메뉴 건너뛰기




Volumn 331, Issue 1, 2009, Pages 45-53

Structure-activity relationship studies of fostriecin, cytostatin, and key analogs, with PP1, PP2A, PP5, and (β12-β13)-chimeras (PP1/PP2A and PP5/PP2A), provide further insight into the inhibitory actions of fostriecin family inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 OXO 5,6 DIHYDRO 2H PYRAN 6 YL] 3,4,6,13 TETRAHYDROXY 3 METHYL 1,7,9,11 TRIDECATETRAENE 3,4 CYCLOPHOSPHATE; 1,5,8,11,18 PENTAHYDROXY 8 METHYLOCTADECA 6,12,14,16 TETRAEN 9 YL DIHYDROGEN PHOSPHATE; 11 DESHYDROXYCYTOSTATIN; 11 METHYL 2,4,6 DODECATRIENE 1,8,10,11 TETRAOL 10 PHOSPHATE; 4 AMINO 7 TERT BUTYL 5 (4 CHLOROPHENYL)PYRAZOLO[3,4 D]PYRIMIDINE; 4 AMINO 7 TERT BUTYL 5 (4 METHYLPHENYL)PYRAZOLO[3,4 D]PYRIMIDINE; ANTINEOPLASTIC AGENT; CYSTEINE; DEPHOSPHOCYTOSTATIN; DEPHOSPHOFOSTRIECIN; EPI CYTOSTATIN; FOSTRIECIN; HEXESTROL DIPHOSPHATE; LACTONE; PHOSPHATASE; SERINE THREONINE PROTEIN PHOSPHATASE 1; SERINE THREONINE PROTEIN PHOSPHATASE 1 CATALYTIC SUBUNIT; SERINE THREONINE PROTEIN PHOSPHATASE 2A CATALYTIC SUBUNIT; SERINE THREONINE PROTEIN PHOSPHATASE 5 CATALYTIC SUBUNIT; UNCLASSIFIED DRUG;

EID: 70349312573     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.109.155630     Document Type: Article
Times cited : (51)

References (40)
  • 1
    • 3042663533 scopus 로고    scopus 로고
    • Total synthesis and biological evaluation of the protein phosphatase 2A inhibitor cytostatin and analogues
    • Bialy L and Waldmann H (2004) Total synthesis and biological evaluation of the protein phosphatase 2A inhibitor cytostatin and analogues. Chemistry 10:2759-2780.
    • (2004) Chemistry , vol.10 , pp. 2759-2780
    • Bialy, L.1    Waldmann, H.2
  • 2
    • 0034800738 scopus 로고    scopus 로고
    • Total synthesis of fostriecin (CI-920)
    • Boger DL, Ichikawa S, and Zhong W (2001) Total synthesis of fostriecin (CI-920). J Am Chem Soc 123:4161-4167.
    • (2001) J Am Chem Soc , vol.123 , pp. 4161-4167
    • Boger, D.L.1    Ichikawa, S.2    Zhong, W.3
  • 5
    • 33846630833 scopus 로고    scopus 로고
    • SODOCK: Swarm optimization for highly flexible protein-ligand docking
    • Chen HM, Liu BF, Huang HL, Hwang SF, and Ho SY (2007) SODOCK: swarm optimization for highly flexible protein-ligand docking. J Comput Chem 28:612-623.
    • (2007) J Comput Chem , vol.28 , pp. 612-623
    • Chen, H.M.1    Liu, B.F.2    Huang, H.L.3    Hwang, S.F.4    Ho, S.Y.5
  • 6
    • 33846118688 scopus 로고    scopus 로고
    • Crystal structure of a protein phosphatase 2A heterotrimeric holoenzyme
    • DOI 10.1038/nature05351, PII NATURE05351
    • Cho US and Xu W (2007) Crystal structure of a protein phosphatase 2A heterotrimeric holoenzyme. Nature 445:53-57. (Pubitemid 46067298)
    • (2007) Nature , vol.445 , Issue.7123 , pp. 53-57
    • Cho, U.S.1    Xu, W.2
  • 7
    • 33745092075 scopus 로고    scopus 로고
    • Pharmacophore identification: The case of the Ser/Thr protein phosphatase inhibitors
    • Colby DA and Chamberlin AR (2006) Pharmacophore identification: the case of the Ser/Thr protein phosphatase inhibitors. Mini Rev Med Chem 6:657-665.
    • (2006) Mini Rev Med Chem , vol.6 , pp. 657-665
    • Colby, D.A.1    Chamberlin, A.R.2
  • 9
    • 0036923391 scopus 로고    scopus 로고
    • Versatile enantiocontrolled synthesis of (+)-fostriecin
    • Esumi T, Okamoto N, and Hatakeyama S (2002) Versatile enantiocontrolled synthesis of (+)-fostriecin. Chem Commun (Camb) 24:3042-3043.
    • (2002) Chem Commun (Camb) , vol.24 , pp. 3042-3043
    • Esumi, T.1    Okamoto, N.2    Hatakeyama, S.3
  • 10
    • 0035354316 scopus 로고    scopus 로고
    • The predicted beta12-beta13 loop is important for inhibition of PP2Acalpha by the antitumor drug fostriecin
    • Evans DR and Simon JA (2001) The predicted beta12-beta13 loop is important for inhibition of PP2Acalpha by the antitumor drug fostriecin. FEBS Lett 498:110-115.
    • (2001) FEBS Lett , vol.498 , pp. 110-115
    • Evans, D.R.1    Simon, J.A.2
  • 11
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity - A rapid access to atomic charges
    • Gasteiger J and Marsili M (1980) Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges. Tetrahedron 36:3219-3228.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 12
    • 0029094754 scopus 로고
    • Three-dimensional structure of the catalytic subunit of protein serine/threonine phosphatase-1
    • Goldberg J, Huang HB, Kwon YG, Greengard P, Nairn AC, and Kuriyan J (1995) Three-dimensional structure of the catalytic subunit of protein serine/threonine phosphatase-1. Nature 376:745-753.
    • (1995) Nature , vol.376 , pp. 745-753
    • Goldberg, J.1    Huang, H.B.2    Kwon, Y.G.3    Greengard, P.4    Nairn, A.C.5    Kuriyan, J.6
  • 13
    • 0035451848 scopus 로고    scopus 로고
    • New energy terms for reduced protein models implemented in an off-lattice force field
    • Hassinen T and Peräkylä M (2001) New energy terms for reduced protein models implemented in an off-lattice force field. J Comput Chem 22:1229-1242.
    • (2001) J Comput Chem , vol.22 , pp. 1229-1242
    • Hassinen, T.1    Peräkylä, M.2
  • 14
    • 20444424775 scopus 로고    scopus 로고
    • Serine/threonine protein phosphatase inhibitors with anti-tumor activity
    • Honkanen RE (2005) Serine/threonine protein phosphatase inhibitors with anti-tumor activity. Handbk Exp Pharm 167:295-317.
    • (2005) Handbk Exp Pharm , vol.167 , pp. 295-317
    • Honkanen, R.E.1
  • 17
    • 0032991501 scopus 로고    scopus 로고
    • Differential induction of apoptosis in B16 melanoma and EL-4 lymphoma cells by cytostatin and bactobolin
    • Kawada M, Amemiya M, Ishizuka M, and Takeuchi T (1999) Differential induction of apoptosis in B16 melanoma and EL-4 lymphoma cells by cytostatin and bactobolin. Jpn J Cancer Res 90:219-225. (Pubitemid 29112323)
    • (1999) Japanese Journal of Cancer Research , vol.90 , Issue.2 , pp. 219-225
    • Kawada, M.1    Amemiya, M.2    Ishizuka, M.3    Takeuchi, T.4
  • 21
    • 1442277086 scopus 로고    scopus 로고
    • Phase I and pharmacokinetic study of fostriecin given as an intravenous bolus daily for five consecutive days
    • DOI 10.1023/B:DRUG.0000011792.13160.b0
    • Lê LH, Erlichman C, Pillon L, Thiessen JJ, Day A, Wainman N, Eisenhauer EA, and Moore MJ (2004) Phase I and pharmacokinetic study of fostriecin given as an intravenous bolus daily for five consecutive days. Invest New Drugs 22:159-167. (Pubitemid 38270471)
    • (2004) Investigational New Drugs , vol.22 , Issue.2 , pp. 159-167
    • Le, L.H.1    Erlichman, C.2    Pillon, L.3    Thiessen, J.J.4    Day, A.5    Wainman, N.6    Eisenhauer, E.A.7    Moore, M.J.8
  • 25
    • 0029014647 scopus 로고
    • Inhibitory effect of cytostatin on spontaneous lung metastases of B16-BL6 melanoma cells
    • Masuda T, Watanabe S, Amemiya M, Ishizuka M, and Takeuchi T (1995) Inhibitory effect of cytostatin on spontaneous lung metastases of B16-BL6 melanoma cells. J Antibiot (Tokyo) 48:528-529.
    • (1995) J Antibiot (Tokyo) , vol.48 , pp. 528-529
    • Masuda, T.1    Watanabe, S.2    Amemiya, M.3    Ishizuka, M.4    Takeuchi, T.5
  • 28
    • 0037149632 scopus 로고    scopus 로고
    • Asymmetric total synthesis of (+)-fostriecin
    • Reddy YK and Falck JR (2002) Asymmetric total synthesis of (+)-fostriecin. Org Lett 4:969-971.
    • (2002) Org Lett , vol.4 , pp. 969-971
    • Reddy, Y.K.1    Falck, J.R.2
  • 29
    • 22844440711 scopus 로고    scopus 로고
    • New and fast statistical-thermodynamic method for computation of protein-ligand binding entropy substantially improves docking accuracy
    • Ruvinsky AM and Kozintsev AV (2005) New and fast statistical- thermodynamic method for computation of protein-ligand binding entropy substantially improves docking accuracy. J Comput Chem 26:1089-1095.
    • (2005) J Comput Chem , vol.26 , pp. 1089-1095
    • Ruvinsky, A.M.1    Kozintsev, A.V.2
  • 30
    • 0027804108 scopus 로고
    • An effective solvation term based on atomic occupancies for use in protein simulations
    • Stouten PFW, Frömmel C, Nakamura H, and Sander C (1993) An effective solvation term based on atomic occupancies for use in protein simulations. Mol Simulat 10:97-120.
    • (1993) Mol Simulat , vol.10 , pp. 97-120
    • Stouten, P.F.W.1    Frömmel, C.2    Nakamura, H.3    Sander, C.4
  • 31
    • 0025007779 scopus 로고
    • Preclinical toxicological evaluation of fostriecin, a novel anticancer antibiotic, in rats
    • Susick RL Jr, Hawkins KL, and Pegg DG (1990) Preclinical toxicological evaluation of fostriecin, a novel anticancer antibiotic, in rats. Fundam Appl Toxicol 15:258-269.
    • (1990) Fundam Appl Toxicol , vol.15 , pp. 258-269
    • Susick Jr., R.L.1    Hawkins, K.L.2    Pegg, D.G.3
  • 32
    • 34447275978 scopus 로고    scopus 로고
    • Small-molecule inhibitors of Ser/Thr protein phosphatases: Specificity, use and common forms of abuse
    • Swingle M, Ni L, and Honkanen RE (2007) Small-molecule inhibitors of Ser/Thr protein phosphatases: specificity, use and common forms of abuse. Methods Mol Biol 365:23-38.
    • (2007) Methods Mol Biol , vol.365 , pp. 23-38
    • Swingle, M.1    Ni, L.2    Honkanen, R.E.3
  • 33
    • 4043101125 scopus 로고    scopus 로고
    • Structural basis for the catalytic activity of human serine/threonine protein phosphatase-5
    • DOI 10.1074/jbc.M402855200
    • Swingle MR, Honkanen RE, and Ciszak EM (2004) Structural basis for the catalytic activity of human serine/threonine protein phosphatase-5. J Biol Chem 279: 33992-33999. (Pubitemid 39063050)
    • (2004) Journal of Biological Chemistry , vol.279 , Issue.32 , pp. 33992-33999
    • Swingle, M.R.1    Honkanen, R.E.2    Ciszak, E.M.3
  • 35
    • 0032981362 scopus 로고    scopus 로고
    • Protein phosphatase 2A inhibitors, phoslactomycins, effects on the cytoskeleton in NIH/3T3 cells
    • Usui T, Marriott G, Inagaki M, Swarup G, and Osada H (1999) Protein phosphatase 2A inhibitors, phoslactomycins. Effects on the cytoskeleton in NIH/3T3 cells. J Biochem 125:960-965. (Pubitemid 29253567)
    • (1999) Journal of Biochemistry , vol.125 , Issue.5 , pp. 960-965
    • Usui, T.1    Marriott, G.2    Inagaki, M.3    Swarup, G.4    Osada, H.5
  • 36
    • 0030720062 scopus 로고    scopus 로고
    • Fostriecin, an antitumor antibiotic with inhibitory activity against serine/threonine protein phosphatases types 1 (PP1) and 2A (PP2A), is highly selective for PP2A
    • DOI 10.1016/S0014-5793(97)01210-6, PII S0014579397012106
    • Walsh AH, Cheng A, and Honkanen RE (1997) Fostriecin, an antitumor antibiotic with inhibitory activity against serine/threonine protein phosphatases types 1 (PP1) and 2A (PP2A), is highly selective for PP2A. FEBS Lett 416:230-234. (Pubitemid 27475370)
    • (1997) FEBS Letters , vol.416 , Issue.3 , pp. 230-234
    • Walsh, A.H.1    Cheng, A.2    Honkanen, R.E.3
  • 38
    • 33750006297 scopus 로고    scopus 로고
    • Structure of Protein Phosphatase 2A Core Enzyme Bound to Tumor-Inducing Toxins
    • DOI 10.1016/j.cell.2006.09.025, PII S0092867406012293
    • Xing Y, Xu Y, Chen Y, Jeffrey PD, Chao Y, Lin Z, Li Z, Strack S, Stock JB, and Shi Y (2006) Structure of protein phosphatase 2A core enzyme bound to tumorinducing toxins. Cell 127:341-353. (Pubitemid 44572378)
    • (2006) Cell , vol.127 , Issue.2 , pp. 341-353
    • Xing, Y.1    Xu, Y.2    Chen, Y.3    Jeffrey, P.D.4    Chao, Y.5    Lin, Z.6    Li, Z.7    Strack, S.8    Stock, J.B.9    Shi, Y.10
  • 39
    • 0029934685 scopus 로고    scopus 로고
    • Mutational analysis of the catalytic subunit of muscle protein phosphatase-1
    • DOI 10.1021/bi952954l
    • Zhang J, Zhang Z, Brew K, and Lee EY (1996) Mutational analysis of the catalytic subunit of muscle protein phosphatase-1. Biochemistry 35:6276-6282. (Pubitemid 26164057)
    • (1996) Biochemistry , vol.35 , Issue.20 , pp. 6276-6282
    • Zhang, J.1    Zhang, Z.2    Brew, K.3    Lee, E.Y.C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.