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Volumn 31, Issue 6, 2011, Pages 863-894

Selective MMP13 inhibitors

Author keywords

Collagen; Inflammation; Inhibitor; MMP13; Osteroarthritis

Indexed keywords

4 [[[4 (4 CHLOROPHENOXY)PHENYL]SULFONYL]METHYL]TETRAHYDRO 2H PYRAN 4 CARBOHYDROXAMIC ACID; ACETOHYDROXAMIC ACID; ALPHA AMINO SULFONYL HYDROXAMIC ACID; BATIMASTAT; CARBOXYLIC ACID; CGS 27023A; CL 82198; COLLAGENASE 3; DICARBOXAMIDE; DOXYCYCLINE; HYDROXAMIC ACID DERIVATIVE; ILOMASTAT; MARIMASTAT; MATRIX METALLOPROTEINASE INHIBITOR; N (BENZOFURANCARBONYLAMINOBIPHENYLSULFONYL)VALINE; PRINOMASTAT; PYRIDO[3,4 D]PYRIMIDIN 4 ONE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG; WAY 152177; WAY 170523; ZINC ION;

EID: 80053959979     PISSN: 01986325     EISSN: 10981128     Source Type: Journal    
DOI: 10.1002/med.20204     Document Type: Review
Times cited : (19)

References (93)
  • 1
    • 0028322352 scopus 로고
    • Molecular cloning and expression of collagenase-3, a novel human matrix metalloproteinase produced by breast carcinoma
    • Freije JMP, Díez-Itza I, Balbín M, Sánchez LM, Blasco R, Tolivia J, López-Otín C. Molecular cloning and expression of collagenase-3, a novel human matrix metalloproteinase produced by breast carcinoma. J Biol Chem 1994;269:16766-16773.
    • (1994) J Biol Chem , vol.269 , pp. 16766-16773
    • Freije, J.M.P.1    Díez-Itza, I.2    Balbín, M.3    Sánchez, L.M.4    Blasco, R.5    Tolivia, J.6    López-Otín, C.7
  • 2
    • 0021052777 scopus 로고
    • The collagen substrate specificity of rat uterus collagenase
    • Welgus HG, Kobayashi DK, Jeffrey JJ. The collagen substrate specificity of rat uterus collagenase. J Biol Chem 1983;258:14162-14165.
    • (1983) J Biol Chem , vol.258 , pp. 14162-14165
    • Welgus, H.G.1    Kobayashi, D.K.2    Jeffrey, J.J.3
  • 5
    • 58149229308 scopus 로고    scopus 로고
    • A critical role for collagen II in cartilage matrix degradation: Collagen II induces pro-inflammatory cytokines and MMPs in primary human chondrocytes
    • Klatt AR, Paul-Klausch B, Klinger G, Kühn G, Renno JH, Bannerjee M, Malchau G, Wielckens K. A critical role for collagen II in cartilage matrix degradation: Collagen II induces pro-inflammatory cytokines and MMPs in primary human chondrocytes. J Orthop Res 2009;27:65-70.
    • (2009) J Orthop Res , vol.27 , pp. 65-70
    • Klatt, A.R.1    Paul-Klausch, B.2    Klinger, G.3    Kühn, G.4    Renno, J.H.5    Bannerjee, M.6    Malchau, G.7    Wielckens, K.8
  • 6
    • 33644870385 scopus 로고    scopus 로고
    • Collagen degradation products modulate matrix metalloproteinase expression in cultured articular chondrocytes
    • Fichter M, Körner U, Schömburg J, Jennings L, Cole AA, Mollenhauer J. Collagen degradation products modulate matrix metalloproteinase expression in cultured articular chondrocytes. J Orthop Res 2006;24:63-70.
    • (2006) J Orthop Res , vol.24 , pp. 63-70
    • Fichter, M.1    Körner, U.2    Schömburg, J.3    Jennings, L.4    Cole, A.A.5    Mollenhauer, J.6
  • 8
    • 0030007277 scopus 로고    scopus 로고
    • Cloning of collagenase-3 from the synovial membrane and its expression in rheumatoid arthritis and osteoarthritis
    • Wernicke D, Seyfert C, Hinzmann B, Gromnica-Ihle E. Cloning of collagenase-3 from the synovial membrane and its expression in rheumatoid arthritis and osteoarthritis. J Rheumatol 1996;23:590-595.
    • (1996) J Rheumatol , vol.23 , pp. 590-595
    • Wernicke, D.1    Seyfert, C.2    Hinzmann, B.3    Gromnica-Ihle, E.4
  • 10
    • 0034041424 scopus 로고    scopus 로고
    • Comparison of the degradation of type II collagen and proteoglycan in nasal and articular cartilages induced by interleukin-1 and the selective inhibition of type II collagen cleavage by collagenase
    • Billinghurst RC, Wu W, Ionescu M, Reiner A, Dahlberg L, Chen J, Van Wart H, Poole AR. Comparison of the degradation of type II collagen and proteoglycan in nasal and articular cartilages induced by interleukin-1 and the selective inhibition of type II collagen cleavage by collagenase. Arthritis Rheum 2000;43:664-672.
    • (2000) Arthritis Rheum , vol.43 , pp. 664-672
    • Billinghurst, R.C.1    Wu, W.2    Ionescu, M.3    Reiner, A.4    Dahlberg, L.5    Chen, J.6    Van Wart, H.7    Poole, A.R.8
  • 14
    • 10344245561 scopus 로고    scopus 로고
    • Critical roles for collagenase-3 (Mmp13) in development of growth plate cartilage and in endochondral ossification
    • Inada M, Wang Y, Byrne MH, Rahman MU, Miyaura C, López-Otín C, Krane SM. Critical roles for collagenase-3 (Mmp13) in development of growth plate cartilage and in endochondral ossification. Proc Natl Acad Sci USA 2004;101:17192-17197.
    • (2004) Proc Natl Acad Sci USA , vol.101 , pp. 17192-17197
    • Inada, M.1    Wang, Y.2    Byrne, M.H.3    Rahman, M.U.4    Miyaura, C.5    López-Otín, C.6    Krane, S.M.7
  • 16
    • 73249137617 scopus 로고    scopus 로고
    • Matrix metalloproteinase 13-deficient mice are resistant to osteoarthritic cartilage erosion but not chondrocyte hypertrophy or osteophyte development
    • Little CB, Barai A, Burkhardt D, Smith SM, Fosang AJ, Werb Z, Shah M, Thompson EW. Matrix metalloproteinase 13-deficient mice are resistant to osteoarthritic cartilage erosion but not chondrocyte hypertrophy or osteophyte development. Arthritis Rheum 2009;60:3723-3733.
    • (2009) Arthritis Rheum , vol.60 , pp. 3723-3733
    • Little, C.B.1    Barai, A.2    Burkhardt, D.3    Smith, S.M.4    Fosang, A.J.5    Werb, Z.6    Shah, M.7    Thompson, E.W.8
  • 17
    • 0030843734 scopus 로고    scopus 로고
    • Expression of collagenase-3 (matrix metalloproteinase-13) in squamous cell carcinomas of the head and neck
    • Johansson N, Airola K, Grenman R, Kariniemi AL, Saarialho-Kere U, Kähäri V-M. Expression of collagenase-3 (matrix metalloproteinase-13) in squamous cell carcinomas of the head and neck. Am J Pathol 1997;151:499-508.
    • (1997) Am J Pathol , vol.151 , pp. 499-508
    • Johansson, N.1    Airola, K.2    Grenman, R.3    Kariniemi, A.L.4    Saarialho-Kere, U.5    Kähäri, V.-M.6
  • 19
    • 0033945337 scopus 로고    scopus 로고
    • Increased expression of collagenase-3 (MMP-13) and MT1-MMP in oesophageal cancer is related to cancer aggressiveness
    • Etoh T, Inoue H, Yoshikawa Y, Barnard GF, Kitano S, Mori M. Increased expression of collagenase-3 (MMP-13) and MT1-MMP in oesophageal cancer is related to cancer aggressiveness. Gut 2000;47:50-56.
    • (2000) Gut , vol.47 , pp. 50-56
    • Etoh, T.1    Inoue, H.2    Yoshikawa, Y.3    Barnard, G.F.4    Kitano, S.5    Mori, M.6
  • 20
    • 0036774674 scopus 로고    scopus 로고
    • Matrix metalloproteinase 13 activity is associated with poor prognosis in colorectal cancer
    • Leeman MF, McKay JA, Murray GI. Matrix metalloproteinase 13 activity is associated with poor prognosis in colorectal cancer. J Clin Pathol 2002;55:758-762.
    • (2002) J Clin Pathol , vol.55 , pp. 758-762
    • Leeman, M.F.1    McKay, J.A.2    Murray, G.I.3
  • 21
    • 33144469825 scopus 로고    scopus 로고
    • Association between high collagenase-3 expression levels and poor prognosis in patients with head and neck cancer
    • Luukkaa M, Vihinen P, Kronqvist P, Vahlberg T, Pyrhönen S, Kähäri V-M, Grénman R. Association between high collagenase-3 expression levels and poor prognosis in patients with head and neck cancer. Head Neck 2006;28:225-234.
    • (2006) Head Neck , vol.28 , pp. 225-234
    • Luukkaa, M.1    Vihinen, P.2    Kronqvist, P.3    Vahlberg, T.4    Pyrhönen, S.5    Kähäri, V.-M.6    Grénman, R.7
  • 25
    • 0034751435 scopus 로고    scopus 로고
    • Matrix metalloproteinase inhibitors: Current developments and future perspectives
    • Hoekstra R, Eskens FALM, Verweij J. Matrix metalloproteinase inhibitors: Current developments and future perspectives. Oncologist 2001;6:415-427.
    • (2001) Oncologist , vol.6 , pp. 415-427
    • Hoekstra, R.1    Eskens, F.A.L.M.2    Verweij, J.3
  • 26
    • 1042263796 scopus 로고    scopus 로고
    • Matrix metalloproteinase inhibitor development and the remodeling of drug discovery
    • Peterson JT. Matrix metalloproteinase inhibitor development and the remodeling of drug discovery. Heart Fail Rev 2004;9:63-79.
    • (2004) Heart Fail Rev , vol.9 , pp. 63-79
    • Peterson, J.T.1
  • 27
    • 31344456635 scopus 로고    scopus 로고
    • The importance of estimating the therapeutic index in the development of matrix metalloproteinase inhibitors
    • Peterson JT. The importance of estimating the therapeutic index in the development of matrix metalloproteinase inhibitors. Cardiovasc Res 2006;69:677-687.
    • (2006) Cardiovasc Res , vol.69 , pp. 677-687
    • Peterson, J.T.1
  • 31
    • 80053945836 scopus 로고    scopus 로고
    • Method for identifying metalloenzyme inhibitors. US Patent Application 0129672 (2003 Warner-Lambert).
    • Dyer RD, Hupe DJ, Johnson AR. Method for identifying metalloenzyme inhibitors. US Patent Application 0129672 (2003 Warner-Lambert).
    • Dyer, R.D.1    Hupe, D.J.2    Johnson, A.R.3
  • 35
    • 40349087284 scopus 로고    scopus 로고
    • Reappraising metalloproteinases in rheumatoid arthritis and osteoarthritis: Destruction or repair?
    • Murphy G, Nagase H. Reappraising metalloproteinases in rheumatoid arthritis and osteoarthritis: Destruction or repair? Nat Clin Prac Rheumatol 2008;4:128-135.
    • (2008) Nat Clin Prac Rheumatol , vol.4 , pp. 128-135
    • Murphy, G.1    Nagase, H.2
  • 36
    • 77149131528 scopus 로고    scopus 로고
    • To bind zinc or not to bind zinc: An examination of innovative approaches to improved matrix metalloproteinase inhibition
    • DOI: 10.1016/j.bbamcr.2009.08.006.
    • Jacobsen JA, Major Jourden JL, Miller MT, Cohen SM. To bind zinc or not to bind zinc: An examination of innovative approaches to improved matrix metalloproteinase inhibition. Biochim Biophys Acta 2009. DOI: 10.1016/j.bbamcr.2009.08.006.
    • (2009) Biochim Biophys Acta
    • Jacobsen, J.A.1    Major Jourden, J.L.2    Miller, M.T.3    Cohen, S.M.4
  • 37
    • 84900154002 scopus 로고    scopus 로고
    • Third-generation MMP inhibitors: Recent advances in the development of highly selective inhibitors
    • Edwards D, Høyer-Hansen G, Blasi F, Sloane BF (Eds). Springer New York
    • Yiotakis A, Dive V. Third-generation MMP inhibitors: Recent advances in the development of highly selective inhibitors. In: Edwards D, Høyer-Hansen G, Blasi F, Sloane BF (Eds). Springer New York. The cancer degradome: Proteases and cancer biology. 2008. pp 811-825.
    • (2008) The cancer degradome: Proteases and cancer biology , pp. 811-825
    • Yiotakis, A.1    Dive, V.2
  • 38
    • 15544373919 scopus 로고    scopus 로고
    • Recent non-hydroxamate matrix metalloproteinase inhibitors
    • Breuer E, Frant J, Reich R. Recent non-hydroxamate matrix metalloproteinase inhibitors. Expert Opin Ther Pat 2005;15:253-269.
    • (2005) Expert Opin Ther Pat , vol.15 , pp. 253-269
    • Breuer, E.1    Frant, J.2    Reich, R.3
  • 40
    • 0019407381 scopus 로고
    • On the attribution and additivity of binding energies
    • Jencks WP. On the attribution and additivity of binding energies. Proc Natl Acad Sci USA 1981;78:4046-4050.
    • (1981) Proc Natl Acad Sci USA , vol.78 , pp. 4046-4050
    • Jencks, W.P.1
  • 42
    • 80054002533 scopus 로고    scopus 로고
    • Cyclic compounds containing zinc binding groups as matrix metalloproteinase inhibitors. US Patent Application 0063673 (2004 Warner-Lambert).
    • Johnson AR. Cyclic compounds containing zinc binding groups as matrix metalloproteinase inhibitors. US Patent Application 0063673 (2004 Warner-Lambert).
    • Johnson, A.R.1
  • 45
    • 34548574687 scopus 로고    scopus 로고
    • Transcriptional profiling and pathway analysis of monosodium iodoacetate-induced experimental osteoarthritis in rats: Relevance to human disease
    • Barve RA, Minnerly JC, Weiss DJ, Meyer DM, Aguiar DJ, Sullivan PM, Weinrich SL, Head RD. Transcriptional profiling and pathway analysis of monosodium iodoacetate-induced experimental osteoarthritis in rats: Relevance to human disease. Osteoarthr Cartilage 2007;15:1190-1198.
    • (2007) Osteoarthr Cartilage , vol.15 , pp. 1190-1198
    • Barve, R.A.1    Minnerly, J.C.2    Weiss, D.J.3    Meyer, D.M.4    Aguiar, D.J.5    Sullivan, P.M.6    Weinrich, S.L.7    Head, R.D.8
  • 48
    • 36048952357 scopus 로고    scopus 로고
    • Urinary TIINE concentrations in a randomized controlled trial of doxycycline in knee osteoarthritis. Implications of the lack of association between TIINE levels and joint space narrowing
    • Otterness IG, Brandt KD, Hellio Le Graverand M-P, Mazzuca SA. Urinary TIINE concentrations in a randomized controlled trial of doxycycline in knee osteoarthritis. Implications of the lack of association between TIINE levels and joint space narrowing. Arthritis Rheum 2007;56:3644-3649.
    • (2007) Arthritis Rheum , vol.56 , pp. 3644-3649
    • Otterness, I.G.1    Brandt, K.D.2    Hellio Le Graverand, M.-P.3    Mazzuca, S.A.4
  • 51
    • 60249091336 scopus 로고    scopus 로고
    • Assessment of the renal toxicity of novel anti-inflammatory compounds using cynomolgus monkey and human kidney cells
    • Cai H, Agrawal AK, Putt DA, Hashim M, Reddy A, Brodfuehrer J, Surendran N, Lash LH. Assessment of the renal toxicity of novel anti-inflammatory compounds using cynomolgus monkey and human kidney cells. Toxicology 2009;258:56-63.
    • (2009) Toxicology , vol.258 , pp. 56-63
    • Cai, H.1    Agrawal, A.K.2    Putt, D.A.3    Hashim, M.4    Reddy, A.5    Brodfuehrer, J.6    Surendran, N.7    Lash, L.H.8
  • 53
    • 80053948188 scopus 로고    scopus 로고
    • Renal toxicity and hyperbilirubinemia of a novel matrix metalloproteinase (MMP) inhibitor in cynomolgus monkeys
    • Datta K, Guzman R, Maier WE, Grzemski FA, Robertson DG. Renal toxicity and hyperbilirubinemia of a novel matrix metalloproteinase (MMP) inhibitor in cynomolgus monkeys. Toxicologist 2006;90:343-344.
    • (2006) Toxicologist , vol.90 , pp. 343-344
    • Datta, K.1    Guzman, R.2    Maier, W.E.3    Grzemski, F.A.4    Robertson, D.G.5
  • 55
    • 42949151580 scopus 로고    scopus 로고
    • Matrix metalloproteinase 13 (MMP13) and tissue inhibitor of matrix metalloproteinase 1 (TIMP1), regulated by the MAPK pathway, are both necessary for Madin-Darby canine kidney tubulogenesis
    • Hellman NE, Spector J, Robinson J, Zuo X, Saunier S, Antignac C, Tobias JW, Lipschutz JH. Matrix metalloproteinase 13 (MMP13) and tissue inhibitor of matrix metalloproteinase 1 (TIMP1), regulated by the MAPK pathway, are both necessary for Madin-Darby canine kidney tubulogenesis. J Biol Chem 2008;283:4272-4282.
    • (2008) J Biol Chem , vol.283 , pp. 4272-4282
    • Hellman, N.E.1    Spector, J.2    Robinson, J.3    Zuo, X.4    Saunier, S.5    Antignac, C.6    Tobias, J.W.7    Lipschutz, J.H.8
  • 56
    • 70349766920 scopus 로고    scopus 로고
    • OA Clinical trials: Current targets and trials for OA. Choosing molecular targets: What have we learned and where are we headed?
    • 17:1393-1401.
    • Hellio Le Graverand M-P. OA Clinical trials: Current targets and trials for OA. Choosing molecular targets: What have we learned and where are we headed? Osteoarthr Cartilage 2009; 17:1393-1401.
    • (2009) Osteoarthr Cartilage
    • Hellio Le Graverand, M.-P.1
  • 57
    • 48749106644 scopus 로고    scopus 로고
    • Drug insight: Aggrecanases as therapeutic targets for osteoarthritis
    • Fosang AJ, Little CB. Drug insight: Aggrecanases as therapeutic targets for osteoarthritis. Nat Clin Pract Rheum 2008;4:420-427.
    • (2008) Nat Clin Pract Rheum , vol.4 , pp. 420-427
    • Fosang, A.J.1    Little, C.B.2
  • 62
    • 80053989921 scopus 로고    scopus 로고
    • WO0044709 WO0044711 WO0044749 (2000 American Cyanamid).
    • Levin JI, et al. WO0044709 WO0044711 WO0044749 (2000 American Cyanamid).
    • Levin, J.I.1
  • 63
    • 0033664735 scopus 로고    scopus 로고
    • Anon. Novel cyclic N-hydroxamic acid inhibitors of TNF-α synthesis and MMP13
    • Anon. Novel cyclic N-hydroxamic acid inhibitors of TNF-α synthesis and MMP13. Expert Opin Ther Pat 2000;10:1951-1956.
    • (2000) Expert Opin Ther Pat , vol.10 , pp. 1951-1956
  • 64
    • 33751042569 scopus 로고    scopus 로고
    • Drug evaluation: Apratastat, a novel TACE/MMP inhibitor for rheumatoid arthritis
    • Thabet MM, Huizinga TWJ. Drug evaluation: Apratastat, a novel TACE/MMP inhibitor for rheumatoid arthritis. Curr Opin Invest Dr 2006;7:1014-1019.
    • (2006) Curr Opin Invest Dr , vol.7 , pp. 1014-1019
    • Thabet, M.M.1    Huizinga, T.W.J.2
  • 66
    • 0034638377 scopus 로고    scopus 로고
    • Structure-based design of a novel, potent, and selective inhibitor for MMP13 utilizing NMR spectroscopy and computer-aided molecular design
    • Chen JM, Nelson FC, Levin JI, Mobilio D, Moy FJ, Nilakantan R, Zask A, Powers R. Structure-based design of a novel, potent, and selective inhibitor for MMP13 utilizing NMR spectroscopy and computer-aided molecular design. J Am Chem Soc 2000;122:9648-9654.
    • (2000) J Am Chem Soc , vol.122 , pp. 9648-9654
    • Chen, J.M.1    Nelson, F.C.2    Levin, J.I.3    Mobilio, D.4    Moy, F.J.5    Nilakantan, R.6    Zask, A.7    Powers, R.8
  • 74
    • 80053957966 scopus 로고    scopus 로고
    • WO9907675 (1997 Pfizer).
    • Robinson RP. WO9907675 (1997 Pfizer).
    • Robinson, R.P.1
  • 75
    • 0032874120 scopus 로고    scopus 로고
    • Anon. Arylsulphonamide hydroxamic acids as potent inhibitors of MMP13
    • Anon. Arylsulphonamide hydroxamic acids as potent inhibitors of MMP13. Expert Opin Ther Pat 1999;9:1303-1307.
    • (1999) Expert Opin Ther Pat , vol.9 , pp. 1303-1307
  • 87
    • 0035938352 scopus 로고    scopus 로고
    • Novel 5,5-disubstituted pyrimidine-2,4,6-triones as selective MMP inhibitors
    • Foley LH, Palermo R, Dunten P, Wang P. Novel 5, 5-disubstituted pyrimidine-2, 4, 6-triones as selective MMP inhibitors. Bioorg Med Chem Lett 2001;11:969-972.
    • (2001) Bioorg Med Chem Lett , vol.11 , pp. 969-972
    • Foley, L.H.1    Palermo, R.2    Dunten, P.3    Wang, P.4
  • 90
    • 80053970467 scopus 로고    scopus 로고
    • Imino acid derivatives for use as inhibitors of matrix metalloproteinases. International Patent Application WO2004/060883 (2004 Aventis).
    • Schudok M, Ruf S, Matter H, Wehner V, Kirsch R, Stahl P. Imino acid derivatives for use as inhibitors of matrix metalloproteinases. International Patent Application WO2004/060883 (2004 Aventis).
    • Schudok, M.1    Ruf, S.2    Matter, H.3    Wehner, V.4    Kirsch, R.5    Stahl, P.6
  • 91
    • 80053980080 scopus 로고    scopus 로고
    • Pyrimidine-4,6-dicarboxylic acid diamides for use as selective MMP13 inhibitors. International Patent Application WO2004/060883 (2004 Aventis).
    • Klingler O, Kirsch R, Habermann J, Weithmann KU, Engel CK, Pirard B. Pyrimidine-4, 6-dicarboxylic acid diamides for use as selective MMP13 inhibitors. International Patent Application WO2004/060883 (2004 Aventis).
    • Klingler, O.1    Kirsch, R.2    Habermann, J.3    Weithmann, K.U.4    Engel, C.K.5    Pirard, B.6


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