Irreversible inhibitors of tissue transglutaminase

Advances in Enzymology and Related Areas of Molecular Biology

Volumn 78 1, Issue , 2011, Pages 415-447

  Keillor, Jeffrey W ^a   Chabot, Nicolas ^a   Roy, Isabelle ^a   Mulani, Amina ^a   Leogane, Olivier ^a   Pardin, Christophe ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; EPOXIDE; GUANINE NUCLEOTIDE BINDING PROTEIN; ISOXAZOLE DERIVATIVE; KETONE; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE 2;

BIOLOGICAL MODEL; CHEMISTRY; CLASSIFICATION; DRUG ANTAGONISM; DRUG DESIGN; EVALUATION; HUMAN; METABOLISM; METHODOLOGY; MOLECULAR PROBE; MOLECULARLY TARGETED THERAPY; REVIEW; SYNTHESIS;

DRUG DESIGN; ENZYME INHIBITORS; EPOXY COMPOUNDS; GTP-BINDING PROTEINS; HUMANS; ISOXAZOLES; KETONES; MODELS, BIOLOGICAL; MOLECULAR PROBES; MOLECULAR TARGETED THERAPY; TRANSGLUTAMINASES;

EID: 84856597474     PISSN: 0065258X     EISSN: None     Source Type: Book Series    
DOI: 10.1002/9781118105771.ch10     Document Type: Article

References (75)

1. Folk, J. E. (1983) Mechanism and basis for specificity of transglutaminase-catalyzed epsilon-(gamma-glutamyl) lysine bond formation, Adv. Enzymol. Relat. Areas Mol. Bio. 54, 1-56.
2. Folk, J. E. and Chung, S. I. (1985) Transglutaminases, Methods Enzymol. 113, 358-375.
3. Folk, J. E. and Chung, S. I. (1973) Molecular and catalytic properties of transglutaminases, Adv. Enzymol. Relat. Areas Mol. Biol. 38, 109-191.
4. Leblanc, A., et al. (2001) Kinetic studies of guinea pig liver transglutaminase reveal a general-base-catalyzed deacylation mechanism, Biochemistry 40(28), 8335-8342.
5. Case, A. and Stein, R. L. (2003) Kinetic analysis of the action of tissue transglutaminase on peptide and protein substrates, Biochemistry 42(31), 9466-9481.
6. Day, N. and Keillor, J. W. (1999) A continuous spectrophotometric linked enzyme assay for transglutaminase activity, Anal. Biochem. 274(1), 141-144.
7. de Macedo, P., et al. (2000) A direct continuous spectrophotometric assay for transglutaminase activity, Anal. Biochem. 285(1), 16-20.
8. Case, A., et al. (2005) Development of a mechanism-based assay for tissue transglutaminase-results of a high-throughput screen and discovery of inhibitors, Anal. Biochem. 338(2), 237-244.
9. Murthy, S. N. P., et al. (2002) Conserved tryptophan in the core domain of transglutaminase is essential for catalytic activity, Proc. Natl. Acad. Sci. U.S.A. 99(5), 2738-2742.
10. Chica, R. A., et al. (2004) Tissue trans glutaminase acylation: proposed role of conserved active site Tyr and Trp residues revealed by molecular modeling of peptide substrate binding, Protein Sci. 13(4), 979-991.
11. Gravel, C., et al. (2007) Acyl transfer from carboxylate, carbonate, and thiocarbonate esters to enzymatic and nonenzymatic thiolates, Can. J. Chem.-Revue Canadienne De Chimie 85(3), 164-174.
12. Griffin, M., et al. (2002) Transglutaminases: nature's biological glues, Biochem. J. 368, 377-396.
13. Lorand, L. and Graham, R. M. (2003) Transglutaminases: crosslinking enzymes with pleiotropic functions, Nat. Rev. Mol. Cell Biol. 4(2), 140-156.
14. Mehta, K. (2005) Mammalian transglutaminases: a family portrait, Prog. Exp. Tumor Res. 38, 1-18.15.
15. Davies, P. J., et al. (1980) Transglutaminase is essential in receptor-mediated endocytosis of alpha 2-macroglobulin and polypeptide hormones, Nature 283(5743), 162-167.
16. Levitzki, A., et al. (1980) Evidence for participation of transglutaminase in receptormediated endocytosis, Proc. Natl. Acad. Sci. USA 77(5), 2706-2710.
17. Fesus, L., et al. (1987) Induction and activation of tissue transglutaminase during programmed cell death, FEBS Lett. 224, 104.
18. Birckbichler, P. J., et al. (1983) Enhanced transglutaminase activity in transformed human lung fibroblast cells after exposure to sodium butyrate, Biochim. Biophys. Acta 763, 27.
19. Aeschlimann, D. and Thomazy, V. (2000) Protein crosslinking in assembly and remodelling of extracellular matrices: the role of transglutaminases, Connect. Tissue Res. 41(1), 1-27.
20. De Young, L., et al. (1984) Transglutaminase activity in human and rabbit ear comedogenesis: a histochemical study, J. Invest. Dermatol. 82, 275.
21. Azari, P., et al. (1981) Transglutaminase activity in normal and hereditary cataractous rat lens and its partial purification, Curr. Eye Res. 1(8), 463.
22. Fesus, L. (1982) Transglutaminase activation: significance with respect to immunologic phenomena, Surv. Immunol. Res. 1, 297.
23. Schroeder,W. T., et al. (1992) Type I keratinocyte transglutaminase: expression in human skin and psoriasis, J. Invest. Dermatol. 99, 27-34.
24. Selkoe, D. J., et al. (1982) Brain transglutaminase: in vitro crosslinking of human neurofilament proteins into insoluble polymers, Proc. Natl. Acad. Sci. U.S.A. 79, 6070.
25. Norlund, M. A., et al. (1999) Elevated transglutaminase-induced bonds in PHF tau in Alzheimer's disease, Brain Res. 851, 154.
26. Dedeoglu, A., et al. (2002) Therapeutic effects of cystamine in a murine model of Huntington's disease, J. Neurosci. 22(20), 8942-8950.
27. Mastroberardino, P., et al. (2002) " Tissue" transglutaminase ablation reduces neuronal death and prolongs survival in a mouse model of Huntington's disease, Cell Death Differ. 9, 873-880.
28. Piper, J. L., et al. (2002) High selectivity of human tissue transglutaminase for immunoactive gliadin peptides: implications for Celiac sprue, Biochemistry 41(1), 386-393.
29. Choi, K., et al. (2005) Chemistry and biology of dihydroisoxazole derivatives: selective inhibitors of human transglutaminase 2, Chem. Biol. 12(4), 469-475.
30. Mehta, K. (2009) Biological and therapeutic significance of tissue transglutaminase in pancreatic cancer, Amino Acids 36(4), 709-716.
31. Siegel, M. and Khosla, C. (2007) Transglutaminase 2 inhibitors and their therapeutic role in disease states, Pharmacol. Ther. 115(2), 232-245.
32. Silverman, R. B. (1988) Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology. CRC Press, Boca Raton, FL.
33. Silverman, R. B. (2000) The Organic Chemistry of Enzyme-Catalyzed Reactions. Academic Press, San Diego, CA.
34. Kitz, R. andWilson, I. B. (1962) Esters ofMethanesulfonic Acid as Irreversible Inhibitors of Acetylcholinesterase, J. Biol. Chem. 237(10), 3245-3249.35.
35. Tian,W. X. and Tsou, C. L. (1982) Determination of the rate-constant of enzyme modification by measuring the substrate reaction in the presence of the modifier, Biochemistry 21(5), 1028-1032.
36. Gray, P. J. and Duggleby, R. G. (1989) Analysis of kinetic data for irreversible enzyme inhibition, Biochem. J. 257(2), 419-424.
37. Powers, J. C., et al. (2002) Irreversible inhibitors of serine, cysteine, and threonine proteases, Chem. Rev. 102(12), 4639-4750.
38. Beynon, R. J. and Bond, J. S. (1989) Proteolytic Enzymes: A Practical Approach. IRL Press, Oxford, England.
39. Folk, J. E. and Cole, P. W. (1966) Identification of a functional cysteine essential for the activity of guinea pig liver transglutaminase, J. Biol. Chem. 241(13), 3238-3240.
40. Pardin, C., et al. (2006) Synthesis and evaluation of peptidic irreversible inhibitors of tissue transglutaminase, Bioorg. Med. Chem. 14(24), 8379-8385.
41. Castelhano, A. L., et al. (1988) Synthesis, chemistry, and absolute-configuration of novel transglutaminase inhibitors containing a 3-halo-4,5-dihydroisoxazole, Bioorg. Chem. 16(3), 335-340.
42. Tso, J. Y., et al. (1980) Mechanism of inactivation of glutamine amidotransferases by the antitumor drug L-(alpha S, 5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125), J. Biol. Chem. 255(14), 6734-6738.
43. Auger, M., et al. (1993) Solid-state C-13 NMR-study of a transglutaminase inhibitor adduct, Biochemistry 32(15), 3930-3934.
44. Watts, R. E., et al. (2006) Structure-activity relationship analysis of the selective inhibition of transglutaminase 2 by dihydroisoxazoles, J. Med. Chem. 49(25), 7493-7501.
45. Hausch, F., et al. (2003) Design, synthesis, and evaluation of gluten peptide analogs as selective inhibitors of human tissue transglutaminase, Chem. Biol. 10(3), 225-231.
46. Shan, L., et al. (2002) Structural basis for gluten intolerance in Celiac sprue, Science 297(5590), 2275-2279.
47. Pliura, D. H., et al. (1992) Irreversible inhibition of transglutaminases by sulfonium methylketones-optimization of specificity and potency with omega-aminoacyl spacers, J. Enzyme Inhib. 6(3), 181-194.
48. Griffin, M., et al. (2008) Synthesis of potent water-soluble tissue transglutaminase inhibitors, Bioorg. Med. Chem. Lett. 18(20), 5559-5562.
49. Slaughter, T. F., et al. (1992) A microtiter plate transglutaminase assay utilizing 5-(biotinamido)pentylamine as substrate, Anal. Biochem. 205(1), 166-171.
50. Freund, K. F., et al. (1994) Transglutaminase inhibition by 2-[(2-oxopropyl)thio]imidazolium derivatives: mechanism of factor XIIIa inactivation, Biochemistry 33(33), 10109-10119.
51. Leung-Toung, R., et al. (2002) Thiol-dependent enzymes and their inhibitors: a review, Curr. Med. Chem. 9(9), 979-1002.
52. Tam, T. F., et al. (2005) Medicinal chemistry and properties of 1,2,4-thiadiazoles, Mini-Rev. Med. Chem. 5(4), 367-379.53.
53. Marrano, C., et al. (2001a) Synthesis and evaluation of novel dipeptide-bound 1,2,4-thiadiazoles as irreversible inhibitors of guinea pig liver transglutaminase, Bioorg. Med. Chem. 9(12), 3231-3241.
54. Keillor, J. W., et al. (2008) The bioorganic chemistry of transglutaminase-from mechanism to inhibition and engineering, Can. J. Chem.-Revue Canadienne De Chimie 86(4), 271-276.
55. Gillet, S. M. F. G., et al. (2004) Expression and rapid purification of highly active hexahistidine-tagged guinea pig liver transglutaminase, Protein Expr. Purifi. 33(2), 256-264.
56. Gillet, S. M. F. G., et al. (2005) A direct fluorometric assay for tissue transglutaminase, Anal. Biochem. 347(2), 221-226.
57. Halim, D., et al. (2007) Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors, Bioorg. Med. Chem. Lett. 17(2), 305-308.
58. de Macedo, P., et al. (2002) Synthesis of dipeptide-bound epoxides and alpha,betaunsaturated amides as potential irreversible transglutaminase inhibitors, Bioorg. Med. Chem. 10(2), 355-360.
59. Marrano, C., et al. (2001b) Evaluation of novel dipeptide-bound a,b-unsaturated amides and epoxides as irreversible inhibitors of guinea pig liver transglutaminase, Bioorg. Med. Chem. 9, 1923-1928.
60. Tate, S. S. and Meister, A. (1985) Gamma-glutamyl-transferase transpeptidase from kidney, Methods Enzymol. 113, 400-419.
61. Pinkas, D. M., et al. (2007) Transglutaminase 2 undergoes a large conformational change upon activation, Plos Biol. 5(12), 2788-2796.
62. Lai, T. S., et al. (2008) Identification of chemical inhibitors to human tissue transglutaminase by screening existing drug libraries, Chem. Biol. 15(9), 969-978.
63. Case, A. and Stein, R. L. (2007) Kinetic analysis of the interaction of tissue transglutaminase with a nonpeptidic slow-binding inhibitor, Biochemistry 46(4), 1106-1115.
64. Casadio, R., et al. (1999) The structural basis for the regulation of tissue transglutaminase by calcium ions, Eur. J. Biochem. 262(3), 672-679.
65. Di Venere, A., et al. (2000) Opposite effects of Ca2+ and GTP binding on tissue transglutaminase tertiary structure, J. Biol. Chem. 275(6), 3915-3921.
66. Begg, G. E., et al. (2006) Mechanism of allosteric regulation of transglutaminase 2 by GTP, Proc. Natl. Acad. Sci. U.S.A. 103(52), 19683-19688.
67. Pardin, C., et al. (2009) Photolabeling of tissue transglutaminase reveals the binding mode of potent cinnamoyl inhibitors, Biochemistry 48(15), 3346-3353.
68. Silverman, R. B. (1992) The Organic Chemistry of Drug Design and Drug Action. Academic Press, San Diego.
69. Barsigian, C., et al. (1991) Tissue (type II) transglutaminase covalently incorporates itself, fibrinogen, or fibronectin into high molecular weight complexes on the extracellular surface of isolated hepatocytes. Use of 2-[(2-oxopropyl)thio] imidazolium derivatives as cellular transglutaminase inactivators, J. Biol. Chem. 266(33), 22501-22509.70.
70. Balklava, Z., et al. (2002) Analysis of tissue transglutaminase function in the migration of Swiss 3T3 fibroblasts, J. Biol. Chem. 277(19), 16567-16575.
71. Maiuri, L., et al. (2005) Unexpected role of surface transglutaminase type II in celiac disease, Gastroenterology 129(5), 1400-1413.
72. Yuan, L., et al. (2005) Tissue transglutaminase 2 inhibition promotes cell death and chemosensitivity in glioblastomas, Molecular Cancer Therapeutics, 4(9), 1293-1302.
73. Yuan, L., et al. (2007) Transglutaminase 2 inhibitor, KCC009, disrupts fibronectin assembly in the extracellular matrix and sensitizes orthotopic glioblastomas to chemotherapy, Oncogene 26(18), 2563-2573.
74. Al-Jallad,H. F., et al. (2009) Inhibition of osteoblast differentiation by a transglutaminasespecific inhibitor targets crosslinking activity of cell surface and extracellular factor XIIIIA, but not transglutaminase 2, Bone 44(2), S310-S310.
75. Chabot, N., et al. (2010) Fluorescent probes of tissue transglutaminase reveal its role in arterial stiffening, Chem. Biol. 17(10), 1143-1150.