A chemiluminescent catalytic antibody†

(Note: The full text of this document is currently only available in the PDF Version )

James D. Stevenson, Anja Dietel and Neil R. Thomas


Abstract

A monoclonal antibody elicited against a phosphonate transition state analogue was shown to initiate chemiluminescence from luminogenic spiro[adamantane-2,3′-(1,2-dioxetane)] substrates by selectively cleaving a benzoate ester triggering group.


References

  1. Reviews: D. R. Liu and P. G. Schultz, Angew. Chem., Int. Ed., 1999, 38, 36 Search PubMed; J.-L. Reymond, Top. Curr. Chem., 1999, 200, 59 CrossRef; G. M. Blackburn, A. Datta, H. Denham and P. Wentworth, Adv. Phys. Org. Chem., 1998, 31, 249 CAS; N. R. Thomas, Nat. Prod. Rep., 1996, 13, 479 CAS.
  2. J. R. Crowther, ELISA Theory & Practice, Humana Press, Totowa, New Jersey, 1995 Search PubMed.
  3. A synthesis for an alternative hapten and proposed antibody chemiluminescence reaction was reported during the course of this work: M. Sawa, Y. Imaeda, J. Hiratake, R. Fujii, R. Umeshita, M. Watanabe, H. Kondo and J. Oda, Bioorg. Med. Chem. Lett., 1998, 8, 647 Search PubMed However the generaion of an antibody catalyst by these workers has yet to be reported. A catalytic antibody for the luminol-peroxidase reaction has also been reported: L. J. Kricka and X. Ji, Biolumin. Chemilum.: Proc. Int. Symp. 7th 1993, 1993, 518 CrossRef CAS The authors were not able to demonstrate unequivocally that this activity, which was short-lived, was not due to a contaminating enzyme, or purely a hydrophobic effect.
  4. J. A. Smiley and S. J. Benkovic, Proc. Natl. Acad. Sci. U.S.A., 1994, 91, 8319 CAS.
  5. N. Bensel, N. Bahr, M. T. Reymond, C. Schenkels and J.-L. Reymond, Helv. Chim. Acta, 1999, 82, 44 CrossRef CAS.
  6. B. Avalle, S. Vanwetswinkel and J. Fastrez, Bioog. Med. Chem. Lett., 1997, 7, 479 Search PubMed; C. F. Barbas, A. Heine, G. F. Zhong, T. Hoffman, S. Gramatikova, R. Bjornestedt, B. List, J. Anderson, E. A. Stura, I. A. Wilson and R. A. Lerner, Science, 1997, 278, 2085 CrossRef.
  7. F. Taran, P. Y. Renard, C. Creminon, A. Valleix, Y. Frobert, P. Pradelles, J. Grassi and C. Mioskowski, Tetrahedron Lett., 1999, 40, 1887 1891; G. Macbeath and D. Hilvert, J. Am. Chem. Soc., 1994, 116, 6106; D. S. Tawfik, B. S. Green, R. Chap, M. Sela and Z. Eshhar, Proc. Natl. Acad. Sci. U.S.A., 1993, 90, 373 CAS.
  8. J.-L. Jestin, P. Kristensen and G. Winter, Angew. Chem., Int. Ed., 1999, 38, 1196 CrossRef; H. Pedersen, S. Hölder, D. P. Sutherlin, U. Schwitter, D. S. King and P. G. Schultz, Proc. Natl. Acad. Sci. U.S.A., 1998, 95, 10 523 CrossRef CAS.
  9. L. E. Janes, A. C. Lowendahl and R. J. Kazlauskas, Chem. Eur. J., 1998, 4, 2324 CrossRef CAS.
  10. A. P. Schaap, R. S. Handley and B. P. Giri, Tetrahedron Lett., 1987, 28, 935 CrossRef; S. Beck and H. Köster, Anal. Chem., 1990, 62, 2258 CrossRef CAS; A. P. Schaap and H. Akhavan-Tafti, US Patent (U.S.P. WO90/07511) 1990; W. Adam, I. Bronstein, A. V. Tromfimov and R. F. Vasilev, J. Am. Chem. Soc., 1999, 121, 958 Search PubMed.
  11. G. T. Hermanson, Bioconjugate Techniques, AP, San Diego, 1996, p. 169 Search PubMed.
  12. R. B. Saishidhar, A. K. Capoor and D. Ramana, J. Immunol. Methods, 1994, 167, 121 CrossRef CAS An average hapten density of 24 copies of 1 per BSA was found, whilst 49% of the free lysines in the polymeric KLH had been derivatised.
  13. E. Harlow and D. Lane, Antibodies: A Laboratory Manual, Cold Spring Harbor, New York, 1988 Search PubMed.
  14. R. Curci, L. Lopez, L. Troisi, S. M. K. Rashid and A. P. Schaap, Tetrahedron Lett., 1987, 28, 5319 CrossRef CAS.
  15. R. E. Kontermann, P. Martineau, C. E. Cummings, A. Karpas, D. Allen, E. Derbyshire and G. Winter, Immunotechnology, 1997, 3, 137 CrossRef CAS.