메뉴 건너뛰기




Volumn 55, Issue 20, 2012, Pages 8859-8878

Synthetic silvestrol analogues as potent and selective protein synthesis inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PROTEIN SYNTHESIS INHIBITOR; SILVESTROL ANALOGUE; UNCLASSIFIED DRUG;

EID: 84867760869     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3011542     Document Type: Article
Times cited : (61)

References (49)
  • 2
    • 79955637310 scopus 로고    scopus 로고
    • The biological and therapeutic relevance of mRNA translation in cancer
    • Blagden, S. P.; Willis, A. E. The biological and therapeutic relevance of mRNA translation in cancer Nat. Rev. Clin. Oncol. 2011, 8, 280-291
    • (2011) Nat. Rev. Clin. Oncol. , vol.8 , pp. 280-291
    • Blagden, S.P.1    Willis, A.E.2
  • 3
    • 2342639670 scopus 로고    scopus 로고
    • Signaling control of mRNA translation in cancer pathogenesis
    • Holland, E. C.; Sonenberg, N.; Pandolfi, P. P.; Thomas, G. Signaling control of mRNA translation in cancer pathogenesis Oncogene 2004, 23, 3138-3144
    • (2004) Oncogene , vol.23 , pp. 3138-3144
    • Holland, E.C.1    Sonenberg, N.2    Pandolfi, P.P.3    Thomas, G.4
  • 4
    • 77958027783 scopus 로고    scopus 로고
    • Targeting eukaryotic translation initiation factor 4E (eIF4E) in cancer
    • Hsieh, A. G.; Ruggero, D. Targeting eukaryotic translation initiation factor 4E (eIF4E) in cancer Clin. Cancer Res. 2010, 16, 4914-4920
    • (2010) Clin. Cancer Res. , vol.16 , pp. 4914-4920
    • Hsieh, A.G.1    Ruggero, D.2
  • 5
    • 38849180436 scopus 로고    scopus 로고
    • Targeting the eurkaryotic translation initiation factor 4E for cancer therapy
    • Graff, J. R.; Konicek, B. W.; Carter, J. H.; Marcusson, E. G. Targeting the eurkaryotic translation initiation factor 4E for cancer therapy Cancer Res. 2008, 68, 631-634
    • (2008) Cancer Res. , vol.68 , pp. 631-634
    • Graff, J.R.1    Konicek, B.W.2    Carter, J.H.3    Marcusson, E.G.4
  • 6
    • 2342489456 scopus 로고    scopus 로고
    • EIF-4E expression and its role in malignancies and metastases
    • DeBenedetti, A.; Graff, J. R. eIF-4E expression and its role in malignancies and metastases Oncogene 2004, 23, 3189-3199
    • (2004) Oncogene , vol.23 , pp. 3189-3199
    • Debenedetti, A.1    Graff, J.R.2
  • 7
    • 0025314596 scopus 로고
    • Malignant transformation by a eukaryotic initiation factor subunit that binds to mRNA 5 cap
    • Lazaris-Karatzas, A.; Montine, K. S.; Sonenberg, N. Malignant transformation by a eukaryotic initiation factor subunit that binds to mRNA 5 cap Nature 1990, 345, 544-547
    • (1990) Nature , vol.345 , pp. 544-547
    • Lazaris-Karatzas, A.1    Montine, K.S.2    Sonenberg, N.3
  • 8
    • 77954296394 scopus 로고    scopus 로고
    • 4E-BP1 is a key effector of the oncogenic activation of the AKT and ERK signaling pathways that integrates their function in tumors
    • She, Q.-B.; Halilovic, E.; Ye, Q.; Zhen, W.; Shirasawa, S.; Sasazuki, T.; Solit, D. B.; Rosen, N. 4E-BP1 is a key effector of the oncogenic activation of the AKT and ERK signaling pathways that integrates their function in tumors Cancer Cell 2010, 18, 39-51
    • (2010) Cancer Cell , vol.18 , pp. 39-51
    • She, Q.-B.1    Halilovic, E.2    Ye, Q.3    Zhen, W.4    Shirasawa, S.5    Sasazuki, T.6    Solit, D.B.7    Rosen, N.8
  • 9
    • 77649286736 scopus 로고    scopus 로고
    • Genetic dissection of the oncogenic mTOR pathway reveals druggable addiction to translational control via 4EBP-eIF4E
    • Hsieh, A. G.; Costa, M.; Zollo, O.; Davis, C.; Feldman, M. E.; Testa, J. R.; Meyuhas, O.; Shokat, K. M.; Ruggero, D. Genetic dissection of the oncogenic mTOR pathway reveals druggable addiction to translational control via 4EBP-eIF4E Cancer Cell 2010, 17, 249-261
    • (2010) Cancer Cell , vol.17 , pp. 249-261
    • Hsieh, A.G.1    Costa, M.2    Zollo, O.3    Davis, C.4    Feldman, M.E.5    Testa, J.R.6    Meyuhas, O.7    Shokat, K.M.8    Ruggero, D.9
  • 11
    • 4444285717 scopus 로고    scopus 로고
    • Characterization of programmed cell death 4 in multiple human cancers reveals a novel enhancer of drug sensitivity
    • Jansen, A. P.; Camalier, C. E.; Stark, C.; Colburn, N. H. Characterization of programmed cell death 4 in multiple human cancers reveals a novel enhancer of drug sensitivity Mol. Cancer Ther. 2004, 3, 103-110
    • (2004) Mol. Cancer Ther. , vol.3 , pp. 103-110
    • Jansen, A.P.1    Camalier, C.E.2    Stark, C.3    Colburn, N.H.4
  • 12
    • 0035032444 scopus 로고    scopus 로고
    • The requirement for eukaryotic initiation factor 4A (eIF4A) in translation is in direct proportion to the degree of mRNA 59 secondary structure
    • Svitkin, Y. V.; Pause, A.; Haghighat, A.; Pyronnet, S.; Witherell, G.; Belsham, G. J.; Sonenberg, N. The requirement for eukaryotic initiation factor 4A (eIF4A) in translation is in direct proportion to the degree of mRNA 59 secondary structure RNA 2001, 7, 382-394
    • (2001) RNA , vol.7 , pp. 382-394
    • Svitkin, Y.V.1    Pause, A.2    Haghighat, A.3    Pyronnet, S.4    Witherell, G.5    Belsham, G.J.6    Sonenberg, N.7
  • 13
    • 0026342613 scopus 로고
    • An analysis of vertebrate mRNA sequences: Intimations of translational control
    • Kozak, M. An analysis of vertebrate mRNA sequences: intimations of translational control J. Cell Biol. 1991, 115, 887-903
    • (1991) J. Cell Biol. , vol.115 , pp. 887-903
    • Kozak, M.1
  • 14
    • 80054104822 scopus 로고    scopus 로고
    • Inhibition of translation initiation as a novel paradigm for cancer therapy
    • Aktas, B. H.; Halperin, J. A.; Wagner, G.; Chorev, M. Inhibition of translation initiation as a novel paradigm for cancer therapy Annu. Rep. Med. Chem. 2011, 46, 189-210
    • (2011) Annu. Rep. Med. Chem. , vol.46 , pp. 189-210
    • Aktas, B.H.1    Halperin, J.A.2    Wagner, G.3    Chorev, M.4
  • 15
    • 77953422876 scopus 로고    scopus 로고
    • Inhibitors of translation initiation as cancer therapeutics
    • Lindqvist, L.; Pelletier, J. Inhibitors of translation initiation as cancer therapeutics Future Med. Chem. 2009, 1, 1709-1722
    • (2009) Future Med. Chem. , vol.1 , pp. 1709-1722
    • Lindqvist, L.1    Pelletier, J.2
  • 22
    • 84857919771 scopus 로고    scopus 로고
    • Recent advances in the biology and chemistry of flavaglines
    • Ribeiro, N.; Thuaud, F.; Nebigil, C.; Désaubry, L. Recent advances in the biology and chemistry of flavaglines Bioorg. Med. Chem. 2012, 20, 1857-1864
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 1857-1864
    • Ribeiro, N.1    Thuaud, F.2    Nebigil, C.3    Désaubry, L.4
  • 23
    • 33745851542 scopus 로고    scopus 로고
    • Potential of cyclopenta[ b ]benzofurans from Aglaia species in cancer chemotherapy
    • Kim, S.; Salimb, A. A.; Swanson, S. M.; Kinghorn, A. D. Potential of cyclopenta[ b ]benzofurans from Aglaia species in cancer chemotherapy Anti-Cancer Agents Med. Chem. 2006, 6, 318-345
    • (2006) Anti-Cancer Agents Med. Chem. , vol.6 , pp. 318-345
    • Kim, S.1    Salimb, A.A.2    Swanson, S.M.3    Kinghorn, A.D.4
  • 24
    • 0035174453 scopus 로고    scopus 로고
    • Chemistry and biological activity of rocaglamide derivatives and related compounds in Aglaia species (meliaceae)
    • Proksch, P.; Edrada, R.; Ebel, R.; Bohnenstengel, F. I.; Nugroho, B. W. Chemistry and biological activity of rocaglamide derivatives and related compounds in Aglaia species (meliaceae) Curr. Org. Chem. 2001, 5, 923-938
    • (2001) Curr. Org. Chem. , vol.5 , pp. 923-938
    • Proksch, P.1    Edrada, R.2    Ebel, R.3    Bohnenstengel, F.I.4    Nugroho, B.W.5
  • 25
    • 0032476106 scopus 로고    scopus 로고
    • Cytostatic mechanism and antitumor potential of novel 1 H -cyclopenta[ b ]benzofuran lignans isolated from Aglaia elliptica
    • Lee, S. K.; Cui, B.; Mehta, R. R.; Kinghorn, A. D.; Pezzuto, J. M. Cytostatic mechanism and antitumor potential of novel 1 H -cyclopenta[ b ]benzofuran lignans isolated from Aglaia elliptica Chem.-Biol. Interact. 1998, 115, 215-228
    • (1998) Chem.-Biol. Interact. , vol.115 , pp. 215-228
    • Lee, S.K.1    Cui, B.2    Mehta, R.R.3    Kinghorn, A.D.4    Pezzuto, J.M.5
  • 26
    • 0033394019 scopus 로고    scopus 로고
    • 1H-Cyclopenta[ b ]benzofuran lignans from Aglaia species inhibit cell proliferation and alter cell cycle distribution in human monocytic leukemia cell lines
    • Bohnenstengel, F. I.; Steube, K. G.; Meyer, C.; Quentmeier, H.; Nugroho, B. W.; Proksch, P. 1H-Cyclopenta[ b ]benzofuran lignans from Aglaia species inhibit cell proliferation and alter cell cycle distribution in human monocytic leukemia cell lines Z. Naturforsch., C: J. Biosci. 1999, 54, 1075-1083
    • (1999) Z. Naturforsch., C: J. Biosci. , vol.54 , pp. 1075-1083
    • Bohnenstengel, F.I.1    Steube, K.G.2    Meyer, C.3    Quentmeier, H.4    Nugroho, B.W.5    Proksch, P.6
  • 27
  • 28
    • 62149099451 scopus 로고    scopus 로고
    • Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4′-desmethoxyepisilvestrol
    • Adams, T. E.; El Sous, M.; Hawkins, B. C.; Hirner, S.; Holloway, G.; Khoo, M. L.; Owen, D. J.; Savage, G. P.; Scammells, P. J.; Rizzacasa, M. A. Total synthesis of the potent anticancer Aglaia metabolites (-)-silvestrol and (-)-episilvestrol and the active analogue (-)-4′-desmethoxyepisilvestrol J. Am. Chem. Soc. 2009, 131, 1607-1616
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 1607-1616
    • Adams, T.E.1    El Sous, M.2    Hawkins, B.C.3    Hirner, S.4    Holloway, G.5    Khoo, M.L.6    Owen, D.J.7    Savage, G.P.8    Scammells, P.J.9    Rizzacasa, M.A.10
  • 30
    • 84865482828 scopus 로고    scopus 로고
    • Total synthesis of 2,5-diepisilvestrol and its C1 epimer: Key structure activity relationships at C1 and C2
    • Chambers, J. M.; Huang, D. C. S.; Lindqvist, L. M.; Savage, G. P.; White, J. M.; Rizzacasa, M. A. Total synthesis of 2,5-diepisilvestrol and its C1 epimer: key structure activity relationships at C1 and C2 J. Nat. Prod. 2012, 75, 1500-1504
    • (2012) J. Nat. Prod. , vol.75 , pp. 1500-1504
    • Chambers, J.M.1    Huang, D.C.S.2    Lindqvist, L.M.3    Savage, G.P.4    White, J.M.5    Rizzacasa, M.A.6
  • 31
  • 32
    • 34547774721 scopus 로고    scopus 로고
    • Silvestrol, a potential anticancer rocaglate derivative from Aglaia foveolata, induces apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7
    • Kim, S.; Hwang, B. Y.; Su, B.-N.; Chai, H.; Mi, Q.; Kinghorn, A. D.; Wild, R.; Swanson, S. M. Silvestrol, a potential anticancer rocaglate derivative from Aglaia foveolata, induces apoptosis in LNCaP cells through the mitochondrial/apoptosome pathway without activation of executioner caspase-3 or -7 Anticancer Res. 2007, 27, 2175-2183
    • (2007) Anticancer Res. , vol.27 , pp. 2175-2183
    • Kim, S.1    Hwang, B.Y.2    Su, B.-N.3    Chai, H.4    Mi, Q.5    Kinghorn, A.D.6    Wild, R.7    Swanson, S.M.8
  • 34
    • 10044251347 scopus 로고    scopus 로고
    • Biomimetic synthesis of the novel 1,4-dioxanyloxy fragment of silvestrol and episilvestrol
    • El Sous, M.; Rizzacasa, M. A. Biomimetic synthesis of the novel 1,4-dioxanyloxy fragment of silvestrol and episilvestrol Tetrahedron Lett. 2005, 46, 293-295
    • (2005) Tetrahedron Lett. , vol.46 , pp. 293-295
    • El Sous, M.1    Rizzacasa, M.A.2
  • 37
    • 84855855153 scopus 로고    scopus 로고
    • Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: Synthetic and biological studies
    • Rodrigo, C. M.; Cencic, R.; Roche, S. P.; Pelletier, J.; Porco, J. A., Jr. Synthesis of rocaglamide hydroxamates and related compounds as eukaryotic translation inhibitors: synthetic and biological studies J. Med. Chem. 2012, 55, 558-562
    • (2012) J. Med. Chem. , vol.55 , pp. 558-562
    • Rodrigo, C.M.1    Cencic, R.2    Roche, S.P.3    Pelletier, J.4    Porco Jr., J.A.5
  • 38
    • 77956529509 scopus 로고    scopus 로고
    • Biomimetic photocycloaddition of 3-hydroxyflavones: Synthesis and evaluation of rocaglate derivatives as inhibitors of eukaryotic translation
    • Roche, S. P.; Cencic, R.; Pelletier, J.; Porco, J. A., Jr. Biomimetic photocycloaddition of 3-hydroxyflavones: synthesis and evaluation of rocaglate derivatives as inhibitors of eukaryotic translation Angew. Chem., Int. Ed. 2010, 49, 6533-6538
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 6533-6538
    • Roche, S.P.1    Cencic, R.2    Pelletier, J.3    Porco Jr., J.A.4
  • 39
    • 0000626006 scopus 로고
    • Peracid oxidation of trimethylsilyl enol ethers. Facile α-hydroxylation procedure
    • Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Peracid oxidation of trimethylsilyl enol ethers. Facile α-hydroxylation procedure Tetrahedron Lett. 1974, 4319-4322
    • (1974) Tetrahedron Lett. , pp. 4319-4322
    • Rubottom, G.M.1    Vazquez, M.A.2    Pelegrina, D.R.3
  • 40
    • 0034723443 scopus 로고    scopus 로고
    • A convenient method for synthesizing 2-aryl-3-hydroxy-4-oxo-4 H -1-benzopyrans or flavonols
    • Fougerousse, A.; Gonzalez, E.; Brouillard, R. A convenient method for synthesizing 2-aryl-3-hydroxy-4-oxo-4 H -1-benzopyrans or flavonols J. Org. Chem. 2000, 65, 583-586
    • (2000) J. Org. Chem. , vol.65 , pp. 583-586
    • Fougerousse, A.1    Gonzalez, E.2    Brouillard, R.3
  • 41
    • 1842787600 scopus 로고    scopus 로고
    • Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin e to effectively inhibit microsomal lipid peroxidation
    • Bennett, C. J.; Caldwell, S. T.; McPhail, D. B.; Morrice, P. C.; Duthie, G. G.; Hartley, R. C. Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation Bioorg. Med. Chem. 2004, 12, 2079-2098
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 2079-2098
    • Bennett, C.J.1    Caldwell, S.T.2    McPhail, D.B.3    Morrice, P.C.4    Duthie, G.G.5    Hartley, R.C.6
  • 42
    • 34248504625 scopus 로고    scopus 로고
    • Di-2-methoxyethyl azodicarboxylate (DMEAD): An inexpensive and separation-friendly alternative reagent for the Mitsunobu reaction
    • Sugimura, T.; Hagiya, Z. Di-2-methoxyethyl azodicarboxylate (DMEAD): an inexpensive and separation-friendly alternative reagent for the Mitsunobu reaction Chem. Lett. 2007, 36, 566-567
    • (2007) Chem. Lett. , vol.36 , pp. 566-567
    • Sugimura, T.1    Hagiya, Z.2
  • 43
    • 33750821137 scopus 로고
    • Conformational analysis of trans -2,3-diaryloxy-1,4-dioxanes. A tool for discrimating between steric and electronic effects in the position of the conformational equilibria of substituted dioxanes
    • Pericas, M. A.; Riera, A.; Giralt, E. Conformational analysis of trans -2,3-diaryloxy-1,4-dioxanes. A tool for discrimating between steric and electronic effects in the position of the conformational equilibria of substituted dioxanes Tetrahedron 1985, 41, 3785-3789
    • (1985) Tetrahedron , vol.41 , pp. 3785-3789
    • Pericas, M.A.1    Riera, A.2    Giralt, E.3
  • 47
    • 0043123153 scopus 로고    scopus 로고
    • Vienna RNA secondary structure server
    • Hofacker, I. L. Vienna RNA secondary structure server Nucleic Acids Res. 2003, 31, 3429-3431
    • (2003) Nucleic Acids Res. , vol.31 , pp. 3429-3431
    • Hofacker, I.L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.