Cinnamoyl inhibitors of tissue transglutaminase

Journal of Organic Chemistry

Volumn 73, Issue 15, 2008, Pages 5766-5775

  Pardin, Christophe ^a   Pelletier, Joelle N ^a   Lubell, William D ^a   Keillor, Jeffrey W ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; PLANTS (BOTANY);

BIOLOGICAL PROCESSING; GUINEA PIGS; INTERMOLECULAR CROSS-LINKING; KINETIC EVALUATION; POTENT INHIBITORS; TISSUE TRANSGLUTAMINASE (TTGASE); TRANSGLUTAMINASE (TGASE); TRANSGLUTAMINASES;

HYDROGELS;

3 (4 NITROPHENYL) 1 (PYRIDIN 3 YL)PROP 2 EN 1 ONE; 4 NITROCINNAMOYL IMIDAZOLYL AMIDE; 4 NITROCINNAMOYL OXYBENZOTRIAZOLYL AMIDE; AMIDE; BENZOTRIAZOLE DERIVATIVE; CHALCONE DERIVATIVE; CINNAMIC ACID DERIVATIVE; ENZYME INHIBITOR; HETEROCYCLIC COMPOUND; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE; PYRIDINE DERIVATIVE; TISSUE TRANSGLUTAMINASE INHIBITOR;

ARTICLE; BINDING COMPETITION; CHEMICAL REACTION KINETICS; COMPETITIVE INHIBITION; CROSS LINKING; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SUBSTRATE; GUINEA PIG; IC 50; MOLECULAR INTERACTION;

AMIDES; CINNAMATES; CROSS-LINKING REAGENTS; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; GTP-BINDING PROTEINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSGLUTAMINASES;

EID: 48249124215     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8004843     Document Type: Article

References (50)

1. Levistzki, A.; Willingham, M.; Pastan, I. H. Evidence for participation of transglutaminase in receptor-mediated endocytosis. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2706-2710.
2. Davies, P. J.; Davies, D. R.; Levitzki, A.; Maxfield, F. R.; Milhaud, P.; Willingham, M. C.; Pastan, I. H. Transglutaminase is essential in receptor-mediated endocytosis of α2-macroglobulin and polypeptide hormones. Nature (London) 1980, 283, 162-167.
3. Fesus, L.; Thomazy, V.; Falus, A. Induction and activation of tissue transglutaminase during programmed cell death. FEBS Lett. 1987, 224, 104-108.
4. Birckbichler, P. J.; Orr, G. R.; Patterson, M. K.; Conway, E.; Carter, H. A.; Maxwell, M. D. Enhanced transglutaminase activity in transformed human lung fibroblast cells after exposure to sodium butyrate. Biochim. Biophys. Acta 1983, 763, 27-34.
5. Lorand, L. Fibrinoligase: the fibrin-stabilizing factor system of blood plasma. Ann. N.Y. Acad. Sci. 1972, 202, 6-30.
6. Pisano, J. J.; Finlayson, J. S.; Peyton, M. P. Cross-link in Fibrin Polymerized by Factor XIII: ∈-(γ-Glutamyl)lysine. Science 1968, 160, 892-893.
7. Candi, E.; Tarcsa, E.; Digiovanna, J. J.; Compton, J. G.; Elias, P. M.; Marekov, L. N.; Steinert, P. M. A highly conserved lysine residue on the head domain of type II keratins is essential for the attachment of keratin intermediate filaments to the cornified cell envelope through isopeptide crosslinking by transglutaminases. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 2067-2072.
8. De Young, L.; Ballaron, S.; Epstein, W. Transglutaminase Activity in Human and Rabbit Ear Comedogenesis: A Histochemical Study. J. Invest. Dermatol. 1984, 82, 275-279.
9. Azari, P.; Rahim, J.; Clarkson, D. P. Transglutaminase activity in normal and hereditary cataractous rat lens and its partial purification. Curr. Eye. Res. 1981, 463-469.
10. Fesus, L. Transglutaminase activation: significance with respect to immunologic phenomena. Surv. Immunol. Res. 1982, 1, 297-304.
11. Schroeder, W. T.; Thatcher, S. M.; Stewart-Galetka, S.; Annarella, M.; Chema, D.; Siciliano, M. J.; Davies, P. J. A.; Tang, H. Y.; Sowa, B. A.; Duvic, M. Type I Keratinocyte Transglutaminase: Expression in Human Skin and Psoriasis. J. Invest. Dermatol. 1992, 99, 27-34.
12. Selkoe, D. J.; Abraham, C.; Ihara, Y. Brain Transglutaminase: In vitro Crosslinking of Human Neurofilament Proteins into Insoluble Polymers. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 6070-6074.
13. Norlund, M. A.; Lee, J. M.; Zainelli, G. M.; Muma, N. A. Elevated transglutaminase-induced bonds in PHF tau in Alzheimer's disease. Brain Res. 1999, 851, 154-163.
14. Dedeoglu, A.; Kubilus, J. K.; Jeitner, T. M.; Matson, S. A.; Bogdanov, M.; Kowall, N. W.; Matson, W. R.; Cooper, A. J. L.; Ratan, R. R.; Beal, M. F. Therapeutic Effects of Cystamine in a Murine Model of Huntington's Disease. J. Neurosci. 2002, 22, 8942-8950.
15. Mastroberardino, P. G.; Iannicola, C.; Nardacci, R.; Bernassola, F.; De Laurenzi, V.; Melino, G.; Moreno, S.; Pavone, F.; Oliverio, S.; Fesus, L. 'Tissue' transglutaminase ablation reduces neuronal death and prolongs survival in a mouse model of Huntington's disease. Cell Death Differ. 2002, 9, 873-880.
16. Piper, J. L.; Gray, G. M.; Khosla, C. High Selectivity of Human Tissue Transglutaminase for Immunoactive Gliadin Peptides: Implications for Celiac Sprue. Biochemistry 2002, 41, 386-393.
17. Choi, K.; Siegel, M.; Piper, J. L.; Yuan, L.; Cho, E.; Strnad, P.; Omary, B.; Rich, K. M.; Khosla, C. Chemistry and Biology of Dihydroisoxazole Derivatives: Selective Inhibitors of Human Transglutaminase 2. Chem. Biol. 2005, 12, 469-475.
18. Keillor, J. W. Tissue Transglutaminase Inhibitors. Chem. Biol. 2005, 12, 410-412.
19. Lorand, L.; Rule, N. G.; Ong, H. H.; Furlanetto, R.; Jacobsen, A.; Downey, J.; Oner, N.; Bruner-Lorand, J. Amine specificity in transpeptidation. Inhibition of fibrin cross-linking. Biochemistry 1968, 7, 1214-1223.
20. Stenberg, P.; Nilsson, I.; Erickson, O.; Lunden, R. Fibrin-stabilizing factor inhibitors. II. The inhibitory properties of various aliphatic amines. Acta Pharm. Sued. 1971, 8, 415-422.
21. Holbrook, J. J.; Cooke, R. D.; Kingston, I. B. The amino acid sequence around the reactive cysteine residue in human plasma Factor XIII. Biochem. J. 1973, 135, 901-903.
22. Chung, S. I.; Lewis, M. S.; Folk, J. E. Relationships of the Catalytic Properties of Human Plasma and Platelet Transglutaminases (Activated Blood Coagulation Factor XIII) to Their Subunit Structures. J. Biol. Chem. 1974, 249, 940-950.
23. Curtis, C. G.; Brown, K. L.; Credo, R. B.; Domanik, R. A.; Gray, A.; Stenberg, P.; Lorand, L. Calcium-dependent unmasking of active center cysteine during activation of fibrin stabilizing factor. Biochemistry 1974, 13, 3774-3780.
24. Folk, J. E.; Finlayson, J. S. The epsilon-(gamma-glutamyl)lysine crosslink and the catalytic role of transglutaminases. Adv. Protein Chem. 1977, 31, 1-133.
25. Gross, M.; Whetzel, N. K.; Folk, J. E. Alkyl isocyanates as active site-directed inactivators of guinea pig liver transglutaminase. J. Biol. Chem. 1975, 250, 7693-7699.
26. Lee, K. N.; Fesus, L.; Yancey, S. T.; Girard, J. E.; Chung, S. I. Development of selective inhibitors of transglutaminase. Phenylthiourea derivatives. J. Biol. Chem. 1985, 260, 14689-14694.
27. Castelhano, A. L.; Billedeau, R.; Pliura, D. H.; Bonaventura, B. J.; Krantz, A. Synthesis, chemistry and absolute configuration of novel transglutaminase inhibitors containing a 3-halo-4,5-dihydroisoxazole. Bioorg. Chem. 1988, 16, 335-340.
28. 13C NMR study of a transglutaminase-inhibitor adduct. Biochemistry 1993, 32, 3930-3934.
29. Pliura, D. H.; Bonaventura, B. J.; Pauls, H. W.; Killackey, J. F.; Krantz, A. Irreversible inhibition of transglutaminases by sulfonium methylketones: optimization of specificity and potency with ω-aminoacyl spacers. J. Enzyme Inhib. 1992, 6, 181-194.
30. Freund, K. F.; Doshi, K. P.; Gaul, S. L.; Claremon, D. A.; Remy, D. C.; Baldwin, J. J.; Pitzenberger, S. M.; Stern, A. M. Transglutaminase inhibition by 2-[(2-oxopropyl)thio]imidazolium derivatives: mechanism of factor XIIIa inactivation. Biochemistry 1994, 33, 10109-10119.
31. Doyle, P. M.; Harris, C. J.; Carter, K. R.; Simpkin, D. S. A.; Bailey-Smith, P.; Stone, D.; Russel, L.; Blackwell, G. Peptides incorporating electrophilic glutamine analogues as potential transglutaminase inhibitors. Biochem. Soc. Trans. 1990, 18, 1318-1320.
32. Marrano, C.; de Macedo, P.; Gagnon, P.; Lapierre, D.; Gravel, C.; Keillor, J. W. Synthesis and Evaluation of Dipeptide-Bound 1,2,4-Thiadiazoles as Irreversible Transglutaminase Inhibitors. Bioorg. Med. Chem. 2001, 9, 3231-3241.
33. Marrano, C.; de Macedo, P.; Keillor, J. W. Evaluation of Novel Dipeptide-Bound α,β-Unsaturated Amides and Epoxides as Irreversible Inhibitors of Guinea Pig Liver Transglutaminase. Bioorg. Med. Chem. 2001, 9, 1923-1928.
34. Keillor, J. W.; Lubell, W. D.; Pardin, C. Cinnamoyl Inhibitors of transglutaminase. PCT Int. Appl. filed 29 May 2008 from U.S. Patent 60,940,523.
35. Duval, E.; Case, A.; Stein, R. L.; Cuny, G. D. Structure-activity relationship study of novel tissue transglutaminase inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 1885-1889.
36. Chica, R. A.; Gagnon, P.; Keillor, J. W.; Pelletier, J. N. Tissue transglutaminase acylation: proposed role of conserved active site Tyr and Trp residues revealed by molecular modelling of peptide substrate binding. Protein Sci. 2004, 13, 979-991.
37. Gobec, S.; Sova, M.; Kristan, K.; Rižner, T. L. Cinnamic acid esters as potent inhibitors of fungal 17β-hydroxysteroid dehydrogenase - a model enzyme of the short-chain dehydrogenase/reductase superfamily. Bioorg. Med. Chem. Lett. 2004, 14, 3933-3936.
38. Penning, T. D.; Russell, M. A.; Chen, B. B.; Chen, H. Y.; Desai, B. N.; Docter, S. H.; Edwards, D. J.; Gesiki, G. J.; Freeman, S. K.; Hanneke, M. L.; Shannon, K. E.; Westlin, M, M.; Nickols, G. A. Synthesis of cinnamic acids and related isosteres as potent and selective αvβ3 receptor antagonists. Bioorg. Med. Chem. Lett. 2004, 14, 1471-1476.
39. Adisakwattana, S.; Sookkongwareeb, K.; Roengsumran, S.; Petsom, A.; Ngamrojnavanich, N.; Chavasiri, W.; Deesamer, S.; Yibchok-anun, S. Structure - activity relationships of trans-cinnamic acid derivatives on α-glucosidase inhibition. Bioorg. Med. Chem. Lett. 2004, 14, 2893-2896.
40. Bellamy, F. D.; Ou, K. Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium. Tetrahedron Lett. 1984, 25, 839-842.
41. Nelson, A. T.; Houlihan, W. J., The Aldol Condensation in Organic Reactions. Wiley: New York, 1968; p 44.
42. Gagnon, P.; Huang, X.; Therrien, E.; Keillor, J. W. Peptide Coupling of Unprotected Amino Acids Through In Situ p-Nitrophenyl Ester Formation. Tetrahedron Lett. 2002, 43, 7717-7719.
43. Gillet, S. M. F. G.; Chica, R. A.; Keillor, J. W.; Pelletier, J. N. Expression in Escherichia coli and Purification of Hexahistidine-Tagged Guinea Pig Liver Transglutaminase. Prot. Exp. Purif. 2004, 33, 256-264.
44. Aeschlimann, D.; Paulsson, M. Transglutaminases: protein cross-linking enzymes in tissues and body fluids. Thromb. Haemost. 1994, 71, 402-415.
45. Leblanc, A.; Gravel, C.; Labelle, J.; Keillor, J. W. Kinetic Studies of Guinea Pig Liver Transglutaminase Reveal a General Base Catalyzed Deacylation Mechanism. Biochemistry 2001, 40, 8335-8342.
46. Case, A.; Stein, R. L. Kinetic Analysis of the Interaction of Tissue Transglutaminase with a Nonpeptidic Slow-Binding Inhibitor. Biochemistry 2007, 46, 1106-1115.
47. Pinkas, D. M.; Strop, P.; Brunger, A. T.; Khosla, C. Transglutaminase 2 undergoes a large conformational change upon activation. PLoS Biol. 2007, 5, e327.
48. Liu, S.; Cerione, R. A.; Clardy, J. Structural basis for the guanine nucleotide-binding activity of tissue transglutaminase and its regulation of transamidation activity. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 2743-2747.
49. Nogushi, K.; Ishikawa, K.; Yokoyama, K.-I.; Ohtsuka, T.; Nio, N.; Suzuki, E.-I. Crystal Structure of Red Sea Bream Transglutaminase. J. Biol. Chem. 2001, 276, 12055-12059.
50. Day, N.; Keillor, J. W. A Continuous Spectrophotometric Linked-Enzyme Assay for Transglutaminase Mediated Transpeptidation Activity. Anal. Biochem. 1999, 274, 141-144.