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Volumn 16, Issue 13, 2016, Pages 1478-1488

Methionine aminopeptidase type-2 inhibitors targeting angiogenesis

Author keywords

ADME; Angiogenesis; Angiogenic inhibitors; Anti angiogenic compounds; Cancer; Drug design; Fumagillin; MetAP 2; Methionine aminiopeptidase; Ovalicin; Pharmacophore; TNP 470

Indexed keywords

BELORANIB; EPIDERMAL GROWTH FACTOR; FIBROBLAST GROWTH FACTOR; FUMAGILLIN; FUMAGILLOL CHLOROACETYLCARBAMATE; INTERLEUKIN 8; MATRIX METALLOPROTEINASE; METHIONYL AMINOPEPTIDASE 2; SCATTER FACTOR; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; VASCULOTROPIN; ZGN 440; AMINOPEPTIDASE; CYCLOHEXANE DERIVATIVE; ENZYME INHIBITOR; GLYCOPROTEIN; METAP2 PROTEIN, HUMAN; O-(CHLOROACETYLCARBAMOYL)FUMAGILLOL; SESQUITERPENE;

EID: 84961684977     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026615666150915121204     Document Type: Article
Times cited : (21)

References (61)
  • 1
    • 0242590529 scopus 로고    scopus 로고
    • Baguley, B. C.; Kerr, D. J., Eds.; Academic Press, San Diego
    • Baguley, B.C. In: Anticancer Drug Development; Baguley, B. C.; Kerr, D. J., Eds.; Academic Press, San Diego, 2002; pp. 1-11.
    • (2002) Anticancer Drug Development , pp. 1-11
    • Baguley, B.C.1
  • 3
    • 77956830880 scopus 로고
    • Bristol J. A., Ed. Academic Press, San Diego
    • Barrett, J.F.; Isaacson, R.E. In: Annual Rep. Med. Chem. Bristol J. A., Ed. Academic Press, San Diego, 1995, pp. 111-118.
    • (1995) Annual Rep. Med. Chem , pp. 111-118
    • Barrett, J.F.1    Isaacson, R.E.2
  • 4
    • 0015311426 scopus 로고
    • Anti-angiogenesis: New concept for therapy of solid tumors
    • Folkman, J. Anti-angiogenesis: new concept for therapy of solid tumors. Ann. Surg. 1972, 175, 409-416.
    • (1972) Ann. Surg , vol.175 , pp. 409-416
    • Folkman, J.1
  • 5
    • 0035254648 scopus 로고    scopus 로고
    • Angiogenesis: Regulators and clinical applications
    • Liekens, S.; De Clercq, E.; Neyts, J. Angiogenesis: regulators and clinical applications. Biochem. Pharmacol., 2001, 61, 253-270.
    • (2001) Biochem. Pharmacol , vol.61 , pp. 253-270
    • Liekens, S.1    De Clercq, E.2    Neyts, J.3
  • 6
    • 0036088478 scopus 로고    scopus 로고
    • Mechanisms of normal and tumorderived angiogenesis
    • Papetti, M.; Herman, I.M. Mechanisms of normal and tumorderived angiogenesis. Am. J. Physiol.-Cell Physiol., 2002, 282, C947-C970.
    • (2002) Am. J. Physiol.-Cell Physiol , vol.282 , pp. C947-C970
    • Papetti, M.1    Herman, I.M.2
  • 7
    • 84975525035 scopus 로고
    • Seminars in Medicine of the Beth Israel Hospital, Boston. Clinical applications of research on angiogenesis
    • Folkman, J. Seminars in Medicine of the Beth Israel Hospital, Boston. Clinical applications of research on angiogenesis. N. Engl. J. Med., 1995, 333, 1757-1763.
    • (1995) N. Engl. J. Med , vol.333 , pp. 1757-1763
    • Folkman, J.1
  • 9
    • 0025204095 scopus 로고
    • Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth
    • Ingber, D.; Fujita, T.; Kishimoto, S.; Sudo, K.; Kanamaru, T.; Brem, H.; Folkman, J. Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth. Nature, 1990, 348, 555-557.
    • (1990) Nature , vol.348 , pp. 555-557
    • Ingber, D.1    Fujita, T.2    Kishimoto, S.3    Sudo, K.4    Kanamaru, T.5    Brem, H.6    Folkman, J.7
  • 11
    • 44049102210 scopus 로고
    • Fumagillin, an antibiotic from Aspergillus fumigatus H-3
    • Eble, T E.; Hanson, F.R. Fumagillin, an antibiotic from Aspergillus fumigatus H-3. Antibiot. Chemother., 1951, 1, 54-58.
    • (1951) Antibiot. Chemother , vol.1 , pp. 54-58
    • Eble, T.E.1    Hanson, F.R.2
  • 12
    • 0025204095 scopus 로고
    • Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth
    • Ingber, D.; Fujita, T.; Kishimoto, S.; Sudo, K.; Kanamaru, T.; Brem, H.; Folkman, J. Synthetic analogues of fumagillin that inhibit angiogenesis and suppress tumour growth. Nature, 1990, 348, 555-557.
    • (1990) Nature , vol.348 , pp. 555-557
    • Ingber, D.1    Fujita, T.2    Kishimoto, S.3    Sudo, K.4    Kanamaru, T.5    Brem, H.6    Folkman, J.7
  • 13
    • 0030924753 scopus 로고    scopus 로고
    • The anti-angiogenic agent fumagillin covalently binds and inhibits the methionine aminopeptidase, MetAP-2
    • Sin, N.; Meng, L.; Wang, M.Q.; Wen, J.J.; Bornmann, W.G.; and Crews, C.M. The anti-angiogenic agent fumagillin covalently binds and inhibits the methionine aminopeptidase, MetAP-2. Proc. Natl. Acad. Sci. U. S. A., 1997, 94, 6099-6103.
    • (1997) Proc. Natl. Acad. Sci. U. S. A , vol.94 , pp. 6099-6103
    • Sin, N.1    Meng, L.2    Wang, M.Q.3    Wen, J.J.4    Bornmann, W.G.5    Crews, C.M.6
  • 14
    • 0031661585 scopus 로고    scopus 로고
    • Synthetic analogues of TNP-470 and ovalicin reveal a common molecular basis for inhibition of angiogenesis and immunosuppression
    • Turk, B.E.; Su, Z.; Liu, J.O. Synthetic analogues of TNP-470 and ovalicin reveal a common molecular basis for inhibition of angiogenesis and immunosuppression. Bioorg. Med. Chem., 1998, 6, 1163-1169.
    • (1998) Bioorg. Med. Chem , vol.6 , pp. 1163-1169
    • Turk, B.E.1    Su, Z.2    Liu, J.O.3
  • 16
    • 0030959441 scopus 로고    scopus 로고
    • Critical components of the female reproductive pathway are suppressed by the angiogenesis inhibitor AGM-1470
    • Klauber, N.; Rohan, R.M.; Flynn, E.; D'Amato, R.J. Critical components of the female reproductive pathway are suppressed by the angiogenesis inhibitor AGM-1470. Nat. Med., 1997, 3, 443-446.
    • (1997) Nat. Med , vol.3 , pp. 443-446
    • Klauber, N.1    Rohan, R.M.2    Flynn, E.3    D'amato, R.J.4
  • 17
    • 0031171961 scopus 로고    scopus 로고
    • Methionine aminopeptidase (Type 2) is the common target for angiogenesis inhibitors AGM-1470 and ovalicin
    • Griffith, E.C.; Su, Z.; Turk, B.E.; Chen, S.; Chang, Y.H.; Wu, Z.; Biemann, K.; Liu, J.O. Methionine aminopeptidase (type 2) is the common target for angiogenesis inhibitors AGM-1470 and ovalicin. Chem. Biol., 1997, 4, 461-471.
    • (1997) Chem. Biol , vol.4 , pp. 461-471
    • Griffith, E.C.1    Su, Z.2    Turk, B.E.3    Chen, S.4    Chang, Y.H.5    Wu, Z.6    Biemann, K.7    Liu, J.O.8
  • 18
    • 0031469819 scopus 로고    scopus 로고
    • Antiangiogenic therapy of experimental cancer does not induce acquired drug resistance
    • Boehm, T.; Folkman, J.; Browder, T.; O’Reilly, M.S. Antiangiogenic therapy of experimental cancer does not induce acquired drug resistance. Nature, 1997, 390, 404-407.
    • (1997) Nature , vol.390 , pp. 404-407
    • Boehm, T.1    Folkman, J.2    Browder, T.3    O’Reilly, M.S.4
  • 21
    • 0032515029 scopus 로고    scopus 로고
    • Structure of human methionine aminopeptidase-2 complexed with fumagillin
    • Liu, S.; Widom, J.; Kemp, C.W.; Crews, C.M.; Clardy, J. Structure of human methionine aminopeptidase-2 complexed with fumagillin. Science, 1998, 282, 1324-1327.
    • (1998) Science , vol.282 , pp. 1324-1327
    • Liu, S.1    Widom, J.2    Kemp, C.W.3    Crews, C.M.4    Clardy, J.5
  • 23
    • 33645846607 scopus 로고    scopus 로고
    • Human methionine aminopeptidase type 2 in complex with L- and D-methionine
    • Nonato, M.C.; Widom, J.; Clardy, J. Human methionine aminopeptidase type 2 in complex with L- and D-methionine. Bioorg. Med. Chem. Lett., 2006, 16, 2580-2583.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 2580-2583
    • Nonato, M.C.1    Widom, J.2    Clardy, J.3
  • 27
    • 0033600583 scopus 로고    scopus 로고
    • The methionyl aminopeptidase from Escherichia coli can function as an iron(II) enzyme
    • D'souza, V.M.; Holz, R.C. The methionyl aminopeptidase from Escherichia coli can function as an iron(II) enzyme. Biochemistry, 1999, 38, 11079-11085.
    • (1999) Biochemistry , vol.38 , pp. 11079-11085
    • D'souza, V.M.1    Holz, R.C.2
  • 28
    • 84961982737 scopus 로고    scopus 로고
    • Which one among Zn(II), Co(II), Mn(II), and Fe(II) is the most efficient ion for the methionine aminopeptidase catalyzed reaction
    • Leopoldini, M.; Russo, N.; Toscano, M. Which one among Zn(II), Co(II), Mn(II), and Fe(II) is the most efficient ion for the methionine aminopeptidase catalyzed reaction? J. Am. Chem. Soc., 2007, 129, 7776-7784.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 7776-7784
    • Leopoldini, M.1    Russo, N.2    Toscano, M.3
  • 29
    • 27744565323 scopus 로고    scopus 로고
    • Structural basis for the functional differences between type I and type II human methionine aminopeptidases
    • Addlagatta, A.; Hu, X.; Liu, J.O.; Matthews, B.W. Structural basis for the functional differences between type I and type II human methionine aminopeptidases. Biochemistry, 2005, 44, 14741-14749.
    • (2005) Biochemistry , vol.44 , pp. 14741-14749
    • Addlagatta, A.1    Hu, X.2    Liu, J.O.3    Matthews, B.W.4
  • 30
    • 0033230999 scopus 로고    scopus 로고
    • Selective inhibition of amino-terminal methionine processing by TNP-470 and ovalicin in endothelial cells
    • Turk, B.E.; Griffith, E.C.; Wolf, S.; Biemann, K.; Chang, Y.H.; Liu, J.O. Selective inhibition of amino-terminal methionine processing by TNP-470 and ovalicin in endothelial cells. Chem. Biol., 1999, 6, 823-833.
    • (1999) Chem. Biol , vol.6 , pp. 823-833
    • Turk, B.E.1    Griffith, E.C.2    Wolf, S.3    Biemann, K.4    Chang, Y.H.5    Liu, J.O.6
  • 31
    • 0034612236 scopus 로고    scopus 로고
    • Cell cycle inhibition by the anti-angiogenic agent TNP-470 is mediated by p53 and p21WAF1/CIP1
    • Zhang, Y.; Griffith, E.C.; Sage, J.; Jacks, T.; Liu, J.O. Cell cycle inhibition by the anti-angiogenic agent TNP-470 is mediated by p53 and p21WAF1/CIP1. Proc. Natl. Acad. Sci. U. S. A., 2000, 97, 6427-6432.
    • (2000) Proc. Natl. Acad. Sci. U. S. A , vol.97 , pp. 6427-6432
    • Zhang, Y.1    Griffith, E.C.2    Sage, J.3    Jacks, T.4    Liu, J.O.5
  • 33
    • 38849143209 scopus 로고    scopus 로고
    • Hybrid angiogenesis inhibitors: Synthesis and biological evaluation of bifunctional compounds based on 1-deoxynojirimycin and aryl-1,2,3- triazoles
    • Zhou, Y.; Zhao, Y.; O'Boyle, K.M.; Murphy, P.V. Hybrid angiogenesis inhibitors: Synthesis and biological evaluation of bifunctional compounds based on 1-deoxynojirimycin and aryl-1,2,3- triazoles. Bioorg. Med. Chem. Lett., 2008, 18, 954-958.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 954-958
    • Zhou, Y.1    Zhao, Y.2    O'boyle, K.M.3    Murphy, P.V.4
  • 34
    • 34248598317 scopus 로고    scopus 로고
    • Inhibition of angiogenesis by the antifungal drug itraconazole. ACS
    • Chong, C. R.; Xu, J.; Lu, J.; Bhat, S.; Sullivan, D.J. Jr.; Liu, J.O. Inhibition of angiogenesis by the antifungal drug itraconazole. ACS Chem. Biol., 2007, 2, 263-270.
    • (2007) Chem. Biol , vol.2 , pp. 263-270
    • Chong, C.R.1    Xu, J.2    Lu, J.3    Bhat, S.4    Sullivan, D.J.5    Liu, J.O.6
  • 38
    • 71849110329 scopus 로고    scopus 로고
    • Metal-mediated inhibition is a viable approach for inhibiting cellular methionine aminopeptidase
    • Chai, S.C.; Ye, Q.Z. Metal-mediated inhibition is a viable approach for inhibiting cellular methionine aminopeptidase. Bioorg. Med. Chem. Lett., 2009, 19, 6862-6864.
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , pp. 6862-6864
    • Chai, S.C.1    Ye, Q.Z.2
  • 45
    • 84961746711 scopus 로고    scopus 로고
    • The clinical trials website
    • The clinical trials website: http://clinicaltrials.gov (Accessed August 24, 2015).
  • 46
    • 3242680935 scopus 로고    scopus 로고
    • RK-805, an endothelial-cell-growth inhibitor produced by Neosartorya sp., and a docking model with methionine aminopeptidase- 2
    • Asami, Y.; Kakeya, H.; Onose, R.; Chang, Y.-H.; Toi, M.; Osada, H. RK-805, an endothelial-cell-growth inhibitor produced by Neosartorya sp., and a docking model with methionine aminopeptidase- 2. Tetrahedron, 2004, 60, 7085-7091.
    • (2004) Tetrahedron , vol.60 , pp. 7085-7091
    • Asami, Y.1    Kakeya, H.2    Onose, R.3    Chang, Y.-H.4    Toi, M.5    Osada, H.6
  • 47
    • 84961746717 scopus 로고    scopus 로고
    • Discovery Studio Modeling Environment, San Diego: Accelrys Software Inc
    • Accelrys Software Inc., Discovery Studio Modeling Environment, San Diego: Accelrys Software Inc., 2012.
    • (2012)
  • 48
    • 84986505827 scopus 로고
    • Validation of the general purpose QUANTA 3.2/CHARMm force field
    • Momany, F.A.; Rone, R. Validation of the general purpose QUANTA 3.2/CHARMm force field. J. Comput. Chem., 1992, 13, 888-900.
    • (1992) J. Comput. Chem , vol.13 , pp. 888-900
    • Momany, F.A.1    Rone, R.2
  • 50
    • 0001398008 scopus 로고    scopus 로고
    • How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules
    • Wang, J.M.; Cieplak, P.; Kollman, P.A. How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J. Comput. Chem., 2000, 21, 1049-1074.
    • (2000) J. Comput. Chem , vol.21 , pp. 1049-1074
    • Wang, J.M.1    Cieplak, P.2    Kollman, P.A.3
  • 51
    • 55549111898 scopus 로고    scopus 로고
    • A fast and accurate computational approach to protein ionization
    • Spassov, V.Z.; Yan, L. A fast and accurate computational approach to protein ionization. Protein Sci., 2008, 17, 1955-1970.
    • (2008) Protein Sci , vol.17 , pp. 1955-1970
    • Spassov, V.Z.1    Yan, L.2
  • 55
    • 0032767386 scopus 로고    scopus 로고
    • Multi-institutional study of the angiogenesis inhibitor TNP-470 in metastatic renal carcinoma
    • Stadler, W.M.; Kuzel, T.; Shapiro, C.; Sosman, J.; Clark, J.; Vogelzang, N.J. Multi-institutional study of the angiogenesis inhibitor TNP-470 in metastatic renal carcinoma. J. Clin. Oncol., 1999, 17, 2541-2545.
    • (1999) J. Clin. Oncol , vol.17 , pp. 2541-2545
    • Stadler, W.M.1    Kuzel, T.2    Shapiro, C.3    Sosman, J.4    Clark, J.5    Vogelzang, N.J.6
  • 56
    • 0034901968 scopus 로고    scopus 로고
    • Phase I trial of the angiogenesis inhibitor TNP-470 for progressive androgen-independent prostate cancer
    • Logothetis, C.J.; Wu, K.K.; Finn, L.D.; Daliani, D.; Figg, W.; Ghaddar, H.; Gutterman, J.U. Phase I trial of the angiogenesis inhibitor TNP-470 for progressive androgen-independent prostate cancer. Clin. Cancer Res., 2001, 7, 1198-1203.
    • (2001) Clin. Cancer Res , vol.7 , pp. 1198-1203
    • Logothetis, C.J.1    Wu, K.K.2    Finn, L.D.3    Daliani, D.4    Figg, W.5    Ghaddar, H.6    Gutterman, J.U.7
  • 57
    • 34447095334 scopus 로고    scopus 로고
    • Design, synthesis, and antiangiogenic effects of a series of potent novel fumagillin analogues
    • Lee, H.W.; Cho, C.S.; Kang, S.K.; Yoo, Y.S.; Shin, J.S.; Ahn, S.K. Design, synthesis, and antiangiogenic effects of a series of potent novel fumagillin analogues. Chem. Pharm. Bull. (Tokyo), 2007, 55, 1024-1029.
    • (2007) Chem. Pharm. Bull. (Tokyo) , vol.55 , pp. 1024-1029
    • Lee, H.W.1    Cho, C.S.2    Kang, S.K.3    Yoo, Y.S.4    Shin, J.S.5    Ahn, S.K.6
  • 58
    • 19444379385 scopus 로고    scopus 로고
    • General pharmacology of CKD-732, a new anticancer agent: Effects on central nervous, cardiovascular, and respiratory system
    • Kim, E.J.; Shin, W.H. General pharmacology of CKD-732, a new anticancer agent: effects on central nervous, cardiovascular, and respiratory system. Biol. Pharm. Bull., 2005, 28, 217.
    • (2005) Biol. Pharm. Bull , vol.28 , pp. 217
    • Kim, E.J.1    Shin, W.H.2


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