Flavonoids with an oligopolysulfated moiety: A new class of anticoagulant agents

Journal of Medicinal Chemistry

Volumn 54, Issue 1, 2011, Pages 95-106

  Correia Da Silva, Marta ^a   Sousa, Emília ^a   Duarte, Bárbara ^a   Marques, Franklim ^a   Carvalho, Félix ^a   Cunha Ribeiro, Luís M ^b   Pinto, Madalena M M ^a  

^a UNIVERSITY OF PORTO   (Portugal)

^b HOSPITAL DE SÃO JOÃO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

3'',4'' BIS(2 O SULFATE ETHOXY) 7 (2 O SULFATE ETHOXY)RUTIN; ANTITHROMBIN III; BLOOD CLOTTING FACTOR 10A; DIOSMIN 2'',2'',3'',3'''',4'',4'''' O HEXASULFATE; FLAVONOID; HESPERIDIN 2'',2''',3'',3''',4'',4'''' O HEXASULFATE; POLYSACCHARIDE SULFATE; RUTIN 2'',2''',3',3'',3'''',4',4'',4'''',5, 7 O DECASULFATE; THROMBIN; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTICOAGULANT THERAPY; ARTICLE; BLOOD CLOTTING TIME; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DETERMINATION; DRUG SAFETY; DRUG SULFATION; DRUG SYNTHESIS; HUMAN; IN VITRO STUDY; IN VIVO STUDY; MALE; MOLECULAR HYBRIDIZATION; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; THROMBOELASTOGRAPHY;

ADULT; ANIMALS; ANTICOAGULANTS; ANTITHROMBIN III; FACTOR XA; FLAVONOIDS; GLUCOSIDES; HUMANS; MICE; MIDDLE AGED; PARTIAL THROMBOPLASTIN TIME; PLATELET AGGREGATION; PROTHROMBIN TIME; RUTIN; STRUCTURE-ACTIVITY RELATIONSHIP; SULFURIC ACID ESTERS; THROMBELASTOGRAPHY; THROMBIN; THROMBIN TIME; YOUNG ADULT;

EID: 78651081744     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1013117     Document Type: Article

References (64)

1. Linhardt, R. J. Heparin: an important drug enters its seventh decade Chem. Ind. 1991, 2, 45-50
2. Linhardt, R. J.; Claude, S. 2003 Hudson Award Address in Carbohydrate Chemistry: Heparin-Structure and Activity. J. Med. Chem. 2003, 46, 2551 - 2564.
3. Hirsh, J.; Anand, S. S.; Halperin, J. L.; Fuster, V. Mechanism of Action and Pharmacology of Unfractionated Heparin Arterioscler., Thromb., Vasc. Biol. 2001, 21, 1094-1096
4. Loganathan, D.; Wang, H. M.; Mallis, L. M.; Linhardt, R. J. Structural variation in the antithrombin III binding site region and its occurrence in heparin from different sources Biochemistry 1990, 29, 4362-4368
5. Ahsan, A.; Jeske, W.; Hoppensteadt, D.; Lormeau, J. C.; Wolf, H.; Fareed, J. Molecular profiling and weight determination of heparins and depolymerized heparins J. Pharm. Sci. 1995, 84, 724-727
6. Hull, R. D.; Raskob, G. E.; Hirsh, J.; Jay, R. M.; Leclerc, J. R.; Geerts, W. H.; Rosenbloom, D.; Sackett, D. L.; Anderson, C.; Harrison, L. Continuous intravenous heparin compared with intermittent subcutaneous heparin in the initial treatment of proximal-vein thrombosis N. Engl. J. Med. 1986, 315, 1109-1114
7. Mant, M. J.; OBrien, B. D.; Thong, K. L.; Hammond, G. W.; Birtwhistle, R. V.; Grace, M. G. Haemorrhagic complications of heparin therapy Lancet 1977, 1, 1133-1135
8. Sonnenblick, M.; Oren, A.; Jacobsohn, W. Hypertransaminasemia with heparin therapy Br. Med. J. 1975, 3-77
9. Chong, B. H. Heparin-induced thrombocytopenia J. Thromb. Haemostasis 2003, 1, 1471-1478
10. Hirsh, J.; Warkentin, T. E.; Shaughnessy, S. G.; Anand, S. S.; Halperin, J. L.; Raschke, R.; Granger, C.; Ohman, E. M.; Dalen, J. E. Pharmacokinetics, Dosing, Monitoring, Efficacy, and Safety Heparin and Low-Molecular-Weight Heparin Mechanisms of Action Chest 2001, 119, 64S-94S
11. Mousa, S. A.; Fareed, J. Overview: from heparin to low molecular weight heparin: beyond anticoagulation Curr. Opin. Invest. Drugs 2001, 2, 1077-1080
12. Hirsh, J.; Levine, M. N. Low molecular weight heparin Blood 1992, 79, 1-17
13. Bara, L.; Billaud, E.; Gramond, G.; Kher, A.; Samama, M. Comparative pharmacokinetics of low molecular weight heparin (PK 10169) and unfractionated heparin after intravenous and subcutaneous administration Thromb. Res. 1985, 39, 631-636 (Pubitemid 15228564)
14. Fareed, J.; Jeske, W.; Hoppensteadt, D.; Clarizio, R.; Walenga, J. M. Low-molecular-weight heparins: pharmacologic profile and product differentiation Am. J. Cardiol. 1998, 82, 3L-10L
15. Linhardt, R. J.; Loganathan, D.; Al-Hakim, A.; Wang, H. M.; Walenga, J. M.; Hoppensteadt, D.; Fareed, J. Oligosaccharide Mapping of Low Molecular Weight Heparins: Structure and Activity Differences J. Med. Chem. 1990, 33, 1639-1645
16. Walenga, J. M.; Koza, M. J.; Lewis, B. E.; Pifarré, R. Relative heparin induced thrombocytopenic potential of low molecular weight heparins and new antithrombotic agents Clin. Appl. Thromb./Hemostasis 1996, 2, S21-S27
17. Greinacher, A.; Alban, S.; Dummel, V.; Franz, G.; Mueller-Eckhardt, C. Characterization of the structural requirements for a carbohydrate based anticoagulant with a reduced risk of inducing the immunological type of heparin-associated thrombocytopenia Thromb. Haemostasis 1995, 74, 886-892
18. Walenga, J. M.; Jeske, W. P.; Bara, L.; Samama, M. M.; Fareed, J. State of the art article, biochemical and pharmacologic rationale for the development of a Heparin pentasaccharide Thromb. Res. 1997, 86, 1-36
19. Kuo, K. H. M.; Kovacs, M. J. Successful treatment of heparin induced thrombocytopenia (HIT) with fondaparinux Thromb. Haemostasis 2005, 93, 999-100
20. Sinay, P.; Jacquinet, J.-C.; Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Torri, G. Total synthesis of a heparin pentasaccharide fragment having high affinity for antithrombin III Carbohydr. Res. 1984, 132, C5-C9
21. Van Boeckel, C. A. A.; Petitou, M. The unique antithrombin III binding domain of heparin: a lead to new synthetic antithrombotics Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1818
22. Sousa, M. E.; Correia-da-Silva, M.; Pinto, M. M. M. Sulfated Flavonoids: Nature Playing with the Hydrophilic-Hydrophobic Balance. In Natural Products: Chemistry, Biochemistry and Pharmacology, 1 st ed.; Brahmachari, G., Eds.; Narosa Publishing House: New Delhi, India, 2008; pp 392 - 416.
23. Guglielmone, H. A.; Agnese, A. M.; Montoya, S. C. N.; Cabrera, J. L. Anticoagulant effect and action mechanism of sulphated flavonoids from Flaveria bidentis Thromb. Res. 2002, 105, 183-188
24. Guglielmone, H. A.; Agnese, A. M.; Montoya, S. C. N.; Cabrera, J. L. Inhibitory effects of sulphated flavonoids isolated from Flaveria bidentis on platelet aggregation Thromb. Res. 2005, 115, 495-502
25. Liu, W.; Song, Z. J.; Liang, N. C.; She, J.; Mo, L. E. Inhibitory effects of sodium quercetin monosulfate on pig platelet aggregation induced by thrombin Zhongguo Yao Li Xue Bao 1999, 20, 623-626
26. Liu, W.; Liang, N.-C. Inhibitory effect of disodium quercetin-7,4′- disulfate on aggregation of pig platelets induced by thrombin and its mechanism Acta Pharmacol. Sin. 2000, 21, 737-741
27. Gunnarsson, G. T.; Desai, U. R. Interaction of designed sulfated flavonoids with antithrombin: lessons on the design of organic activators J. Med. Chem. 2002, 45, 4460-4470
28. Gunnarsson, G. T.; Desai, U. R. Exploring new non-sugar sulfated molecules as activators of antithrombin Bioorg. Med. Chem. Lett. 2003, 13, 679-683
29. Gunnarsson, G. T.; Desai, U. R. Hydropathic interaction analyses of small organic activators binding to antithrombin Bioorg. Med. Chem. 2004, 12, 633-640
30. Gunnarsson, G. T.; Riaz, M.; Adams, J.; Desai, U. R. Synthesis of per-sulfated flavonoids using 2,2,2-trichloro ethyl protecting group and their factor Xa inhibition potential Bioorg. Med. Chem. 2005, 13, 1783-1789
31. Wermuth, C. G. Selective Optimization of Side Activities: Another Way for Drug Discovery J. Med. Chem. 2004, 47, 1304-1313
32. Lyseng-Williamson, K. A.; Perry, C. M. Micronised purified flavonoid fraction: a review of its use in chronic venous insufficiency, venous ulcers and haemorrhoids Drugs 2003, 63, 71-100
33. Lorette, N. B.; Gage, T. B.; Wender, S. H. The use of n -bromosuccikimide and pyridinium bromide perbromide in the conversion of flavanones into flavones J. Org. Chem. 1951, 16, 930-933
34. Barron, D.; Ibrahim, R. K. Synthesis of Flavonoid Sulphates: 1. Stepwise Sulfation of Position 3, 7, and 4′ Using N, N ′- Dicyclohexylcarbodiimide and Tetrabutylammonium Hydrogen Sulphate Tetrahedron 1987, 43, 5197-5202
35. Williams, C. A.; Harborne, J. B. Tricetin, diosmetin and luteolin sulphates in leaves of Lachenalia unifolia Phytochemistry 1976, 15, 349-350
36. -) sulfates, method for their preparation and pharmaceutical compositions containing them. Patent EP0013470, 1980.
37. Raghuramana, A.; Muhammad, R.; Hindleb, M.; Desai, U. R. Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds Tetrahedron Lett. 2007, 48, 6754-6758
38. -) sulfonate sodium by ion-pairing reversed-phase liquid chromatography J. Chromatogr., A 2004, 1036, 229-232
39. Mabry, T. J.; Markam, K. R.; Thomas, M. B. The Determination and Interpretation of NMR Spectra of Flavonoids. In The Systematic Identification of Flavonoids, 1st ed.; Mabry, T. J.; Markam, K. R.; Thomas, M. B., Eds.; Springer: New York, 1970; pp 253 - 344.
40. Agrawal, P. K.; Bansal, M. C., Flavonoid Glycosides. In Carbon-13 NMR of Flavonoids, 1st ed.; Agrawal, P. K., Eds.; Elsevier: Netherlands, 1989; pp 283 - 364.
41. Mackman, N.; Tilley, R. E.; Nigel, S. Key Role of the Extrinsic Pathway of Blood Coagulation in Hemostasis and Thrombosis Arterioscler., Thromb., Vasc. Biol. 2007, 27, 1687-1693
42. Monien, B. H.; Henry, B. L.; Raghuraman, A.; Hindle, M.; Desai, U. R. Novel chemo-enzymatic oligomers of cinnamic acids as direct and indirect inhibitors of coagulation proteinases Bioorg. Med. Chem. 2006, 14, 7988-7998
43. Donahue, S. M.; Otto, C. M. Thromboelastography: a tool for measuring hypercoagulability, hypocoagulability, and fibrinolysis J. Vet. Emerg. Critical Care 2005, 15, 9-16
44. Salat, A.; Kroess, S.; Felfernig-Boehm, D.; Felfernig, M.; Fleck, T.; Schmidt, D.; Pulaki, S.; Mueller, M. R. Comparison of in vitro closure time (PFA-100) with whole blood electrical aggregometry and platelet surface antigen expression in healthy volunteers Thromb. Res. 2002, 105, 205-208
45. Kundu, S. K.; Heilmann, E. J.; Sio, R.; Garcia, C.; Davidson, R.; Ostgaard, R. A. Description of an in vitro platelet function analyzer PFA-100 Semin. Thromb. Haemostasis 1995, 21, 106-112
46. Eikelboom, J. W.; Hirsh, J. Combined antiplatelet and anticoagulant therapy: clinical benefits and risks J. Thromb. Haemostasis 2007, 5, 255-263
47. Henry, B. L.; Desai, U. R. Recent Research Developments in the Direct Inhibition of Coagulation Proteinases-Inhibitors of the Initiation Phase Cardiovasc. Hematol. Agents Med. Chem. 2008, 6, 323-336
48. Kubitza, D.; Becka, M.; Wensing, G.; Voith, B.; Zuehlsdorf, M. Safety, pharmacodynamics, and pharmacokinetics of BAY 59-7939-an oral, direct Factor Xa inhibitor-after multiple dosing in healthy male subjects Eur. J. Clin. Pharmacol. 2005, 61, 873-880
49. Lassen, M. R.; Raskob, G. E.; Gallus, A.; Pineo, G.; Chen, D.; Portman, R. J. Apixaban or enoxaparin for thromboprophylaxis after knee replacement N. Engl. J. Med. 2009, 361, 594-604
50. Stangier, J.; Rathgen, K.; Stahle, H.; Gansser, D.; Roth, W. The pharmacokinetics, pharmacodynamics and tolerability of dabigatran etexilate, a new oral direct thrombin inhibitor, in healthy male subjects Br. J. Clin. Pharmacol. 2007, 64, 292-303
51. Garcia, D.; Libby, E.; Crowther, M. A. The new oral anticoagulants Blood 2010, 115, 15-20
52. Weitz, J. I. Factor Xa or thrombin: is thrombin a better target? J. Thromb. Haemostasis 2007, 5, 65-67
53. Al-Obeidi, F.; Ostrem, J. A. Factor Xa inhibitors by classical and combinatorial chemistry DDT 1998, 3, 223-231
54. Ansell, J. Factor Xa or thrombin: is factor Xa a better target? J. Thromb. Haemostasis 2007, 5, 60-64
55. -) sulfate sodium in rat plasma using ion-pairing liquid chromatography after ion-pairing solid-phase extraction J. Chromatogr., B: Anal. Technol. Biomed. Life Sci. 2006, 833, 231-235
56. Sanders, S. W.; Dukes, G. E., Jr.; Gray, P.; Tolman, K. G. Toxicity of heparin in isolated rat hepatocytes Biochem. Pharmacol. 1984, 33, 2223-2226
57. Carlson, M. K.; Gleason, P. P.; Sen, S. Elevation of hepatic transaminases after enoxaparin use: case report and review of unfractionated and low-molecular-weight heparin-induced hepatotoxicity Pharmacotherapy 2001, 21, 108-113
58. Huang, X.-J.; Choi, Y.-K.; Im, H.-S.; Yarimaga, O.; Yoon, E.; Kim, H.-S. Aspartate Aminotransferase (AST/GOT) and Alanine Aminotransferase (ALT/GPT) Detection Techniques Sensors 2006, 6, 756-782
59. Winkler, A. M.; Sheppard, C. A.; Fantz, C. R. Laboratory Monitoring of Heparin: Challenges and Opportunities Lab Med. 2007, 38, 499-502
60. Canavese, C.; Salomone, M.; Mangiarotti, G.; Pacitti, A.; Trucco, S.; Scaglia, C.; Assone, F.; Lunghi, F.; Vercellone, A. Heparin transfer across the rabbit peritoneal membrane Clin. Nephrol. 1986, 26, 116-120
61. Swart, C. A. M.; Nijmeyer, B.; Roelofs, J. M. M.; Sixma, J. J. Kinetics of intravenously administered heparin in normal humans Blood 1982, 60, 1251-1258
62. Olsson, P.; Lagergren, H.; Ek, S. The elimination from plasma of intravenous heparin: an experimental study on dogs and humans Acta Med. Scand. 1963, 173, 619-630
63. -) sulfonate sodium across Caco-2 cell monolayers J. Pharm. Pharmacol. 2005, 57, 1-7
64. Mousa, S. A.; Zhang, F.; Aljada, A.; Chaturvedi, S.; Takieddin, M.; Zhang, H.; Chi, L.; Castelli, M. C.; Friedman, K.; Goldberg, M. M.; Linhardt, R. J. Pharmacokinetics and Pharmacodynamics of Oral Heparin Solid Dosage Form in Healthy Human Subjects J. Clin. Pharmacol. 2007, 47, 1508-1520