Covalent binding of catechols to Src family SH2 domains

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 2, 1997, Pages 113-116

  Jagoe, Christopher T ^a   Kreifels, Scott E ^a   Li, Jongming ^a  

^a Sandoz Pharma Ltd   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CATECHOL DERIVATIVE; CYSTEINE; QUINONE DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; AUTOOXIDATION; COVALENT BOND; DRUG SYNTHESIS; PROTEIN CONFORMATION; PROTEIN DOMAIN; PROTEIN PROTEIN INTERACTION; REACTION ANALYSIS;

EID: 0031031538     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00589-6     Document Type: Article

References (22)

1. Src Homology 2 (SH2) domains first reported in 1986. Sadowski, I.; Stone J. C.; Pawson, T. Mol. Cell. Biol. 1986, 6, 4396.
2. Koch, C. A.; Anderson, D.; Moran, M. F.; Ellis, C.; Pawson, T. Science 1991, 252, 668. Mayer, B. J.; Baltimore, D. Trends Cell Bio. 1993, 3, 8.
3. Koch, C. A.; Anderson, D.; Moran, M. F.; Ellis, C.; Pawson, T. Science 1991, 252, 668. Mayer, B. J.; Baltimore, D. Trends Cell Bio. 1993, 3, 8.
4. For example, breast cancer see: Daly, R. J. Breast Cancer Res. Treat. 1995, 34, 85.
5. One might argue that certain phosphotyrosine peptides meet the criterion; however, we disqualify them because of poor cell permeability and low enzymatic stability. Also, protein tyrosine kinase inhibitors are fundamentally different because they inhibit enzymatic activity of the kinase domain and not protein-protein binding.
6. Brugge, J. S. Science 1993, 260, 918.
7. A single concentration of 25 μM was used to screen compounds in a 96-well microtiter plate format. The SH2 ELISA detects inhibition of GST-SH2 fusion proteins binding to immobilized phosphotyrosine peptides through a colorimetric signal read at 410 nm. The assay buffer is 50 nmM tris-buffered saline (pH 7.5) containing 0.05% tween-20 (TBST) with 0.25% bovine serum albumin (BSA) and 1.0% sheep serum. Mallon, R. M.; Yu, K.; Williams, C. A.; Feldberg, L. R. Sandoz Pharmaceuticals Corp.
8. Haadsma-svensson, S. R.; Andersson, B. R.; Sonesson, C. A.; Lin, C.; Waters, R. N; Svensson, K. A. I.; Carlsson, P. A. E.; Hansson, L. O.; Stjernlof, N. P. WO 95/04713, 1995.
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10. By high sequence homology the Src family of includes: Src, Yes, Fgr, Fyn, Lck, Lyn, Hck, and Blk.
11. The general procedures described by Cannon (ref 8) were applied for the preparation of all compounds that were not commercially available.
12. The data presented for Fyn are representative of data not shown for Src, Lyn, and Lck SH2 domains.
13. Walling, X. Free Radicals in Solution; Wiley: New York, 1957; pp 457-461.
14. The assay buffer contains BSA (see note 6), which has one free cysteine. We conclude that it must be less accessible than the one on the SH2 domain.
15. Teuber, H.-J. Org. Synth. VI, 1988, 480.
16. Tse, D. C. S.; McCreey, R. L.; Adams, R. N. J. Med. Chem. 1976, 19, 37; and ref in note 18.
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19. Mallon, R. M.; Feldberg, L. R.; Nalin, C. M., Sandoz Pharmaceuticals Corp., unpublished results.
20. It has been suggested that nucleophilic attack by sulfyhdryl groups is more rapid than cyclization when dopamine is oxidized by tyrosinase to an o-quinone. Ito, S.; Kato, T.; Fujita, K. Biochem. Pharmacol. 1988, 37, 1707.
21. James, T. H.; Snell, J. M.; Weissberger, A. J. Am. Chem. Soc. 1938, 60, 2084. LuValle, J. E.; Weissberger, A. J. Am. Chem. Soc. 1947, 69, 1576.
22. James, T. H.; Snell, J. M.; Weissberger, A. J. Am. Chem. Soc. 1938, 60, 2084. LuValle, J. E.; Weissberger, A. J. Am. Chem. Soc. 1947, 69, 1576.