메뉴 건너뛰기




Volumn 24, Issue 5, 2017, Pages 605-613.e5

Inhibition of Eukaryotic Translation by the Antitumor Natural Product Agelastatin A

Author keywords

agelastatin A; brain cancer; chemical footprinting; drug design; marine alkaloid; molecular docking; peptidyl transferase center; ribosome; rRNA seq; translation elongation

Indexed keywords

AGELASTATIN A; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG; ALKALOID; BIOLOGICAL PRODUCT; OXAZOLIDINONE DERIVATIVE;

EID: 85018190156     PISSN: 24519456     EISSN: 24519448     Source Type: Journal    
DOI: 10.1016/j.chembiol.2017.04.006     Document Type: Article
Times cited : (41)

References (50)
  • 1
    • 0033544957 scopus 로고    scopus 로고
    • Translational regulation of ribonucleotide reductase by eukaryotic initiation factor 4E Links protein synthesis to the control of DNA replication
    • Abid, M.R., Li, Y., Anthony, C., De Benedetti, A., Translational regulation of ribonucleotide reductase by eukaryotic initiation factor 4E Links protein synthesis to the control of DNA replication. J. Biol. Chem. 274 (1999), 35991–35998.
    • (1999) J. Biol. Chem. , vol.274 , pp. 35991-35998
    • Abid, M.R.1    Li, Y.2    Anthony, C.3    De Benedetti, A.4
  • 5
    • 69749093258 scopus 로고    scopus 로고
    • When DNA replication and protein synthesis come together
    • Berthon, J., Fujikane, R., Forterre, P., When DNA replication and protein synthesis come together. Trends Biochem. Sci. 34 (2009), 429–434.
    • (2009) Trends Biochem. Sci. , vol.34 , pp. 429-434
    • Berthon, J.1    Fujikane, R.2    Forterre, P.3
  • 7
    • 47949094068 scopus 로고    scopus 로고
    • Peptide release on the ribosome depends critically on the 2’ OH of the peptidyl-tRNA substrate
    • Brunelle, J.L., Shaw, J.J., Youngman, E.M., Green, R., Peptide release on the ribosome depends critically on the 2’ OH of the peptidyl-tRNA substrate. RNA 14 (2008), 1526–1531.
    • (2008) RNA , vol.14 , pp. 1526-1531
    • Brunelle, J.L.1    Shaw, J.J.2    Youngman, E.M.3    Green, R.4
  • 8
    • 1242341504 scopus 로고    scopus 로고
    • Eukaryotic protein synthesis inhibitors identified by comparison of cytotoxicity profiles
    • Chan, J., Eukaryotic protein synthesis inhibitors identified by comparison of cytotoxicity profiles. RNA 10 (2004), 528–543.
    • (2004) RNA , vol.10 , pp. 528-543
    • Chan, J.1
  • 10
    • 67650675111 scopus 로고    scopus 로고
    • Impact of natural products on developing new anti-cancer agents
    • Cragg, G.M., Grothaus, P.G., Newman, D.J., Impact of natural products on developing new anti-cancer agents. Chem. Rev. 109 (2009), 3012–3043.
    • (2009) Chem. Rev. , vol.109 , pp. 3012-3043
    • Cragg, G.M.1    Grothaus, P.G.2    Newman, D.J.3
  • 11
    • 0027170397 scopus 로고
    • Agelastatin a, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the coral sea
    • D'Ambrosio, M., Guerriero, A., Debitus, C.c., Ribes, O., Pusset, J., Leroy, S., Pietra, F., Agelastatin a, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the coral sea. J. Chem. Soc. Chem. Comm, 1993, 1305.
    • (1993) J. Chem. Soc. Chem. Comm , pp. 1305
    • D'Ambrosio, M.1    Guerriero, A.2    Debitus, C.C.3    Ribes, O.4    Pusset, J.5    Leroy, S.6    Pietra, F.7
  • 12
    • 33845950751 scopus 로고    scopus 로고
    • Eukaryotic initiation factor 2alpha-independent pathway of stress granule induction by the natural product pateamine A
    • Dang, Y., Kedersha, N., Low, W.K., Romo, D., Gorospe, M., Kaufman, R., Anderson, P., Liu, J.O., Eukaryotic initiation factor 2alpha-independent pathway of stress granule induction by the natural product pateamine A. J. Biol. Chem. 281 (2006), 32870–32878.
    • (2006) J. Biol. Chem. , vol.281 , pp. 32870-32878
    • Dang, Y.1    Kedersha, N.2    Low, W.K.3    Romo, D.4    Gorospe, M.5    Kaufman, R.6    Anderson, P.7    Liu, J.O.8
  • 13
    • 79960440718 scopus 로고    scopus 로고
    • Inhibition of eukaryotic translation elongation by the antitumor natural product Mycalamide B
    • Dang, Y., Schneider-Poetsch, T., Eyler, D.E., Jewett, J.C., Bhat, S., Rawal, V.H., Green, R., Liu, J.O., Inhibition of eukaryotic translation elongation by the antitumor natural product Mycalamide B. RNA 17 (2011), 1578–1588.
    • (2011) RNA , vol.17 , pp. 1578-1588
    • Dang, Y.1    Schneider-Poetsch, T.2    Eyler, D.E.3    Jewett, J.C.4    Bhat, S.5    Rawal, V.H.6    Green, R.7    Liu, J.O.8
  • 14
    • 84893427735 scopus 로고    scopus 로고
    • In vivo genome-wide profiling of RNA secondary structure reveals novel regulatory features
    • Ding, Y., Tang, Y., Kwok, C.K., Zhang, Y., Bevilacqua, P.C., Assmann, S.M., In vivo genome-wide profiling of RNA secondary structure reveals novel regulatory features. Nature 505 (2013), 696–700.
    • (2013) Nature , vol.505 , pp. 696-700
    • Ding, Y.1    Tang, Y.2    Kwok, C.K.3    Zhang, Y.4    Bevilacqua, P.C.5    Assmann, S.M.6
  • 15
    • 78649809107 scopus 로고    scopus 로고
    • Recent advances in the total synthesis of agelastatins
    • Dong, G., Recent advances in the total synthesis of agelastatins. Pure Appl. Chem. 82 (2010), 2231–2246.
    • (2010) Pure Appl. Chem. , vol.82 , pp. 2231-2246
    • Dong, G.1
  • 16
  • 17
    • 79955028699 scopus 로고    scopus 로고
    • Distinct response of yeast ribosomes to a miscoding event during translation
    • Eyler, D.E., Green, R., Distinct response of yeast ribosomes to a miscoding event during translation. RNA 17 (2011), 925–932.
    • (2011) RNA , vol.17 , pp. 925-932
    • Eyler, D.E.1    Green, R.2
  • 18
    • 84898757160 scopus 로고    scopus 로고
    • Omacetaxine: a protein translation inhibitor for treatment of chronic myelogenous leukemia
    • Gandhi, V., Plunkett, W., Cortes, J.E., Omacetaxine: a protein translation inhibitor for treatment of chronic myelogenous leukemia. Clin. Cancer Res. 20 (2014), 1735–1740.
    • (2014) Clin. Cancer Res. , vol.20 , pp. 1735-1740
    • Gandhi, V.1    Plunkett, W.2    Cortes, J.E.3
  • 20
    • 84890215732 scopus 로고    scopus 로고
    • Synthesis and anticancer activity of all known (−)-Agelastatin alkaloids
    • Han, S., Siegel, D.S., Morrison, K.C., Hergenrother, P.J., Movassaghi, M., Synthesis and anticancer activity of all known (−)-Agelastatin alkaloids. J. Org. Chem. 78 (2013), 11970–11984.
    • (2013) J. Org. Chem. , vol.78 , pp. 11970-11984
    • Han, S.1    Siegel, D.S.2    Morrison, K.C.3    Hergenrother, P.J.4    Movassaghi, M.5
  • 22
    • 75149196287 scopus 로고    scopus 로고
    • The mechanism of eukaryotic translation initiation and principles of its regulation
    • Jackson, R.J., Hellen, C.U.T., Pestova, T.V., The mechanism of eukaryotic translation initiation and principles of its regulation. Nat. Rev. Mol. Cell Biol. 11 (2010), 113–127.
    • (2010) Nat. Rev. Mol. Cell Biol. , vol.11 , pp. 113-127
    • Jackson, R.J.1    Hellen, C.U.T.2    Pestova, T.V.3
  • 24
    • 76449106188 scopus 로고    scopus 로고
    • Integration, scaling, space-group assignment and post-refinement
    • Kabsch, W., Integration, scaling, space-group assignment and post-refinement. Acta Cryst. D66 (2010), 133–144.
    • (2010) Acta Cryst. , vol.D66 , pp. 133-144
    • Kabsch, W.1
  • 25
    • 3943080710 scopus 로고    scopus 로고
    • The molecular mechanics of eukaryotic translation
    • Kapp, L.D., Lorsch, J.R., The molecular mechanics of eukaryotic translation. Annu. Rev. Biochem. 73 (2004), 657–704.
    • (2004) Annu. Rev. Biochem. , vol.73 , pp. 657-704
    • Kapp, L.D.1    Lorsch, J.R.2
  • 26
    • 66849113670 scopus 로고    scopus 로고
    • Potent in vitro and in vivo anticancer activities of des-methyl, des-amino pateamine A, a synthetic analogue of marine natural product pateamine A
    • Kuznetsov, G., Xu, Q., Rudolph-Owen, L., Tendyke, K., Liu, J., Towle, M., Zhao, N., Marsh, J., Agoulnik, S., Twine, N., et al. Potent in vitro and in vivo anticancer activities of des-methyl, des-amino pateamine A, a synthetic analogue of marine natural product pateamine A. Mol. Cancer Ther. 8 (2009), 1250–1260.
    • (2009) Mol. Cancer Ther. , vol.8 , pp. 1250-1260
    • Kuznetsov, G.1    Xu, Q.2    Rudolph-Owen, L.3    Tendyke, K.4    Liu, J.5    Towle, M.6    Zhao, N.7    Marsh, J.8    Agoulnik, S.9    Twine, N.10
  • 27
    • 84879863287 scopus 로고    scopus 로고
    • An integrated approach to the discovery of potent agelastatin A analogues for brain tumors: chemical synthesis and biological, physicochemical and CNS pharmacokinetic analyses
    • Li, Z., Shigeoka, D., Caulfield, T.R., Kawachi, T., Qiu, Y., Kamon, T., Arai, M., Tun, H.W., Yoshimitsu, T., An integrated approach to the discovery of potent agelastatin A analogues for brain tumors: chemical synthesis and biological, physicochemical and CNS pharmacokinetic analyses. MedChemComm, 4, 2013, 1093.
    • (2013) MedChemComm , vol.4 , pp. 1093
    • Li, Z.1    Shigeoka, D.2    Caulfield, T.R.3    Kawachi, T.4    Qiu, Y.5    Kamon, T.6    Arai, M.7    Tun, H.W.8    Yoshimitsu, T.9
  • 31
    • 0022470564 scopus 로고
    • Rapid chemical probing of conformation in 16 S ribosomal RNA and 30 S ribosomal subunits using primer extension
    • Moazed, D., Stern, S., Noller, H.F., Rapid chemical probing of conformation in 16 S ribosomal RNA and 30 S ribosomal subunits using primer extension. J. Mol. Biol. 187 (1986), 399–416.
    • (1986) J. Mol. Biol. , vol.187 , pp. 399-416
    • Moazed, D.1    Stern, S.2    Noller, H.F.3
  • 32
    • 33847057304 scopus 로고    scopus 로고
    • Imatinib: a review of its use in chronic myeloid leukaemia
    • Moen, M.D., McKeage, K., Plosker, G.L., Siddiqui, M.A.A., Imatinib: a review of its use in chronic myeloid leukaemia. Drugs 67 (2007), 299–320.
    • (2007) Drugs , vol.67 , pp. 299-320
    • Moen, M.D.1    McKeage, K.2    Plosker, G.L.3    Siddiqui, M.A.A.4
  • 33
    • 79952607810 scopus 로고    scopus 로고
    • Total synthesis of all (-)-Agelastatin alkaloids
    • Movassaghi, M., Siegel, D.S., Han, S., Total synthesis of all (-)-Agelastatin alkaloids. Chem. Sci. 1 (2010), 561–566.
    • (2010) Chem. Sci. , vol.1 , pp. 561-566
    • Movassaghi, M.1    Siegel, D.S.2    Han, S.3
  • 34
    • 84962367258 scopus 로고    scopus 로고
    • Natural products as sources of new drugs from 1981 to 2014
    • Newman, D.J., Cragg, G.M., Natural products as sources of new drugs from 1981 to 2014. J. Nat. Prod. 79 (2016), 629–661.
    • (2016) J. Nat. Prod. , vol.79 , pp. 629-661
    • Newman, D.J.1    Cragg, G.M.2
  • 35
    • 0018499594 scopus 로고
    • The mode of inhibitory action by aphidicolin on eukaryotic DNA polymerase alpha
    • Oguro, M., Suzuki-Hori, C., Nagano, H., Mano, Y., Ikegami, S., The mode of inhibitory action by aphidicolin on eukaryotic DNA polymerase alpha. Eur. J. Biochem. 97 (1979), 603–607.
    • (1979) Eur. J. Biochem. , vol.97 , pp. 603-607
    • Oguro, M.1    Suzuki-Hori, C.2    Nagano, H.3    Mano, Y.4    Ikegami, S.5
  • 36
    • 0031905698 scopus 로고    scopus 로고
    • A prokaryotic-like mode of cytoplasmic eukaryotic ribosome binding to the initiation codon during internal translation initiation of hepatitis C and classical swine fever virus RNAs
    • Pestova, T.V., Shatsky, I.N., Fletcher, S.P., Jackson, R.J., Hellen, C.U., A prokaryotic-like mode of cytoplasmic eukaryotic ribosome binding to the initiation codon during internal translation initiation of hepatitis C and classical swine fever virus RNAs. Genes Dev. 12 (1998), 67–83.
    • (1998) Genes Dev. , vol.12 , pp. 67-83
    • Pestova, T.V.1    Shatsky, I.N.2    Fletcher, S.P.3    Jackson, R.J.4    Hellen, C.U.5
  • 37
    • 16344396159 scopus 로고    scopus 로고
    • Antineoplastic agents 470. Absolute configuration of the marine sponge bromopyrrole agelastatin A
    • Pettit, G.R., Ducki, S., Herald, D.L., Doubek, D.L., Schmidt, J.M., Chapuis, J.C., Antineoplastic agents 470. Absolute configuration of the marine sponge bromopyrrole agelastatin A. Oncol. Res. 15 (2005), 11–20.
    • (2005) Oncol. Res. , vol.15 , pp. 11-20
    • Pettit, G.R.1    Ducki, S.2    Herald, D.L.3    Doubek, D.L.4    Schmidt, J.M.5    Chapuis, J.C.6
  • 39
    • 84890951257 scopus 로고    scopus 로고
    • pi-Stacking, C-H/pi, and halogen bonding interactions in bromobenzene and mixed bromobenzene-benzene clusters
    • Reid, S.A., Nyambo, S., Muzangwa, L., Uhler, B., pi-Stacking, C-H/pi, and halogen bonding interactions in bromobenzene and mixed bromobenzene-benzene clusters. J. Phys. Chem. A 117 (2013), 13556–13563.
    • (2013) J. Phys. Chem. A , vol.117 , pp. 13556-13563
    • Reid, S.A.1    Nyambo, S.2    Muzangwa, L.3    Uhler, B.4
  • 40
    • 84863694084 scopus 로고    scopus 로고
    • Bioinspired total synthesis of agelastatin A
    • Reyes, J.C.P., Romo, D., Bioinspired total synthesis of agelastatin A. Angew. Chem. Int. Ed 51 (2012), 6870–6873.
    • (2012) Angew. Chem. Int. Ed , vol.51 , pp. 6870-6873
    • Reyes, J.C.P.1    Romo, D.2
  • 41
    • 0028924641 scopus 로고
    • Fine structure of the peptidyl transferase centre on 23 S-like rRNAs deduced from chemical probing of antibiotic-ribosome complexes
    • Rodriguez-Fonseca, C., Amils, R., Garrett, R.A., Fine structure of the peptidyl transferase centre on 23 S-like rRNAs deduced from chemical probing of antibiotic-ribosome complexes. J. Mol. Biol. 247 (1995), 224–235.
    • (1995) J. Mol. Biol. , vol.247 , pp. 224-235
    • Rodriguez-Fonseca, C.1    Amils, R.2    Garrett, R.A.3
  • 42
    • 84893351549 scopus 로고    scopus 로고
    • Genome-wide probing of RNA structure reveals active unfolding of mRNA structures in vivo
    • Rouskin, S., Zubradt, M., Washietl, S., Kellis, M., Weissman, J.S., Genome-wide probing of RNA structure reveals active unfolding of mRNA structures in vivo. Nature 505 (2013), 701–705.
    • (2013) Nature , vol.505 , pp. 701-705
    • Rouskin, S.1    Zubradt, M.2    Washietl, S.3    Kellis, M.4    Weissman, J.S.5
  • 44
  • 45
    • 0002574670 scopus 로고
    • Aphidicolin: a specific inhibitor of nuclear DNA replication in eukaryotes
    • Spadari, S., Sala, F., Pedrali-Noy, G., Aphidicolin: a specific inhibitor of nuclear DNA replication in eukaryotes. Trends Biochem. Sci. 7 (1982), 29–32.
    • (1982) Trends Biochem. Sci. , vol.7 , pp. 29-32
    • Spadari, S.1    Sala, F.2    Pedrali-Noy, G.3
  • 46
    • 84903523658 scopus 로고    scopus 로고
    • Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies
    • Stout, E.P., Choi, M.Y., Castro, J.E., Molinski, T.F., Potent fluorinated agelastatin analogues for chronic lymphocytic leukemia: design, synthesis, and pharmacokinetic studies. J. Med. Chem. 57 (2014), 5085–5093.
    • (2014) J. Med. Chem. , vol.57 , pp. 5085-5093
    • Stout, E.P.1    Choi, M.Y.2    Castro, J.E.3    Molinski, T.F.4
  • 47
    • 84857922851 scopus 로고    scopus 로고
    • Identification and validation of protein targets of bioactive small molecules
    • Titov, D.V., Liu, J.O., Identification and validation of protein targets of bioactive small molecules. Bioorg. Med. Chem. 20 (2012), 1902–1909.
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 1902-1909
    • Titov, D.V.1    Liu, J.O.2
  • 49
    • 0014528003 scopus 로고
    • Effects of cycloheximide on DNA and protein synthesis in rat liver
    • Tornheim, K., O'Dell, R.G., Prosky, L., Effects of cycloheximide on DNA and protein synthesis in rat liver. Proc. Soc. Exp. Biol. Med. 131 (1969), 601–605.
    • (1969) Proc. Soc. Exp. Biol. Med. , vol.131 , pp. 601-605
    • Tornheim, K.1    O'Dell, R.G.2    Prosky, L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.