New amphiphilic hyaluronan derivatives based on modification with alkenyl and aryl succinic anhydrides

Carbohydrate Polymers

Volumn 85, Issue 1, 2011, Pages 173-179

  Tømmeraas, Kristoffer ^a   Mellergaard, Martin ^a   Malle, Birgitte M ^a   Skagerlind, Peter ^a  

^a NOVOZYMES A S   (Denmark)

Author keywords

1H NMR spectroscopy; Amphiphilic; Derivatization; Hyaluronan; SEC MALLS RI

Indexed keywords

AMPHIPHILIC; DERIVATIZATION; H NMR SPECTROSCOPY; HYALURONAN; SEC-MALLS;

EMULSIFICATION; ORGANIC ACIDS; SODIUM CHLORIDE; SURFACE PROPERTIES; SURFACE TENSION;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

OSA;

EID: 79953652088     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2011.02.011     Document Type: Article

References (43)

1. D.C. Armstrong, and M.R. Johns Culture conditions affect the molecular weight properties of hyaluronic acid produced by Streptococcus zooepidemicus Applied and Environmental Microbiology 63 1997 2759 2764 (Pubitemid 27292872)
2. J. Bao, J. Xing, D.L. Phillips, and H. Corke Physical properties of octenyl succinic anhydride modified rice, wheat and potato starches Journal of Agricultural and Food Chemistry 51 2003 2283 2287
3. R. Bhosale, and R. Singhal Process optimization for the synthesis of octenyl succinyl derivative of waxy corn and amaranth starches Carbohydrate Polymers 66 2006 521 527 (Pubitemid 44648318)
4. A. Biswas, R.L. Shogren, S. Kim, and J.L. Willett Rapid preparation of starch maleate half-esters Carbohydrate Polymers 64 2006 484 487
5. G.C.I. Chen, and T.W. Woodward Optimization of alkenyl succinic anhydride emulsification and sizing Tappi Journal 8 1986 95 97
6. M. Chytil, S. Strand, B.E. Christensen, and M. Pekar Calorimetric and light scattering study of interactions and macromolecular properties of native and hydrophobically modified hyaluronan Carbohydrate Polymers 81 2010 855 863
7. M. Chytil, and M. Pekař Effect of new hydrophobic modification of hyaluronan on its solution properties: Evaluation of self-aggregation Carbohydrate Polymers 76 2009 443 448
8. C. Duval-Terrié, J. Huguet, and G. Miller Self assembly and hydrophobic clusters of amphiphilic polysaccharides Colloids and Surfaces A: Physiochemical and Engineering Aspects 220 2003 105 115 (Pubitemid 36724611)
9. 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 Carbohydrate Polymers 79 2010 597 605
10. S. Furlan, G. La Penna, A. Perico, and A. Cesro Hyaluronan chain conformation and dynamics Carbohydrate Research 340 2005 959 970 (Pubitemid 40380825)
11. J. Gang-Biao, Q. Daping, L. Kairong, and W. Haihua Preparation of polymeric micelles based on chitosan bearing a small amount of highly hydrophobic groups Carbohydrate Polymers 66 2006 514 520
12. D.A. Gibbs, E.W. Merrill, K.A. Smith, and P. Chabrecek Rheology of hyaluronic acid Biopolymers 6 1968 777 791
13. K. Hayashi, K. Tsutsumi, T. Norisuye, and A. Teramoto Electrostatic contributions to chain stiffness and excluded-volume effects in sodium hyaluronate solutions Polymer Journal 28 1996 922 928 (Pubitemid 126587212)
14. P.M. Heacock, S.R. Hertzler, and B. Wolf The glycemic, insulinemic, and breath hydrogen responses in humans to a food starch esterified by 1-octenyl succinic anhydride Nutrition Research 24 2004 581 592 (Pubitemid 39094294)
15. D. Heinegrd, S. Björnsson, M. Mörgelin, and Y. Sommarin Hyaluronan-binding proteins T.C. Laurent, The chemistry, biology and medical applications of hyaluronan and its derivatives 1998 Portland Press London 113 122
16. A. Jansson, and L. Järnström Barrier and mechanical properties of modified starches Cellulose 12 2005 423 433 (Pubitemid 41600139)
17. W. Jarowenko Acetylated starch and miscellaneous organic esters O. Wurzburg, Properties and uses of modified starches 1986 CRC Press Florida 55 77
18. Y.-S. Jeon, A. Viswanathan, and R.A. Gross Study of starch esterification: Reaction with alkenyl - succinates in aqueous slurry system Starch/Stärke 51 1999 90 93
19. J.H. Jeong, H.S. Kang, S.R. Yang, K. Park, and J.-D. Kim Biodegradable poly(asparagine) grafted with poly(caprolactone) and the effect of substitution on self-aggregation Colloids and Surfaces A: Physiochemical and Engineering Aspects 264 2005 187 194 (Pubitemid 41246345)
20. R.I. Kelley Octenylsuccinic aciduria in children fed protein-hydrolysate formulas containing modified cornstarch Pediatric Research 30 1991 564 569
21. W. Knudson, and R.S. Peterson The hyaluronan 388 receptor: CD44 H.G. Garg, C.A. Hales, Chemistry and biology of hyaluronan 2004 Elsevier Ltd. Oxford 83 124
22. L. Lapcik, L. Lapcik, S. De Smedt, and J. Demeester Hyaluronan: Preparation, structure, properties, and applications Chemical Reviews 98 1998 2663 2684
23. O.S. Lawal Succinyl and acetyl starch derivatives of a hybrid maize: Physicochemical characteristics and retrogradation properties monitored by differential scanning calorimetry Carbohydrate Research 339 2004 2673 2682 (Pubitemid 39425138)
24. H.G. Lee, and M.K. Cowman An agarose gel electrophoretic method for analysis of hyaluronan molecular weight distribution Analytical Biochemistry 219 1994 278 287 (Pubitemid 24206807)
25. G. Lepperdinger, C. Fehrer, and S. Reitinger Biodegradation of hyaluronan H.G. Garg, C.A. Hales, Chemistry and biology of hyaluronan 2004 Elsevier Ltd. Oxford 71 82
26. C. Melander, and K. Tømmeraas Heterogeneous hydrolysis of hyaluronic acid in ethanolic HCl slurry Carbohydrate Polymers 82 2010 874 879
27. M.T. Neves-Petersen, S. Klitsgaard, E. Skovsen, S.B. Petersen, K. Tømmeraas, and K. Schwach-Abdellaoui Biophysical properties of phenyl succinic acid derivatised hyaluronic acid Journal of Fluorescence 20 2010 483 492
28. L. Nilsson, and B. Bergensthl Adsorption of hydrophobically modified starch at oil/water interfaces during emulsification Langmuir 22 2006 8770 8776 (Pubitemid 44626137)
29. L. Nilsson, M. Leeman, K.-G. Wahlund, and B. Bergensthl Mechanical degradation and changes in conformation of hydrophobically modified starch Biomacromolecules 7 2006 2671 2679 (Pubitemid 44530506)
30. S. Park, M.-G. Chung, and B. Yoo Rheological properties of octenyl succinated corn starch pastes Starch 56 2004 399 406
31. R.L. Shogren, A. Viswanathan, F. Felker, and R.A. Gross Distribution of octenyl succinate groups in octenyl succinic anhydride modified waxy maize starch Starch 52 2000 196 204
32. X.Z. Shu, and G.D. Prestwich Therapeutic biomaterials from chemically modified hyaluronan H.G. Garg, C.A. Hales, Chemistry and biology of hyaluronan 2004 Elsevier Ltd. Oxford 475 504
33. 13C NMR study of repeating disaccharide of hyaluronan: The effects of temperature and counterion type Carbohydrate Research 242 1993 29 51 (Pubitemid 23107498)
34. O. Smidsrød, and A. Haug Estimation of the relative stiffness of the molecular chain in polyelectrolytes from measurements of viscosity at different ionic strengths Biopolymers 10 1971 1213 1227
35. I.W. Sutherland Biotechnology of exopolysaccharides 1990 Cambridge University Press Cambridge
36. T. Takihara, Y. Yoshida, and A. Isogai Reactions between cellulose diacetate and alkenylsuccinic anhydrides and characterization of the reaction products Cellulose 14 2007 357 366 (Pubitemid 47103553)
37. A. Tawada, T. Masa, Y. Oonuki, A. Watanabe, Y. Matsuzaki, and A. Asari Large-scale preparation, purification, and characterization of hyaluronan oligosaccharides from 4-mers to 52-mers Glycobiology 12 2002 421 426
38. P.C. Trubiano Succinate and substituted succinate derivatives of starch O. Wurzburg, Properties and uses of modified starches 1986 CRC Press Florida 131 147
39. C. Tölg, S.R. Hamilton, and E.A. Turley The role of the hyaluronan receptor RHAMM in wound repair and tumorigenesis H.G. Garg, C.A. Hales, Chemistry and biology of hyaluronan 2004 Elsevier Ltd. Oxford 125 152
40. K. Tømmeraas, and C. Melander Kinetics of hyaluronan hydrolysis in acidic solution at various pH values Biomacromolecules 9 2008 1535 1540 (Pubitemid 351954426)
41. K. Tømmeraas, and P.-O. Wahlund Poly-acid properties of biosynthetic hyaluronan studied by titration Carbohydrate Polymers 77 2009 194 200
42. B. Widner, R. Behr, S. Von Dollen, M. Tang, T. Heu, and A. Sloma Hyaluronic acid production in Bacillus subtilis Applied and Environmental Microbiology 71 2005 3747 3752 (Pubitemid 40980543)
43. O.B. Wurzburg Modified starches A.M. Stephen, Food polysaccharides 1995 Marcel Dekker, Inc. New York 67 97