Download PDF
Synthesis 2006(3): 509-513  
DOI: 10.1055/s-2005-918518
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Photoactivatable Analogues of Glutathione Disulfide

Dan Bernardi, Amadou Dicko, Gilbert Kirsch*
Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, Université Paul Verlaine-Metz, 1 Boulevard Arago, 57078 METZ Cedex 3, France
Fax: +33(38)7315801; e-Mail: kirsch@sciences.univ-metz.fr;
Further Information

Publication History

Received 12 July 2005
Publication Date:
21 December 2005 (online)

    Permissions and Reprints All articles of this category

Abstract

New photoactivatable analogues of glutathione disulfide (GSSG) bearing new benzophenone-like photophores were synthesized by using an improved coupling reaction.

Key words

glutathione disulfide - photoaffinity labeling - benzo­phenone - heterocycles

    References

  • 1a Lyon RP. Hill JJ. Atkins WM. Biochemistry  2003,  42:  10418 
    Google Scholar
  • 1b Lim MLR. Lum M. Hansen TM. Roucou X. Nagley P. J. Biomed. Sci.  2002,  9:  488 
    Google Scholar
  • 1c Hanigan MH. Chemico-Biol. Interact.  1998,  111-112:  333 
    Google Scholar
  • 1d Keppler D. Leier I. Jedlitischky G. König J. Chemico-Biol. Interact.  1998,  111-112:  153 
    Google Scholar
  • 1e Kauvar LS. Sanderson PE. Henner WD. Chemico-Biol. Interact.  1998,  111-112:  225 
    Google Scholar
  • 2a Quian Y. Grant CE. Westlake CJ. Zhang D. Lander PA. Shepard RL. Dantzig AH. Cole SPC. Deeley RG. J. Biol. Chem.  2002,  277:  35225 
    CrossrefGoogle Scholar
  • 2b Furuta K. Tomokiyo K. Kuo MT. Ishikawa T. Suzuki M. Tetrahedron  1999,  55:  7529 
    CrossrefGoogle Scholar
  • 2c Furuta K. Hosoya T. Tomokiyo K. Okuda S. Kuniyasu A. Nakayama H. Ishikawa T. Suzuki M. Bioorg. Med. Chem. Lett.  1999,  9:  2661 
    CrossrefGoogle Scholar
  • 3 Hall AG. Eur. J. Clin. Invest.  1999,  29:  238 
    CrossrefGoogle Scholar
  • 4 Filomeni G. Rotilio G. Ciriolo MR. FASEB J.  2003,  17:  64 
    Google Scholar
  • 5 D’Silva C. Seddon AP. Douglas KT. J. Chem. Soc., Perkin Trans. 1  1981,  3029 
    CrossrefGoogle Scholar
  • 6 Douglas KT. Seddon AP. D’Silva C. Bunni M. Biochem. Soc. Trans.  1982,  10:  124 
    CrossrefGoogle Scholar
  • 7 Brault L. Migianu E. Néguesque A. Battaglia E. Bagrel D. Kirsch G. Eur. J. Med. Chem.  2005,  in press 
    Google Scholar
  • 8 Dorman G. Prestwich GD. Biochemistry  1994,  33:  5661 
    CrossrefGoogle Scholar
  • 9a Bosca F. Miranda MA. J. Photochem. Photobiol., B: Biology  1998,  43:  1 
    CrossrefGoogle Scholar
  • 9b Lahoz A. Hernandez D. Miranda MA. Perz-Prieto J. Morera IM. Castell JV. Chem. Res. Toxicol.  2001,  14:  1486 
    CrossrefGoogle Scholar
  • 9c Moser J. Hye A. Lovell WW. Earl LK. Castell JV. Miranda MA. Toxicol. in Vitro  2001,  15:  333 
    CrossrefGoogle Scholar
  • 9d Arnold DR. Birtwell RJ. J. Am. Chem. Soc.  1973,  95:  4599 
    CrossrefGoogle Scholar
  • 10 Holland GF. inventors; US Patent,  4282246.  ; Chem. Abstr. 1981, 95, 203733a
  • 11 Green TW. Wuts PGM. Protective Groups in Organic Synthesis   2nd ed.:  Wiley; New York: 1991. 
    Google Scholar
  • 12 Gartner CA. Wen B. Wan J. Becker RS. Jones G. Gygi SP. Nelson SD. Biochemistry  2005,  44:  1846 
    CrossrefGoogle Scholar
  • 13 Cadamuro S. Degani I. Dughera S. Fochi R. Gatti A. Piscopo L. J. Chem. Soc., Perkin Trans. 1  1993,  273 
    CrossrefGoogle Scholar
  • 14 Zu J. Wang X. Chen Y. Jiang X. Chen X. Li Z. J. Org. Chem.  2004,  69:  6221 
    CrossrefGoogle Scholar
  • 15 Anderson GW. Zimmerman JE. Callahan FM. J. Am. Chem. Soc.  1964,  86:  1839 
    CrossrefGoogle Scholar