Applications of tailored ferrocenyl molecules as electrochemical probes of biochemical interactions

Bioconjugate Chemistry

Volumn 18, Issue 1, 2007, Pages 199-208

  Tranchant, Isabelle ^a,d   Hervé, Anne Cécile ^b,c   Carlisle, Stephen ^b   Lowe, Phillip ^b,e   Slevin, Christopher J ^b,e   Forssten, Camilla ^b   Dilleen, John ^b,e   Tabor, Alethea B ^a   Williams, David E ^b,f   Hailes, Helen C ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b Unipath   (United Kingdom)

^c Diatos NV   (Belgium)

^d Diatos SA   (France)

^e UNIVERSITY OF STIRLING   (United Kingdom)

^f UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING SITES; CHAIN LENGTH; CHAINS; FATTY ACIDS; IRON COMPOUNDS; MOLECULES; PROBES;

BINDING-SITES; BIOCHEMICAL INTERACTIONS; CHAINS LENGTH; DRUG BINDING SITES; ELECTROCHEMICAL PROBE; FATTY ACID BINDING; FATTY ACID CHAINS; FERROCENES; FERROCENYL; HUMAN SERUM ALBUMINS;

ORGANOMETALLICS;

BOVINE SERUM ALBUMIN; FATTY ACID; FATTY ACID BINDING PROTEIN; FERROCENE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG BINDING SITE; ELECTROCHEMISTRY; HUMAN; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR INTERACTION; PROTEIN BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33846415439     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060039e     Document Type: Article

References (38)

1. Peters, T. (1996) All About Albumin: Biochemistry, Genetics and Medical Applications, Academic Press: San Diego.
2. (a) Ghuman, J., Zunszain, P. A., Petitpas, I., Bhattacharya, A. A., Otagiri, M., and Curry, S. (2005) Structural basis of the drug-binding specificity of human serum albumin. J. Mol. Biol. 353, 38-52.
3. (b) Curry, S. (2002) Beyond expansion: structural studies of the transport roles of human serum albumin. Vox Sang. 83, 315-319.
4. (c) Emerson, T. E. (1989) Unique features of albumin - a brief review. Crit. Care Med. 17, 690-694.
5. (d) Kragh-Hansen, U., Chuang, V. T. G., and Otagiri, M. (2002) Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. Biol. Pharm. Bull. 25, 695-704.
6. (e) Fasano, M., Curry, C., Terreno, E., Galliano, M., Fanali, G., Narciso, P., Notari, S., and Ascenzi, P. (2005) The extraordinary ligand binding properties of human serum albumin. Life 57, 787-796.
7. (a) Seidel, P., Gurachevsky, A., Muravsky, V., Schnurr, K., Seibt, G., and Matthes, G. (2005) Recognition of malignant processes with neural nets from ESR spectra of serum albumin. Z. Med. Phys. 15, 265-272.
8. (b) Muravskaya, E. V., Lapko, A. G., and Muravskii, V. A. (2003) Modification of transport function of plasma albumin during atherosclerosis and diabetes mellitus. Bull. Exp. Biol. Med. 135, 433-435.
9. Zaton, A. M. L., Ferrer, J. M., Ruizde G.orda, J. C., and Marquín, M. A. (1995) Binding of coumarins to site I of human serum albumin. Effects of fatty acids. Chem.-Biol. Interact. 97, 169-174.
10. (a) Apple, F. S., Kleinfeld, A. M., and Adams, J. (2004) Unbound free fatty acid concentrations are increased in cardiac ischemia. Clin. Proteomics 1, 41-44.
11. (b) Kleinfeld, A. (2003) Diagnostic markers for ischemia. PCT Int. Appl., WO 2003025571.
12. Hamilton, J. A. (2002) How fatty acids bind to proteins: the inside story from protein structures. Prostaglandins, Leukotrienes Essent. Fatty Acids 67, 65-72.
13. (a) Curry, S., Brick, P., and Franks, N. P. (1999) Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim. Biophys. Acta 1441, 131-140.
14. (b) Petitpas, I., Grüne, T., Bhattacharya, and A. A., Curry, S. (2001) Crystal Structures of Human Serum Albumin Complexed with Monounsaturated and Polyunsaturated Fatty Acids. J. Mol. Biol. 314, 955-960.
15. (c) Bhattacharya, A. A., Grüne, T., and Curry, S. (2000) Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. J. Mol. Biol. 303, 721-732.
16. (d) Sacchettini, J. C., Gordon, J. I., and Banaszak, L. J. (1989) Crystal structure of rat intestinal fatty acid binding protein. Refinement and analysis of the Escherichia coli-derived protein with bound palmitate. J. Mol. Biol. 208, 327-339.
17. (e) Simard, J. R., Zunszain, P. A., Ha, C. E., Yang, J. S., Bhagavan, N. V., Petitpas, I., Curry, S., and Hamilton, J. A. (2005) Locating high-affinity fatty acid-binding sites on albumin by X-ray crystallography and NMR spectroscopy. Proc. Natl. Acad. Sci. U.S.A. 102, 17958-17963.
18. Narazaki, R., Maruyama, T., and Otagiri, M. (1997) Probing the cysteine 34 residue in human serum albumin using fluorescence techniques. Biochem. Biophys. Acta 1338, 275-281.
19. Wilton, D. C. (1990) The fatty acid analogue 11-(dansylamino)-undecanoic acid is a fluorescent probe for the bilirubin-binding sites of albumin and not for the high-affinity fatty acid-binding sites. Biochem. J. 270, 163-166.
20. (a) Kennedy, M. W., Scott, J. C., Lo, S., Beauchamp, J., and McManus, D. P. (2000) Sj-FABPc fatty-acid-binding protein of the human blood fluke Schistosoma japonicum: structural and functional characterisation and unusual solvent exposure of a portal-proximal tryptophan residue. Biochem. J. 349, 377-384.
21. (b) Veerkamp, J. H., van Moerkerk, H. T. B., Prisen, C. F. M., and van Kuppeveit, T. H. (1999) Structural and functional studies on different human FABP types. Mol. Cell. Biochem. 192, 137-142.
22. (a) Spector, A. A. (1975) Fatty acid binding to plasma albumin. J. Lipid Res. 16, 165-179.
23. (b) Ashbrook, J. D., Spector, A. A., and Reicher, J. E. (1972) Medium chain fatty acid binding to human plasma albumin. J. Biol. Chem. 247, 7038-7042.
24. (c) Ashbrook, J. D., Spector, A. A., Santos, E. C., and Fletcher, J. E. (1975) Long chain fatty acid binding to human plasma albumin. J. Biol. Chem. 250, 2333-2338.
25. Richieri, G. V., Anel, A., and Kleinfeld, A. M. (1993) Interactions of long-chain fatty acids and albumin: determination of free fatty acid levels using the fluorescent probe ADIFAB. Biochemistry 32, 7574-7580.
26. Tranchant, I., Hervé, A.-C., Carlisle, S., Lowe, P., Slevin, C. J., Forssten, C., Dilleen, J., Williams, D. E., Tabor, A. B., and Hailes, H. C. (2006) Design and synthesis of ferrocene probe molecules for detection by electrochemical methods. Bioconjugate Chem. 17, 1256-1264.
27. Klotz, I. M., Walker, F. M., and Pivan, R. B. (1946) The binding of organic ions by proteins. J. Am. Chem. Soc. 68, 1486-1490.
28. Abumrad, N. A., Perkins, R. C., Park, J. H., and Park, C. H. (1981) Mechanism of long chain fatty acid permeation in the isolated adipocyte. J. Biol. Chem. 256, 9183-9191.
29. Huenig, S., Graessmann, W., Luecke, E., and Brenninger, W. (1967) Syntheses with enamines. XIV. Synthesis of long-chain α-amino acids. Chem. Ber. 100, 3039-3044.
30. Oshida, N., Mimaki, Y., Satoh, H., Yokoyama, S., Muraki, Y., Nishimura, K., Hamada, T., Sakurai, E., Sakai, H., Sugai, T., Tonoike, T., and Itoh, K. Preparation of pyridinecarboxamide derivatives as brain protectants. PCT Int. Appl. 1998, WO 9822439.
31. Dobner, B., and Nuhn, P. (1991) Synthesis of deuterium-labeled methyl branched fatty-acids. Chem. Phys. Lipids 60, 21-28.
32. Takahashi, T., Mizuno, T., Ido, T., Iwata, R., and Watanabe, K.-I. (2003) Improved synthesis of pure [18F]fluoro-compounds for PET studies from bromo-compounds. Appl. Radiat. Isotopes 58, 557-566.
33. Lubas, B., Soltysik-Rasek, M., and Lesniewska, I. (1979) Proton NMR study of association of monovalent and divalent alcohols with bovine serum albumin. Biochemistry 18, 4943-4951.
34. Demant, E. J. F., Richieri, G. V., and Kleinfeld, A. M. (2002) Stopped-flow kinetic analysis of long-chain fatty acid dissociation from bovine serum albumin. Biochem. J. 363, 809-815.
35. Southampton Electrochemistry Group (1990) Instrumental Methods in Electrochemistry, p 182, Ellis Horwood, Chichester, U.K.
36. Rosenberg, R. M., Rogers, D. W., Haebig, J. E., and Steck, T. L. (1962) The interaction of serum albumin with ethanol. Arch. Biochem. Biophys. 97, 433-441.
37. Avdulov, N. A., Chochina, S. V., Daragan, V. A., Schroeder, F., Mayo, K. H., and Wood, W. G. (1996) Direct binding of ethanol to bovine serum albumin: A fluorescent and C-13 NMR multiplet relaxation study. Biochemistry 35, 340-347.
38. Ha, C. E., Petersen, C. E., Park, D. S., Harohalli, K., and Bhagavan, N. V. (2000) Investigations of the effects of ethanol on warfarin binding to human serum albumin. J. Biomed. Sci. 7, 114-121.