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Volumn 52, Issue 12, 2009, Pages 3814-3828

Sesterterpenes as tubulin tyrosine ligase inhibitors. First insight of structure-activity relationships and discovery of new lead

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TUBULIN; LIGASE; LIGASE INHIBITOR; PLANT EXTRACT; SALVIA DOMINICA EXTRACT; SESTERTERPENE; TUBULIN TYROSINE LIGASE; UNCLASSIFIED DRUG;

EID: 67549128952     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801637f     Document Type: Article
Times cited : (53)

References (52)
  • 3
    • 0036059869 scopus 로고    scopus 로고
    • Antioxidant and free radical scavenging activities of eight Salvia species
    • Bozan, B.; Ozturk, N.; Kosar, M.; Tunalier, Z.; Baser, K. H. C. Antioxidant and free radical scavenging activities of eight Salvia species. Chem. Nat. Compounds 2002, 38 (2), 198-200.
    • (2002) Chem. Nat. Compounds , vol.38 , Issue.2 , pp. 198-200
    • Bozan, B.1    Ozturk, N.2    Kosar, M.3    Tunalier, Z.4    Baser, K.H.C.5
  • 5
    • 33645960092 scopus 로고    scopus 로고
    • Bioactive triterpenoids from Salvia species
    • Topcu, G. Bioactive triterpenoids from Salvia species. J. Nat. Prod. 2006, 69, 482-487.
    • (2006) J. Nat. Prod. , vol.69 , pp. 482-487
    • Topcu, G.1
  • 8
  • 11
    • 34447556014 scopus 로고    scopus 로고
    • Chemical proteomics for drug discovery based on compound-immobilized affinity chromatography
    • Katayama, H.; Oda, Y. Chemical proteomics for drug discovery based on compound-immobilized affinity chromatography. J. Chromatogr., B. 2007, 855, 21-27.
    • (2007) J. Chromatogr., B , vol.855 , pp. 21-27
    • Katayama, H.1    Oda, Y.2
  • 12
    • 0024020919 scopus 로고
    • Posttranslational tyrosination/ detyrosination of tubulin
    • Barra, H. S.; Arce, C. A.; Argarana, C. E. Posttranslational tyrosination/ detyrosination of tubulin. Mol. Neurobiol. 1988, 2, 133-153.
    • (1988) Mol. Neurobiol. , vol.2 , pp. 133-153
    • Barra, H.S.1    Arce, C.A.2    Argarana, C.E.3
  • 16
    • 6344255193 scopus 로고    scopus 로고
    • Low expression of human tubulin tyrosine ligase and suppressed tubulin tyrosination/detyrosination cycle are associated with impaired neuronal differentiation in neuroblastomas with poor prognosis
    • DOI 10.1002/ijc.20431
    • Kato, C.; Miyazaki, K.; Nakagawa, A.; Ohira, M.; Nakamura, Y.; Ozaki, T.; Imai, T.; Nakagawara, A. Low expression of human tubulin tyrosine ligase and suppressed tubulin tyrosination/detyrosination cycle are associated with impaired neuronal differentiation in neuroblastomas with poor prognosis. Int. J. Cancer 2004, 112, 365-375 (Pubitemid 39390599)
    • (2004) International Journal of Cancer , vol.112 , Issue.3 , pp. 365-375
    • Kato, C.1    Miyazaki, K.2    Nakagawa, A.3    Ohira, M.4    Nakamura, Y.5    Ozaki, T.6    Imai, T.7    Nakagawara, A.8
  • 17
    • 33744901133 scopus 로고    scopus 로고
    • Normal and prostate cancer cells display distinct molecular profiles of R-tubulin posttranslational modifications
    • DOI 10.1002/pros.20416
    • Soucek, K.; Kamaid, A.; Phung, A. D.; Kubala, L.; Bulinski, J. C.; Harper, R. W.; Eiserich, J. P. Normal and prostate cancer cells display distinct molecular profiles of R-tubulin posttranslational modifications. Prostate 2006, 66, 954-965. (Pubitemid 43849594)
    • (2006) Prostate , vol.66 , Issue.9 , pp. 954-965
    • Soucek, K.1    Kamaid, A.2    Phung, A.D.3    Kubala, L.4    Bulinski, J.C.5    Harper, R.W.6    Eiserich, J.P.7
  • 18
    • 0032956022 scopus 로고    scopus 로고
    • Two Novel Lanostane- Type Triterpenes from the Stem Bark of Abies mariesii
    • Tanaka, R.; Aoki, H.; Wada, S.; Matsunaga, S. Two Novel Lanostane- Type Triterpenes from the Stem Bark of Abies mariesii. J. Nat. Prod. 1999, 62, 198-200.
    • (1999) J. Nat. Prod. , vol.62 , pp. 198-200
    • Tanaka, R.1    Aoki, H.2    Wada, S.3    Matsunaga, S.4
  • 19
    • 0001259244 scopus 로고
    • Salvisyriacolide, a sesterterpene from Salvia syriaca
    • Rustaiyan, A.; Sadjadi, A. Salvisyriacolide, a sesterterpene from Salvia syriaca. Phytochemistry 1987, 26, 3078-3079.
    • (1987) Phytochemistry , vol.26 , pp. 3078-3079
    • Rustaiyan, A.1    Sadjadi, A.2
  • 20
    • 0036240214 scopus 로고    scopus 로고
    • Thorectandrols C, D, and E, new sesterterpenes from the marine sponge Thorectandra sp
    • Charan, R. D.; McKee, T. C.; Boyd, M. R. Thorectandrols C, D, and E, new sesterterpenes from the marine sponge Thorectandra sp. J. Nat. Prod. 2002, 65, 492-495.
    • (2002) J. Nat. Prod. , vol.65 , pp. 492-495
    • Charan, R.D.1    McKee, T.C.2    Boyd, M.R.3
  • 21
    • 0030021191 scopus 로고    scopus 로고
    • The absolute configuration of salvileucolide methyl ester, a sesterterpene from Iranian Salvia species
    • DOI 10.1016/0031-9422(95)00655-9
    • Linden, A.; Juch, M.; Moghaddam, F. M.; Zaynizadeh, B.; Rueedi, P. The absolute configuration of salvileucolide methyl ester, a sesterterpene from Iranian Salvia species. Phytochemistry 1996, 41, 589-590. (Pubitemid 3021209)
    • (1996) Phytochemistry , vol.41 , Issue.2 , pp. 589-590
    • Linden, A.1    Juch, M.2    Moghaddam, F.M.3    Zaynizadeh, B.4    Ruedi, P.5
  • 22
    • 0023712085 scopus 로고
    • Absolute configurations of cytotoxic marine cembranolides; consideration of Mosher's method
    • DOI 10.1016/S0040-4039(00)80593-6
    • Kusumi, T.; Ohtani, I.; Inouye, Y.; Kakisawa, H. Absolute configurations of cytotoxic marine cembranolides; consideration of Mosher's method. Tetrahedron Lett. 1988, 29, 4731-4734. (Pubitemid 18247340)
    • (1988) Tetrahedron Letters , vol.29 , Issue.37 , pp. 4731-4734
    • Kusumi, T.1    Ohtani, I.2    Inouye, Y.3    Kakisawa, H.4
  • 23
    • 2142858450 scopus 로고
    • High-field FT NMR application of Mosher's method. the absolute configurations of marine terpenoids
    • Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 1991, 113, 4092-4096.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4092-4096
    • Ohtani, I.1    Kusumi, T.2    Kashman, Y.3    Kakisawa, H.4
  • 24
    • 0029814889 scopus 로고    scopus 로고
    • Structural and stereochemical studies of C-21 terpenoids from Mediterranean Spongiidae Sponges
    • Fontana, A.; Albarella, L.; Scognamiglio, G.; Uriz, M.; Cimino, G. Structural and stereochemical studies of C-21 terpenoids from Mediterranean Spongiidae Sponges. J. Nat. Prod. 1996, 59, 869-872.
    • (1996) J. Nat. Prod. , vol.59 , pp. 869-872
    • Fontana, A.1    Albarella, L.2    Scognamiglio, G.3    Uriz, M.4    Cimino, G.5
  • 25
    • 0028198112 scopus 로고
    • Novel cytotoxic annonaceous acetogenins: (2,4-cis and trans)-bulladecinones from Annona bullata (Annonaceae)
    • Gu, Z. M.; Fang, X. P.; Zeng, L.; Kozlowski, J. F.; McLaughlin, J. L. Novel cytotoxic annonaceous acetogenins: (2,4-cis and trans)-bulladecinones from Annona bullata (Annonaceae). Bioorg. Med. Chem. Lett. 1994, 4, 473-478.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 473-478
    • Gu, Z.M.1    Fang, X.P.2    Zeng, L.3    Kozlowski, J.F.4    McLaughlin, J.L.5
  • 26
    • 0029101038 scopus 로고
    • New bioactive monotetrahydrofuran annonaceous acetogenins, annomuricin C and muricatocin C, from the leaves of Annona muricata
    • Wu, F. E.; Zeng, L.; Gu, Z. M.; Zhao, G. X.; Zhang, Y.; Schwedler, J. T.; McLaughlin, J. L.; Sastrodihardjo, S. New bioactive monotetrahydrofuran annonaceous acetogenins, annomuricin C and muricatocin C, from the leaves of Annona muricata. J. Nat. Prod. 1995, 58, 909-915.
    • (1995) J. Nat. Prod. , vol.58 , pp. 909-915
    • Wu, F.E.1    Zeng, L.2    Gu, Z.M.3    Zhao, G.X.4    Zhang, Y.5    Schwedler, J.T.6    McLaughlin, J.L.7    Sastrodihardjo, S.8
  • 27
    • 39149139595 scopus 로고    scopus 로고
    • Secondary metabolites from the aerial parts of Salvia palaestina Bentham
    • Cioffi, G.; Bader, A.; Malafronte, A.; Dal Piaz, F.; De Tommasi, N. Secondary metabolites from the aerial parts of Salvia palaestina Bentham. Phytochemistry 2008, 69, 1005-1012.
    • (2008) Phytochemistry , vol.69 , pp. 1005-1012
    • Cioffi, G.1    Bader, A.2    Malafronte, A.3    Dal Piaz, F.4    De Tommasi, N.5
  • 28
    • 0001259244 scopus 로고
    • Salvisyriacolide, a sesterterpene from Salvia syriaca
    • Rustaiyan, A.; Sadjadi, A. Salvisyriacolide, a sesterterpene from Salvia syriaca. Phytochemistry 1987, 26, 3078-3079.
    • (1987) Phytochemistry , vol.26 , pp. 3078-3079
    • Rustaiyan, A.1    Sadjadi, A.2
  • 29
    • 0030184066 scopus 로고    scopus 로고
    • Sesterterpenes and other constituents of Salvia yosgadensis
    • Topcu, G.; Ulubelen, A.; Tam, T. C. M.; Chin, T. C. Sesterterpenes and other constituents of Salvia yosgadensis. Phytochemistry 1996, 42, 1089-1092.
    • (1996) Phytochemistry , vol.42 , pp. 1089-1092
    • Topcu, G.1    Ulubelen, A.2    Tam, T.C.M.3    Chin, T.C.4
  • 30
    • 0032901678 scopus 로고    scopus 로고
    • Crotonadiol, a labdane diterpenoid from the stem bark of Croton zambesicus
    • DOI 10.1016/S0031-9422(98)00706-7, PII S0031942298007067
    • Ngadjui, B. T.; Folefoc, G. G.; Keumedjio, F.; Dongo, E.; Sondengam, B. L.; Connolly, J. D. Crotonadiol, a labdane diterpenoid from the stem bark of Croton zambesicus. Phytochemistry 1999, 51, 171-174. (Pubitemid 29232803)
    • (1999) Phytochemistry , vol.51 , Issue.1 , pp. 171-174
    • Ngadjui, B.T.1    Folefoc, G.G.2    Keumedjio, F.3    Dongo, E.4    Sondengam, B.L.5    Connolly, J.D.6
  • 31
    • 0026721551 scopus 로고
    • Luffariolides A-E, new cytotoxic sesterterpenes from the Okinawan marine sponge Luffariella sp.
    • Tsuda, M.; Shigemori, H.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. Luffariolides A-E, new cytotoxic sesterterpenes from the Okinawan marine sponge Luffariella sp. J. Org. Chem. 1992, 57, 3503-3507.
    • (1992) J. Org. Chem. , vol.57 , pp. 3503-3507
    • Tsuda, M.1    Shigemori, H.2    Ishibashi, M.3    Sasaki, T.4    Kobayashi, J.5
  • 32
    • 0028797867 scopus 로고
    • Salvileucolide methyl ester, a sesterterpene from Salvia sahendica
    • Moghaddam, F. M.; Zaynizadeh, B.; Rueedi, P. Salvileucolide methyl ester, a sesterterpene from Salvia sahendica. Phytochemistry 1995, 39, 715-716.
    • (1995) Phytochemistry , vol.39 , pp. 715-716
    • Moghaddam, F.M.1    Zaynizadeh, B.2    Rueedi, P.3
  • 33
    • 0242383456 scopus 로고    scopus 로고
    • New Pyrrolizidine Alkaloids and Glycosides from Anchusa strigosa
    • DOI 10.1055/s-2003-43202
    • Braca, A.; Bader, A.; Siciliano, T.; Morelli, I.; De Tommasi, N. New pyrrolizidine alkaloids and glycosides from Anchusa strigosa. Planta Med. 2003, 69, 835-841. (Pubitemid 37346572)
    • (2003) Planta Medica , vol.69 , Issue.9 , pp. 835-841
    • Braca, A.1    Bader, A.2    Siciliano, T.3    Morelli, I.4    De Tommasi, N.5
  • 35
    • 40849130043 scopus 로고    scopus 로고
    • Proteomic methods for drug target discovery
    • Sleno, L.; Emili, A. Proteomic methods for drug target discovery. Curr. Opin. Chem. Biol. 2008, 12, 46-54.
    • (2008) Curr. Opin. Chem. Biol. , vol.12 , pp. 46-54
    • Sleno, L.1    Emili, A.2
  • 37
    • 1542787841 scopus 로고    scopus 로고
    • Label-free screening of biomolecular interactions
    • Cooper, M. A. Label-free screening of biomolecular interactions. Anal. Bioanal. Chem. 2003, 377, 834-842.
    • (2003) Anal. Bioanal. Chem. , vol.377 , pp. 834-842
    • Cooper, M.A.1
  • 38
    • 0345169048 scopus 로고    scopus 로고
    • Post-translational modifications regulate microtubule function
    • Westermann, S.; Weber, K. Post-translational modifications regulate microtubule function. Nat. Rev. Mol. Cell Biol. 2003, 4, 938-947.
    • (2003) Nat. Rev. Mol. Cell Biol. , vol.4 , pp. 938-947
    • Westermann, S.1    Weber, K.2
  • 40
    • 47549094913 scopus 로고    scopus 로고
    • Aplysinoplides A-C, cytotoxic sesterterpenes from the marine sponge Aplysinopsis digitata
    • Ueoka, R.; Nakao, Y.; Fujii, S.; van Soest, R. W.; Matsunaga, S. Aplysinoplides A-C, cytotoxic sesterterpenes from the marine sponge Aplysinopsis digitata. J. Nat. Prod. 2008, 71, 1089-1091.
    • (2008) J. Nat. Prod. , vol.71 , pp. 1089-1091
    • Ueoka, R.1    Nakao, Y.2    Fujii, S.3    Van Soest, R.W.4    Matsunaga, S.5
  • 41
    • 33845918629 scopus 로고    scopus 로고
    • Mooloolabenes A-E, norsesterterpenes from the Australian sponge Hyattella intestinalis
    • Somerville, M. J.; Hooper, J. N.; Garson, M. J. Mooloolabenes A-E, norsesterterpenes from the Australian sponge Hyattella intestinalis. J. Nat. Prod. 2006, 69, 1587-1590.
    • (2006) J. Nat. Prod. , vol.69 , pp. 1587-1590
    • Somerville, M.J.1    Hooper, J.N.2    Garson, M.J.3
  • 42
    • 0017903434 scopus 로고
    • 14C] tyrosine by brain extract: Separation of a carboxypeptidase from tubulin-tyrosine ligase
    • 14C]tyrosine by brain extract: separation of a carboxypeptidase from tubulin-tyrosine ligase. Mol. Cell. Biochem. 1978, 19, 17-21.
    • (1978) Mol. Cell. Biochem. , vol.19 , pp. 17-21
    • Argarana, C.E.1    Barra, H.S.2    Caputto, R.3
  • 43
    • 0030709242 scopus 로고    scopus 로고
    • Multiple forms of tubulin: Different gene products and covalent modifications
    • Luduena, R. F. Multiple forms of tubulin: different gene products and covalent modifications. Int. Rev. Cytol. 1998, 178, 207-275.
    • (1998) Int. Rev. Cytol. , vol.178 , pp. 207-275
    • Luduena, R.F.1
  • 44
    • 0017406215 scopus 로고
    • Enzyme which specifically adds tyrosine to the alpha chain of tubulin
    • Raybin, D.; Flavin, M. Enzyme which specifically adds tyrosine to the alpha chain of tubulin. Biochemistry 1977, 16, 2189-2194. (Pubitemid 8120887)
    • (1977) Biochemistry , vol.16 , Issue.10 , pp. 2189-2194
    • Raybin, D.1    Flavin, M.2
  • 45
    • 0018104825 scopus 로고
    • Capability of tubulin and microtubules to incorporate and to release tyrosine and phenylalanine and the effect of the incorporation of these amino acids on tubulin assembly
    • Arce, A.; Hallak, M. E.; Rodriguez, J. A.; Barra, H. S.; Caputto, R. Capability of tubulin and microtubules to incorporate and to release tyrosine and phenylalanine and the effect of the incorporation of these amino acids on tubulin assembly. J. Neurochem. 1978, 31, 205-210. (Pubitemid 8390994)
    • (1978) Journal of Neurochemistry , vol.31 , Issue.1 , pp. 205-210
    • Arce, C.A.1    Hallak, M.E.2    Rodriguez, J.A.3
  • 47
    • 0035059140 scopus 로고    scopus 로고
    • Evidence for a role of the (alpha)-tubulin C terminus in the regulation of cyclin B synthesis in developing oocytes
    • Vee, S.; Lafanechere, L.; Fisher, D.; Wehland, J.; Job, D.; Picard, A. Evidence for a role of the (alpha)-tubulin C terminus in the regulation of cyclin B synthesis in developing oocytes. J. Cell Sci. 2001, 114, 887-898. (Pubitemid 32266260)
    • (2001) Journal of Cell Science , vol.114 , Issue.5 , pp. 887-898
    • Vee, S.1    Lafanechere, L.2    Fisher, D.3    Wehland, J.4    Job, D.5    Picard, A.6
  • 48
    • 0032992466 scopus 로고    scopus 로고
    • Microtubule dysfunction by posttranslational nitrotyrosination of alpha-tubulin: A nitric oxide dependent mechanism of cellular injury
    • Eiserich, P.; Estevez, A. G.; Bamberg, T. V.; Ye, Y. Z.; Chumley, P. H.; Beckman, J. S.; Freeman, B. A. Microtubule dysfunction by posttranslational nitrotyrosination of alpha-tubulin: a nitric oxide dependent mechanism of cellular injury. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 6365-6370.
    • (1999) Proc. Natl. Acad. Sci. U.S.A. , vol.96 , pp. 6365-6370
    • Eiserich, P.1    Estevez, A.G.2    Bamberg, T.V.3    Ye, Y.Z.4    Chumley, P.H.5    Beckman, J.S.6    Freeman, B.A.7
  • 49
    • 34548178909 scopus 로고    scopus 로고
    • In-gel digestion for mass spectrometric characterization of proteins and proteomes
    • Shevchenko, A.; Tomas, H.; Havlis, J.; Olsen, J. V.; Mann, M. In-gel digestion for mass spectrometric characterization of proteins and proteomes. Nat. Protoc. 2006, 1, 2856-2860.
    • (2006) Nat. Protoc. , vol.1 , pp. 2856-2860
    • Shevchenko, A.1    Tomas, H.2    Havlis, J.3    Olsen, J.V.4    Mann, M.5
  • 50
    • 0025944815 scopus 로고
    • Immobilization of proteins to a carboxymethyldextran-modified gold surface for biospecific interaction analysis in surface plasmon resonance sensors
    • Johnsson, B.; Loefaas, S.; Lindquist, G. Immobilization of proteins to a carboxymethyldextran-modified gold surface for biospecific interaction analysis in surface plasmon resonance sensors. Anal. Biochem. 1991, 198, 268-277.
    • (1991) Anal. Biochem. , vol.198 , pp. 268-277
    • Johnsson, B.1    Loefaas, S.2    Lindquist, G.3
  • 51
    • 0032701484 scopus 로고    scopus 로고
    • Improving biosensor analysis
    • Myszka, D. G. Improving biosensor analysis. J. Mol. Recogn. 1999, 12, 279-284.
    • (1999) J. Mol. Recogn. , vol.12 , pp. 279-284
    • Myszka, D.G.1


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