Synthetic human serum albumin Sudlow i binding site mimics

Journal of Medicinal Chemistry

Volumn 53, Issue 22, 2010, Pages 7932-7937

  Karlsson, Björn C G ^a   Rosengren, Annika M ^a   Näslund, Inga ^b   Andersson, Per Ola ^b   Nicholls, Ian A ^a,c  

^a LINNAEUS UNIVERSITY   (Sweden)

^b SWEDISH DEFENCE RESEARCH AGENCY   (Sweden)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

COUMACHLOR; COUMARIN; ETHYLENE GLYCOL DIMETHACRYLATE; HUMAN SERUM ALBUMIN; METHACRYLIC ACID; MOLECULARLY IMPRINTED POLYMER; POLYMER; RODENTICIDE; UNCLASSIFIED DRUG; WARFARIN;

ARTICLE; BINDING AFFINITY; BINDING SITE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; LIGAND BINDING; MOLECULAR DYNAMICS; MOLECULAR IMPRINTING; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY;

ANTICOAGULANTS; BINDING SITES; BINDING, COMPETITIVE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR DYNAMICS SIMULATION; MOLECULAR IMPRINTING; MOLECULAR MIMICRY; POLYMETHACRYLIC ACIDS; RADIOLIGAND ASSAY; SERUM ALBUMIN; WARFARIN;

EID: 78649517838     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100491v     Document Type: Article

References (41)

1. Landefeld, C. S.; Beyth, R. J. Anticoagulant-related bleeding-Clinical epidemiology, prediction, and prevention Am. J. Med. 1993, 95, 315-328
2. Yacobi, A.; Udall, J. A.; Levy, G. Serum-protein binding as a determinant of warfarin body clearance and anticoagulant effect Clin. Pharmacol. Ther. 1976, 19, 552-558
3. Lucas, F. V.; Duncan, A.; Jay, R.; Coleman, R.; Craft, P.; Chan, B.; Winfrey, L.; Mungall, D. R.; Hirsch, J. A novel whole-blood capillary technique for measuring the prothrombin time Am. J. Clin. Pathol. 1987, 88, 442-446
4. Cromheecke, M. E.; Levi, M.; Colly, L. P.; de Mol, B. J. M.; Prins, M. H.; Hutten, B. A.; Mak, R.; Keyzers, K. C. J.; Buller, H. R. Oral anticoagulation self-management and management by a specialist anticoagulation clinic: A randomised cross-over comparison Lancet 2000, 356, 97-102
5. Quin, J.; Markwell, S.; Rogers, L. Q.; McLafferty, R.; Reinersman, M.; Hazelrigg, S. Home anticoagulation testing: Predictors of rural patient interest J. Surg. Res. 2006, 136, 232-237
6. Chianella, I.; Piletsky, S. A.; Tothill, I. E.; Chen, B.; Turner, A. P. F. MIP-based solid phase extraction cartridges combined with MIP-based sensors for the detection of microcystin-LR Biosens. Bioelectron. 2003, 18, 119-127
7. Ye, L.; Mosbach, K. Polymers recognizing biomolecules based on a combination of molecular imprinting and proximity scintillation: A new sensor concept J. Am. Chem. Soc. 2001, 123, 2901-2902
8. Subrahmanyam, S.; Piletsky, S. A.; Piletska, E. V.; Chen, B. N.; Karim, K.; Turner, A. P. F. "Bite-and-Switch" approach using computationally designed molecularly imprinted polymers for sensing of creatinine Biosens. Bioelectron. 2001, 16, 631-637 (Pubitemid 33000191)
9. Diñeiro, Y.; Menéndez, M. I.; Blanco-López, M. C.; Lobo-Castañón, M. J.; Miranda-Ordieres, A. J.; Tuñón- Blanco, P. Computational approach to the rational design of molecularly imprinted polymers for voltammetric sensing of homovanillic acid Anal. Chem. 2005, 77, 6741-6746
10. Cao, L.; Zhou, X. C.; Li, S. F. Y. Enantioselective sensor based on microgravimetric quartz crystal microbalance with molecularly imprinted polymer film Analyst 2001, 126, 184-188
11. Vlatakis, G.; Andersson, L. I.; Müller, R.; Mosbach, K. Drug assay using antibody mimics made by molecular imprinting Nature 1993, 361, 645-647
12. Sellergren, B.; Lepistö, M.; Mosbach, K. Highly enantioselective and substrate-selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition J. Am. Chem. Soc. 1988, 110, 5853-5860
13. Wulff, G.; Sarhan, A. The use of polymers with enzyme-analogous structures for resolution of racemates Angew. Chem., Int. Ed. 1972, 11, 341
14. Andersson, L. I.; Müller, R.; Vlatakis, G.; Mosbach, K. Mimics of the binding sites of opioid receptors obtained by molecular imprinting of enkephalin and morphine Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 4788-4792
15. Jenik, M.; Schirhagl, R.; Schirk, C.; Hayden, O.; Lieberzeit, P.; Blaas, D.; Paul, G.; Dickert, F. L. Sensing picornaviruses using molecular imprinting techniques on a quartz crystal microbalance Anal. Chem. 2009, 81, 5320-5326
16. Berglund, J.; Lindbladh, C.; Nicholls, I.; Mosbach, K. Selection of phage display combinatorial library peptides with affinity for a yohimbine imprinted methacrylate polymer Anal. Commun. 1998, 35, 3-7 (Pubitemid 128492533)
17. Kempe, M.; Mosbach, K. Separation of amino acids, peptides and proteins on molecularly imprinted stationary phases J. Chromatogr. A 1995, 691, 317-323
18. O'Connor, N. A.; Paisner, D. A.; Huryn, D.; Shea, K. J. Screening of 5-HT1A receptor antagonists using molecularly imprinted polymers J. Am. Chem. Soc. 2007, 129, 1680-1689
19. Liao, J. L.; Wang, Y.; Hjertén, S. Novel support with artificially created recognition for the selective removal of proteins and for affinity chromatography Chromatographia 1996, 42, 259-262
20. Ramström, O.; Ye, L.; Mosbach, K. Artificial antibodies to corticosteroids prepared by molecular imprinting Chem. Biol. 1996, 3, 471-477 (Pubitemid 126663347)
21. Svenson, J.; Nicholls, I. A. On the thermal and chemical stability of molecularly imprinted polymers Anal. Chim. Acta 2001, 435, 19-24
22. Petitpas, I.; Bhattacharya, A. A.; Twine, S.; East, M.; Curry, S. Crystal structure analysis of warfarin binding to human serum albumin J. Biol. Chem. 2001, 276, 22804-22809
23. Alexander, C.; Andersson, H. S.; Andersson, L. I.; Ansell, R. J.; Kirsch, N.; Nicholls, I. A.; O'Mahony, J.; Whitcombe, M. J. Molecular imprinting science and technology: A survey of the literature for the years up to and including 2003 J. Mol. Recognit. 2006, 19, 106-180
24. O'Mahony, J.; Karlsson, B. C. G.; Mizaikoff, B.; Nicholls, I. A. Correlated theoretical, spectroscopic and X-ray crystallographic studies of a non-covalent molecularly imprinted polymerisation system Analyst 2007, 132, 1161-1168
25. Svenson, J.; Karlsson, J. G.; Nicholls, I. A. 1H Nuclear magnetic resonance study of the molecular imprinting of (-)-nicotine: Template self-association, a molecular basis for cooperative ligand binding J. Chromatogr. A 2004, 1024, 39-44
26. Svenson, J.; Andersson, H. S.; Piletsky, S. A.; Nicholls, I. A. Spectroscopic studies of the molecular imprinting self-assembly process J. Mol. Recognit. 1998, 11, 83-86
27. Andersson, H. S.; Nicholls, I. A. Spectroscopic evaluation of molecular imprinting polymerization systems Bioorg. Chem. 1997, 25, 203-211
28. Karlsson, B. C. G.; O'Mahony, J.; Karlsson, J. G.; Bengtsson, H.; Eriksson, L. A.; Nicholls, I. A. Structure and dynamics of monomer-template complexation: An explanation for molecularly imprinted polymer recognition site heterogeneity J. Am. Chem. Soc. 2009, 131, 13297-13304
29. Nicholls, I. A.; Andersson, H. S.; Charlton, C.; Henschel, H.; Karlsson, B. C.; Karlsson, J. G.; O'Mahony, J.; Rosengren, A. M.; Rosengren, K. J.; Wikman, S. Theoretical and computational strategies for rational molecularly imprinted polymer design Biosens. Bioelectron. 2009, 25, 543-552
30. Piletska, E.; Piletsky, S.; Karim, K.; Terpetschnig, E.; Turner, A. Biotin-specific synthetic receptors prepared using molecular imprinting Anal. Chim. Acta 2004, 504, 179-183
31. Piletska, E. V.; Turner, N. W.; Turner, A. P. F.; Piletsky, S. A. Controlled release of the herbicide simazine from computationally designed molecularly imprinted polymers J. Controlled Release 2005, 108, 132-139
32. Valente, E. J.; Lingafelter, E. C.; Porter, W. R.; Trager, W. F. Structure of warfarin in solution J. Med. Chem. 1977, 20, 1489-1493
33. Karlsson, J. G.; Andersson, L. I.; Nicholls, I. A. Probing the molecular basis for ligand-selective recognition in molecularly imprinted polymers selective for the local anaesthetic bupivacaine Anal. Chim. Acta 2001, 435, 57-64
34. Svenson, J.; Zheng, N.; Nicholls, I. A. A molecularly imprinted polymer-based synthetic transaminase J. Am. Chem. Soc. 2004, 126, 8554-8560
35. Andersson, L. I. Application of molecular imprinting to the development of aqueous buffer and organic solvent based radioligand binding assays for (S)-propranolol Anal. Chem. 1996, 68, 111-117
36. Karlsson, J. G.; Karlsson, B.; Andersson, L. I.; Nicholls, I. A. The roles of template complexation and ligand binding conditions on recognition in bupivacaine molecularly imprinted polymers Analyst 2004, 129, 456-462
37. Pinkerton, T. C.; Koeplinger, K. A. Determination of warfarin-human serum albumin protein binding parameters by an improved Hummel-Dreyer high-performance liquid chromatographic method using internal surface reversed-phase columns Anal. Chem. 1990, 62, 2114-2122
38. Karlsson, B. C. G.; Rosengren, A. M.; Andersson, P. O.; Nicholls, I. A. The spectrophysics of warfarin: Implications for protein binding J. Phys. Chem. B 2007, 111, 10520-10528
39. Karlsson, B. C. G.; Rosengren, A. M.; Andersson, P. O.; Nicholls, I. A. Molecular insights on the two fluorescence lifetimes displayed by warfarin from fluorescence anisotropy and molecular dynamics studies J. Phys. Chem. B 2009, 113, 7945-7949
40. Nicholls, I. A.; Karlsson, B. C. G.; Rosengren, A. M.; Henschel, H. Warfarin: An environment-dependent switchable molecular probe. J. Mol. Recognit. DOI: 10.1002/jmr.1058
41. Kasai, K.; Oda, Y.; Nishikata, M.; Ishii, S. Frontal affinity chromatography: Theory for its application to studies on specific interactions of biomolecules J. Chromatogr. A 1986, 376, 33-47