Ion exchange chromatographic separation and isolation of oligosaccharides of intact low-molecular-weight heparin for the determination of their anticoagulant and anti-inflammatory properties

Analytical and Bioanalytical Chemistry

Volumn 405, Issue 18, 2013, Pages 6043-6052

  Shastri, Madhur D ^a   Johns, Cameron ^b   Hutchinson, Joseph P ^b   Khandagale, Manish ^b   Patel, Rahul P ^a  

^a UNIVERSITY OF TASMANIA   (Australia)

^b UNIVERSITY OF TASMANIA   (Australia)

Author keywords

Anti inflammatory activity; Anticoagulant oligosaccharides; Enoxaparin; Ion exchange chromatography; Non anticoagulant oligosaccharides

Indexed keywords

ANTI-INFLAMMATORY ACTIVITY; ANTICOAGULANT ACTIVITIES; CHROMATOGRAPHIC SEPARATIONS; ENOXAPARIN; INFLAMMATORY CONDITIONS; INFLAMMATORY DISORDERS; ION EXCHANGE CHROMATOGRAPHY; LOW-MOLECULAR WEIGHT HEPARINS;

CHROMATOGRAPHIC ANALYSIS; ION EXCHANGE; LIQUID CHROMATOGRAPHY; OLIGOSACCHARIDES; POLYSACCHARIDES;

DRUG PRODUCTS;

ANTICOAGULANT AGENT; BLOOD CLOTTING FACTOR 10A; ENOXAPARIN; LOW MOLECULAR WEIGHT HEPARIN; NONSTEROID ANTIINFLAMMATORY AGENT; OLIGOSACCHARIDE;

ANIMAL; CARBOHYDRATE ANALYSIS; CELL LINE; CHEMISTRY; CONFERENCE PAPER; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; EQUIPMENT; EQUIPMENT DESIGN; ION EXCHANGE CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MACROPHAGE; METABOLISM; METHODOLOGY; MOLECULAR GENETICS; MOLECULAR WEIGHT; MOUSE; REPRODUCIBILITY;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTICOAGULANTS; CARBOHYDRATE SEQUENCE; CELL LINE; CHROMATOGRAPHY, ION EXCHANGE; DRUG EVALUATION, PRECLINICAL; ENOXAPARIN; EQUIPMENT DESIGN; FACTOR XA; HEPARIN, LOW-MOLECULAR-WEIGHT; MACROPHAGES; MICE; MOLECULAR SEQUENCE DATA; MOLECULAR WEIGHT; OLIGOSACCHARIDES; REPRODUCIBILITY OF RESULTS;

EID: 84879798595     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-013-6996-9     Document Type: Conference Paper

References (43)

1. Rabenstein DL (2002) Heparin and heparan sulfate: structure and function. Nat Prod Rep 19:312-331
2. McLean J (1959) The discovery of heparin. Circulation 19:75-78
3. Casu B (2005) In: Garg HG, Linhardt RJ, Hales CA (eds) Chemistry and biology of heparin and heparan sulfate, 1st edn. Elsevier Science, Oxfordshire, pp 1-28
4. Hirsh J (1991) Heparin. N Engl J Med 324:1565-1574
5. Weitz JI (1997) Low-molecular-weight heparins. N Engl J Med 337:688-699
6. Hirsh J, Raschke R (2004) Heparin and low-molecular-weight heparin. Chest 126:188S-203S
7. Alexander GGT (1991) Efficacy of a postoperative regimen of enoxaparin in deep vein thrombosis prophylaxis. Am J Surg 161:532-536
8. Casu B, Lindahl U (2001) Structure and biological interactions of heparin and heparan sulfate. Adv Carbohydr Chem Biochem 57:159-206
9. Lever R, Page C (2001) Glycosaminoglycans, airways inflammation and bronchial hyperresponsiveness. Pulm Pharmacol Ther 14:249-254
10. Dotan I, Hallak A, Arber N, Santo M, Alexandrowitz A, Knaani Y, Hershkoviz R, Brazowski E, Halpern Z (2001) Low-dose low-molecular weight heparin (enoxaparin) is effective as adjuvant treatment in active ulcerative colitis: an open trial. Dig Dis Sci 46:2239-2244
11. Hodak E, Yosipovitch G, David M, Ingber A, Chorev L, Lider O, Cahalon L, Cohen IR (1998) Low-dose low-molecular-weight heparin (enoxaparin) is beneficial in lichen planus: a preliminary report. J Am Acad Dermatol 38:564-568
12. Fernández C, Hattan CM, Kerns RJ (2006) Semi-synthetic heparin derivatives: chemical modifications of heparin beyond chain length, sulfate substitution pattern and N-sulfo/N-acetyl groups. Carbohydr Res 341:1253-1265
13. Riesenfeld J, Thunberg L, Höök M, Lindahl U (1981) The antithrombin-binding sequence of heparin. Location of essential N-sulfate groups. J Biol Chem 256:2389-2394
14. Lever R, Page CP (2002) Novel drug development opportunities for heparin. Nat Rev Drug Discov 1:140-148
15. Nelson R, Cecconi O, Roberts W, Aruffo A, Linhardt R, Bevilacqua M (1993) Heparin oligosaccharides bind L- and P-selectin and inhibit acute inflammation. Blood 82:3253-3258
16. Hostettler N, Naggi A, Torri G, Ishai-Michaeli R, Casu B, Vlodavsky I, Borsig L (2007) P-selectin- and heparanase-dependent antimetastatic activity of non-anticoagulant heparins. FASEB J 21:3562-3572
17. Rai R, Kaur I, Kumar B (2002) Low-dose low-molecular-weight heparin in lichen planus. J Am Acad Dermatol 46:141-143
18. Bergamaschini L, Rossi E, Storini C, Pizzimenti S, Distaso M, Perego C, De Luigi A, Vergani C, De Simoni MG (2004) Peripheral treatment with enoxaparin, a low molecular weight heparin, reduces plaques and β-amyloid accumulation in a mouse model of Alzheimer's disease. J Neurosci 24:4181-4186
19. Mousa SA, Petersen LJ (2009) Anti-cancer properties of low-molecular-weight heparin: preclinical evidence. Thromb Haemost 102:258-267
20. Lever R, Lo WT, Faraidoun M, Amin V, Brown RA, Gallagher J, Page CP (2007) Size-fractionated heparins have differential effects on human neutrophil function in vitro. Br J Pharmacol 151:837-843
21. Nelson RM, Cecconi O, Roberts WG, Aruffo A, Linhardt RJ, Bevilacqua MP (1993) Heparin oligosaccharides bind L- and P-selectin and inhibit acute inflammation. Blood 82:3253-3258
22. Whitelock JM, Murdoch AD, Iozzo RV, Underwood PA (1996) The degradation of human endothelial cell-derived perlecan and release of bound basic fibroblast growth factor by stromelysin, collagenase, plasmin, and heparanases. J Biol Chem 271:10079-10086
23. Turnbull JE, Fernig DG, Ke Y, Wilkinson MC, Gallagher JT (1992) Identification of the basic fibroblast growth factor binding sequence in fibroblast heparan sulfate. J Biol Chem 267:10337-10341
24. Patel RP, Narkowicz C, Jacobson GA (2009) Investigation of the effect of heating on the chemistry and antifactor Xa activity of enoxaparin. J Pharm Sci 98:1700-1711
25. Fryer A, Huang YC, Rao G, Jacoby D, Mancilla E, Whorton R, Piantadosi CA, Kennedy T, Hoidal J (1997) Selective O-desulfation produces nonanticoagulant heparin that retains pharmacological activity in the lung. J Pharmacol Exp Ther 282:208-219
26. Patel RP, Narkowicz C, Jacobson GA (2009) Investigation of freezing- and thawing-induced biological, chemical, and physical changes to enoxaparin solution. J Pharm Sci 98:1118-1128
27. Pervin A, Gallo C, Jandik KA, Han XJ, Linhardt RJ (1995) Preparation and structural characterization of large heparin-derived oligosaccharides. Glycobiology 5:83-95
28. Johnson EA (1987) An approach to a molecular weight calibration for low molecular weight heparins. Thromb Res 45:675-680
29. Ramasamy I, Kennedy J, Tan K (2003) Capillary electrophoresis for characterization of low molecular weight heparins. Lab Hematol 9:64-66
30. Patel RP, Narkowicz C, Hutchinson JP, Hilder EF, Jacobson GA (2008) A simple capillary electrophoresis method for the rapid separation and determination of intact low molecular weight and unfractionated heparins. J Pharm Biomed Anal 46:30-35
31. Pervin A, Alhakim A, Linhardt RJ (1994) Separation of glycosaminoglycan-derived oligosaccharides by capillary electrophoresis using reverse polarity. Anal Biochem 221:182-188
32. Thanawiroon C, Linhardt RJ (2003) Separation of a complex mixture of heparin-derived oligosaccharides using reversed-phase high-performance liquid chromatography. J Chromatogr A 1014:215-223
33. Patel RP, Narkowicz C, Jacobson GA (2009) Effective reversed-phase ion pair high-performance liquid chromatography method for the separation and characterization of intact low-molecular-weight heparins. Anal Biochem 387:113-121
34. Jayasri M (2009) Determination of anti-factor Xa activity of enoxaparin fractions using reversed-phase HPLC separation. Master's thesis, University of Tasmania, Hobart
35. Skidmore MA, Turnbull JE (2005) In: Garg HG, Linhardt RJ, Hales CA (eds) Chemistry and biology of heparin and heparan sulfate, 1st edn. Elsevier Science, Oxfordshire
36. Sumyk GB, Kyle JL, Hawrylewicz EJ (1969) Method for the preparation of heparin. Washington, DC. Patent 3,451,996, June 24
37. Bazin RJL-HG (2002) In: Fraser-Reid B, Tatsuta K, Thiem J (eds) Glycoscience: chemistry and chemistry biology, 1st edn. Springer, Berlin, pp 63-74
38. Miller MJ, Sandoval M (1999) Nitric oxide. III. A molecular prelude to intestinal inflammation. Am J Physiol 276:G795-G799
39. Mahoney JR, Beutler BA, Le Trang N, Vine W, Ikeda Y, Kawakami M, Cerami A (1985) Lipopolysaccharide-treated RAW 264.7 cells produce a mediator that inhibits lipoprotein lipase in 3T3-L1 cells. J Immunol 134:1673-1675
40. Miranda KM, Espey MG, Wink DA (2001) A rapid, simple spectrophotometric method for simultaneous detection of nitrate and nitrite. Nitric Oxide 5:62-71
41. Moncada S, Higgs A (1993) The l-arginine-nitric oxide pathway. N Engl J Med 329:2002-2012
42. Lundberg JO, Lundberg JM, Alving K, Weitzberg E (1997) Nitric oxide and inflammation: the answer is blowing in the wind. Nat Med 3:30-31
43. Turpie AGG (2008) Selective factor Xa inhibition with fondaparinux: from concept to clinical benefit. Eur Heart J Suppl 10:C1-C7