Sulfhydryl-selective, covalent labeling of biomolecules with transition metallocarbonyl complexes. Synthesis of (η5-C5H 5)M(CO)3(η1-N-maleimidato) (M = Mo, W), X-ray structure, and reactivity studies

Bioconjugate Chemistry

Volumn 16, Issue 5, 2005, Pages 1218-1224

  Rudolf, Bogna ^a   Palusiak, Marcin ^a   Zakrzewski, Janusz ^a   Salmain, Michèle ^b   Jaouen, Gérard ^b  

^a UNIVERSITY OF LODZ   (Poland)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOMOLECULES; BODY FLUIDS; CRYSTAL ATOMIC STRUCTURE; LIGANDS; METALS; PHOTOCHEMICAL REACTIONS; SINGLE CRYSTALS; THALLIUM COMPOUNDS;

BIOCONJUGATES; BOVINE SERUM ALBUMINS; COVALENT LABELING; GLUTHATHIONE; LABELINGS; MALEIMIDES; REACTIVITY STUDIES; SH GROUPS; SULFHYDRYL; X-RAY STRUCTURE;

PEPTIDES;

BOVINE SERUM ALBUMIN; CARBONYL DERIVATIVE; CYSTEINE ETHYL ESTER; GLUTATHIONE; LIGAND; MALEIMIDE DERIVATIVE; MOLYBDENUM COMPLEX; N ETHYLMALEIMIDE; PROPYLAMINE; REAGENT; THALLIUM; THIOL DERIVATIVE; TRANSITION ELEMENT; TUNGSTEN DERIVATIVE;

ARTICLE; CHEMICAL LABELING; CONJUGATE; COVALENT BOND; CRYSTAL STRUCTURE; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; PHOTOCHEMISTRY; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BOVINAE;

EID: 25444500972     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc050073d     Document Type: Article

References (31)

1. Van Staveren, D. R., and Metzler-Nolte, N. (2004) Bioorganometallic chemistry of ferrocene. Chem. Rev. 104, 5931-5985.
2. Salmain, M., and Jaouen, G. (2003) Side-chain selective and covalent labelling of proteins with transition organometallic complexes. C. R. Chimie 6, 249-258.
3. (a) Guo, X. Q., Castellano, F. N., Li, L., and Lakowicz, J. R. (1998) Use of a long-lifetime Re(I)complex in fluorescence polarization immunoassays of high-molecular-weight analytes. Anal. Chem. 70, 632-637.
4. (b) Dattelbaum, J. D., Abugo, O. O., and Lakowicz, J. R. (2000) Synthesis and characterization of a sulfhydryl-reactive rhenium metal-ligand complex. Bioconjugate Chem. 11, 533-536.
5. (c) Lo, K. K., Hui, W. K., Ng, D. C., and Cheung, K. K. (2002) Synthesis, characterization, photophysical properties, and biological labeling studies of a series of luminescent rhenium(I) polypyridine maleimide complexes. Inorg. Chem. 41, 40-46.
6. Blundell, T. L., and Johnson, L. N. (1976) Protein Crystallography, Academic Press, London.
7. Hermanson, G. T. (1996) Bioconjugate Techniques, Academic Press, San Diego CA.
8. Jahn, W. (1989) Synthesis of water soluble tetrairidium clusteres suitable for heavy atom labelling of proteins. Z. Naturforsch. 44b, 79-82.
9. Weinstein, S., Jahn, W., Hansen, H., Wittmann, H. G. and Yonath, A. (1989) Novel procedures for derivatization of ribosomes for crystallographic studies. J. Biol. Chem. 264, 19138-19142.
10. Cheng, N. Conway, J. F., Watts, N. R., Hainfeld, J. F., Joshi, V., Powell, R. D., Stahl, S. J., Wingfield, P. E., and Steven, A. C. (1999) Tetrairidium, a four-atom cluster as a density label in three-dimensional cryo-EM maps of proteins at 10-25 Å resolution. J. Struct. Biol. 127, 169-176.
11. cam: enzymatic properties and electrochemistry. FEBS Lett. 451, 342-346.
12. cam as revealed by the crystal structure of the modified protein. J. Am. Chem. Soc. 120, 46-52.
13. (c) Di Gleria, K., Hill, H. A. O., and Wong, L.-L. (1996) N-(2-Ferrocene-ethyl)-maleimide: a new electroactive sulfhydryl-specific reagent for cysteine-containing peptides and proteins. FEBS Lett. 390, 142-144.
14. Di Gleria, K., Halliwell, C. M., Jacob, C., and Hill, H. A. (1997) Site-specific introduction of an electroactive label into a non-electroactive enzyme (β-lactamase I). FEBS Lett. 400, 155-157.
15. 2-complex of maleimide anion: An organometallic carbonyl probe for biomolecules containing HS groups. Tetrahedron Lett. 35, 9611-9612.
16. 1- N- imidato) system as protein labelling reagents: reactivity and selectivity studies using bovine serum albumin as a model protein. New J. Chem. 813-818.
17. 1-N- succinimidato]glutathione. J. Organomet. Chem. 589, 98-102.
18. (a) Salmain, M., Fischer-Durand, N., Cavalier, L., Rudolf, B., Zakrzewski, J., and Jaouen, G. (2002) Transition metalcarbonyl labeling of biotin and avidin for use in solid-phase Carbonyl Metallo Immunoassay (CMIA). Bioconjugate Chem. 18, 693-698.
19. (b) Rudolf, B., Zakrzewski, J., Celichowski, G., Salmain, M., Vessières, A., and Jaouen, G. (2004) (b) Specific binding of a biotinylated, metallocarbonyl-labelled dendrimer to immobilised avidin detected by Diffuse Reflectance Infrared Fourier Transform (DRIFT) spectroscopy. Appl. Organomet. Chem. 18, 105-110.
20. (c) Fischer-Durand, N., Salmain, M., Rudolf, B., Vessières, A., Zakrzewski, J., and Jaouen, G. (2004) Synthesis of metal carbonyl-dendrimer- antibody immunoconjugates: towards a new format for Carbonyl Metallo ImmunoAssay (CMIA). ChemBioChem. 5, 519-525.
21. (a) Abel, A. E., Singh, W., and Wilkinson, G. (1960) Some π-cyclopentadienyl- molybdenum and -tungsten halides. J. Chem. Soc. 1321-1324.
22. (b) Burckett- St. Laurent, J. C. T. R., Field, J. S., Haines, R. J., and McMahon, M. (1978) Halogenation of bis (η- cyclopentadienyltricarbonylmolybdenum and -tungsten) via bridged intermediates- formation of some monocyclopentadienyl derivatives of molybdenum (IV). J. Organomet. Chem. 153, C19-C22.
23. Ellman, G. L. (1958) A colorimetric method for determining low concentrations of mercaptans. Arch. Biochem. Biophys. 74, 443-450.
24. Peters, P. J. (1985) Serum albumin. Adv. Protein Chem. 37, 161-245.
25. (a) Alway, D. G., and Barnett, K. W. (1978) Photochemical processes in cyclopentadienylmetal carbonyl complexes. Adv. Chem. Ser. 168, 115-131.
26. (b) Alway, D. G., Barnett, K. W. (1975) Photochemical isomerization of cyclopentadienylmetal complexes. J. Organomet. Chem. 99, C52-C54.
27. (c) Alway, D. G., and Barnett, K. W. (1980) Photochemistry of cyclopentadienylmolybdenum and cyclopentadienyltungsten carbonyl halide complexes. Inorg. Chem. 19, 1533-1543.
28. (d) Pan, X., Philbin, C. E., Castellani, M. P., and Tyler, D. R. (1988) Photochemistry of organometallic halide complexes. Mechanism for the formation of ionic products. Inorg. Chem. 27, 671-676.
29. 4CO)] and the nature of the metal-nitrogen bond. J. Chem. Soc., Dalton Trans. 813-821.
30. 3HgCl. Inorg. Chem. 20, 2197-2202.
31. Allen, F. H., Baalham, C. A., Lommerse, J. P. M., and Raithby, P. R. (1998) Carbonyl-carbonyl interaction can be competitive with hydrogen bond. Acta Crystallogr. B54, 320-329.