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Volumn 58, Issue 18, 2015, Pages 7224-7240

N-O-Isopropyl Sulfonamido-Based Hydroxamates as Matrix Metalloproteinase Inhibitors: Hit Selection and in Vivo Antiangiogenic Activity

Author keywords

[No Author keywords available]

Indexed keywords

4 (1,3 DIOXOISOINDOLIN 2 YL) N HYDROXY 2 (N ISOPROPOXY 4' METHOXYBIPHENYL 4 YLSULFONAMIDO)BUTANAMIDE; GELATINASE A; GELATINASE B; HYDROXAMIC ACID DERIVATIVE; MATRIX METALLOPROTEINASE; MATRIX METALLOPROTEINASE 14; METALLOPROTEINASE INHIBITOR; N O ISOPROPYL SULFONAMIDO DERIVATIVE; UNCLASSIFIED DRUG; ANGIOGENESIS INHIBITOR; HYDROXAMIC ACID; MATRIX METALLOPROTEINASE INHIBITOR; SULFONAMIDE;

EID: 84942346084     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b00367     Document Type: Article
Times cited : (65)

References (54)
  • 1
    • 0033134622 scopus 로고    scopus 로고
    • Matrix metalloproteinases in angiogenesis: A moving target for therapeutic intervention
    • Stetler-Stevenson, W. G. Matrix metalloproteinases in angiogenesis: a moving target for therapeutic intervention J. Clin. Invest. 1999, 103, 1237-1241 10.1172/JCI6870
    • (1999) J. Clin. Invest. , vol.103 , pp. 1237-1241
    • Stetler-Stevenson, W.G.1
  • 2
    • 84857422770 scopus 로고    scopus 로고
    • A heterogeneous in vitro three dimensional model of tumour-stroma interactions regulating sprouting angiogenesis
    • Correa de Sampaio, P.; Auslaender, D.; Krubasik, D.; Failla, A. V.; Skepper, J. N.; Murphy, G.; English, W. R. A heterogeneous in vitro three dimensional model of tumour-stroma interactions regulating sprouting angiogenesis PLoS One 2012, 7, e30753 10.1371/journal.pone.0030753
    • (2012) PLoS One , vol.7 , pp. e30753
    • Correa De Sampaio, P.1    Auslaender, D.2    Krubasik, D.3    Failla, A.V.4    Skepper, J.N.5    Murphy, G.6    English, W.R.7
  • 3
    • 24044459285 scopus 로고    scopus 로고
    • Matrix metalloproteinases and angiogenesis
    • Rundhaug, J. E. Matrix metalloproteinases and angiogenesis J. Cell. Mol. Med. 2005, 9, 267-285 10.1111/j.1582-4934.2005.tb00355.x
    • (2005) J. Cell. Mol. Med. , vol.9 , pp. 267-285
    • Rundhaug, J.E.1
  • 5
    • 33646576169 scopus 로고    scopus 로고
    • Matrix metalloproteinases and tumor metastasis
    • Deryugina, E. I.; Quigley, J. P. Matrix metalloproteinases and tumor metastasis Cancer Metastasis Rev. 2006, 25, 9-34 10.1007/s10555-006-7886-9
    • (2006) Cancer Metastasis Rev. , vol.25 , pp. 9-34
    • Deryugina, E.I.1    Quigley, J.P.2
  • 6
    • 34250307200 scopus 로고    scopus 로고
    • MT1-MMP controls tumor-induced angiogenesis through the release of semaphorin 4D
    • Basile, J. R.; Holmbeck, K.; Bugge, T. H.; Gutkind, J. S. MT1-MMP controls tumor-induced angiogenesis through the release of semaphorin 4D J. Biol. Chem. 2007, 282, 6899-6905 10.1074/jbc.M609570200
    • (2007) J. Biol. Chem. , vol.282 , pp. 6899-6905
    • Basile, J.R.1    Holmbeck, K.2    Bugge, T.H.3    Gutkind, J.S.4
  • 7
    • 77957281923 scopus 로고    scopus 로고
    • Coordinate action of membrane-type matrix metalloproteinase-1 (MT1-MMP) and MMP-2 enhances pericellular proteolysis and invasion
    • Sato, H.; Takino, T. Coordinate action of membrane-type matrix metalloproteinase-1 (MT1-MMP) and MMP-2 enhances pericellular proteolysis and invasion Cancer Sci. 2010, 101, 843-847 10.1111/j.1349-7006.2010.01498.x
    • (2010) Cancer Sci. , vol.101 , pp. 843-847
    • Sato, H.1    Takino, T.2
  • 9
    • 0037192458 scopus 로고    scopus 로고
    • Matrix metalloproteinase inhibitors and cancer: Trials and tribulations
    • Coussens, L. M.; Fingleton, B.; Matrisian, L. M. Matrix metalloproteinase inhibitors and cancer: trials and tribulations Science 2002, 295, 2387-2392 10.1126/science.1067100
    • (2002) Science , vol.295 , pp. 2387-2392
    • Coussens, L.M.1    Fingleton, B.2    Matrisian, L.M.3
  • 13
    • 41349106390 scopus 로고    scopus 로고
    • Carbamoylphosphonate matrix metalloproteinase inhibitors 6: Cis-2-aminocyclohexylcarbamoylphosphonic acid, a novel orally active antimetastatic matrix metalloproteinase-2 selective inhibitor - Synthesis and pharmacodynamic and pharmacokinetic analysis
    • Hoffman, A.; Qadri, B.; Frant, J.; Katz, Y.; Bhusare, S. R.; Breuer, E.; Hadar, R.; Reich, R. Carbamoylphosphonate matrix metalloproteinase inhibitors 6: cis-2-aminocyclohexylcarbamoylphosphonic acid, a novel orally active antimetastatic matrix metalloproteinase-2 selective inhibitor - synthesis and pharmacodynamic and pharmacokinetic analysis J. Med. Chem. 2008, 51, 1406-1414 10.1021/jm701087n
    • (2008) J. Med. Chem. , vol.51 , pp. 1406-1414
    • Hoffman, A.1    Qadri, B.2    Frant, J.3    Katz, Y.4    Bhusare, S.R.5    Breuer, E.6    Hadar, R.7    Reich, R.8
  • 16
    • 33646175469 scopus 로고    scopus 로고
    • Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides
    • Tuccinardi, T.; Martinelli, A.; Nuti, E.; Carelli, P.; Balzano, F.; Uccello-Barretta, G.; Murphy, G.; Rossello, A. Amber force field implementation, molecular modelling study, synthesis and MMP-1/MMP-2 inhibition profile of (R)- and (S)-N-hydroxy-2-(N-isopropoxybiphenyl-4-ylsulfonamido)-3-methylbutanamides Bioorg. Med. Chem. 2006, 14, 4260-4276 10.1016/j.bmc.2006.01.056
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 4260-4276
    • Tuccinardi, T.1    Martinelli, A.2    Nuti, E.3    Carelli, P.4    Balzano, F.5    Uccello-Barretta, G.6    Murphy, G.7    Rossello, A.8
  • 23
    • 2142828483 scopus 로고    scopus 로고
    • 2, a fluorogenic substrate with increased specificity constants for collagenases and tumor necrosis factor converting enzyme
    • 2, a fluorogenic substrate with increased specificity constants for collagenases and tumor necrosis factor converting enzyme Anal. Biochem. 2004, 328, 166-173 10.1016/j.ab.2003.12.035
    • (2004) Anal. Biochem. , vol.328 , pp. 166-173
    • Neumann, U.1    Kubota, H.2    Frei, K.3    Ganu, V.4    Leppert, D.5
  • 25
    • 33644545381 scopus 로고    scopus 로고
    • Tumour microenvironment - Opinion: Validating matrix metalloproteinases as drug targets and anti-targets for cancer therapy
    • Overall, C. M.; Kleifeld, O. Tumour microenvironment-opinion: validating matrix metalloproteinases as drug targets and anti-targets for cancer therapy Nat. Rev. Cancer 2006, 6, 227-239 10.1038/nrc1821
    • (2006) Nat. Rev. Cancer , vol.6 , pp. 227-239
    • Overall, C.M.1    Kleifeld, O.2
  • 26
    • 84930764392 scopus 로고    scopus 로고
    • Tumor angiogenesis: MMP-mediated induction of intravasation- and metastasis-sustaining neovasculature
    • Deryugina, E. I.; Quigley, J. P. Tumor angiogenesis: MMP-mediated induction of intravasation- and metastasis-sustaining neovasculature Matrix Biol. 2015, 44-46, 94-112 10.1016/j.matbio.2015.04.004
    • (2015) Matrix Biol. , vol.4446 , pp. 94-112
    • Deryugina, E.I.1    Quigley, J.P.2
  • 27
    • 77949813516 scopus 로고    scopus 로고
    • Drug design of sulfonylated MMP inhibitors
    • Wiley Series in Drug Discovery and Development; Wang, B. Series; John Wiley & Sons, Inc. New York
    • Rossello, A.; Nuti, E. Drug design of sulfonylated MMP inhibitors. In Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications; Wiley Series in Drug Discovery and Development; Wang, B., Series Ed.; John Wiley & Sons, Inc.: New York, 2009; pp 549-589.
    • (2009) Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications , pp. 549-589
    • Rossello, A.1    Nuti, E.2
  • 32
    • 0346887176 scopus 로고    scopus 로고
    • Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors
    • Ma, D.; Wu, W.; Yang, G.; Li, J.; Li, J.; Ye, Q. Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors Bioorg. Med. Chem. Lett. 2004, 14, 47-50 10.1016/j.bmcl.2003.10.026
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 47-50
    • Ma, D.1    Wu, W.2    Yang, G.3    Li, J.4    Li, J.5    Ye, Q.6
  • 33
    • 50349090567 scopus 로고    scopus 로고
    • Synthesis of new sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors
    • Cheng, X. C.; Wang, Q.; Fang, H.; Tang, W.; Xu, W. F. Synthesis of new sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors Bioorg. Med. Chem. 2008, 16, 7932-7938 10.1016/j.bmc.2008.07.073
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 7932-7938
    • Cheng, X.C.1    Wang, Q.2    Fang, H.3    Tang, W.4    Xu, W.F.5
  • 36
    • 34347234200 scopus 로고    scopus 로고
    • The chemoinvasion assay: A method to assess tumor and endothelial cell invasion and its modulation
    • Albini, A.; Benelli, R. The chemoinvasion assay: a method to assess tumor and endothelial cell invasion and its modulation Nat. Protoc. 2007, 2, 504-511 10.1038/nprot.2006.466
    • (2007) Nat. Protoc. , vol.2 , pp. 504-511
    • Albini, A.1    Benelli, R.2
  • 37
    • 0027981273 scopus 로고
    • Angiogenic potential in vivo by Kaposis sarcoma cell-free supernatants and HIV-1 tat product: Inhibition of KS-like lesions by tissue inhibitor of metalloproteinase-2
    • Albini, A.; Fontanini, G.; Masiello, L.; Tacchetti, C.; Bigini, D.; Luzzi, P.; Noonan, D. M.; Stetler-Stevenson, W. G. Angiogenic potential in vivo by Kaposis sarcoma cell-free supernatants and HIV-1 tat product: inhibition of KS-like lesions by tissue inhibitor of metalloproteinase-2 AIDS 1994, 8, 1237-1244 10.1097/00002030-199409000-00004
    • (1994) AIDS , vol.8 , pp. 1237-1244
    • Albini, A.1    Fontanini, G.2    Masiello, L.3    Tacchetti, C.4    Bigini, D.5    Luzzi, P.6    Noonan, D.M.7    Stetler-Stevenson, W.G.8
  • 38
    • 70350085639 scopus 로고    scopus 로고
    • Molecular Devices: Sunnyvale, CA
    • SoftMax Pro 4.7.1; Molecular Devices: Sunnyvale, CA, 2004.
    • (2004) SoftMax Pro 4.7.1
  • 39
    • 77949835201 scopus 로고    scopus 로고
    • Erithecus Software: Staines, Middlesex, UK
    • GraFit version 4; Erithecus Software: Staines, Middlesex, UK, 1998.
    • (1998) GraFit Version 4
  • 40
    • 84902009927 scopus 로고    scopus 로고
    • Contribution: Angiogenesis Analyzer
    • Carpentier, G. Contribution: Angiogenesis Analyzer. ImageJ. News http://imagej.nih.gov/ij/notes.html, 2012
    • (2012) ImageJ. News
    • Carpentier, G.1
  • 41
    • 0033990048 scopus 로고    scopus 로고
    • Primer3 on the WWW for general users and for biologist programmers
    • Rozen, S.; Skaletsky, H. Primer3 on the WWW for general users and for biologist programmers Methods Mol. Biol. 1999, 132, 365-386 10.1385/1-59259-192-2:365
    • (1999) Methods Mol. Biol. , vol.132 , pp. 365-386
    • Rozen, S.1    Skaletsky, H.2
  • 44
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
    • Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 1998, 19, 1639-1662 10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 46
    • 36449007976 scopus 로고
    • The effect of long range electrostatic interactions in simulations of macromolecular crystals: A comparison of the Ewald and truncated list methods
    • York, D. M.; Darden, T. A.; Pedersen, L. G. The effect of long range electrostatic interactions in simulations of macromolecular crystals: a comparison of the Ewald and truncated list methods J. Chem. Phys. 1993, 99, 8345-8348 10.1063/1.465608
    • (1993) J. Chem. Phys. , vol.99 , pp. 8345-8348
    • York, D.M.1    Darden, T.A.2    Pedersen, L.G.3
  • 48
    • 84893676573 scopus 로고    scopus 로고
    • Strategies for Protein Cryocrystallography
    • Vera, L.; Stura, E. A. Strategies for Protein Cryocrystallography Cryst. Growth Des. 2014, 14, 427-435 10.1021/cg301531f
    • (2014) Cryst. Growth Des. , vol.14 , pp. 427-435
    • Vera, L.1    Stura, E.A.2
  • 54
    • 0026117693 scopus 로고
    • Applications of the streak seeding technique in protein crystallization
    • Stura, E. A.; Wilson, I. A. Applications of the streak seeding technique in protein crystallization J. Cryst. Growth 1991, 110, 270-282 10.1016/0022-0248(91)90896-D
    • (1991) J. Cryst. Growth , vol.110 , pp. 270-282
    • Stura, E.A.1    Wilson, I.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.