Fluorogenic Peptide-Based Substrates for Monitoring Thrombin Activity

ChemMedChem

Volumn 7, Issue 4, 2012, Pages 606-617

  vanBerkel, Sander S ^a   vanderLee, Bas ^a   vanDelft, Floris L ^a   Wagenvoord, Rob ^b   Hemker, H Coenraad ^b   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b MAASTRICHT UNIVERSITY   (Netherlands)

Author keywords

ETP; Fluorogenic substrates; Peptide synthesis; Thrombin; Thrombograms

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; ALANINE; ALPHA 2 MACROGLOBULIN; AMIDE; AMINO 4 METHYLCOUMARIN; ARGININE; BLOOD CLOTTING FACTOR 10A; COUMARIN DERIVATIVE; GLYCINE; MALONIC ACID DERIVATIVE; PROLINE; THROMBIN; UNCLASSIFIED DRUG; VALINE; WATER;

AMINO ACID COMPOSITION; AMINO ACID SUBSTITUTION; ARTICLE; BIOLOGICAL MONITORING; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLOADDITION; FREEZE DRYING; HUMAN; HYDROGENATION; HYDROLYSIS; KINETICS; PRIORITY JOURNAL; PROTEIN SYNTHESIS;

AMIDES; COUMARINS; DIPEPTIDES; FACTOR XA; FLUORESCENT DYES; HUMANS; HYDROLYSIS; KINETICS; MALONATES; PEPTIDES; THROMBIN; TRIAZOLES;

EID: 84859171454     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201100560     Document Type: Article

References (87)

1. M. J. Costanzo, H. R. Almond, Jr., L. R. Hecker, M. R. Schott, S. C. Yabut, H.-C. Zhang, P. Andrade-Gordon, T. W. Corcoran, E. C. Giardino, J. A. Kauffman, J. M. Lewis, L. deGaravilla, B. J. Haertlein, B. E. Maryanoff, J. Med. Chem. 2005, 48, 1984-2008.
2. D. J. Angiolillo, P. Capranzano, Am. Heart J. 2008, 156, 10S-15S.
3. A. T. Askari, A. W. Messerli, A. M. Lincoff, Management Strategies in Antithrombotic Therapy, Wiley, Chichester, 2007.
4. W. Bode, I. Mayr, U. Baumann, R. Huber, S. R. Stone, J. Hofsteenge, EMBO J. 1989, 8, 3467-3475.
5. A. Schwienhorst, Cell. Mol. Life Sci. 2006, 63, 2773-2791;
6. P. C. A. Kam, N. Kaur, C. L. Thong, Anaesthesia 2005, 60, 565-574;
7. L.-A. Linkins, J. I. Weitz, Curr. Pharm. Des. 2005, 11, 3877-3884.
8. For reviews on thrombin inhibitors, see:
9. J. Das, S. D. Kimball, Bioorg. Med. Chem. 1995, 3, 999-1007;
10. K. Menear, Expert Opin. Invest. Drugs 1999, 8, 1373-1384;
11. C. A. Kontogiorgis, D. Hadjipavlou-Litina, Curr. Med. Chem. 2003, 10, 525-577;
12. C. Becattini, A. Lignani, G. Agnelli, Drug Des. Devel. Ther. 2010, 4, 49-60.
13. A. Tripodi, P. M. Mannucci, Clin. Chem. 1984, 30, 1392-1395.
14. D. A. Triplett, Clin. Chem. 2000, 46, 1260-1269.
15. K. G. Mann, K. Brummel, S. Butenas, J. Thromb. Haemostasis 2003, 1, 1504-1514.
16. N. Salooja, D. J. Perry, Blood Coagulation Fibrinolysis 2001, 12, 327-337.
17. J. L. Francis, Platelets (Ed.: A.D. Michelson), Academic Press, San Diego, 2002, pp.325-335.
18. T. W. Barrowcliffe, M. Cattaneo, G. M. Podda, P. Bucciarelli, F. Lussana, A. Lecchi, C. H. Toh, H. C. Hemker, S. Béguin, J. Ingerslev, B. Sørensen, Haemophilia 2006, 12, 76-81.
19. G. T. Gerotziafas, F. Depasse, J. Busson, L. Leflem, I. Elalamy, M. M. Samama, Thromb. J. 2005, 3, 16-26.
20. A. Beilfu, M. Grandoch, F. Wenzel, T. Hohlfeld, K. Schrör, A.-A. Weber, Ther. Drug Monit. 2008, 30, 740-743.
21. H. C. Hemker, R. AlDieri, E. deSmedt, S. Béguin, Thromb. Haemostasis 2006, 96, 553-561.
22. R. G. Macfarlane, R. Biggs, J. Clin. Pathol. 1953, 6, 3-8.
23. W. R. Pitney, J. V. Dacie, J. Clin. Pathol. 1953, 6, 9-14.
24. H. C. Hemker, G. M. Willems, S. Béguin, Thromb. Haemostasis 1986, 56, 9-17.
25. For the development of thrombin-specific, chromogenic peptide substrates, see the pioneering work by: L. Svendsen, B. Blomback, M. Blomback, P. I. Olsson, Thromb. Res. 1972, 1, 267-278;
26. L. G. Svendsen, J. Fareed, J. M. Walenga, D. Hoppensteadt, Semin. Thromb. Hemostasis 1983, 9, 250-262.
27. H. C. Hemker, S. Wielders, H. Kessels, S. Béguin, Thromb. Haemostasis 1993, 70, 617-624;
28. D. T. S. Rijkers, S. J. H. Wielders, G. I. Tesser, H. C. Hemker, Thromb. Res. 1995, 79, 491-499.
29. S. Langlet, G. Quentin, G. Contant, J. C. Ghnassia, Ann. Biol. Clin. 1999, 57, 191-196.
30. K. Vanschoonbeek, M. A. H. Feijge, R. J. W. vanKampen, H. Kenis, H. C. Hemker, P. L. A. Giesen, J. W. M. Heemskerk, J. Thromb. Haemostasis 2004, 2, 476-484.
31. H. C. Hemker, P. L. Giesen, M. Ramjee, R. Wagenvoord, S. Béguin, Thromb. Haemostasis 2000, 83, 589-591.
32. M. K. Ramjee, Anal. Biochem. 2000, 277, 11-18.
33. H. C. Hemker, P. Giesen, R. AlDieri, V. Regnault, E. deSmedt, R. Wagenvoord, T. Lecompte, S. Béguin, Pathophysiol. Haemostasis Thromb. 2003, 33, 4-15.
34. M. Zimmerman, B. Ashe, E. C. Yurewicz, G. Patel, Anal. Biochem. 1977, 78, 47-51.
35. Y. Kanaoka, T. Takahashi, H. Nakayama, Chem. Pharm. Bull. 1977, 25, 3126-3128.
36. T. Kato, T. Hama, K. Kojima, T. Nagatsu, S. Sakakibara, Clin. Chem. 1978, 24, 1163-1166.
37. S. Kunugi, M. Fukuda, R. Hayashi, Eur. J. Biochem. 1985, 153, 37-40.
38. T. Morita, H. Kato, S. Iwanaga, K. Takada, T. Kimura, S. Sakakibara, J. Biochem. 1977, 82, 1495-1498.
39. S. Kawabatal, T. Miura, T. Morita, H. Kato, K. Fujikawa, S. Iwanaga, K. Takada, T. Kimura, S. Sakakibara, Eur. J. Biochem. 1988, 172, 17-25.
40. Y. Ohno, H. Kato, T. Morita, S. Iwanaga, K. Takada, S. Sakakibara, J. Stenflo, J. Biochem. 1981, 90, 1387-1395.
41. H. Kato, N. Adachi, Y. Ohno, S. Iwanaga, K. Takada, S. Sakakibara, J. Biochem. 1980, 88, 183-190.
42. B. J. Backes, J. L. Harris, F. Leonetti, C. S. Craik, J. A. Ellman, Nat. Biotechnol. 2000, 18, 187-193.
43. S. T. Furlong, R. C. Mauger, A. M. Strimpler, Y.-P. Liu, F. X. Morris, P. D. Edwards, Bioorg. Med. Chem. 2002, 10, 3637-3647.
44. A. J. Dirks, S. S. vanBerkel, H. I. V. Amatdjais-Groenen, F. L. vanDelft, F. P. J. T. Rutjes, J. J. L. M. Cornelissen, R. J. M. Nolte, Soft Matter 2009, 5, 1692-1704;
45. K. Koch, S. S. vanBerkel, M. M. E. B. van de Wal, P. J. Nieuwland, J. C. M. vanHest, F. P. J. T. Rutjes, J. Appl. Phys. 2009, 105, 102012/1-102012/5;
46. S. S. vanBerkel, B. van der Lee, F. L. vanDelft, F. P. J. T. Rutjes, Chem. Commun. 2009, 4272-4274.
47. Available from Bachem AG, Switzerland, I-1140, Cat.no. 102601-58-1.
48. F. Jean, A. Boudreault, A. Basak, N. G. Seidah, C. Lazure, J. Biol. Chem. 1995, 270, 19225-19231;
49. P. D. Edwards, R. C. Mauger, K. M. Cottrell, F. X. Morris, K. K. Pine, M. A. Sylvester, C. W. Scott, S. T. Furlong, Bioorg. Med. Chem. Lett. 2000, 10, 2291-2294;
50. D. J. Maly, F. Leonetti, B. J. Backes, D. S. Dauber, J. L. Harris, C. S. Craik, J. A. Ellman, J. Org. Chem. 2002, 67, 910-915.
51. D. T. S. Rijkers, H. P. H. M. Adams, H. C. Hemker, G. I. Tesser, Tetrahedron 1995, 51, 11235-11250.
52. An elegant enzymatic approach was recently published: T. Nuijens, C. Cusan, J. A. W. Kruijtzer, D. T. S. Rijkers, R. M. J. Liskamp, P. J. L. M. Quaedflieg, J. Org. Chem. 2009, 74, 5145-5150.
53. For an overview of coupling methods, see: S.-Y. Han, Y.-A. Kim, Tetrahedron 2004, 60, 2447-2467.
54. G. Freyburger, M. Dubreuil, A. Audebert, S. Labrouche, J. C. Pistre, I. Molinari, F. Dubecq, C. Laville, X. Villanove, Haemostasis 2001, 31, 32-41.
55. For a review, see:
56. Y. L. Angell, K. Burgess, Chem. Soc. Rev. 2007, 36, 1674-1689. Selected publications:
57. W. S. Horne, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2003, 125, 9372-9376;
58. W. S. Horne, M. K. Yadav, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2004, 126, 15366-15367;
59. V. D. Bock, D. Speijer, H. Hiemstra, J. H. vanMaarseveen, Org. Biomol. Chem. 2007, 5, 971-975.
60. For examples of biologically active triazoles, see:
61. R. Alvarez, S. Velazquez, F. San, S. Aquaro, C. De, C. F. Perno, A. Karlsson, J. Balzarini, M. Camarasa, J. Med. Chem. 1994, 37, 4185-4191;
62. J. S. Tullis, J. C. Van-Rens, M. G. Natchus, M. P. Clark, B. De, L. C. Hsieh, M. J. Janusz, Bioorg. Med. Chem. Lett. 2003, 13, 1665-1668;
63. C. W. Tornøe, S. J. Sanderson, J. C. Mottram, G. H. Coombs, M. Meldal, J. Comb. Chem. 2004, 6, 312-324;
64. D.-K. Kim, J. Kim, H.-J. Park, Bioorg. Med. Chem. Lett. 2004, 14, 2401-2405;
65. A. Brik, J. Alexandratos, Y.-C. Lin, J. H. Elder, A. J. Olson, A. Wlodawer, D. S. Goodsell, C.-H. Wong, ChemBioChem 2005, 6, 1167-1169.
66. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064;
67. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711; Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
68. P. L. Golas, K. Matyjaszewski, QSAR Comb. Sci. 2007, 26, 1116-1134.
69. H. C. Hemker, "The Mode of Action of Heparin in Plasma" in Thrombosis and Haemostasis (Eds.: M. Verstraete, J. Vermylen, R. Lijnen, J. Arnout), Leuven University Press, Leuven, 1987, pp.17-36.
70. V. Chantarangkul, M. Clerici, C. Bressi, P. L. A. Giesen, A. Tripodi, Haematologica 2003, 88, 547-554;
71. Y. Dargaud, S. Béguin, A. Lienhart, R. AlDieri, C. Trzeciak, J. C. Bordet, H. C. Hemker, C. Negrier, Thromb. Haemostasis 2005, 93, 475-480.
72. T. Siegemund, S. Petros, A. Siegemund, U. Scholz, L. Engelmann, Thromb. Haemostasis 2003, 90, 781-786.
73. L. Rugeri, S. Béguin, C. Hemker, J. C. Bordet, R. Fleury, B. Chatard, C. Negrier, Y. Dargaud, Haematologica 2007, 92, 1639-1646;
74. S. Béguin, I. Keularts, R. AlDieri, S. Bellucci, J. Caen, H. C. Hemker, J. Thromb. Haemostasis 2004, 2, 170-176.
75. S. Petros, T. Siegemund, A. Siegemund, L. Engelmann, Blood Coagulation Fibrinolysis 2006, 17, 131-137;
76. S. L. Boström, G. F. H. Hansson, T. C. Sarich, M. Wolzt, Thromb. Res. 2004, 113, 85-91.
77. H. C. Hemker, S. Béguin, Thromb. Haemostasis 1995, 74, 134-138.
78. A. S. Wolberg, Thromb. Res. 2007, 119, 663-665.
79. T. Baglin, Br. J. Haematol. 2005, 130, 653-661.
80. More on inner-filter effects: S. P. Srinivas, R. Mutharasan, Biotechnol. Bioeng. 1987, 30, 769-774.
81. R. Wagenvoord, P. W. Hemker, H. C. Hemker, J. Thromb. Haemostasis 2006, 4, 1331-1338.
82. S. Butenas, K. G. Mann, J. Thromb. Haemostasis 2007, 5, 1084-1085;
83. H. C. Hemker, E. deSmedt, J. Thromb. Haemostasis 2007, 5, 1085-1087.
84. As a result of competition between the substrate and natural enzyme inhibitors, the ETP, as a rule, is increased by the presence of substrate.
85. H. C. Hemker, R. AlDieri, S. Béguin, Curr. Opin. Hematol. 2004, 11, 170-175.
86. H. C. Hemker, P. W. Hemker, R. AlDieri, Thromb. Haemostasis 2009, 101, 171-177.
87. V. Regnault, S. Béguin, T. Lecompte, Pathophysiol. Haemostasis Thromb. 2003, 33, 23-29.