New activities of a catalytic antibody with a peroxidase activity: Formation of Fe(II)-RNO complexes and stereoselective oxidation of sulfides

European Journal of Biochemistry

Volumn 271, Issue 7, 2004, Pages 1277-1283

  Ricoux, Rémy ^a   Lukowska, Edyta ^a   Pezzotti, Fabio ^a   Mahy, Jean Pierre ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

Abzymes; Artificial hemoproteins; Microperoxidase 8; Nitrosoalcanes; S oxidation

Indexed keywords

CATALYTIC ANTIBODY; HEMOPROTEIN; HYDROGEN PEROXIDE; IRON COMPLEX; MONOCLONAL ANTIBODY; PEROXIDASE; SULFIDE; TERT BUTYL HYDROPEROXIDE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; ENANTIOMER; ENZYME ACTIVITY; METAL BINDING; OXIDATION; PRIORITY JOURNAL; PROTEIN BINDING; STEREOCHEMISTRY;

ANIMALS; BINDING SITES; CYTOCHROMES C; HEME; HORSES; HYDROGEN PEROXIDE; HYDROXYLAMINES; IRON; KINETICS; MODELS, BIOLOGICAL; MODELS, CHEMICAL; OXYGEN; PEROXIDASES; PORPHYRINS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STEREOISOMERISM; SULFIDES; TERT-BUTYLHYDROPEROXIDE; TIME FACTORS; ULTRAVIOLET RAYS;

EID: 1942520299     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.2004.04032.x     Document Type: Article

References (25)

1. Mahy, J.P., Desfosses, B., de Lauzon, S., Quilez, R., Desfosses, B., Lion, L. & Mansuy, D. (1998) Hemoabzymes. Different strategies for obtaining artificial hemoproteins based on antibodies. Appl. Biochem. Biotechnol. 75, 103-127.
2. Ricoux, R., Sauriat-Dorizon, H., Girgenti, E., Blanchard, D. & Mahy, J.P. (2002) Hemoabzymes: towards new biocatalysts for selective oxidations. J. Immunol. Methods 269, 39-57.
3. Ricoux, R., Girgenti, E., Sauriat-Dorizon, H., Blanchard, D. & Mahy, J.P. (2002) Regioselective nitration of phenol induced by catalytic antibodies. J. Protein Chem. 21, 473-477.
4. Damani, L.A. (1989) Sulphur-Containing Drugs and Related Organic Compounds, Vol. 1, Ellis Horwood, Chichester.
5. Hofstra, A.H. & Uetrecht, J.P. (1993) Myeloperoxidase-mediated activation of xenobiotics by human leukocytes. Toxicology 82, 221-242.
6. Colonna, S., Gaggero, N., Manfredi, A., Casella, L., Gullotti, M., Carrea, G. & Pasta, P. (1990) Enantioselective oxidations of sulphides catalyzed by chloroperoxidase. Biochemistry 29, 10465-10468.
7. Tuynman, A., Vink, M.K., Dekker, H.L., Schoemaker, H.E. & Wever, R. (1998) The sulphoxidation of thioanisole catalysed by lactoperoxidase and Coprinus cinereus peroxidase: evidence for an oxygen-rebound mechanism. Eur. J. Biochem. 258, 906-913.
8. Capeillere-Blandin, C., Martin, C., Gaggero, N., Pasta, P., Carrea, G. & Colonna, S. (1998) Sulphoxidation reaction catalysed by myeloperoxidase from human leucocytes. Biochem. J. 335, 27-33.
9. Colonna, S., Gaggero, N., Carrea, G. & Pasta, P. (1992) Horse-radish peroxidase catalysed sulfoxidation is enantioselective. J. Chem. Soc. Chem. Com. 4, 357-358.
10. Miller, V.P., DePillis, G.D., Ferrer, J.C., Mauk, A.G. & Ortid de Montellano, P.R. (1992) Monooxygenase activity of cytochrome c peroxidase. J. Biol. Chem. 267, 8936-8942.
11. Blée, E. & Schuber, F. (1989) Mechanism of S-oxidation reaction catalysed by a soybean hydroperoxide dependent oxygenase. Biochemistry 28, 4962-4967.
12. Aron, J., Baldwin, D.A., Marques, H.M., Pratt, J.M. & Adams, P.A. (1986) Hemes and hemoproteins 1: preparation and analysis of heme containing octapeptide (Microperoxidase-8) and identification of the monomeric form in aqueous solution. J. Inorg. Biochem. 27, 227-243.
13. Tresca, J.P., Ricoux, R., Pontet, M. & Engler, R. (1995) Comparative activity of peroxidase-antibody conjugates with periodate and glutaraldehyde coupling according to an enzyme immunoassay. Ann. Biol. Clin. 53, 227-231.
14. Köhler, G. & Milstein, C. (1975) Continuous culture of fused cells secreting antibodies of predefined specificity. Nature 256, 495-497.
15. de Lauzon, S., Desfosses, B., Moreau, M., Le Trang, N., Rajkovski, K. & Cittanova, N. (1990) Comparison of monoclonal antibodies to estradiol obtained from structurally different immunogens. Hybridoma 9, 481-491.
16. Gairaud, C.B. & Lappin, G.R. (1953) The synthesis of ω-nitrostyrenes. J. Org. Chem. 18, 1-3.
17. Gilsdorf, R.T. & Nord, F.F. (1952) Reverse addition of lithium aluminum hydride to nitroolefins. J. Am. Chem. Soc. 74, 1837-1843.
18. Maasen, J.A. & De Boer, T.J. (1971) Silver carbonate, a convenient reagent for preparing C-nitroso compounds from hydroxylamines. Recl. Trav. Chim. Pays-Bas 90, 371-376.
19. Mansuy, D., Battioni, P., Chottard, J.C., Riche, C. & Chiaroni, A. (1983) Nitrosoalkane complexes of iron-porphyrins: analogy between the bonding properties of nitrosoalkanes and dioxygen. J. Am. Chem. Soc. 105, 455-463.
20. Ricoux, R., Boucher, J.L., Mansuy, D. & Mahy, J.P. (2000) Formation of iron (II)-nitrosoalkane complexes: a new activity of microperoxidase 8. Biochem. Biophys. Res. Commun. 278, 217-223.
21. Mansuy, D., Gans, P., Chottard, J.C. & Bartoli, J.F. (1977) Nitrosoalkanes as Fe(II) ligands in the 455-nm-absorbing cytochrome P-450 complexes formed from nitroalkanes in reducing conditions. Eur. J. Biochem. 76, 607-615.
22. Marques, H.M., Baldwin, D.A. & Pratt, J.M. (1987) Hemes and hemoproteins. 3. The reaction of microperoxidase-8 with cyanide: comparison with aquocobalamin and hemoproteins. J. Inorg. Biochem. 29, 77-91.
23. Dai, L. & Klibanov, A.M. (2000) Peroxidase-catalyzed asymmetric sulfoxidation in organic solvents versus in water. Biotechnol. Bioeng. 70, 353-357.
24. De Gioia, L., Ghibaudi, E., Laurenti, E., Salmona, M. & Ferrari, R.P. (1996) A theoretical three-dimensional model for lactoperoxidase and eosinophil peroxidase, built on the scaffold of the myeloperoxidase. J. Biol. Inorg. Chem. 1, 476-485.
25. Shai, S. & Keinan, E. (1999) Antibody-metalloporphyrin catalytic assembly mimics natural oxidation enzymes. J. Am. Chem. Soc. 121, 8978-8982.