Disruption of rosetting in Plasmodium falciparum malaria with chemically modified heparin and low molecular weight derivatives possessing reduced anticoagulant and other serine protease inhibition activities

Journal of Medicinal Chemistry

Volumn 51, Issue 5, 2008, Pages 1453-1458

  Skidmore, Mark A ^a   Dumax Vorzet, Audrey F ^b   Guimond, Scott E ^a   Rudd, Timothy R ^a   Edwards, Elizabeth A ^a   Turnbull, Jeremy E ^a   Craig, Alister G ^c   Yates, Edwin A ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

^c LIVERPOOL SCHOOL OF TROPICAL MEDICINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HEPARIN DERIVATIVE; LOW MOLECULAR WEIGHT HEPARIN; PROTEINASE; THROMBOCYTE FACTOR 4;

ANTICOAGULATION; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG ACTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; MALARIA; NONHUMAN; PLASMODIUM FALCIPARUM;

ANIMALS; ANTICOAGULANTS; ERYTHROCYTES; HEPARIN; MALARIA, FALCIPARUM; MOLECULAR WEIGHT; PLASMODIUM FALCIPARUM; PLATELET FACTOR 4; POLYMERS; PROTEIN BINDING; PROTEIN CONFORMATION; SERINE PROTEINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 41649094162     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701337t     Document Type: Article

References (28)

1. Afonso, A.; Hunt, P.; Cheeseman, S.; Alves, A. C.; Canha, C. V. Malaria parasites can develop stable resistance to artemisinin but lack mutations in candidate genes atp6 (encoding the sarcoplasmic and endoplasmic reticulum Ca2+ ATPase, tctp, mdr1, and cg10. Antimicrob. Agents Chemother. 2006, 50, 480-489.
2. Jambou, R.; Legrand, E.; Niang, M.; Khim, N.; Lim, P. Resistance of Plasmodium falciparum field isolates to in-vitro artemether and point mutations of the SERCA-type PfATPase6. Lancet 2005, 366, 1960-1963.
3. Rowe, J. A.; Obeiro, J.; Newbold, C. I.; Marsh, K. Plasmodium falciparum rosetting is associated with malaria severity in Kenya. Infect. Immun. 1995, 63, 2323-2326.
4. Chen, Q.; Barragan, A.; Fernandez, V.; Sundstrum, A.; Schlichtherle, M.; et al. Identification of Plasmodium falciparum erythrocyte membrane protein 1 (PfEMP1) as the rosetting ligand of the malaria parasite P. falciparum. J. Exp. Med. 1998, 187, 15-23.
5. Rowe, J. A. P. falciparum rosetting mediated by a parasite-variant erythrocyte membrane protein and complement-receptor 1. Nature 1998, 388, 292-295.
6. Rostand, K. S.; Esko, J. D. Microbial adherence to and invasion through proteoglycans. Infect. Immun. 1997, 65, 1-8.
7. Barragan, A.; Spillmann., D.; Kremsner, P. G.; Wahlgren, M.; Carlson, A. Plasmodium falciparum: molecular background to strain-specific rosette disruption by glycosaminoglycans and sulphated glycoconjugates. J. Exp. Para. 1999, 91, 133-143.
8. Vogt, A. M.; Barragan, A.; Chen, Q.; Kironde, F.; Spillmann, D.; et al. Heparan sulphate on endothelial cells mediates the binding of Plasmodium falciparum-infected eryhtrocytes via the DBL1alpha domain of PfEMP1. Blood 2003, 101, 2405-2411.
9. Westling, C.; Lindahl, U. Location of N-unsubstituted glucosamine residues in heparan sulphate. J. Biol. Chem. 2002, 277, 49247-49255.
10. Barragan, A.; Fernandez, V.; Chen, Q.; von Eurler, A.; Wahlgren, M. The Duffy-binding-like domain lof Plasmodium falciparum erythrocyte membrane protein 1 (PfEMP1) is a heparan sulphate ligand that requires 12mers for binding. Blood 2000, 95, 3594-3599.
11. Rowe, A.; Berendt, A. R.; Marsh, K. and Newbold C. I. Plasmodium falciparum: a family of sulphated glycoconjugates disrupts erythrocyte rosettes. Exp. Parasitol. 1994, 79, 506-516.
12. Jepsen, H. H.; Svehag, S. E.; Jarlbaek, L.; Baatrup, G. Interaction of complement-solubilized immune complexes with CR1 receptors on human erythrocytes. The binding reaction. Scand. J. Immunol. 1986, 23 (1), 65-73.
13. Jepsen, H. H.; Ekre, H. P.; Svehag, S. E. Interaction of complement-solubilized immune complexes (IC) with CR1 receptors on human erythrocytes. Polysulphated compounds inhibit IC binding and induce IC-release from CR1. Int. J. Immunopharmacol. 1987, 9 (5), 587-95.
14. Kelton, J.; Smith, J.; Warkentin, T.; Hayward, C.; Denomme, G.; et al. Immunoglobulin G from patients with heparin-induced thrombocytopenia binds to a complex of heparin and platelet factor 4. Blood 1994, 83, 3232-3239.
15. Ferro, D. R.; Provasoli, A.; Ragazzi, M.; Torri, G.; Casu, B.; et al. Evidence for Conformational Equilibrium of the Sulphated L-Iduronate Residue in Heparin and in Synthetic Heparin Monosaccharides and Oligosaccharides - NMR and Force-Field Studies. J. Am. Chem. Soc. 1986, 108, 6773-6778.
16. Yates, E. A.; Santini, F.; De Cristofano, B.; Payre, N.; Cosentino, C.; et al. Effect of substitution pattern on H-1, C-13 NMR chemical shifts and (1)J(CH) coupling constants in heparin derivatives. Carbohydr. Res. 2000, 329, 239-247.
17. Rudd, T. R.; Guimond, S. E.; Skidmore, M. A.; Duchesne, L.; Guerrini, M. et al. Influence of substitution pattern and cation binding on conformation and activity in heparin derivatives. Glycobiology 2007, 17, 983-993.
18. 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, 1671-1690.
19. Liu, Z.; Perlin, A. S. Regioselectivity in the sulfation of some chemically-modified heparins, and observations on their cation binding characteristics. Carbohydr. Res. 1992, 236, 121-133.
20. Santini, F.; Bisio, A.; Guerrini, M.; Yates, E. A. Modifications under basic conditions of the minor sequences of heparin containing 2,3 or 2,3,6 sulphated D-glucosamine residues. Carbohydr. Res. 1997, 302, 103-108.
21. Naggi, A.; De Cristofano, B.; Bisio, A.; Torri, G.; Casu, B. Generation of anti-factor Xa active, 3-O-sulphated glucosamine-rich sequences by controlled desulfation of oversulphated heparins. Carbohydr. Res. 2001, 336, 283-290.
22. Fabris, F.; Luzzatto, G.; Stefani, P. M.; Girolami, B.; Cella, G.; et al. Heparin-induced thrombocytopenia. Heamatalogica 2000, 85, 72-81.
23. Wallace, B. A. Conformational changes by synchrotron radiation circular dichroism spectroscopy. Nat. Struct. Biol. 2000, 7, 708-709.
24. Patey, S. J.; Edwards, E. A.; Yates, E. A.; Turnbull, J. E. (2006) Heparin derivatives as inhibitors of BACE-1, the Alzheimer's beta-secretase, with reduced activity against factor Xa and other proteases. J. Med. Chem. 2006, 49, 6129-6132.
25. Jaseja, M.; Rej, R. N.; Sauriol, F.; Perlin, A. S. Novel regioselective and stereoselective modifications of heparin in alkaline solution - nuclear magnetic-resonance spectroscopic evidence. Can. J. Chem. 1989, 67, 1449-1456.
26. Inoue, S.; Miyawaki, M. Quantitative-Analysis of Iduronic Acid and Glucuronic Acid in Sulphated Galactosaminoglycuronans by Gas-Chromatography. Anal. Biochem. 1975, 65, 164-174.
27. Yates, E. A.; Santini, F.; Guerrini, M.; Naggi, A.; Torri, G.; et al. H-1 and C-13 NMR spectral assignments of the major sequences of twelve systematically modified heparin derivatives. Carbohydr. Res. 1996, 294, 15-27.
28. Lloyd, A. G.; Embery, G.; Fowler, L. J. Studies on heparin degradation - I: Preparation of [35S] sulphamate derivatives for studies on heparin degrading enzymes of mammalian origin. Biochem. Pharmacol. 1971, 20, 637-648.