Tumor necrosis factor alpha converting enzyme: An encouraging target for various inflammatory disorders

Chemical Biology and Drug Design

Volumn 75, Issue 5, 2010, Pages 415-443

  Bahia, Malkeet S ^a   Silakari, Om ^a  

^a PUNJABI UNIVERSITY   (India)

Author keywords

Autoimmune diseases; Cancer; Inflammatory disorders; Rheumatoid arthritis; Tumor necrosis factor alpha; Tumor necrosis factor converting enzyme (TACE)

Indexed keywords

BB 1101; BMS 561392; CGS 27023 A; CGS 27023A; DPC 333; GELATINASE B; GW 3333; GW 9471; HYDROXAMIC ACID; IK 682; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; MARIMASTAT; MATRIX METALLOPROTEINASE INHIBITOR; MITOGEN ACTIVATED PROTEIN KINASE; N1 [2,2 DIMETHYL 1 [(METHYLAMINO)CARBONYL]PROPYL] N4 HYDROXY 2 (2 METHYLPROPYL)BUTANEDIAMIDE; PKF 242 484; PRINOMASTAT; RO 32 7315; THIOL DERIVATIVE; TMI 1; TUMOR NECROSIS FACTOR ALPHA; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME INHIBITOR; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AUTOIMMUNE DISEASE; BINDING SITE; CATALYSIS; DISEASE COURSE; DRUG DESIGN; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SPECIFICITY; ENZYME STRUCTURE; HUMAN; LIVER TOXICITY; MUSCLE ATROPHY; MUSCULOSKELETAL DISEASE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; REVIEW; RHEUMATOID ARTHRITIS; STRUCTURE ACTIVITY RELATION;

ADAM PROTEINS; ANTIRHEUMATIC AGENTS; ARTHRITIS, RHEUMATOID; CATALYTIC DOMAIN; HUMANS; MATRIX METALLOPROTEINASES; NF-KAPPA B; PROTEASE INHIBITORS; TUMOR NECROSIS FACTOR-ALPHA;

EID: 77950003296     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2010.00950.x     Document Type: Review

References (125)

1. Aggarwal B.B., Kohr W.J., Hass P.E., Moffat B., Spencer S.A., Henzel W.J., Bringman T.S., Nedwin G.E., Goeddel D.V., Harkins R.N. (1985) Human tumor necrosis factor production, purification and characterization. J Biol Chem 260 : 2345 2354.
2. Bemelmans M.H.A., Tits L.J.V., Buurman W.A. (1996) Tumor necrosis factor: function, release and clearance. Crit Rev Immunol 16 : 1 11.
3. Bazzoni F., Beutler B. (1996) The tumor necrosis factor ligand and receptor families. N Engl J Med 334 : 1717 1725.
4. Marcia L.M., Judith M.W., Millard H.L., Robert C.A. (2001) TACE and other ADAM proteases as targets for drug discovery. Drug Discov Today 6 : 417 426.
5. Sekut L., Connolly K.M. (1996) Pathophysiology and regulation of TNF-α in inflammation. Drug News Perspect 9 : 261 269.
6. Rink L., Kirchner H. (1996) Recent progress in the tumor necrosis factor-α field. Int Arch Allergy Immunol 111 : 199 209.
7. Brennan F.M., Maini R.N., Walport M. (1992) TNF-α: a pivotal role in rheumatoid arthritis? Br J Rheumatol 31 : 293 298.
8. Maini R.N., Brennan F.M., Williams R., Chu C.Q., Cope A.P., Gibbons D., Elliot M., Feldmann M. (1993) TNF-α in rheumatoid arthritis and prospects of anti-TNF therapy. Clin Exp Rheumatol 11 : S173 S175.
9. Philip M., Rowley D.A., Schreiber H. (2004) Inflammation as a tumor promoter in cancer induction. Semin Cancer Biol 14 : 433 439.
10. Kitano K., Rivas C.I., Baldwin G.C., Vera J.C., Golde D.W. (1993) Tumor necrosis factor dependent production of human immunodeficiency virus 1 in chronically infected HL-60 cells. Blood 82 : 2742 2748.
11. Hotamisligil G.S., Spiegelman B.M. (1994) Tumor necrosis factor-α: a key component of the obesity diabetes link. Diabetes 43 : 1271 1278.
12. Black R.A. (2002) Tumor necrosis factor-α converting enzyme. Int J Biochem Cell Biol 34 : 1 5.
13. Lucas M.L., Rothwell N.J., Gibson R.M. (2006) The role of inflammation in CNS injury and disease. Br J Pharmacol 147 : S232 S240.
14. Kim J., Remick D.G. (2007) Tumor necrosis factor inhibitors for treatment of asthma. Curr Allergy Asthma Rep 7 : 151 156.
15. Maeda K., Hirota M., Kimura Y., Inoue K., Kuwata K., Ohmuraya M., Ogawa M. (2003) The effect of TNF-α converting enzyme inhibitors on cytokine responses in acute pancreatitis. Int Congr Ser 1255 : 173 175.
16. Amin A.R. (1999) Regulation of tumor necrosis factor-α and tumor necrosis factor converting enzyme in human osteoarthritis. Osteoarthr Cartil 7 : 392 394.
17. Deventer S.J.H.V. (2002) A place of TACE. Gut 51 : 5 6.
18. Grootveld M., McDermott M.F. (2003) BMS-561392 (Bristol-Myers Squibb). Curr Opin Investig Drugs 4 : 598 602.
19. Duan J.J.W., Lu Z., Xue C.B., He X., Seng J.L., Roderick J.J., Wasserman Z.R., Liu R.Q., Covington M.B., Magolda R.L., Newton R.C., Trzaskos J.M., Decicco C.P. (2003) Discovery of N-hydroxy-2(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of TNF-α converting enzyme. Bioorg Med Chem Lett 13 : 2035 2040.
20. Newton R.C., Decicco C.P. (1999) Therapeutic potential and strategies for inhibiting tumor necrosis factor-α. J Med Chem 42 : 2295 2314.
21. Nelson F.C., Zask A. (1999) The therapeutic potential of small molecule TACE inhibitors. Expert Opin Investig Drugs 8 : 383 392.
22. Levin J.I. (2004) The design and synthesis of aryl hydroxamic acid inhibitors of MMPs and TACE. Curr Top Med Chem 4 : 1289 1310.
23. DasGupta S., Murumkar P.R., Giridhar R., Yadav M.R. (2009) Current perspective of TACE inhibitors: a review. Bioorg Med Chem 17 : 444 459.
24. Carswell E.A., Old L.L., Kassel R.L., Green S., Fiore N., Williamson B. (1975) An endotoxin induced serum factor that causes necrosis of tumors. Proc Natl Acad Sci USA 72 : 3666 3670.
25. Muller U., Jongeneel C.V., Nedospasov S.A., Lindahl K.F., Steinmetz M. (1987) Tumor necrosis factor and lymphotoxin genes map close to H-2D in the mouse major histocompatibility complex. Nature 325 : 265 267.
26. Perez C., Albert I., DeFay K., Zachariades N., Gooding L., Kriegler M. (1990) A non-secretable cell surface mutant of tumor necrosis factor (TNF) kills by cell to cell contact. Cell 63 : 251 258.
27. Beutler B., Greenwald D., Hulmes J., Chang M., Pan Y.C.E., Mathison J., Ulevitch R., Cerami A. (1985) Identification of tumor necrosis factor and the macrophage secreted factor cachectin. Nature 316 : 552 554.
28. Aggarwal B.B., Eessalu T.E., Hass P.E. (1985) Characterization of receptors for human tumor necrosis factor and their regulation by gamma interferon. Nature 318 : 665 667.
29. Kolb W.P., Granger G.A. (1968) Lymphocyte in vitro cytotoxicity: characterization of human lymphotoxin. Proc Natl Acad Sci USA 61 : 1250 1255.
30. Xue C.B., He X., Roderick J., Corbett R.L., Duan J.J.W., Liu R.Q., Covington M.B., Newton R.C., Trzaskos J.M., Magolda R.L., Wexler R.R., Decicco C.P. (2003) Rational design, synthesis and structure activity relationships of a cyclic succinate series of TNF-α converting enzyme inhibitors. Part 1: lead identication. Bioorg Med Chem Lett 13 : 4293 4297.
31. Horssen R.V., TenHagen T.L.M., Eggermont A.M.M. (2006) TNF-α in cancer treatment: molecular insights, antitumor effects, and clinical utility. Oncologist 11 : 397 408.
32. Chan F.K.M., Siegel R.M., Lenardo M.J. (2000) Signaling by the TNF receptor superfamily and T-cell homeostasis. Immunity 13 : 419 422.
33. Vandenabeele P., Declercq W., Beyaert R., Fiers W. (1995) Two tumor necrosis factor receptors: structure and function. Trends Cell Biol 5 : 392 399.
34. Tartaglia L.A., Goeddel D.V. (1992) Two TNF receptors. Immunol Today 13 : 151 153.
35. Aggarwal B.B. (2003) Signalling pathways of the TNF superfamily: a double edged sword. Nat Rev Immunol 3 : 745 756.
36. Ashkenazi A., Dixit V.M. (1998) Death receptors: signaling and modulation. Science 281 : 1305 1308.
37. Murray J.A.F., Barbara J., Dunkley S.A., Lopez A.F., Ostade X.V., Condliffe A.M., Haslett C., Dransfield I., Chilvers E.R. (1997) Regulation of neutrophil apoptosis by tumor necrosis factor-α: Requirements for TNF-R55 and TNF-R75 for induction of apoptosis in vitro. Blood 90 : 2772 2783.
38. Jones E.Y., Stuart D.I., Walker N.P.C. (1989) Structure of tumor necrosis factor. Nature 338 : 225 228.
39. Strieter R.M., Kunkel S.L., Bone R.C. (1993) Role of tumor necrosis factor-α in disease states and inflammation. Crit Care Med 21 : S447 S463.
40. Pfeffer K., Matsuyama T., Kundig T.M., Wakeham A., Kishihara K., Shahinian A., Wiegmann K., Ohashi P.S., Kronke M., Mak T.W.(. (1993) Mice deficient for the 55 kD tumor necrosis factor receptor are resistant to endotoxic shock, yet succumb to L. Monocytogenes infection. Cell 73 : 457 467.
41. Chen G., Goeddel D.V. (2002) TNF-R1 signaling: a beautiful pathway. Science 296 : 1634 1635.
42. Wajant H., Pfizenmaier K., Scheurich P. (2003) Tumor necrosis factor signaling. Cell Death Differ 10 : 45 65.
43. Dam H.V., Castellazzi M. (2001) Distinct role of Jun: Fos and Jun: ATF dimmers in oncogenesis. Oncogene 20 : 2453 2464.
44. Gaur U., Aggarwal B.B. (2003) Regulation of proliferation, survival and apoptosis by members of the TNF superfamily. Biochem Pharmacol 66 : 1403 1408.
45. Tracey K., Cerami A. (1990) Metabolic response to cachectin/TNF. N Y Acad Sci 587 : 325 330.
46. Duan J.J.W., Lu Z., Wasserman Z.R., Liu R.Q., Covington M.B., Decicco C.P. (2005) Non-hydroxamate 5-phenylpyrimdine-2,4,6-trione derivatives as selective inhibitors of TACE. Bioorg Med Chem Lett 15 : 2970 2973.
47. Cherney R.C., King W.B., Gilmore J.L., Liu R.Q., Covington M.B., Duan J.J.W., Decicco C.P. (2006) Conversion of potent MMP inhibitors into selective TACE inhibitors. Bioorg Med Chem Lett 16 : 1028 1031.
48. Stocker W., Grams F., Baumann U., Reinemer P., Ruth F.X.G., McKay D.B., Bode W. (1995) The metzincins topological and sequential relations between the astacins, adamalysins, serralysins, and matrixins (collagenases) define a superfamily of zinc peptidases. Protein Sci 4 : 823 840.
49. Black R.A., Rauch C.T., Kozlosky C.J., Peschon J.J., Slack J.L., Wolfson M.F., Castner B.J. et al. (1997) A metalloproteinase disintegrin that releases tumor necrosis factor-α from cells. Nature 385 : 729 733.
50. Gearing A.J.H., Beckett P., Christodoulou M., Churchill M., Clements J., Davidson A.H., Drummond A.H. et al. (1994) Processing of tumor necrosis factor-α precursor by metalloproteinases. Nature 370 : 555 557.
51. Mohler K.M., Sleath P.R., Fitzner J.N., Cerretti D.P., Alderson M., Kerwar S.S., Dauphine S.T. et al. (1994) Protection against a lethal dose of endotoxin by an inhibitor of tumor necrosis factor processing. Nature 370 : 218 220.
52. McGeehan G.M., Becherer J.D., Bast R.C., Boyer C.M., Champion B., Connolly K.M., Conway J.G. et al. (1994) Regulation of tumor necrosis factor-α processing by a metalloproteinase inhibitor. Nature 370 : 558 561.
53. Moss M.L., Jin S.L.C., Millam E., Burkhart W., Carter H.L., Chen W.J., Clay W.C. et al. (1997) Cloning of a disintegrin metalloproteinase that processes precursor tumor necrosis factor-α. Nature 385 : 733 736.
54. Peschon J.J., Slack J.L., Reddy P., Stocking K.L., Sunnaeburg S.W., Lee D.C., Russel W.E. et al. (1998) An essential role for ectodomain shedding in mammalian development. Science 282 : 1281 1284.
55. Mezyk R., Bzowska M., Bereta J. (2003) Structure and functions of tumor necrosis factor-α converting enzyme. Acta Biochim Pol 50 : 625 645.
56. Buxbaum J.D., Liu K.N., Luo Y., Slack J.L., Stocking K.L., Peschon J.J., Johnson R.S., Castner B.J., Cerretti D.P., Black R.A. (1998) Evidence that tumor necrosis factor-α converting enzyme is involved in regulated α-Secretase cleavage of the alzheimer amyloid protein precursor. J Biol Chem 273 : 27765 27767.
57. Marcia L.M., Jorg W.B. (2004) Therapeutic benefits from targeting of ADAM family members. Biochemistry 43 : 7228 7235.
58. Borrell P.M., Rojo F., Albanell J., Baselga J., Arribas J. (2003) TACE is required for the activation of the EGFR by TGF-α in tumors. EMBO J 22 : 1114 1124.
59. Letavic M.A., Axt M.Z., Barberia J.T., Carty T.J., Danley D.E., Geoghegan K.F., Halim N.S. et al. (2002) Synthesis and biological activity of selective pipecolic acid based TNF-α converting enzyme (TACE) inhibitors. Bioorg Med Chem Lett 12 : 1387 1390.
60. Milla M.E., Gonzales P.E., Leonard J.D. (2006) The TACE zymogen. Cell Biochem Biophys 44 : 342 348.
61. Galazka G., Windsor L.J., Hanser H.B., Engler J.A. (1996) APMA (4-aminophenylmercuric acetate) activation of stromelysin-1 involves protein interactions in addition to those with cysteine-75 in the propeptide. Biochemistry 35 : 11221 11227.
62. Wart H.E.V., Hansen H.B. (1990) The cysteine switch: a principle of regulation of metalloprotease activity with potential applicability to the entire matrix metalloprotease gene family. Proc Natl Acad Sci USA 87 : 5578 5581.
63. Milla M.E., Leesnitzer A., Moss M.L., Clay W.C., Carter H.L., Miller A.B., Su J.L. et al. (1999) Specific sequence elements are required for the expression of functional tumor necrosis factor-α converting enzyme (TACE). J Biol Chem 274 : 30563 30570.
64. Zhang Z., Cork J., Ye P., Le D., Schwarzenberger P., Summer W.R., Shellito J.E., Nelson S., Kolls J.K. (2000) Inhibitors of TNF-α processing and TACE mediated ectodomain shedding by ethanol. J Leukoc Biol 67 : 856 862.
65. Schlondorff J., Becherer J.D., Blobel C.P. (2000) Intracellular maturation and localization of the tumor necrosis factor-α convertase (TACE). Biochem J 347 : 131 138.
66. Gould R.J., Polokoff M.A., Friedman P.A., Huang T.F., Holt J.C., Cook J.J., Niewiarowski S. (1990) Disintegrins: a family of integrin inhibitory proteins from viper venoms. Proc Soc Exp Biol Med 195 : 168 171.
67. Schlondorff J., Blobel C.P. (1999) Metalloporotease disintegrins: modular proteins capable of promoting cell-cell interactions and triggering signals by protein ectodomain shedding. J Cell Sci 112 : 3603 3617.
68. Lukacova V., Zhang Y., Kroll D.M., Raha S., Comez D., Balaz S. (2005) A comparison of the binding sites of matrix metalloproteinases and tumor necrosis factor-α converting Enzyme: implications for selectivity. J Med Chem 48 : 2361 2370.
69. Sheppeck J.E., Tebben A., Gilmore J.L., Yang A., Wasserman Z.R., Decicco C.P., Duan J.J.W. (2007) A molecular modeling analysis of novel non hydroxamate inhibitors of TACE. Bioorg Med Chem Lett 17 : 1408 1412.
70. Moss M.L., Tavron L.S., Nudelman R. (2008) Drug insight: tumor necrosis factor converting enzyme as a pharmaceutical target for rheumatoid arthritis. Nat Clin Pract Rheumatol 4 : 300 309.
71. Gilmore J.L., King B.W., Harris C., Maduskuie T., Mercer S.E., Liu R.Q., Covington M.B., Qian M., Ribadeneria M.D., Vaddi K., Trzaskos J.M., Newton R.C., Decicco C.P., Duan J.J.W. (2006) Synthesis and structure activity relationship of a novel, achiral series of TNF-α converting enzyme inhibitors. Bioorg Med Chem Lett 16 : 2699 2704.
72. Kamei N., Tanaka T., Kawai K., Miyawaki K., Okuyama A., Murakami Y., Arakawa Y., Haino M., Harada T., Shimano M. (2004) Reverse hydroxamate based selective TACE inhibitors. Bioorg Med Chem Lett 14 : 2897 2900.
73. Sawa M., Kurokawa K., Inoue Y., Kondo H., Yoshino K. (2003) Discovery of selective phosphonamide based inhibitors of tumor necrosis factor-α converting enzyme (TACE). Bioorg Med Chem Lett 13 : 2021 2024.
74. Rabinowitz M.H., Andrews R.C., Becherer J.D., Bickett D.M., Bubacz D.G., Conway J.G., Cowan D.J., Gaul M., Glennon K., Lambert M.H., Leesnitzer M.A., McDougald D.L., Moss M.L., Musso D.L., Rizzolio M.C. (2001) Design of selective and soluble inhibitors of tumor necrosis factor-α converting enzyme (TACE). J Med Chem 44 : 4252 4267.
75. Xue C.B., Voss M.E., Nelson D.J., Duan J.J.W., Cherney R.J., Jacobson I.C., He X. et al. (2001) Design, synthesis and structure activity relationships of macrocyclic hydroxamic acids that inhibit tumor necrosis factor-α release in vitro and in vivo. J Med Chem 44 : 2636 2660.
76. Xue C.B., He X., Corbett R.L., Roderick J., Wasserman Z.R., Liu R.Q., Jaffee B.D., Covington M.B., Qian M., Trzaskos J.M., Newton R.C., Magolda R.L., Wexler R.R., Decicco C.P. (2001) Discovery of macrocyclic hydroxamic acids containing biphenylmethyl derivatives at P1', a series of selective TNF-α converting enzyme inhibitors with potent cellular activity in the inhibition of TNF-α release. J Med Chem 44 : 3351 3354.
77. Holms J., Mast K., Marcotte P., Elmore I., Li J., Pease L., Glaser K., Morgan D., Michaelides M., Davidsen S. (2001) Discovery of selective hydroxamic acid inhibitors of tumor necrosis factor-α converting enzyme. Bioorg Med Chem Lett 11 : 2907 2910.
78. Chen J.M., Jin G., Sung A., Levin J.I. (2002) Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 1: structure based design of novel acetylenic P1' groups. Bioorg Med Chem Lett 12 : 1195 1198.
79. Levitt N.C., Eskens F.A.L.M., O'Byrne K.J., Propper D.J., Denis L.J., Owen S.J., Choi L., Foekens J.A., Wilner S., Wood J.M., Nakajima M., Talbot D.C., Steward W.P., Harris A.L., Verwei J. (2001) Phase-I and pharmacological study of the oral matrix metalloproteinase inhibitor, MMI270 (CGS27023A), in patients with advanced solid Cancer. Clin Cancer Res 7 : 1912 1922.
80. Praga S.W., Torri J., Johnson M., Steen V., Marshall J., Ness E., Dickson R., Sale M., Rasmussen H.S., Chiodo T.A., Hawkins M.J. (1998) Phase-I trial of Marimastat, a novel matrix metalloproteinase inhibitor, administered orally to patients with advanced lung cancer. J Clin Oncol 16 : 2150 2156.
81. Maskos K., Catala C.F., Huber R., Bourenkov G.P., Bartunik H., Ellestad G.A., Reddy P. et al. (1998) Crystal structure of the catalytic domain of human tumor necrosis factor-α converting enzyme. Proc Natl Acad Sci USA 95 : 3408 3412.
82. Zhu Z., Mazzola R., Sinning L., McKittrick B., Niu X., Lundell D., Sun J., Orth P., Guo Z., Madison V., Ingram R., Beyer B.M. (2008) Discovery of novel hydroxamates as highly potent tumor necrosis factor converting enzyme inhibitors. Part II: discovery of two binding modes. J Med Chem 51 : 725 736.
83. Letavic M.A., Barberia J.T., Carty T.J., Hardink J.R., Liras J., Morrow L.L.L., Mitchell P.G., Noe M.C., Reeves L.M., Snow S.L., Stam E.J., Sweeney F.J., Vaughn M.L., Yu C.H. (2003) Synthesis and biological activity of piperazine based dual MMP-13 and TNF-α converting enzyme inhibitors. Bioorg Med Chem Lett 13 : 3243 3246.
84. Huang A., McCarthy D.J., Lovering F., Sun L., Wang W., Xu W., Zhu Y., Cui J., Zhang Y., Levin J.I. (2007) Structure based design of TACE selective inhibitors: manipulations in the S1'-S3' Pocket. Bioorg Med Chem Lett 15 : 6170 6181.
85. Kottirsch G., Koch G., Feifel R., Neumann U. (2002) β-aryl-succinic acid hydroxamates as dual inhibitors of matrix metalloproteinases and TACE. J Med Chem 45 : 2289 2293.
86. Koch G., Kottirsch G., Wietfeld B., Kusters E. (2002) Process development of dual MMP/TACE inhibitors (SDZ 242-484). Org Process Res Dev 6 : 652 659.
87. Trifilieff A., Walker C., Keller T., Kottirsch G., Neumann U. (2002) Pharmacological profile of PKF 242-484 and PKF 241-466, novel dual inhibitors of TACE and matrix metalloproteinases in models of airway inflammation. Br J Pharmacol 135 : 1655 1664.
88. Levin J.I., Chen J.M., Laakso L.M., Du M., Schmid J., Xu W., Cummons T., Xu J., Jin G., Barone D., Skotnicki J.S. (2006) Acetylenic TACE inhibitors. Part 3: thiomorpholine sulfonamide hydroxamates. Bioorg Med Chem Lett 16 : 1605 1609.
89. Berlaam B., Bird T.G., Brempt C.L., Campbell D., Foster S.J., Maciewicz R. (1999) New α-substituted succinate based hydroxamic acids as TNF-α convertase inhibitors. J Med Chem 42 : 4890 4908.
90. Skiles J.W., Gonnella N.C., Jeng A.Y. (2001) The design, structure and therapeutic application of matrix metalloproteinase inhibitors. Curr Med Chem 8 : 425 474.
91. Skotnicki J.S., Levin J.I., Killar L.M., Zask A. (1999) Metalloproteinases as targets for anti in ammatory drugs. In : Bottomley K.M.K., Bradshaw D., Nixon J.S., editor. Matrix Metalloproteinase Inhibitors. Berlin : Birkhaüser, p p. 17.
92. Montana J., Baxter A. (2000) The design of selective non substrate based matrix metalloproteinase inhibitors. Curr Opin Drug Discov Devel 3 : 353 361.
93. MacPherson L.J., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L. et al. (1997) Discovery of CGS 27023A, a non-peptidic, potent and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits. J Med Chem 40 : 2525 2532.
94. Close D.R. (2001) Matrix metalloproteinase inhibitors in rheumatic diseases. Ann Rheum Dis 60 : 62 67.
95. Yip D., Ahmad A., Karapetis C.S., Hawkins C.A., Harper P.G. (1999) Matrix metalloproteinases inhibitors: applications in oncology. Invest New Drugs 17 : 387 399.
96. Nelson A.R., Fingleton B., Rothenberg M.L., Matrisian L.M. (2000) Matrix metalloproteinases: biological activity and clinical implications. J Clin Oncol 18 : 1135 1149.
97. Bottomley K.M., Johnson W.H., Walter D.S. (1998) Matrix metalloproteinase inhibitors in arthritis. J Enzyme Inhib 13 : 79 101.
98. Moss M.J., Becherer D., Millia M., Pahel G., Lambert M., Andrews R., Frye S. et al. (1999) Metalloproteinases as targets for anti-inflammatory drugs. In : Bottomley K.M.K., Bradshaw D., Nixon J.S., editors. TNF-α Converting Enzyme. Berlin : Birkhaüser p. 187 204.
99. Eli B., Julia F., Reuven R. (2005) Recent non hydroxamate matrix metalloproteinase inhibitors. Expert Opin Ther Pat 15 : 253 269.
100. Michaelides M.R., Dellaria J.F., Gong J., Holms J.H., Bouska J.J., Stacey J., Wada C.K. et al. (2001) Biaryl ether retrohydroxamates as potent, long lived, orally bioavailable MMP inhibitors. Bioorg Med Chem Lett 11 : 1553 1556.
101. Schroder J., Henke A., Wenzel H., Brandstetter H., Stammler H.G., Stammler A., Pfeiffer W.D., Tschesche H. (2001) Structure based design and synthesis of potent matrix metalloproteinase inhibitors derived from 6H-1,3,4-thiadiazine scaffold. J Med Chem 44 : 3231 3243.
102. Grams F., Brandstetter H., D'Alo S., Geppert D., Krell H.W., Leinert H., Livi V., Menta E., Oliva A., Zimmerman G. (2001) Pyrimidine-2,4,6-triones: a new effective and selective class of matrix metalloproteinase inhibitors. Biol Chem 382 : 1277 1285.
103. Levin J.I., Chen J.M., Du M.T., Nelson F.C., Killar L.M., Skala S., Sung A., Jin G., Cowling R., Barone D., March C.J., Mohler K.M., Black R.A., Skotnicki J.S. (2002) Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 2: SAR of the acetylenic P1' group. Bioorg Med Chem Lett 12 : 1199 1202.
104. Levin J.I., Chen J., Du M., Hogan M., Kincaid S., Nelson F.C., Venkatesan A.M. et al. (2001) The discovery of anthranilic acid based MMP inhibitors. Part 2: SAR of the 5-position and P1' groups. Bioorg Med Chem Lett 11 : 2189 2192.
105. Levin J.I., Chen J.M., Du M.T., Nelson F.C., Wehr V., DiJoseph J.F., Killar L.M. et al. (2001) The discovery of anthranilic acid based MMP inhibitors. Part 3: incorporation of basic amines. Bioorg Med Chem Lett 11 : 2975 2978.
106. Nelson F.C., Santos E.D., Levin J.I., Chen J.M., Skotnicki J.S., DiJoseph J.F., Sharr M.A., Sung A., Killar L.M., Cowling R., Jin G., Roth C.E., Albright J.D. (2002) Benzodiazepine inhibitors of the MMPs and TACE. Bioorg Med Chem Lett 12 : 2867 2870.
107. Levin J.I., Nelson F.C., Santos E.D., Du M.T., MacEwan G., Chen J.M., Kaloustian S.A., Xu J., Jin G., Cummons T., Barone D. (2004) Benzodiazepine inhibitors of the MMPs and TACE. Part 2. Bioorg Med Chem Lett 14 : 4147 4151.
108. Zask A., Kaplan J., Du X., MacEwan G., Sandanayaka V., Eudy N., Levin J., Jin G., Xu J., Cummons T., Barone D., Kaloustiana S.A., Skotnicki J. (2005) Synthesis and SAR of diazepine and thiazepine TACE and MMP inhibitors. Bioorg Med Chem Lett 15 : 1641 1645.
109. Levin J.I., Chen J.M., Laakso L.M., Du M., Du X., Venkatesan A.M., Sandanayaka V., Zask A., Xu J., Xu W., Zhang Y., Skotnicki J.S. (2005) Acetylenic TACE inhibitors. Part 2: SAR of six membered cyclic sulfonamide hydroxamates. Bioorg Med Chem Lett 15 : 4345 4349.
110. Condon J.S., McCarthy D.J., Levin J.I., Lombart H.G., Lovering F.E., Sun L., Wang W., Xu W., Zhang Y. (2007) Identication of potent and selective TACE inhibitors via the S1 pocket. Bioorg Med Chem Lett 17 : 34 39.
111. Lombart H.G., Feyfant E., McCarthy D.J., Huang A., Lovering F., Sun L., Zhu Y., Zeng C., Zhang Y., Levin J.I. (2007) Design and synthesis of 3,3-piperidine hydroxamate analogs as selective TACE inhibitors. Bioorg Med Chem Lett 17 : 4333 4337.
112. Mazzola R.D., Zhu Z., Sinning L., McKittrick B., Lavey B., Spitler J., Kozlowski J., Yang S.N., Zhou G., Guo Z., Orth P., Madison V., Sun J., Lundell D., Niu X. (2008) Discovery of novel hydroxamates as highly potent tumor necrosis factor-α converting enzyme inhibitors. Part II: optimization of the S3' pocket. Bioorg Med Chem Lett 18 : 5809 5814.
113. Guo Z., Orth P., Wong S.C., Lavey B.J., Shih N.Y., Niu X., Lundell D.J., Madison V., Kozlowski J.A. (2009) Discovery of novel spirocyclopropyl hydroxamate and carboxylate compounds as TACE inhibitors. Bioorg Med Chem Lett 19 : 54 57.
114. Park K., Gopalsamy A., Aplasca A., Ellingboe J.W., Xu W., Zhang Y., Levin J.I. (2009) Synthesis and activity of tryptophan sulfonamide derivatives as novel non-hydroxamate TNF-α converting enzyme (TACE) inhibitors. Bioorg Med Chem 17 : 3857 3865.
115. Duan J.J.W., Chen L., Lu Z., Xue C.B., Liu R.Q., Covington M.B., Qian M., Wasserman Z.R., Vaddi K., Christ D.D., Trzaskos J.M., Newton R.C., Decicco C.P. (2008) Discovery of β-benzamido hydroxamic acids as potent, selective and orally bioavailable TACE inhibitors. Bioorg Med Chem Lett 18 : 241 246.
116. Xue C.B., He X., Roderick J., Corbett R.L., Duan J.J.W., Liu R.Q., Covington M.B. et al. (2003) Rational design, synthesis and structure activity relationships of a cyclic succinate series of TNF-α converting enzyme inhibitors. Part 2: lead optimization. Bioorg Med Chem Lett 13 : 4299 4304.
117. Duan J.J.W., Chen L., Lu Z., Jiang B., Asakawa L., Sheppeck J.E., Liu R.Q., Covington M.B., Pitts W., Hoon K.S., Decicco C.P. (2007) Discovery of low nanomolar non hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE). Bioorg Med Chem Lett 17 : 266 271.
118. Sheppeck J.E., Gilmore J.L., Yang A., Chen X.T., Xue C.B., Roderick J., Liu R.Q., Covington M.B., Decicco C.P., Duan J.J.W. (2007) Discovery of novel hydantoins as selective non hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE). Bioorg Med Chem Lett 17 : 1413 1417.
119. Sheppeck J.E., Gilmore J.L., Tebben A., Xue C.B., Liu R.Q., Decicco C.P., Duan J.J.W. (2007) Hydantoins, triazolones and imidazolones as selective non hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE). Bioorg Med Chem Lett 17 : 2769 2774.
120. Ott G.R., Asakawa N., Lu Z., Liu R.Q., Covington M.B., Vaddi K., Qian M., Newton R.C., Christ D.D., Traskos J.M., Decicco C.P., Duan J.J.W. (2008) α,β-Cyclic-β-benzamido hydroxamic acids: novel templates or the design, synthesis and evaluation of selective inhibitors of TNF-α converting enzyme (TACE). Bioorg Med Chem Lett 18 : 694 699.
121. Gilmore J.L., King B.W., Asakawa N., Harrison K., Tebben A., Sheppeck J.E., Liu R.Q., Covington M., Duan J.J.W. (2007) Synthesis and structure activity relationship of a novel, non hydroxamate series of TNF-α converting enzyme inhibitors. Bioorg Med Chem Lett 17 : 4678 4682.
122. Yamamoto M., Tsujishita H., Hori N., Ohishi Y., Inoue S., Ikeda S., Okada Y. (1998) Inhibition of membrane type 1 matrix metalloproteinase by hydroxamate inhibitors: an examination of the subsite pocket. J Med Chem 41 : 1209 1217.
123. Wasserman Z.R., Duan J.J.W., Voss M.E., Xue C.B., Cherney R.J., Nelson D.J., Hardman K.D., Decicco C.P. (2003) Identification of a selectivity determinant for inhibition of tumor necrosis factor-α converting enzyme by comparative modeling. Chem Biol 10 : 215 223.
124. Park K., Aplasca A., Du M.T., Sun L., Zhu Y., Zhang Y., Levin J.I. (2006) Design and synthesis of butynyloxyphenyl β-sulfone piperidine hydroxamates as TACE inhibitors. Bioorg Med Chem Lett 16 : 3927 3931.
125. Duan J.J.W., Chen L., Wasserman Z.R., Lu Z., Liu R.Q., Covington M.B., Qian M., Hardman K.D., Magolda R.L., Newton R.C., Christ D.D., Wexler R.R., Decicco C.P. (2002) Discovery of γ-lactam hydroxamis acids as selective inhibitors of TACE: design, synthesis and structure activity relationship. J Med Chem 45 : 4954 4957.