메뉴 건너뛰기




Volumn 42, Issue 24, 1999, Pages 4932-4941

Structure-activity studies of cerulenin analogues as protein palmitoylation inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

CERULETIDE; FATTY ACID SYNTHASE; PALMITIC ACID; PROTEIN P21;

EID: 0033518174     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980591s     Document Type: Article
Times cited : (89)

References (47)
  • 5
    • 0028331587 scopus 로고
    • Farnesyltransferase inhibitors: Ras research yields a potential cancer therapeutic
    • Gibbs, J. B.; Oliff, A.; Kohl, N. E. Farnesyltransferase inhibitors: ras research yields a potential cancer therapeutic. Cell 1994, 77, 175-178.
    • (1994) Cell , vol.77 , pp. 175-178
    • Gibbs, J.B.1    Oliff, A.2    Kohl, N.E.3
  • 7
    • 0021170342 scopus 로고
    • The p21 ras C-terminus is required for transformation and membrane association
    • Willumsen, B. M.; Christensen, A. The p21 ras C-terminus is required for transformation and membrane association. Nature 1984, 310, 583-586.
    • (1984) Nature , vol.310 , pp. 583-586
    • Willumsen, B.M.1    Christensen, A.2
  • 8
    • 0024406286 scopus 로고
    • All ras proteins are polyisoprenylated but only some are palmitoylated
    • Hancock, J. F.; Magee, A. I.; Childs, J. E.; Marshall, C. J. All ras proteins are polyisoprenylated but only some are palmitoylated. Cell 1989, 57, 1167-1177.
    • (1989) Cell , vol.57 , pp. 1167-1177
    • Hancock, J.F.1    Magee, A.I.2    Childs, J.E.3    Marshall, C.J.4
  • 9
    • 0025013547 scopus 로고
    • A polybasic domain or palmitoylation is required in addition to the CAAX motif to localize p21 ras to the plasma membrane
    • Hancock, J. F.; Paterson, H.; Marshall, C. J. A polybasic domain or palmitoylation is required in addition to the CAAX motif to localize p21 ras to the plasma membrane. Cell 1990, 6, 133-139.
    • (1990) Cell , vol.6 , pp. 133-139
    • Hancock, J.F.1    Paterson, H.2    Marshall, C.J.3
  • 10
    • 0028234577 scopus 로고
    • N-terminally myristoylated ras proteins require palmitoylation or a polybasic domain for plasma membrane localization
    • Cadwallader, K. A.; Paterson, H.; MacDonald, S. G.; Hancock, J. F. N-terminally myristoylated ras proteins require palmitoylation or a polybasic domain for plasma membrane localization. Mol. Cell. Biol. 1994, 14, 4722-4730.
    • (1994) Mol. Cell. Biol. , vol.14 , pp. 4722-4730
    • Cadwallader, K.A.1    Paterson, H.2    MacDonald, S.G.3    Hancock, J.F.4
  • 12
    • 0025871919 scopus 로고
    • cDNA cloning and expression of the peptide binding subunit of rat p21 ras farnesyltransferase, the counterpart of yeast RAM1/DPR1
    • Chen, W.-J.; Andres, D. A.; Goldstein, J. L.; Russell, D. W.; Brown, M. S. cDNA cloning and expression of the peptide binding subunit of rat p21 ras farnesyltransferase, the counterpart of yeast RAM1/DPR1. Cell 1991, 66, 327-334.
    • (1991) Cell , vol.66 , pp. 327-334
    • Chen, W.-J.1    Andres, D.A.2    Goldstein, J.L.3    Russell, D.W.4    Brown, M.S.5
  • 15
    • 0028958919 scopus 로고
    • Polylysine and CVIM sequences of K-RasB dictate specificity of prenylation and confer resistance to benzodiazepine peptidomimetic in vitro
    • James, G. L.; Goldstein, J. L.; Brown, M. S. Polylysine and CVIM sequences of K-RasB dictate specificity of prenylation and confer resistance to benzodiazepine peptidomimetic in vitro. J. Biol. Chem. 1995, 270, 6221-6226.
    • (1995) J. Biol. Chem. , vol.270 , pp. 6221-6226
    • James, G.L.1    Goldstein, J.L.2    Brown, M.S.3
  • 16
    • 0030968859 scopus 로고    scopus 로고
    • Direct demonstration of geranylgeranylation and farnesylation of Kiras in vivo
    • Rowell, C. A.; Kowalczyk, J. J.; Lewis, M. D.; Garcia, A. M. Direct demonstration of geranylgeranylation and farnesylation of Kiras in vivo. J. Biol. Chem. 1997, 272, 14093-14097.
    • (1997) J. Biol. Chem. , vol.272 , pp. 14093-14097
    • Rowell, C.A.1    Kowalczyk, J.J.2    Lewis, M.D.3    Garcia, A.M.4
  • 19
    • 0000081175 scopus 로고
    • Posttranslational modification of the Ha-ras oncogene protein: Evidence for a third class of protein carboxy methyltransferases
    • Clarke, S.; Vogel, J. P.; Deschenes, R. J.; Stock, J. Posttranslational modification of the Ha-ras oncogene protein: Evidence for a third class of protein carboxy methyltransferases. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 4643-4647.
    • (1988) Proc. Natl. Acad. Sci. U.S.A. , vol.85 , pp. 4643-4647
    • Clarke, S.1    Vogel, J.P.2    Deschenes, R.J.3    Stock, J.4
  • 21
    • 0027518208 scopus 로고
    • Purification and properties of a palmitoyl-protein thioesterase that cleaves palmitate from H-ras
    • Camp, L. A.; Hoffmann, S. L. Purification and properties of a palmitoyl-protein thioesterase that cleaves palmitate from H-ras. J. Biol. Chem. 1993, 268, 22566-22574.
    • (1993) J. Biol. Chem. , vol.268 , pp. 22566-22574
    • Camp, L.A.1    Hoffmann, S.L.2
  • 24
    • 0017137380 scopus 로고
    • The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis
    • Omura, S. The antibiotic cerulenin, a novel tool for biochemistry as an inhibitor of fatty acid synthesis. Bacteriol. Rev. 1976, 40, 681-697.
    • (1976) Bacteriol. Rev. , vol.40 , pp. 681-697
    • Omura, S.1
  • 25
    • 0029971427 scopus 로고    scopus 로고
    • Inhibition of fatty acid synthesis delays disease progression in a xenograft model of ovarian cancer
    • Pizer, E. S.; Wood, F. D.; Heine, H. S.; Romantsev, F. E.; Pasternick, G. R.; Kuhajda, F. P. Inhibition of fatty acid synthesis delays disease progression in a xenograft model of ovarian cancer. Cancer Res. 1996, 56, 1189-1193.
    • (1996) Cancer Res. , vol.56 , pp. 1189-1193
    • Pizer, E.S.1    Wood, F.D.2    Heine, H.S.3    Romantsev, F.E.4    Pasternick, G.R.5    Kuhajda, F.P.6
  • 27
  • 28
    • 0020453356 scopus 로고
    • Cerulenin blocks fatty acid acylation of glycoproteins and inhibits vesicular stomatitis and Sinbis virus particle formation
    • Schlessinger, M. J.; Malfer, C. Cerulenin blocks fatty acid acylation of glycoproteins and inhibits vesicular stomatitis and Sinbis virus particle formation. J. Biol. Chem. 1982, 257, 9887-9890.
    • (1982) J. Biol. Chem. , vol.257 , pp. 9887-9890
    • Schlessinger, M.J.1    Malfer, C.2
  • 29
    • 0017385545 scopus 로고
    • A total synthesis of DL-cerulenin: A novel fatty acid antibiotic and lipid synthesis inhibitor
    • Boekman, R. K., Jr.; Thomas, E. W. A total synthesis of DL-cerulenin: a novel fatty acid antibiotic and lipid synthesis inhibitor. J. Am. Chem. Soc. 1977, 99, 2805-2806.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 2805-2806
    • Boekman R.K., Jr.1    Thomas, E.W.2
  • 30
    • 0031027534 scopus 로고    scopus 로고
    • A concise synthesis of (+)-cerulenin from a chiral oxiranyllithium
    • Mani, N. S.; Townsend, C. A. A concise synthesis of (+)-cerulenin from a chiral oxiranyllithium. J. Org. Chem. 1997, 62, 636-640.
    • (1997) J. Org. Chem. , vol.62 , pp. 636-640
    • Mani, N.S.1    Townsend, C.A.2
  • 31
    • 0345179625 scopus 로고
    • Stereoselective synthesis of (+)- and (-)-tetrahydrocerulenin from D-glucose. The absolute configuration of cerulenin
    • Ohri, H.; Emoto, S. Stereoselective synthesis of (+)- and (-)-tetrahydrocerulenin from D-glucose. The absolute configuration of cerulenin. Tetrahedron Lett. 1978, 24, 2095-2098.
    • (1978) Tetrahedron Lett. , vol.24 , pp. 2095-2098
    • Ohri, H.1    Emoto, S.2
  • 32
    • 0019983436 scopus 로고
    • Total synthesis of (±)-cerulenin, (±)-tetrahydrocerulenin, and related compounds
    • Jakubowski, A. A.; Guziec, F. S., Jr.; Sugiera, M.; Tam, C. C.; Tischler, M. Total synthesis of (±)-cerulenin, (±)-tetrahydrocerulenin, and related compounds. J. Org. Chem. 1982, 47, 1221-1228.
    • (1982) J. Org. Chem. , vol.47 , pp. 1221-1228
    • Jakubowski, A.A.1    Guziec F.S., Jr.2    Sugiera, M.3    Tam, C.C.4    Tischler, M.5
  • 33
    • 0000450920 scopus 로고
    • Total synthesis of (±)-cerulenin and (±)-tetrahydrocerulenin
    • Ohta, T.; Tsuchiyama, H.; Nozoe, S. Total synthesis of (±)-cerulenin and (±)-tetrahydrocerulenin. Heterocycles 1986, 24, 1137-1143.
    • (1986) Heterocycles , vol.24 , pp. 1137-1143
    • Ohta, T.1    Tsuchiyama, H.2    Nozoe, S.3
  • 34
    • 0041807380 scopus 로고
    • Preparation and use of tetra-n-butylammonium per-ruthenate (TBAP reagent) and tetra-n-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols
    • Griffith, W. P. Preparation and use of tetra-n-butylammonium per-ruthenate (TBAP reagent) and tetra-n-propylammonium per-ruthenate (TPAP reagent) as new catalytic oxidants for alcohols J. Chem. Soc., Chem. Commun. 1987, 1625-1627.
    • (1987) J. Chem. Soc., Chem. Commun. , pp. 1625-1627
    • Griffith, W.P.1
  • 35
    • 0002455223 scopus 로고
    • TPAP: Tetra-n-propylammonium perruthenate, a mild and convenient oxidant for alcohols
    • Griffith, W. P.; Ley, S. V. TPAP: Tetra-n-propylammonium perruthenate, a mild and convenient oxidant for alcohols. Aldrichim. Acta 1990, 23, 13-19.
    • (1990) Aldrichim. Acta , vol.23 , pp. 13-19
    • Griffith, W.P.1    Ley, S.V.2
  • 42
    • 0002714675 scopus 로고
    • Rapid chromatographic techniques for preparative separation with moderate resolution
    • Still, W. C.; Kahn, M.; Mitra, A. Rapid chromatographic techniques for preparative separation with moderate resolution. J. Org. Chem. 1978, 43, 2923-2924.
    • (1978) J. Org. Chem. , vol.43 , pp. 2923-2924
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 44
    • 2042524507 scopus 로고
    • Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media
    • Corey, E. J.; Schmidt, G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media. Tetrahedron Lett. 1979, 399-402.
    • (1979) Tetrahedron Lett. , pp. 399-402
    • Corey, E.J.1    Schmidt, G.2
  • 45
    • 0032875098 scopus 로고    scopus 로고
    • Fatty acylation of proteins: New insights into membrane targeting of myristoylated and palmitoylated proteins
    • Resh, M. D. Fatty acylation of proteins: new insights into membrane targeting of myristoylated and palmitoylated proteins. Biochim. Biophys. Acta 1999, 1451, 1-16.
    • (1999) Biochim. Biophys. Acta , vol.1451 , pp. 1-16
    • Resh, M.D.1
  • 47
    • 0028973293 scopus 로고
    • Ras CAAX peptidomimetic FTI-277 selectively blocks oncogenic ras signaling by inducing cytoplasmic accumulation of inactive ras-raf complexes
    • Lerner, E. C.; Qian, Y.; Blaskovich, M. A.; Fossum, R. D.; Vogt, A.; Sun, J.; Cox, A. D.; Der, C. J.; Hamilton, A. D.; Sebti, S. M. Ras CAAX peptidomimetic FTI-277 selectively blocks oncogenic ras signaling by inducing cytoplasmic accumulation of inactive ras-raf complexes. J. Biol. Chem. 1995, 260, 26802-26806.
    • (1995) J. Biol. Chem. , vol.260 , pp. 26802-26806
    • Lerner, E.C.1    Qian, Y.2    Blaskovich, M.A.3    Fossum, R.D.4    Vogt, A.5    Sun, J.6    Cox, A.D.7    Der, C.J.8    Hamilton, A.D.9    Sebti, S.M.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.