Recent advances in the development of tissue transglutaminase (TG2) inhibitors

Amino Acids

Volumn 44, Issue 1, 2013, Pages 119-127

  Badarau, E ^a   Collighan, R J ^a   Griffin, M ^a  

^a ASTON UNIVERSITY   (United Kingdom)

Author keywords

Inhibitors; Structure activity relationships (SAR); TG2; Tissue transglutaminase

Indexed keywords

3 (3,5 DIBROMO 4 HYDROXYBENZYLIDENE) 1,3 DIHYDRO 5 IODO 2 INDOLONE; ACYLTRANSFERASE INHIBITOR; BETA AMINOETHYLKETONE DERIVATIVE; BETA LAPACHONE; BLOOD CLOTTING FACTOR 13A; CASPASE 3; CINNAMOYL DERIVATIVE; DIHYDROISOXAZOLE DERIVATIVE; MENADIONE; METHYL 3,4 DEPHOSTATIN; NSC 95397; OXINDOLE; PEPTIDYLMETHYLKETONE DERIVATIVE; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE 2; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE 2 INHIBITOR; TRIAZOLE DERIVATIVE; TYRPHOSTIN 47; UNCLASSIFIED DRUG; ZM 39923;

BINDING AFFINITY; DIABETIC NEPHROPATHY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG STRUCTURE; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; IC 50; KIDNEY SCAR; NONHUMAN; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION;

ANIMALS; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; HUMANS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; INHIBITORY CONCENTRATION 50; MOLECULAR TARGETED THERAPY; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSGLUTAMINASES;

MAMMALIA;

EID: 84871981788     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-011-1188-4     Document Type: Review

References (51)

1. Ahvazi B, Boeshans KM, Idler W, Baxa U, Steinert PM, Rastinejad F (2004) Structural basis for the coordinated regulation of transglutaminase 3 by guanine nucleotides and calcium/magnesium. J Biol Chem 279(8):7180-7192
2. Baumgartner W, Golenhofen N, Weth A, Hiiragi T, Saint R, Griffin M, Drenckhahn D (2004) Role of transglutaminase 1 in stabilisation of intercellular junctions of the vascular endothelium. Histochem Cell Biol 122(1):17-25
3. Brunner J (1993) New photolabeling and crosslinking methods. Annu Rev Biochem 62:483-514
4. Candi E, Paradisi A, Terrinoni A, Pietroni V, Oddi S, Cadot B, Jogini V, Meiyappan M, Clardy J, Finazzi-Agro A, Melino G (2004) Transglutaminase 5 is regulated by guanine-adenine nucleotides. Biochem J 381(Pt 1):313-319
5. Case A, Stein RL (2007) Kinetic analysis of the interaction of tissue transglutaminase with a nonpeptidic slow-binding inhibitor. Biochemistry 46(4):1106-1115
6. Castelhano AL, Billedeau R, Pliura DH, Bonaventura BJ, Krantz A (1988) Synthesis, chemistry, and absolute configuration of novel transglutaminase inhibitors containing a 3-halo-4, 5-dihydroisoxazole. Bioorg Chem 16(3):335-340
7. Chen JS, Mehta K (1999) Tissue transglutaminase: an enzyme with a split personality. Int J Biochem Cell Biol 31(8):817-836
8. Chica RA, Gagnon P, Keillor JW, Pelletier JN (2004) Tissue transglutaminase 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
9. Choi K, Siegel M, Piper JL, Yuan L, Cho E, Strnad P, Omary B, Rich KM, Khosla C (2005) Chemistry and biology of dihydroisoxazole derivatives: selective inhibitors of human transglutaminase 2. Chem Biol 12(4):469-475
10. Chung SI, Folk JE (1970) Mechanism of the inactivation of guinea pig liver transglutaminase by tetrathionate. J Biol Chem 245(4):681-689
11. Colak G, Keillor JW, Johnson GV (2011) Cytosolic guanine nucledotide binding deficient form of transglutaminase 2 (R580a) potentiates cell death in oxygen glucose deprivation. PLoS One 6(1):e16665
12. Connellan JM, Folk JE (1969) Mechanism of the inactivation of guinea pig liver transglutaminase by 5, 5′-dithiobis-(2-nitrobenzoic acid). J Biol Chem 244(12):3173-3181
13. Dafik L, Khosla C (2011) Dihydroisoxazole analogs for labeling and visualization of catalytically active transglutaminase 2. Chem Biol 18(1):58-66
14. de Macedo P, Marrano C, Keillor JW (2002) Synthesis of dipeptide-bound epoxides and alpha, beta-unsaturated amides as potential irreversible transglutaminase inhibitors. Bioorg Med Chem 10(2):355-360
15. Duval E, Case A, Stein RL, Cuny GD (2005) Structure-activity relationship study of novel tissue transglutaminase inhibitors. Bioorg Med Chem Lett 15(7):1885-1889
16. Griffin M, Casadio R, Bergamini CM (2002) Transglutaminases: nature's biological glues. Biochem J 368(Pt 2):377-396
17. Griffin M, Coutts IG, Saint RE (2004) Novel compounds and methods of using the same. World Patent WO 2004/113363 A2, 29 December 2004
18. Griffin M, Mongeot A, Collighan R, Saint RE, Jones RA, Coutts IG, Rathbone DL (2008) Synthesis of potent water-soluble tissue transglutaminase inhibitors. Bioorg Med Chem Lett 18(20):5559-5562
19. Halim D, Caron K, Keillor JW (2007) Synthesis and evaluation of peptidic maleimides as transglutaminase inhibitors. Bioorg Med Chem Lett 17(2):305-308
20. Hitomi K, Kitamura M, Sugimura Y (2009) Preferred substrate sequences for transglutaminase 2: screening using a phage-displayed peptide library. Amino Acids 36(4):619-624
21. Huang L, Haylor JL, Hau Z, Jones RA, Vickers ME, Wagner B, Griffin M, Saint RE, Coutts IG, El Nahas AM, Johnson TS (2009) Transglutaminase inhibition ameliorates experimental diabetic nephropathy. Kidney Int 76(4):383-394
22. Johnson TS, Fisher M, Haylor JL, Hau Z, Skill NJ, Jones R, Saint R, Coutts I, Vickers ME, El Nahas AM, Griffin M (2007) Transglutaminase inhibition reduces fibrosis and preserves function in experimental chronic kidney disease. J Am Soc Nephrol 18(12):3078-3088
23. Johnson T, Fisher M, Haylor J, Hau Z, Skill N, Jones R, Saint R, Coutts I, El Nahas A, Griffin M (2008) Transglutaminase inhibition ameliorates tissue scarring and fibrosis: experience in a kidney model. J Am Soc 14(8):2052
24. Jones RA, Kotsakis P, Johnson TS, Chau DY, Ali S, Melino G, Griffin M (2006) Matrix changes induced by transglutaminase 2 lead to inhibition of angiogenesis and tumor growth. Cell Death Differ 13(9):1442-1453
25. Klock C, Jin X, Choi K, Khosla C, Madrid PB, Spencer A, Raimundo BC, Boardman P, Lanza G, Griffin JH (2011) Acylideneoxoindoles: a new class of reversible inhibitors of human transglutaminase 2. Bioorg Med Chem Lett 21(9):2692-2696
26. Lai TS, Liu Y, Tucker T, Daniel KR, Sane DC, Toone E, Burke JR, Strittmatter WJ, Greenberg CS (2008) Identification of chemical inhibitors to human tissue transglutaminase by screening existing drug libraries. Chem Biol 15(9):969-978
27. Leblanc A, Gravel C, Labelle J, Keillor JW (2001) Kinetic studies of guinea pig liver transglutaminase reveal a general-base-catalyzed deacylation mechanism. Biochemistry 40(28):8335-8342
28. Lorand L, Conrad SM (1984) Transglutaminases. Mol Cell Biochem 58(1):9-35
29. Marrano C, de Macedo P, Gagnon P, Lapierre D, Gravel C, Keillor JW (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
30. Marrano C, de Macedo P, Keillor JW (2001b) Evaluation of novel dipeptide-bound alpha, beta-unsaturated amides and epoxides as irreversible inhibitors of guinea pig liver transglutaminase. Bioorg Med Chem 9(7):1923-1928
31. McGovern SL, Helfand BT, Feng B, Shoichet BK (2003) A specific mechanism of nonspecific inhibition. J Med Chem 46(20):4265-4272
32. Okauchi M, Xi G, Keep RF, Hua Y (2009) Tissue-type transglutaminase and the effects of cystamine on intracerebral hemorrhage-induced brain edema and neurological deficits. Brain Res 1249:229-236
33. Ozaki S, Ebisui E, Hamada K, Goto J, Suzuki AZ, Terauchi A, Mikoshiba K (2010) Potent transglutaminase inhibitors, aryl beta-aminoethyl ketones. Bioorg Med Chem Lett 20(3):1141-1144
34. Ozaki S, Ebisui E, Hamada K, Suzuki AZ, Terauchi A, Mikoshiba K (2011) Potent transglutaminase inhibitors, dithio beta-aminoethyl ketones. Bioorg Med Chem Lett 21(1):377-379
35. Pardin C, Gillet SM, Keillor JW (2006) Synthesis and evaluation of peptidic irreversible inhibitors of tissue transglutaminase. Bioorg Med Chem 14(24):8379-8385
36. Pardin C, Pelletier JN, Lubell WD, Keillor JW (2008a) Cinnamoyl inhibitors of tissue transglutaminase. J Org Chem 73(15):5766-5775
37. Pardin C, Roy I, Lubell WD, Keillor JW (2008b) Reversible and competitive cinnamoyl triazole inhibitors of tissue transglutaminase. Chem Biol Drug Des 72(3):189-196
38. Pardin C, Roy I, Chica RA, Bonneil E, Thibault P, Lubell WD, Pelletier JN, Keillor JW (2009) Photolabeling of tissue transglutaminase reveals the binding mode of potent cinnamoyl inhibitors. Biochemistry 48(15):3346-3353
39. Pinkas DM, Strop P, Brunger AT, Khosla C (2007) Transglutaminase 2 undergoes a large conformational change upon activation. PLoS Biol 5(12):e327
40. Pliura DH, Bonaventura BJ, Pauls HW, Killackey JF, Krantz A (1992) Irreversible inhibition of transglutaminases by sulfonium methylketones: optimization of specificity and potency with omega-aminoacyl spacers. J Enzym Inhib 6(3):181-194
41. Schaertl S, Prime M, Wityak J, Dominguez C, Munoz-Sanjuan I, Pacifici RE, Courtney S, Scheel A, Macdonald D (2010) A profiling platform for the characterization of transglutaminase 2 (TG2) inhibitors. J Biomol Screen 15(5):478-487
42. Siegel M, Khosla C (2007) Transglutaminase 2 inhibitors and their therapeutic role in disease states. Pharmacol Ther 115(2):232-245
43. Siegel M, Strnad P, Watts RE, Choi K, Jabri B, Omary MB, Khosla C (2008) Extracellular transglutaminase 2 is catalytically inactive, but is transiently activated upon tissue injury. PLoS One 3(3):e1861
44. Sletten EM, Bertozzi CR (2009) Bioorthogonal chemistry: fishing for selectivity in a sea of functionality. Angew Chem Int Ed Engl 48(38):6974-6998
45. Strnad P, Siegel M, Toivola DM, Choi K, Kosek JC, Khosla C, Omary MB (2006) Pharmacologic transglutaminase inhibition attenuates drug-primed liver hypertrophy but not Mallory body formation. FEBS Lett 580(9):2351-2357
46. Sugimura Y, Yamashita H, Hitomi K (2011) Screening of substrate peptide sequences for tissue-type transglutaminase (TGase 2) using T7 phage cDNA library. Cytotechnology 63(2):111-118
47. Telci D, Collighan RJ, Basaga H, Griffin M (2009) Increased TG2 expression can result in induction of transforming growth factor β1, causing increased synthesis and deposition of matrix proteins, which can be regulated by nitric oxide. J Biol Chem 284(43):29547-29558
48. Verhaar R, Jongenelen CA, Gerard M, Baekelandt V, Van Dam AM, Wilhelmus MM, Drukarch B (2011) Blockade of enzyme activity inhibits tissue transglutaminase-mediated transamidation of alpha-synuclein in a cellular model of Parkinson's disease. Neurochem Int 58(7):785-793
49. Watts RE, Siegel M, Khosla C (2006) Structure-activity relationship analysis of the selective inhibition of transglutaminase 2 by dihydroisoxazoles. J Med Chem 49(25):7493-7501
50. Wodzinska JM (2005) Transglutaminases as targets for pharmacological inhibition. Mini Rev Med Chem 5(3):279-292
51. Ziebell MR, Nirthanan S, Husain SS, Miller KW, Cohen JB (2004) Identification of binding sites in the nicotinic acetylcholine receptor for [3H]azietomidate, a photoactivatable general anesthetic. J Biol Chem 279(17):17640-17649