Design and synthesis of ferrocene probe molecules for detection by electrochemical methods

Bioconjugate Chemistry

Volumn 17, Issue 5, 2006, Pages 1256-1264

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

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b Unipath   (United Kingdom)

^c Diatos SA   (France)

^d Diatos NV   (Belgium)

^e Scion House   (United Kingdom)

^f UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; BINDING ENERGY; CHEMICAL DETECTION; CYCLIC VOLTAMMETRY; ESTERS; FATTY ACIDS; IRON COMPOUNDS; LEAD COMPOUNDS; MOLECULES; POSITIVE IONS; SYNTHESIS (CHEMICAL);

BINDING STUDIES; BIOMOLECULAR BINDING; ELECTROCHEMICAL METHOD; FERROCENE CONJUGATES; FERROCENES; FERROCENIUM CATIONS; FERROCENYL; PROBE MOLECULES; PROPERTY; SYNTHESISED;

ORGANOMETALLICS;

AMIDE; AMINE; CARBAMIC ACID; CATION; ESTER DERIVATIVE; FATTY ACID; FERROCENE; HUMAN SERUM ALBUMIN; LEAD; LONG CHAIN FATTY ACID; METAL ION; SILVER; SILVER CHLORIDE; SOLUBILIZER;

AMPEROMETRIC BIOSENSOR; ARTICLE; BINDING AFFINITY; BIOMOLECULAR ELECTRONICS; CHEMICAL STRUCTURE; CONJUGATION; ELECTROCHEMICAL ANALYSIS; MOLECULAR IMAGING; MOLECULAR INTERACTION; MOLECULAR MIMICRY; MOLECULAR PROBE; PROTEIN LIPID INTERACTION; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33749025576     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060038m     Document Type: Article

References (30)

1. Cais, M., Slovin, E., and Snarsky, L. (1978) Metalloimmunoassay II. Iron-metallohaptens from estrogen steroids. J. Organomet. Chem. 160, 223-230.
2. Weber, S. G., and Purdy, W. C. (1979) Homogeneous voltammetric immunoassay: a preliminary study. Anal. Lett. 12, 1-19.
3. Tiefenauer, L. X., Kossek, S., Padeste, C., Thiebaud, P. (1997) Towards Amperometric Immunosensor Devices. Biosens. Bioelectron. 12, 213-223.
4. Yu, C. J., Wang, H., Wan, Y., Yowanto, H., Lie, J., Tao, C., James, M. D., Tan, C. L., Blackburn, G. F., and Meade, T. J. (2001) 2-Ribose-ferrocene oligonucleotides for electronic detection of nucleic acids. J. Am. Chem. Soc. 123, 11155-11161.
5. Hillier, S. C., Flower, S. E., Frost, C. G., Jenkins, A. T. A., Keay, R., Braven, H., Clarkson, J. (2004) An electrochemical gene detection assay utilizing T7 exonuclease activity on complementary probe-target oligonucleotide sequences. Electrochem. Commun. 6, 1227-1232.
6. Hillier, S. C., Frost, C. G., Jenkins, A. T. A., Braven, H., Keay, R. W., Flower, S. E., Clarkson, J. M. (2004) An electrochemical study of enzymatic oligonucleotide digestion. Bioelectrochemistry 63, 307-310.
7. Plumb, K., and Kraatz, H.-B. (2003) Interaction of a ferrocenyl-modified peptide with papain: toward protein-sensitive electrochemical probes. Bioconjugate Chem. 14, 601-606.
8. Forrow, N. J., Sanghera, G. S., and Walters, S. J. (2002) The influence of structure in the reaction of electrochemically generated ferrocenium derivatives with reduced glucose oxidase. J. Chem. Soc., Dalton Trans. 3187-3194.
9. Di Gleria, K., Hill, H. A. O., McNeil, C. J., and Green, M. J. (1988) Homogeneous ferrocene-mediated amperometric immunoassay. Anal. Chem. 58, 1203-1205.
10. Forrow, N. J., Foulds, N. C., Frew, J. E., and Law, J. T. (2004) Synthesis, characterization, and evaluation of ferrocene-theophylline conjugates for use in electrochemical enzyme immunoassay. Bioconjugate Chem. 15, 137-144.
11. Zatón, A. M. L., Ferrer, J. M., Ruizde Gorda, 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.
12. Bhattacharya, A. A., Grüne, T., and Curry, S. (2000) Crystallographic analysis reveals common modes of binding medium and long chain fatty acids to human serum albumin. J. Mol. Biol. 303, 721-732.
13. Sacchettini, J. C., Gordon, J. I., and Banaszak, L. J. (1989) Crystal structure of rat intestinal fatty acid binding protein. Refinment and analysis of the Escherichia coli-derived protein with bound palmitate. J. Mol. Biol. 208, 327-339.
14. 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.
15. 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 (1), 163-166.
16. Timanova-Atanasova, A., Jordanova, R., Radoslavov, G., Deevska, G., Bankov, I., and Barrett, J. (2004) A native 13 kDa fatty acid binding protein from the liver fluke Fasciola hepatica. Biochim. Biophys. Acta 1674, 200-204.
17. Richieri, G. V., Ogata, R. T., and Kleinfeld, A. M. (1992) A fluorescently labeled intestinal fatty acid binding protein. Interactions with fatty acids and its use in monitoring free fatty acids. J. Biol. Chem. 33, 23495-23501.
18. Anne, A. (1998) Novel monolabeled redox biomaterials: Amino-ended poly(ethylene oxide) ferrocenes and their biotin-conjugates. Tetrahedron Lett. 39, 561-564.
19. Anne, A., and Moiroux, J. (1999) Quantitative characterization of the flexibility of poly(ethylene glycol) chains attached to a glassy carbon electrode. Macromolecules 32, 5829-5835.
20. Khersonsky, S. M., Jung, D. W., Kang, T. W., Walsh, D. P., Moon, H. S., Jo, H., Jacobson, E. M., Shetty, V., Neubert, T. A., and Chang, Y. T. (2003) A cross-linking method to study protein interactions. J. Am. Chem. Soc. 125, 2416-2425.
21. Rees, G. D., Robinson, B. H., and Stephenson, G. R. (1995) Macrocyclic lactone synthesis by lipases in water-in-oil microemulsions. Biochim. Biophys. Acta 1257, 239-248.
22. Ross, W. C. J. (1962) Some surface active alkylating agents. J. Chem. Soc. 4739-4740.
23. Cooke, G., Radhi, A., Boden, N., Bushby, R. J., Lu, Z., Brown, S., and Heath, S. L. (2000) Synthesis and characterisation of tetrathiafulvalenyl- and ferrocenyl-triphenylenes. Tetrahedron 56, 3385-3390.
24. Schetter, B., and Speiser, B. (2004) Reaction of ferrocenecarboxylic acid with N,N-disubstituted carbodiimides: synthesis, spectroscopic and X-ray crystallographic analysis of N,N′-disubstituted N-ferrocenoylureas and identification of a one-pot coupling reagent for the formation of ferrocenecarboxamides in a non-aqueous solvent. J. Organomet. Chem. 689, 1472-1480.
25. Pravda, M., Junjar, C. M., Iwuoha, E. I., Smyth, M. R., Vytras, K., and Ivaska, A. (1995) Evaluation of amperorneteric glucose biosensors based on co-immobilisation of glucose oxidase with an osmium redox polymer in electrochemically generated polyphenol films. Anal. Chim. Acta 304, 127-138.
26. Rossier, J. S., Roberts, M. A., Ferringo, R., and Girault, H. H. (1999) Electrochemical detection in polymer microchannels. Anal. Chem. 71, 4294-4299.
27. Sheehy, M. J., Gallagher, J. F., Yamashita, M., Ida, Y., White-Colangelo, J., Johnson, J., Orlando, R., and Kenny, P. T. M. (2004) Synthesis and structural characterization of redox-responsive N-ferrocenoyl amino acid esters; the X-ray crystal structure of N-ferrocenoyl alanine methyl ester; electrochemical anion recognition and 1H NMR complexation studies. J. Organomet. Chem. 689, 1511-1520.
28. Yoon, H. C., Yang, H., and Byun, S. Y. (2004) Ferritin immunosensing on microfabricated electrodes based on the integration of immunoprecipitation and electrochemical signaling reactions. Anal. Sci. 20, 1249-1253.
29. Southampton Electrochemistry Group (1990) Instrumental methods in electrochemistry, p 182, Ellis Horwood, Chichester, U.K.
30. Tranchant, I., Hervé, A.-C., Carlisle, S., Lowe, P., Slevin, C. J., Forssten, C., Dilleen, J., Tabor, A. B., Williams, D. E., and Hailes, H. C., manuscript in preparation.