Photochemical preparation of a novel low molecular weight heparin

Carbohydrate Polymers

Volumn 87, Issue 2, 2012, Pages 1737-1743

  Higashi, Kyohei ^a   Hosoyama, Saori ^a   Ohno, Asami ^a   Masuko, Sayaka ^b   Yang, Bo ^b   Sterner, Eric ^c   Wang, Zhenyu ^d   Linhardt, Robert J ^b,c,d   Toida, Toshihiko ^a  

^a CHIBA UNIVERSITY   (Japan)

^b Research Rensselaer Polytechnic Institute   (United States)

^c RENSSELAER POLYTECHNIC INSTITUTE   (United States)

^d RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

LC MS; Low molecular weight heparin; NMR; Photochemical depolymerization; Titanium dioxide

Indexed keywords

ANTICOAGULANT ACTIVITIES; CORE STRUCTURE; H NMR SPECTRA; LC-MS; LIQUID CHROMATOGRAPHY/MASS SPECTROMETRY; LOW-MOLECULAR WEIGHT HEPARINS; NITROUS ACID; PHOTOCHEMICAL PREPARATION; POLYSACCHARIDE CHAIN; PRODUCT QUALITY; REACTION CONDITIONS; REDUCED LENGTH; SIDE REACTIONS; TIO; UNFRACTIONATED HEPARINS;

CENTRIFUGATION; DEPOLYMERIZATION; INORGANIC ACIDS; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDES; PHOTOLYSIS; TITANIUM; TITANIUM DIOXIDE;

POLYSACCHARIDES;

EID: 81255135677     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2011.09.087     Document Type: Article

References (41)

1. L.O. Anderson, T.W. Barrowcliffe, E. Holmer, E.A. Johnson, and G.E. Sims Anticoagulant properties of heparin fractionated by affinity chromatography on matrix-bound antithrombin III and by gel filtration Thrombosis Research 9 1976 575 583 (Pubitemid 8010572)
2. Bianchini, P., Mascellani, G. (1988). Novel oligosaccharides having pharmacological properties by depolymerization of heparin. U.S. Patent 4,791,195 December 13.
3. A. Bisio, S. Guglieri, M. Frigerio, G. Torri, E. Vismara, and U. Cornelli Controlled γ-ray irradiation of heparin generates oligosaccharides enriched in highly sulfated sequences Carbohydrate Polymers 55 2004 101 112
4. A. Blažková, V. Brezová, Z. Soldánová, A. Stasko, M. Soldan, and M. Čeppan Photocatalytic degradation of heparin over titanium dioxide Journal of Materials Science 30 1995 729 733
5. H.K. Breddin, J. Fareed, and N. Bender Low molecular weight heparins Haemostasis 18 Suppl. 3 1988 1 87
6. J. Burana-osot, S. Hosoyama, Y. Nagamoto, S. Suzuki, R.J. Linhardt, and T. Toida Photolytic depolymerization of alginate Carbohydrate Research 344 2009 2023 2027
7. J. Burana-osot, N. Soonthornchareonnon, S. Hosoyama, R.J. Linhardt, and T. Toida Partial depolymerization of pectin by a photochemical reaction Carbohydrate Research 345 2010 1205 1210
8. A. Chaidedgumjorn, A. Suzuki, H. Toyoda, T. Toida, T. Imanari, and R.J. Linhardt Conductivity detection for molecular mass estimation of per-O-sulfonated glycosaminoglycans separated by high-performance size-exclusion chromatography Journal of Chromatography A 959 2002 95 102 (Pubitemid 34607473)
9. M.D. Freedman Pharmacodynamics, clinical indications, and adverse effects of heparin Journal of Clinical Pharmacology 32 1992 584 596
10. Fussi, F. (1978). Oligo-heteropolysaccharides a active semblable a celle de l'heparine, procede pour leur preparation et compositions therapeutiques correspondantes. French Patent #FR 78 23499.
11. Fussi, F. (1981). Process for obtaining low molecular weight heparins endowed with elevated pharmacological properties and products so obtained. U.S. Patent 4,281,108, July 28.
12. Fussi, F. (1982). Process for obtaining low molecular weight heparins. European Patent GB2,002,406B.
13. A.S. Gervin Complications of heparin therapy Surgery Gynecology & Obstetrics 40 1975 789 796
14. D. Green, J. Hirsh, J. Heit, M. Prins, B. Davidson, and A.W. Lensing Low molecular weight heparin: A critical analysis of clinical trials Pharmacological Reviews 46 1994 89 109 (Pubitemid 24100620)
15. 2 dispersions Canadian Journal of Chemistry 63 1985 204 208
16. J. Harenberg Pharmacology of low molecular weight heparins Seminars in Thrombosis and Hemostasis 16 1990 12 18
17. K. Higashi, M. Ly, Z. Wang, S. Masuko, U. Bhaskar, and E. Sterner Controlled photochemical depolymerization of K5 heparosan, a bioengineered heparin precursor Carbohydrate Polymers 86 2011 1365 1370
18. J. Hirsh, and R. Raschke Heparin and low-molecular-weight heparin Chest 126 2004 188S 203S
19. S. Honda, and S. Suzuki Common conditions for high-performance liquid chromatographic microdetermination of aldoses, hexosamines, and sialic acids in glycoproteins Analytical Biochemistry 142 1984 167 174 (Pubitemid 15207562)
20. C.D. Jaeger, and A.J. Bard Spin trapping and electron spin resonance detection of radical intermediates in the photodecomposition of water at titanium dioxide particulate systems Journal of Physical Chemistry 83 1979 3146 3152
21. E.A. Johnson, and B. Mulloy The molecular weight range of mucosal-heparin preparations Carbohydrate Research 51 1976 119 127
22. Lindahl, U., Backstrom, G. E., & Thunberg, J. Y. L. (1980). Heparin fragments having selective anticoagulation activity. U.S. Patent 4,303,651, January 4.
23. R.J. Linhardt Analysis of glycosaminoglycans with polysaccharide lyases Current Protocols in Molecular Biology 2001 (Unit 17.13B.1-17.13B.16)
24. R.J. Linhardt 2003 Claude S. Hudson Award address in carbohydrate chemistry. Heparin: Structure and activity Journal of Medicinal Chemistry 46 2003 2551 2554
25. R.J. Linhardt, and N.S. Gunay Production and chemical processing of low molecular weight heparins Seminars in Thrombosis and Hemostasis 25 Suppl. 3 1999 5 16 (Pubitemid 29517028)
26. R.J. Linhardt, A. Grant, C.L. Cooney, and R. Langer Differential anticoagulant activity of heparin fragments prepared using microbial heparinase Journal of Biological Chemistry 257 1982 7310 7313 (Pubitemid 12002758)
27. R.J. Linhardt, D. Loganathan, A. Al-Hakim, H.M. Wang, J.M. Walenga, and D. Hoppensteadt Oligosaccharide mapping of low molecular weight heparins: Structure and activity differences Journal of Medicinal Chemistry 33 1990 1639 1645 1990 (Pubitemid 20180622)
28. A. Linker, K. Meyer, and P. Hoffman The production of unsaturated uronides by bacterial hyaluronidases Journal of Biological Chemistry 219 1956 13 25
29. D.L. Loshe, and R.J. Linhardt Purification and characterization of heparin lyases from Flavobacterium heparinum Journal of Biological Chemistry 267 1992 24347 24355
30. Mardiguian, J. (1984). Heparin esters and process for their preparation. U.S. Patent 4,440,926, April 3.
31. S. Masuko, K. Higashi, Z. Wang, U. Bhaskar, A.M. Hickey, and F. Zhang Ozonolysis of the double bond of the unsaturated uronate residue in low molecular weight heparin and K5 heparosan Carbohydrate Research 346 13 2011 1962 1966
32. Nielsen, J. I. (1992). Process of using light absorption to control enzymatic depolymerization of heparin to produce low molecular weight heparin. U.S. Patent 5,106,734, April 21.
33. H. Noda, K. Oikawa, and H. Kamada ESR study of active oxygen radicals from photoexcited semiconductors using the spin-trapping technique Bulletin of the Chemical Society of Japan 65 1992 2505 2509
34. T. Ohno, K. Sarukawa, K. Tokeida, and M. Matsumura Morphology of TiO2 photocatalyst (degussa, P-25) consisting of anatase and rutile crystalline phases Journal of Catalysis 203 2001 82 86 (Pubitemid 33092407)
35. J.E. Shivley, and H.E. Conrad Formation of anhydrosugars in the chemical depolymerization of heparin Biochemistry 15 1976 3932 3942
36. K. Solakyildirim, Z. Zhang, and R.J. Linhardt Ultraperformance liquid chromatography with electrospray ion trap mass spectrometry for chondroitin disaccharide analysis Analytical Biochemistry 397 2010 24 28
37. 1H nuclear magnetic resonance spectroscopic analysis for determination of glucuronic and iduronic acids in dermatan sulfate, heparin, and heparin sulfate Analytical Biochemistry 297 2001 42 51 (Pubitemid 32939272)
38. C. Thanawiroom, K.G. Rice, T. Toida, and R.J. Linhardt Liquid chromatography/mass spectrometry sequencing approach for highly heparin-derived oligosaccharides Journal of Biological Chemistry 279 2004 2608 2615 (Pubitemid 38114247)
39. Uzan, A. (1998). Sulfated polysaccharides obtained from heparin, preparation process, pharmaceutical composition and use thereof. U.S. Patent 5,849,721, December 15.
40. E. Vismara, M. Pierini, S. Guglieri, L. Liverani, G. Mascellani, and G. Torri Structural modification induced in heparin by a Fenton-type depolymerization process Seminars in Thrombosis and Hemostasis 33 2007 466 477 (Pubitemid 47105736)
41. 2+ fenton type depolymerization processes Thrombosis and Haemostasis 103 2010 613 622