Discovery of potent inhibitor for matrix metalloproteinase-9 by pharmacophore based modeling and dynamics simulation studies

Journal of Molecular Graphics and Modelling

Volumn 49, Issue , 2014, Pages 25-37

  Kalva, Sukesh ^a   Azhagiya Singam, E R ^b   Rajapandian, V ^b   Saleena, Lilly M ^a   Subramanian, V ^b  

^a SRM INSTITUTE OF SCIENCE AND TECHNOLOGY   (India)

^b CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

Docking; Gelatin zymography; Molecular dynamics simulation; MTT; Pharmacophore modeling

Indexed keywords

DESIGN AND DEVELOPMENT; GELATIN ZYMOGRAPHY; HYDROGEN BOND ACCEPTORS; MATRIX METALLOPROTEINASE 9 (MMP 9); MATRIX METALLOPROTEINASE-9; MOLECULAR DYNAMICS SIMULATIONS; MTT; PHARMACOPHORE MODELING;

BINDING ENERGY; DOCKING; HYDROGEN BONDS; MOLECULAR DYNAMICS;

PHARMACODYNAMICS;

ARCTIIN; CARBOXYL GROUP; COLLAGENASE 3; GELATIN; GELATINASE B; HINOKIFLAVONE; HYDROXYL GROUP; MATRIX METALLOPROTEINASE INHIBITOR; NATURAL PRODUCT; ZINC ION; ENZYME INHIBITOR;

ANTIFUNGAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; BIOLOGICAL ACTIVITY; CELL PROLIFERATION; CELL STRAIN MCF 7; CELL VIABILITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG SCREENING; ENZYME ACTIVE SITE; ENZYME ASSAY; ENZYME INHIBITION; HINGE REGION; HUMAN; HUMAN CELL; HYDROGEN BOND; IC 50; JUNIPERUS; LC 50; METASTASIS INHIBITION; MOLECULAR DOCKING; MOLECULAR DYNAMICS; MTT ASSAY; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN INTERACTION; ZYMOGRAPHY; CHEMICAL PHENOMENA; CHEMISTRY; METABOLISM; PROTEIN SECONDARY STRUCTURE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STRUCTURE ACTIVITY RELATION;

ENZYME INHIBITORS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MATRIX METALLOPROTEINASE 9; MOLECULAR DOCKING SIMULATION; MOLECULAR DYNAMICS SIMULATION; PROTEIN STRUCTURE, SECONDARY; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84893051168     PISSN: 10933263     EISSN: 18734243     Source Type: Journal    
DOI: 10.1016/j.jmgm.2013.12.008     Document Type: Article

References (81)

1. P. Vihinen, R. Ala-aho, and V.M. Kahari Matrix metalloproteinases as therapeutic targets in cancer Current Cancer Drug Targets 5 2005 203 220 (Pubitemid 40694861)
2. P. Vihinen, and V.M. Kahari Matrix metalloproteinases in cancer: prognostic markers and therapeutic targets International Journal of Cancer Journal International du Cancer 99 2002 157 166 (Pubitemid 34309470)
3. N. Johansson, M. Ahonen, and V.M. Kahari Matrix metalloproteinases in tumor invasion Cellular and Molecular Life Sciences 57 2000 5 15 (Pubitemid 30105326)
4. V.M. Kahari, and U. Saarialho-Kere Matrix metalloproteinases and their inhibitors in tumour growth and invasion Annals of Medicine 31 1999 34 45 (Pubitemid 29134483)
5. R.P. Verma, and C. Hansch Matrix metalloproteinases (MMPs): chemical-biological functions and (Q)SARs Bioorganic & Medicinal Chemistry 15 2007 2223 2268 (Pubitemid 46240907)
6. O. Nicolotti, T.F. Miscioscia, F. Leonetti, G. Muncipinto, and A. Carotti Screening of matrix metalloproteinases available from the protein data bank: insights into biological functions, domain organization, and zinc binding groups Journal of Chemical Information and Modeling 47 2007 2439 2448 (Pubitemid 350275108)
7. F. Vasaturo, F. Solai, C. Malacrino, T. Nardo, B. Vincenzi, and M. Modesti et al. Plasma levels of matrix metalloproteinases 2 and 9 correlate with histological grade in breast cancer patients Oncology Letters 5 2013 316 320
8. C. Chang, and Z. Werb The many faces of metalloproteases: cell growth, invasion, angiogenesis and metastasis Trends in Cell Biology 11 2001 S37 S43
9. N.I. Solovyeva, S.V. Vinokurova, O.S. Ryzhakova, T.A. Gureeva, and I.V. Tsvetkova Expression of gelatinases A and B and their endogenous regulators in immortal and transformed fibroblasts Biomeditsinskaia khimiia 55 2009 441 450
10. H.Q. Ye, and D.T. Azar Expression of gelatinases A and B, and TIMPs 1 and 2 during corneal wound healing Investigative Pphthalmology & Visual Science 39 1998 913 921 (Pubitemid 28196677)
11. P.A. Forsyth, T.D. Laing, A.W. Gibson, N.B. Rewcastle, P. Brasher, and G. Sutherland et al. High levels of gelatinase-B and active gelatinase-A in metastatic glioblastoma Journal of Neuro-Oncology 36 1998 21 29 (Pubitemid 28230649)
12. J. Vandooren, P.E. Van den Steen, and G. Opdenakker Biochemistry and molecular biology of gelatinase B or matrix metalloproteinase-9 (MMP-9): the next decade Critical Reviews in Biochemistry and Molecular Biology 48 2013 222 272
13. W.T. Purcell, M.A. Rudek, and M. Hidalgo Development of matrix metalloproteinase inhibitors in cancer therapy Hematology/Oncology Clinics of North America 16 2002 227 1189
14. S. Rowsell, P. Hawtin, C.A. Minshull, H. Jepson, S.M. Brockbank, and D.G. Barratt et al. Crystal structure of human MMP9 in complex with a reverse hydroxamate inhibitor Journal of Molecular Biology 319 2002 173 181 (Pubitemid 34729494)
15. A. Tandon, and S. Sinha Structural insights into the binding of MMP9 inhibitors Bioinformation 5 2011 310 314
16. T. Tuccinardi, E. Nuti, G. Ortore, A. Rossello, S.I. Avramova, and A. Martinelli Development of a receptor-based 3D-QSAR study for the analysis of MMP2, MMP3, and MMP9 inhibitors Bioorganic & Medicinal Chemistry 16 2008 58 7749
17. B.G. Rao Recent developments in the design of specific matrix metalloproteinase inhibitors aided by structural and computational studies Current Pharmaceutical Design 11 2005 295 322 (Pubitemid 40277859)
18. L. Devel, B. Czarny, F. Beau, D. Georgiadis, E. Stura, and V. Dive Third generation of matrix metalloprotease inhibitors: gain in selectivity by targeting the depth of the S1′ cavity Biochimie 92 2010 8 1501
19. A. Agrawal, D. Romero-Perez, J.A. Jacobsen, F.J. Villarreal, and S.M. Cohen Zinc-binding groups modulate selective inhibition of MMPs ChemMedChem 3 2008 812 820
20. F. Mannello, G. Tonti, and S. Papa Matrix metalloproteinase inhibitors as anticancer therapeutics Current Cancer Drug Targets 5 2005 285 298 (Pubitemid 40910561)
21. N.G. Lia, Z.H. Shib, Y.P. Tang, and J.A. Duan Selective matrix metalloproteinase inhibitors for cancer Current Medicinal Chemistry 16 2009 27 3805
22. B. Turk Targeting proteases: successes, failures and future prospects Nature Reviews Drug Discovery 5 2006 785 799 (Pubitemid 44323703)
23. L. Devel, V. Rogakos, A. David, A. Makaritis, F. Beau, and P. Cuniasse et al. Development of selective inhibitors and substrate of matrix metalloproteinase-12 Journal of Biological Chemistry 281 2006 11152 11160 (Pubitemid 43855540)
24. L.A. Reiter, K.D. Freeman-Cook, C.S. Jones, G.J. Martinelli, A.S. Antipas, and M.A. Berliner et al. Potent, selective pyrimidinetrione-based inhibitors of MMP-13 Bioorganic & Medicinal Chemistry Letters 16 2006 5822 5826 (Pubitemid 44486733)
25. K. Maeda, M. Kuzuya, X.W. Cheng, T. Asai, S. Kanda, and N. Tamaya-Mori et al. Green tea catechins inhibit the cultured smooth muscle cell invasion through the basement barrier Atherosclerosis 166 2003 23 30 (Pubitemid 35449597)
26. F. Mannello Natural bio-drugs as matrix metalloproteinase inhibitors: new perspectives on the horizon? Recent Patents on Anti-Cancer Drug Discovery 1 2006 91 103
27. S. Kalva, S. Vadivelan, R. Sanam, S.A. Jagarlapudi, and L.M. Saleena Lead identification and optimization of novel collagenase inhibitors; pharmacophore and structure based studies Bioinformation 8 2012 301
28. T. Le Diguarher, A.M. Chollet, M. Bertrand, P. Hennig, E. Raimbaud, and M. Sabatini et al. Stereospecific synthesis of 5-substituted 2-bisarylthiocyclopentane carboxylic acids as specific matrix metalloproteinase inhibitors Journal of Medicinal Chemistry 46 2003 52 3840
29. C.A. Fink, J.E. Carlson, C. Boehm, P. McTaggart, Y. Qiao, and J. Doughty et al. Design and synthesis of thiol containing inhibitors of matrix metalloproteinases Bioorganic & Medicinal Chemistry Letters 9 1999 195 200 (Pubitemid 29059527)
30. V. Aranapakam, J.M. Davis, G.T. Grosu, J. Baker, J. Ellingboe, and A. Zask et al. Synthesis and structure-activity relationship of N-substituted 4-arylsulfonylpiperidine-4-hydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis Journal of Medicinal Chemistry 46 2003 2376 2396 (Pubitemid 36637922)
31. J.I. Levin, J.M. Chen, K. Cheung, D. Cole, C. Crago, and E.D. Santos et al. Acetylenic TACE inhibitors Part 1. SAR of the acyclic sulfonamide hydroxamates Bioorganic & Medicinal Chemistry Letters 13 2003 2799 2803 (Pubitemid 36851573)
32. A.M. Venkatesan, J.M. Davis, G.T. Grosu, J. Baker, A. Zask, and J.I. Levin et al. Synthesis and structure-activity relationships of 4-alkynyloxy phenyl sulfanyl, sulfinyl, and sulfonyl alkyl hydroxamates as tumor necrosis factor-alpha converting enzyme and matrix metalloproteinase inhibitors, Journal of Medicinal Chemistry 47 2004 6255 6269 (Pubitemid 39587250)
33. S. Hanessian, S. Bouzbouz, A. Boudon, G.C. Tucker, and D. Peyroulan Picking the S1, S1′ and S2′ pockets of matrix metalloproteinases. A niche for potent acyclic sulfonamide inhibitors Bioorganic & Medicinal Chemistry Letters 9 1999 1691 1696 (Pubitemid 29278856)
34. J.I. Levin, J.F. DiJoseph, L.M. Killar, A. Sung, T. Walter, and M.A. Sharr et al. The synthesis and biological activity of a novel series of diazepine MMP inhibitors Bioorganic & Medicinal Chemistry Letters 8 1998 2657 2662 (Pubitemid 28496647)
35. H.J. Breyholz, M. Schafers, S. Wagner, C. Holtke, A. Faust, and H. Rabeneck et al. C-5-disubstituted barbiturates as potential molecular probes for noninvasive matrix metalloproteinase imaging Journal of Medicinal Chemistry 48 2005 3400 3409 (Pubitemid 40628057)
36. V. Aranapakam, G.T. Grosu, J.M. Davis, B. Hu, J. Ellingboe, and J.L. Baker et al. Synthesis and structure-activity relationship of alpha-sulfonylhydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis Journal of Medicinal Chemistry 46 2003 2361 2375 (Pubitemid 36637921)
37. D.J. Osguthorpe, W. Sherman, and A.T. Hagler Generation of receptor structural ensembles for virtual screening using binding site shape analysis and clustering Chemical Biology & Drug Design 80 2012 182 193
38. S.L. Dixon, A.M. Smondyrev, E.H. Knoll, S.N. Rao, D.E. Shaw, and R.A. Friesner PHASE: a new engine for pharmacophore perception 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results, Journal of Computer-Aided Molecular Design 20 2006 647 671 (Pubitemid 46023928)
39. P.R. Murumkar, V.P. Zambre, and M.R. Yadav Development of predictive pharmacophore model for in silico screening, and 3D QSAR CoMFA and CoMSIA studies for lead optimization, for designing of potent tumor necrosis factor alpha converting enzyme inhibitors Journal of Computer-Aided Molecular Design 24 2010 143 156
40. W. Tai, T. Lu, H. Yuan, F. Wang, H. Liu, and S. Lu et al. Pharmacophore modeling and virtual screening studies to identify new c-Met inhibitors Journal of Molecular Modeling 18 2012 3087 3100
41. T.B. Lowinger, B. Riedl, J. Dumas, and R.A. Smith Design and discovery of small molecules targeting raf-1 kinase Current Pharmaceutical Design 8 2002 2269 2278 (Pubitemid 35189900)
42. R.A. Smith, J. Barbosa, C.L. Blum, M.A. Bobko, Y.V. Caringal, and R. Dally et al. Discovery of heterocyclic ureas as a new class of raf kinase inhibitors: identification of a second generation lead by a combinatorial chemistry approach Bioorganic & Medicinal Chemistry Letters 11 2001 2775 2778 (Pubitemid 32925314)
43. R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, and T.A. Halgren et al. Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes Journal of Medicinal Chemistry 49 2006 6177 6196 (Pubitemid 44595196)
44. M.J.G.W.T. Frisch, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision A.1 2003 Gaussian, Inc. Pittsburgh PA
45. J.O. De Kerpel, and U. Ryde Protein strain in blue copper proteins studied by free energy perturbations Proteins 36 1999 157 174 (Pubitemid 29305086)
46. F. Lin, and R. Wang Systematic derivation of AMBER force field parameters applicable to zinc-containing systems Journal of Chemical Theory and Computation 6 2010 1852 1870
47. M.B. Peters, Y. Yang, B. Wang, L. Fusti-Molnar, M.N. Weaver, and K.M. Merz Jr. Structural survey of zinc containing proteins and the development of the zinc AMBER force field (ZAFF) Journal of Chemical Theory and Computation 6 2010 2935 2947
48. V. Rajapandian, V. Hakkim, and V. Subramanian Molecular dynamics studies on native, loop-contracted, and metal ion-substituted azurins Journal of Physical Chemistry B 114 2010 8474 8486
49. U. Ryde, M.H. Olsson, B.O. Roos, and A.C. Borin A theoretical study of the copper-cysteine bond in blue copper proteins Theoretical Chemistry Accounts 105 2001 452 462
50. E.I. Solomon, R.K. Szilagyi, S. DeBeer George, and L. Basumallick Electronic structures of metal sites in proteins and models: contributions to function in blue copper proteins Chemical Reviews 104 2004 419 458
51. C. Dennison Investigating the structure and function of cupredoxins Coordination Chemistry Reviews 249 2005 3025 3054 (Pubitemid 41643179)
52. P. Comba, and M. Kerscher Computation of structures and properties of transition metal compounds Coordination Chemistry Reviews 253 2009 564 574
53. S. Shaik, S. Cohen, Y. Wang, H. Chen, D. Kumar, and W. Thiel P450 enzymes: their structure, reactivity, and selectivity-modeled by QM/MM calculations Chemical Reviews 110 2010 949 1017
54. P.E. Siegbahn, and M.R. Blomberg Quantum chemical studies of proton-coupled electron transfer in metalloenzymes Chemical Reviews 110 2010 7040 7061
55. K. Shahrokh, A. Orendt, G.S. Yost, and T.E.3rd. Cheatham Quantum mechanically derived AMBER-compatible heme parameters for various states of the cytochrome P450 catalytic cycle Journal of Computational Chemistry 33 2012 119 133
56. D.A. Case, T.E.3rd Cheatham, T. Darden, H. Gohlke, R. Luo, and K.M. Merz Jr. et al. The Amber biomolecular simulation programs Journal of Computational Chemistry 26 2005 1668 1688 (Pubitemid 43076180)
57. T. Makarewicz, and R. Kazmierkiewicz Molecular Dynamics Simulation by GROMACS Using GUI Plugin for PyMOL Journal of Chemical Information and Modeling 53 2013 1229 1234
58. B. Hess, H. Bekker, H.J. Berendsen, and J.G. Fraaije LINCS: a linear constraint solver for molecular simulations Journal of Computational Chemistry 18 1997 1463 1472 (Pubitemid 127637344)
59. W. Li, H. Liu, E.E. Scott, F. Gräter, J.R. Halpert, and X. Luo et al. Possible pathway (s) of testosterone egress from the active site of cytochrome P450 2B1: a steered molecular dynamics simulation Drug Metabolism and Disposition 33 2005 910 919 (Pubitemid 41002771)
60. D.C. Marks, L. Belov, M.W. Davey, R.A. Davey, and A.D. Kidman The MTT cell viability assay for cytotoxicity testing in multidrug-resistant human leukemic cells Leukemia Research 16 1992 1165 1173 (Pubitemid 23028819)
61. D.T. Vistica, P. Skehan, D. Scudiero, A. Monks, A. Pittman, and M.R. Boyd Tetrazolium-based assays for cellular viability: a critical examination of selected parameters affecting formazan production Cancer Research 51 1991 2515 2520
62. H. Takeuchi, M. Baba, and S. Shigeta An application of tetrazolium (MTT) colorimetric assay for the screening of anti-herpes simplex virus compounds Journal of Virological Methods 33 1991 61 71
63. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the folin phenol reagent Journal of Biological Chemistry 193 1951 265 275
64. K. Kupai, G. Szucs, S. Cseh, I. Hajdu, C. Csonka, and T. Csont et al. Matrix metalloproteinase activity assays: importance of zymography Journal of Pharmacological and Toxicological Methods 61 2010 205 209
65. M. Osathanunkul, K. Buddhachat, and S. Chomdej A modified colorimetric method of gelatinolytic assay using bacterial collagenase, type II as a model Analytical Biochemistry 433 2013 168 170
66. O.D. Defawe, R.D. Kenagy, C. Choi, S.Y. Wan, C. Deroanne, and B. Nusgens et al. MMP-9 regulates both positively and negatively collagen gel contraction A nonproteolytic function of MMP-9 Cardiovascular Research 66 2005 402 409 (Pubitemid 40471055)
67. G.V. Halade, Y.F. Jin, and M.L. Lindsey Matrix metalloproteinase (MMP)-9: a proximal biomarker for cardiac remodeling and a distal biomarker for inflammation Pharmacology & Therapeutics 139 2013 32 40
68. S. Thangapandian, S. John, S. Sakkiah, and K.W. Lee Ligand and structure based pharmacophore modeling to facilitate novel histone deacetylase 8 inhibitor design European Journal of Medicinal Chemistry 45 2010 4409 4417
69. S.L. Dixon, A.M. Smondyrev, E.H. Knoll, S.N. Rao, D.E. Shaw, and R.A. Friesner PHASE: a new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results Journal of Computer-Aided Molecular Design 20 2006 647 671 (Pubitemid 46023928)
70. R.A. Laskowski, and M.B. Swindells LigPlot+: multiple ligand-protein interaction diagrams for drug discovery Journal of Chemical Information and Modeling 51 2011 2778 2786
71. R.C. Rizzo, S. Toba, and I.D. Kuntz A molecular basis for the selectivity of thiadiazole urea inhibitors with stromelysin-1 and gelatinase-A from generalized born molecular dynamics simulations Journal of Medicinal Chemistry 47 2004 3065 3074 (Pubitemid 38702702)
72. A.C. Saragusti, M.G. Ortega, J.L. Cabrera, D.A. Estrin, M.A. Marti, and G.A. Chiabrando Inhibitory effect of quercetin on matrix metalloproteinase 9 activity molecular mechanism and structure-activity relationship of the flavonoid-enzyme interaction European Journal of Pharmacology 644 2010 138 145
73. Z. Bikadi, E. Hazai, F. Zsila, and S.F. Lockwood Molecular modeling of non-covalent binding of homochiral (3S,3′S)-astaxanthin to matrix metalloproteinase-13 (MMP-13) Bioorganic & Medicinal Chemistry 14 2006 5451 5458 (Pubitemid 43994484)
74. T. Hou, W. Zhang, and X. Xu Binding affinities for a series of selective inhibitors of gelatinase-A using molecular dynamics with a linear interaction energy approach Journal of Physical Chemistry B 105 2001 5304 5315 (Pubitemid 35372632)
75. N. Carrascal, and R.C. Rizzo Calculation of binding free energies for non-zinc chelating pyrimidine dicarboxamide inhibitors with MMP-13 Bioorganic & Medicinal Chemistry Letters 19 2009 47 50
76. L.A. Liotta, K. Tryggvason, S. Garbisa, I. Hart, C.M. Foltz, and S. Shafie Metastatic potential correlates with enzymatic degradation of basement membrane collagen Nature 284 1980 67 68 (Pubitemid 10098769)
77. E.J. Bernhard, S.B. Gruber, and R.J. Muschel Direct evidence linking expression of matrix metalloproteinase 9 (92-kDa gelatinase/collagenase) to the metastatic phenotype in transformed rat embryo cells Proceedings of the National Academy of Sciences of the United States of America 91 1994 4293 4297 (Pubitemid 24143419)
78. Y. Tsunezuka, H. Kinoh, T. Takino, Y. Watanabe, Y. Okada, and A. Shinagawa et al. Expression of membrane-type matrix metalloproteinase 1 (MT1-MMP) in tumor cells enhances pulmonary metastasis in an experimental metastasis assay Cancer Research 56 1996 5678 5683 (Pubitemid 26422172)
79. M. Egeblad, and Z. Werb New functions for the matrix metalloproteinases in cancer progression Nature Reviews. Cancer 2 2002 161 174 (Pubitemid 37328786)
80. G. La Rocca, I. Pucci-Minafra, A. Marrazzo, P. Taormina, and S. Minafra Zymographic detection and clinical correlations of MMP-2 and MMP-9 in breast cancer sera British Journal of Cancer 90 2004 1414 1421 (Pubitemid 38586271)
81. X.M. Zhang, S.P. Huang, and Q. Xu Quercetin inhibits the invasion of murine melanoma B16-BL6 cells by decreasing pro-MMP-9 via the PKC pathway Cancer Chemotherapy and Pharmacology 53 2004 82 88 (Pubitemid 38161193)