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Review

Recent non-hydroxamate matrix metalloproteinase inhibitors

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Pages 253-269 | Published online: 22 Apr 2005

Bibliography

  • HODGSON J: Remodeling MMPIs Biotechnology (1995) 13:554–557.
  • DOHERTY TM, ASOTRA K, PEI DQ et al.: Therapeutic developments in matrix metalloproteinase inhibition. Expert Opin. Ther. Patents (2002) 12:665–707.
  • ••An excellent comprehensive review thatdescribes the MMPs in detail and the clinical rationale for the exploitation of their action.
  • WHIFIAKER M, FLOYD CD, BROWN P, GEARING AJ: Design and therapeutic application of matrix metalloproteinase inhibitors. Chem. Rev. (1999) 99:2735–2776.
  • ••A comprehensive review of MMPs and theinhibitors developed until the date of its publication.
  • WOJTOWICZ-PRAGA S: Clinical potential of matrix metalloproteinase inhibitors. Drugs R D. (1999) 1:117–129.
  • SKILES JW, GONNELLA NC, JENG AY: The design, structure, and therapeutic application of matrix metalloproteinase inhibitors. Curr. Med. Chem. (2001) 8:425–474.
  • ••A comprehensive and useful review of MMPs and the inhibitors developed that includes 3D-structures of human MMPs with and without bound inhibitors determined by X-ray crystallography or by NMR and other tabulated data until the date of publication.
  • SKILES JW, GONNELLA NC, JENG AY: The design, structure, and clinical update of small molecular weight matrix metalloproteinase inhibitors. Curr. Med. Chem. (2004) 11:2911–2977.
  • ••An updated version of the previousreference. A very detailed, useful and most recent review of the area.
  • HIDALGO M, ECKHARDT SG: Development of matrix metalloproteinase inhibitors in cancer therapy. J. Natl. Cancer Inst. (2001) 93:178–193.
  • COUSSENS LM, FINGLETON B, MATRISIAN LM: Matrix metalloproteinase inhibitors and cancer: trials and tribulations. Science (2002) 295:2387–2392.
  • •This article summarises the role of MMPs in cancer and the history of development of MMPIs.
  • EGEBLAD M, WERB Z: New functions for the matrix metalloproteinases in cancer progression. Nat. Rev. Cancer (2002) 2:161–174.
  • •This is an excelent review on the role of MMPs in cancer.
  • OVERALL C, LOPEZ-OTIN C: Strategies for MMP inhibition in cancer: innovations for the post-trial era. Nat. Rev. Cancer (2002) 9:657–672.
  • •This article analyses the reasons why the pharmaceutical industry has failed in developing MMPI.
  • CONNELL RD: Patent focus on cancer chemotherapeutics V. Angiogenesis agents: September 2001 - August 2002. Expert Opin. Ther. Patents (2002) 12:1763–1782
  • ••See also previous reviews I - W.
  • SKILES JW, MONO VISH LG, JENG AY:Matrix metalloproteinase inhibitors for treatment of cancer. Ann. Rep. Med. Chem. (2000) 35:167–176.
  • PAVLAKI M, ZUCKER S: Matrix metalloproteinase inhibitors (MMPIs): The beginning of Phase I or the termination of Phase III clinical trials. Cancer Metastasis Rev. (2003) 22:177–203.
  • •This article describes a new approach to the understanding of the potential roles of future MMPIs.
  • ZUCKER S, VACIRCA J: Role of matrix metalloproteinases (MMPs) in colorectal cancer. Cancer Metastasis Rev. (2004) 23:101–117.
  • JONES LE, HUMPHREYS MJ, CAMPBELL F, NEOPTOLEMOS JP, BOYD MT: Comprehensive analysis of matrix metalloproteinase and tissue inhibitor expression in pancreatic cancer: increased expression of matrix metalloproteinase-7 predicts poor survival. Clin. Cancer Res. (2004) 10:2832–2845.
  • DAHLBERG L, BILLINGHURST RC, MANNER P et al.: Selective enhancement of collagenase-mediated cleavage of resident Type II collagen in cultured osteoarthritic cartilage and arrest with a synthetic inhibitor that spares collagenase 1 (matrix metalloproteinase 1). Arthritis Rheum. (2000) 43:673–682.
  • HENROTIN Y, SANCHEZ C, REGINSTER JY: The inhibition of metalloproteinases to treat osteoarthritis: reality and new perspectives. Expert Opin. Ther. Patents (2002) 12:29–43.
  • SHIRE MG, MULLER GW: TNF-a inhibitors and rheumatoid arthritis. Expert Opin. Ther. Patents (1998) 8:531–544.
  • ISHIGURO N, ITO T, OGUCHI T et aL: Relationships of matrix metalloproteinases and their inhibitors to cartilage proteoglycan and collagen turnover and inflammation as revealed by analyses of synovial fluids from patients with rheumatoid arthritis. Arthritis Rheum. (2001) 44:2503–2511.
  • CHU Q, LOPEZ M, HAYASHI K et aL: Elevation of collagenase generated Type II collagen neoepitope and proteoglycan epitopes in synovial fluid following induction of joint instability in the dog. Osteoarth. CartiL (2002) 10:662–669.
  • IKEDA U, SHIMADA K: Matrix metalloproteinases and coronary artery diseases. Clin. CardioL (2003) 26:55–59.
  • PETERSON JT: Matrix metalloproteinase inhibitor development and the remodeling of drug discovery. Heart Fail. Rev. (2004) 9:63–79.
  • •This article focuses on some of the lessons to be learned from the failure of so many MMP inhibitors across so many indications, and what potential exists in the future for MMP inhibitors.
  • LINDSEY ML: MMP Induction and inhibition in myocardial infarction. Heart Fail. Rev. (2004) 9:7–19.
  • DONNELLY LE, ROGERS DF: Antiproteases and retinoids for treatment of chronic obstructive pulmonary disease. Expert Opin. Ther. Patents (2003) 13:1345–1372.
  • •This article describes recent patent applications of different structural classes of rotease inhibitors and retinoid compounds that may be of benefit in COPD. MMP inhibitors is only one of these classes.
  • SUZUKI R, MIYAZAKI Y, TAKAGI K, TORII K, TANIGUCHI H: Matrix metalloproteinases in the pathogenesis of asthma and COPD: implications for therapy. Treat. Respir. Med. (2004) 3:17–27.
  • •This article describes current views on the role of MMPs in the pathogenesis of bronchial asthma and of COPD.
  • GOLUB LM, MCNAMARA TF, RYAN ME et al.: Adjunctive treatment with subantimicrobial doses of doxycycline: effects on gingival fluid collagenase activity and attachment loss in adult periodontitis. J. Clin. PeriodontoL (2001) 28:146–156.
  • LEE HM, CIANCIO SG, TUTER G, RYAN ME, KOMAROFF E, GOLUB LM: Subantimicrobial dose doxycycline efficacy as a matrix metalloproteinase inhibitor in chronic periodontitis patients is enhanced when combined with a non-steroidal anti-inflammatory drug. J. Periodontol. (2004) 75:453–463.
  • ACHARYA MR, VENITZ J, FIGG WD, SPARREBOOM k Chemically modified tetracyclines as inhibitors of matrix metalloproteinases. Drug Resist. Updat. (2004) 7:195–208.
  • MATTHEWS BW: Structural basis of theaction of thermolysin and related zinc peptidases. Acc. Chem. Res. (1988) 21:333–340.
  • PIKUL S, OHLER NE, CISZEWSKI G et al.: Potent and selective carboxylic acid-based inhibitors of matrix metalloproteinases. J. Med. Chem. (2001) 44:2499–2502.
  • WANG X, CHOE Y, CRAIK CS, ELLMAN JA: Design and synthesis of novel inhibitors of gelatinase B. Bioorg. Med. Chem. Lett. (2002) 12:2201–2204.
  • AUGE F, HORNEBECK W, DECARME M, LARONZE J-Y: Improved gelatinase A selectivity by novel zinc binding groups containing galardin derivatives. Bioorg. Med. Chem. Lett. (2003) 13:1783–1786.
  • FARKAS E, KATZ Y, BHUSARE S et al.:Carbamoylphosphonate based matrix metalloproteinase (MMP) inhibitor metal complexes - solution studies and stability constants, towards a zinc selective binding group. J. Biol. Inorg Chem. (2004) 9:307–315.
  • MOORE WM, SPILBURG CA: Purification of human collagenases with a hydroxamic acid affinity column. Biochemistry (1986) 25:5189–5195.
  • TURBANTI L, CERBAI G, DI BUGNO C et al.: 1,2-Cyclomethylenecarboxylic monoamide hydroxamic derivatives. A novel class of non-amino acid angiotensin converting enzyme inhibitors./ Med. Chem. (1993) 36:699–707.
  • MATTER H, SCHUDOK M: Recent advances in the design of matrix metalloprotease inhibitors. Curr. Opin. Drug Discov. DeveL (2004) 7:513–535.
  • FUJISAWA T, ODAKE S, OGAWA Y, YASUDA J, MORITA Y, MORIKAWA T: Design and synthesis of sulfur based inhibitors of matrix metalloproteinase-1. Chem. Pharm. BulL (2002) 50:239–252.
  • FUJISAWA T, KATAKURA S, ODAKE S et al.: Design and synthesis of carboxylate inhibitors for matrix metalloproteinases. Chem. Pharm. BulL (2001) 49:1272–1279.
  • TULLIS JS, LAUFERSWEILER MJ, VANRENS JC et al.: The development of new carboxylic acid-based MMP inhibitors derived from a cyclohexylglycine scaffold. Bioorg. Med. Chem. Lett. (2001) 11:1975–1979.
  • LE DIGUARHER T, CHOLLET AM, BERTRAND M et aL: Stereospecific synthesis of 5-substituted 2-bisarylthiocyclopentane carboxylic acids as specific matrix metalloproteinase inhibitors. J. Med. Chem. (2003) 46:3840–3852.
  • DELBECQ F, CORDONNIER G, POMMERY N, BARBRY D, HENICHART JP: New heteroaryl benzenesulphonamides as matrix metalloproteinase inhibitors. Bioorg. Med. Chem. Lett. (2004) 14:1119–1121.
  • MATZIARI M, BEAU F, CUNIASSE P, DIVE V YIOTAKIS A: Evaluation of P V-diversified phosphinic peptides leads to the development of highly selective inhibitors of MMP-11. J. Med. Chem. (2004) 47:325–336.
  • 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.
  • GRAMS F, BRANDSTETTER H, D'ALO S et al.: Pyrimidine-2,4,6-triones: a new effective and selective class of matrix metalloproteinase inhibitors. Biol. Chem. (2001) 382:1277–1285.
  • BRANDSTETTER H, GRAMS F, GLITZI D et al.: The 1.8 A crystal structure of a matrix metalloproteinase 8-barbiturate inhibitor complex reveals a previously unobserved mechanism for collagenase substrate recognition. J. Biol Chem. (2001) 276:17405–17412.
  • MAQUOI E, SOUNNI NE, DEVY L et al.: Anti-invasive, antitumoral, and antiangiogenic efficacy of a pyrimidine-2,4,6-trione derivative, an orally active and selective matrix metalloproteinases inhibitor. Clin. Cancer Res. (2004) 10:4038–4047.
  • SCHRODER J, HENKE A, WENZEL H et al.: Structure-based design and synthesis of potent matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. J. Med. Chem. (2001) 44:3231–3243.
  • COOK GR, MANIVANNAN E, UNDERDAHL T, LUKACOVA V, ZHANG Y, BALAZ S: Synthesis and evaluation of novel oxazoline MMP inhibitors. Bioorg. Med. Chem. Lett. (2004) 14:4935–4939.
  • CAINELLI G, GALLETTI P, GARBISA S,GIACOMINI D, SARTOR L, QUINTAVALLA A: 4-Alkylideneazetidin-2-ones: novel inhibitors of leukocyte elastase and gelatinase. Bioorg. Med. Chem. (2003) 11:5391–5399.
  • BREUER E, SALOMON CJ, KATZ Y et al.: Carbamoylphosphonates, a new class of in vivo active matrix metalloproteinase inhibitors. 1. Alkyl- and cycloalkylcarbamoylphosphonic acids. J. Med. Chem. (2004) 47:2826–2832.
  • BREUER E, KATZ Y, HADAR R, REICH R: Carbamoylphosphonate MMP inhibitors 4. The influence of chirality and geometrical isomerism on the potency and selectivity of inhibition. Tetrahedron Asymmetry (2004) 15:2415–2420.
  • REICH R, KATZ Y, HADAR R, BREUER E: Carbamoylphosphonate MMP inhibitors 3. In vivo evaluation of cyclopentylcarbamoylphosphonic acid, CPCPA, in experimental metastasis and angiogenesis. Clin. Cancer Res. in press.
  • BROWN S, BERNARDO MM, LI Z-H et al.: Potent and selective mechanism-based inhibition of gelatinases. J. Am. Chem. Soc. (2000) 122:6799–6800.
  • PERGAMENT I, REICH R, SREBNIK M: Novel matrix metallo-proteinase (MMP-2) phosphonoboronate inhibitors. Bioorg. Med. Chem. Lett. (2002) 12:1215–1218.
  • QUNTAR A, BAUM 0, REICH R, SREBNIK M: Recently synthesized class of vinylphosphonates as potent matrix metalloproteinase (MMP-2) inhibitors. Arch. Pharm. Pharm. Med. Chem. (2004) 337:76–80.
  • ABU ALI H, BERKOVITZ R, REICH R, SREBNIK M: Matrix metallo-proteinase (MMP-2) organoboronate inhibitors. Arch. Pharm. Pharm. Med. Chem. (2004) 37:183–187.
  • PUERTA DT, LEWIS JA, COHEN SM: New beginnings for matrix metalloproteinase inhibitors: identification of high-affinity zinc-binding groups. J. Am. Chem. Soc. (2004) 126:8388–8389.
  • FUJITA M, NAKAO Y, MATSUNAGA S et al.: Ageladine A: an antiangiogenic matrix metalloproteinase inhibitor from the marine sponge Agelas nakamurai. J. Am. Chem. Soc. (2003) 125:15700–15701.
  • MORALES R, PERRIER S, FLORENT JM et al.: Crystal structures of novel non-peptidic, non-zinc chelating inhibitors bound to MMP-12. j MoL Biol. (2004) 341:1063–1076.
  • ENDE C, GEBHART R: Inhibition of matrix metalloproteinase-2 and -9 activities by selected flavanoids. Planta Med. (2004) 70:1006–1008.
  • PATANI Gk LAVOIE EJ: Bioisosterism: a rational approach in drug design. Chem. Rev. (1996) 96:3147–3176.
  • FOLGUERAS AR, PENDAS AM, SANCHEZ LM, LOPEZ-OTIN C: Matrix metalloproteinases in cancer: from new functions to improved inhibition strategies. Int. J. Dev. Biol. (2004) 48:411–424.
  • •A recent review summarising the literature including the complexity of the phenomena (favourable and unfavourable) that may result from the action of broad spectrum MMPIs.
  • BROWNER MF, SMITH WW, CASTELHANO AL: Matrilysin-inhibitor complexes: common themes among metalloproteases. Biochemistry (1995) 34:6602–6610.
  • O'BRIEN EC, FARKAS E, GIL MJ, FITZGERALD D, CASTINERAS A, NOLAN KB: Metal complexes of salicylhydroxamic acid (H2Sha), anthranilic hydroxamic acid and benzohydroxamic acid, crystal and molecular structure of Cu(Phen)2(C1)1- Clph2sha, a model for a peroxidase inhibitor complex. J. Inorg. Biochem. (2000) 79:47–51.
  • FURIA TE: Sequestrants in food (chapter 6). In: CRC Handbook of Food Additives 2"a Ed Furia TE (Ed.) (1972):271–294.
  • CANNAN, RK, KIBRICK A: Complex formation between carboxylic acids and divalent metal cations. J. Am. Chem. Soc. (1938) 60:2314–2320.
  • Textbook of Biochemistry 4th Ed Devlin TM (Ed.) Wiley-Liss, NY, USA (1997):151–152.
  • GARDNER CR, WALSH CT, ALMARSSON 0: Drugs as materials: valuing physical form in drug discovery. Nat. Rev. Drug Dis. (2004) 3:926–934.

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