paclitaxel-hyaluronic acid for intravesical therapy of Bacillus Calmette-Guérin refractory carcinoma in situ of the bladder: Results of a phase I study Journal of Urology 185 2011 445 449
4. K. Bergman, C. Elvingson, J. Hilborn, G. Svensk, and T. Bowden Hyaluronic acid derivatives prepared in aqueous media by triazine-activated amidation Biomacromolecules 8 2007 2190 2195 (Pubitemid 47104305)
5. P. Bulpitt, and D. Aeschlimann New strategy for chemical modification of hyaluronic acid: Preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels Journal of Biomedical Materials Research 47 1999 152 169 (Pubitemid 29409734)
6. S. Cai, S. Thati, T.R. Bagby, H.M. Diab, N.M. Davies, and M.S. Cohen et al. Localized doxorubicin chemotherapy with a biopolymeric nanocarrier improves survival and reduces toxicity in xenografts of human breast cancer Journal of Controlled Release 146 2010 212 218
7. C. Caravaggi, R. De Giglio, C. Pritelli, M. Sommaria, S. Dalla Noce, and E. Faglia et al. HYAFF 11-based autologous dermal and epidermal grafts in the treatment of noninfected diabetic plantar and dorsal foot ulcers: A prospective, multicenter, controlled, randomized clinical trial Diabetes Care 26 2003 2853 2859 (Pubitemid 37205558)
8. J.S. Cha Recent developments in the synthesis of aldehydes by reduction of carboxylic acids and their derivatives with metal hydrides. A review Organic Preparations and Procedures International 21 1989 451 477
9. M.N. Collins, and C. Birkinshaw Hyaluronic acid based scaffolds for tissue engineering - A review Carbohydrate Polymers 92 2013 1262 1279
10. M. D'Este, and D. Eglin Hydrogels in calcium phosphate moldable and injectable bone substitutes: Sticky excipients or advanced 3-D carriers? Acta Biomaterialia 9 2013 5421 5430
11. M. D'Este, M. Alini, and D. Eglin Single step synthesis and characterization of thermoresponsive hyaluronan hydrogels Carbohydrate Polymers 90 2012 1378 1385
12. A. Falchi, G. Giacomelli, A. Porcheddu, and M. Taddei 4-(4,6-Dimethoxy[1,3,5]triazin-2-yl)-4-methyl-morpholinium Chloride (DMTMM): A valuable alternative to PyBOP for solid phase peptide synthesis Synlett 2000 2000 275 277 (Pubitemid 30106389)
13. P. Farkas, and S. Bystricky Efficient activation of carboxyl polysaccharides for the preparation of conjugates Carbohydrate Polymers 68 2007 187 190 (Pubitemid 46204871)
14. P. Gibbs, T.J. Brown, R. Ng, R. Jennens, E. Cinc, and M. Pho et al. A pilot human evaluation of a formulation of irinotecan and hyaluronic acid in 5-fluorouracil-refractory metastatic colorectal cancer patients Chemotherapy 55 2009 49 59
15. P. Gibbs, P. Clingan, V. Ganju, A. Strickland, S. Wong, and N. Tebbutt et al. Hyaluronan-irinotecan improves progression-free survival in 5-fluorouracil refractory patients with metastatic colorectal cancer: A randomized phase II trial Cancer Chemotherapy and Pharmacology 67 2011 153 163
16. M.A. Gilles, A.Q. Hudson, and J. Borders Stability of water-soluble carbodiimides in aqueous solution Analytical Biochemistry 184 1990 244 248 (Pubitemid 20055618)
17. S.Y. Han, and Y.A. Kim Recent development of peptide coupling reagents in organic synthesis Tetrahedron 60 2004 2447 2467
18. Z.J. Kaminski, B. Kolesinska, J. Kolesinska, G. Sabatino, M. Chelli, and P. Rovero et al. N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis Journal of the American Chemical Society 127 2005 16912 16920 (Pubitemid 41772851)
19. M. Kunishima, C. Kawachi, J. Monta, K. Terao, F. Iwasaki, and S. Tani 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: An efficient condensing agent leading to the formation of amides and esters Tetrahedron 55 1999 13159 13170 (Pubitemid 29502265)
20. L. Lapcik, K. Benesova, L. Lapcik, S. De Smedt, and B. Lapcikova Chemical modification of hyaluronic acid: Alkylation International Journal of Polymer Analysis and Characterization 15 2010 486 496
21. T.C. Laurent, and J.R. Fraser Hyaluronan FASEB Journal 6 1992 2397 2404
22. L. Meléndez-Alafort, A. Nadali, E. Zangoni, A. Banzato, M. Rondina, and A. Rosato et al. Biokinetic and dosimetric studies of 188Re-hyaluronic acid: A new radiopharmaceutical for treatment of hepatocellular carcinoma Nuclear Medicine and Biology 36 2009 693 701
23. A. Mero, M. Pasqualin, M. Campisi, D. Renier, and G. Pasut Conjugation of hyaluronan to proteins Carbohydrate Polymers 92 2013 2163 2170
24. D. Mortisen, M. Peroglio, M. Alini, and D. Eglin Tailoring thermoreversible hyaluronan hydrogels by "Click" chemistry and RAFT polymerization for cell and drug therapy Biomacromolecules 11 2010 1261 1272
25. N. Nakajima, and Y. Ikada Mechanism of amide formation by carbodiimide for bioconjugation in aqueous media Bioconjugate Chemistry 6 1995 123 130
26. C.M. Nimmo, S.C. Owen, and M.S. Shoichet Diels-Alder click cross-linked hyaluronic acid hydrogels for tissue engineering Biomacromolecules 12 2011 824 830
27. J.M. Pelet, and D. Putnam An in-depth analysis of polymer-analogous conjugation using DMTMM Bioconjugate Chemistry 22 2011 329 337
28. M. Peroglio, D. Eglin, L.M. Benneker, M. Alini, and S. Grad Thermoreversible hyaluronan-based hydrogel supports in-vitro and ex-vivo disc-like differentiation of human mesenchymal stem cells Spine Journal 13 2013 1627 1639
29. M. Peroglio, S. Grad, D. Mortisen, C. Sprecher, S. Illien-Jünger, and M. Alini et al. Injectable thermoreversible hyaluronan-based hydrogels for nucleus pulposus cell encapsulation European Spine Journal 21 2012 839 849
30. T. Peters The Plasma Proteins F.W. Putman, The Plasma Proteins 2nd ed. 1975 Academic Press New York 133 181
31. T. Pouyani, G.S. Harbison, and G.D. Prestwich Novel hydrogels of hyaluronic acid: Synthesis, surface morphology, and solid-state NMR Journal of the American Chemical Society 116 1994 7515 7522 (Pubitemid 24291810)
32. T. Pouyani, and G.D. Prestwich Functionalized derivatives of hyaluronic acid oligosaccharides: Drug carriers and novel biomaterials Bioconjugate Chemistry 5 1994 339 347
33. S.A. Raw An improved process for the synthesis of DMTMM-based coupling reagents Tetrahedron Letters 50 2009 946 948
34. P.A. Revell, E. Damien, L. Di Silvio, N. Gurav, C. Longinotti, and L. Ambrosio Tissue engineered intervertebral disc repair in the pig using injectable polymers Journal of Materials Science: Materials in Medicine 18 2007 303 308 (Pubitemid 46332852)
35. M.A. Rosenthal, P. Gibbs, T.J. Brown, S. Wong, S. Uren, and A. Ellis et al. Phase I and pharmacokinetic evaluation of intravenous hyaluronic acid in combination with doxorubicin or 5-fluorouracil Chemotherapy 51 2005 132 141 (Pubitemid 40981071)
36. C.E. Schantè, G. Zuber, C. Herlin, and T.F. Vandamme Chemical modifications of hyaluronic acid for the synthesis of derivatives for a broad range of biomedical applications Carbohydrate Polymers 85 2011 469 489
37. W.Y. Su, Y.C. Chen, and F.H. Lin Injectable oxidized hyaluronic acid/adipic acid dihydrazide hydrogel for nucleus pulposus regeneration Acta Biomaterialia 6 2010 3044 3055
38. G. Tringali, F. Bettella, M.C. Greco, M. Campisi, D. Renier, and P. Navarra Pharmacokinetic profile of Oncofid-S after intraperitoneal and intravenous administration in the rat Journal of Pharmacy and Pharmacology 64 2012 360 365
39. ®) as a scaffold for endothelial cells in tissue engineered vascular grafts Biomaterials 25 2004 5955 5964 (Pubitemid 38747018)
40. L. Udabage, G.R. Brownlee, S.K. Nilsson, and T.J. Brown The over-expression of HAS2, Hyal-2 and CD44 is implicated in the invasiveness of breast cancer Experimental Cell Research 310 2005 205 217 (Pubitemid 41393701)
41. F. Yu, X. Cao, Y. Li, L. Zeng, B. Yuan, and X. Chen An injectable hyaluronic acid/PEG hydrogel for cartilage tissue engineering formed by integrating enzymatic crosslinking and Diels-Alder "click chemistry" Polymer Chemistry 5 2014 1082 1090
42. F. Yu, X. Cao, L. Zeng, Q. Zhang, and X. Chen An interpenetrating HA/G/CS biomimic hydrogel via Diels-Alder click chemistry for cartilage tissue engineering Carbohydrate Polymers 97 2013 188 195