메뉴 건너뛰기




Volumn 51, Issue 5, 2008, Pages 1469-1473

Conformational preferences of natural and C3-modified epothilones in aqueous solution

Author keywords

[No Author keywords available]

Indexed keywords

EPOTHILONE A; EPOTHILONE DERIVATIVE;

EID: 41649104278     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm7013452     Document Type: Article
Times cited : (43)

References (41)
  • 1
    • 18744390786 scopus 로고    scopus 로고
    • Recent developments in the chemistry and biology of epothilones
    • (a) Altmann, K.-H. Recent developments in the chemistry and biology of epothilones. Curr. Pharm. Des. 2005, 11, 1595-613.
    • (2005) Curr. Pharm. Des , vol.11 , pp. 1595-1613
    • Altmann, K.-H.1
  • 2
    • 41649096196 scopus 로고    scopus 로고
    • Cragg, G. M, Kingston, D. G. I, Newman D. J, Eds, Taylor & Francis: Boca Raton, FL
    • (b) Höfle G.; Reichenbach H. In Anticancer Agents form Natural Products; Cragg, G. M., Kingston, D. G. I., Newman D. J., Eds.; Taylor & Francis: Boca Raton, FL, 2005; Vol. 41, pp 3-450.
    • (2005) Anticancer Agents form Natural Products , vol.41 , pp. 3-450
    • Höfle, G.1    Reichenbach, H.2
  • 3
    • 1942438028 scopus 로고    scopus 로고
    • Microtubules as a target for anticancer drugs
    • Jordan, M. A.; Wilson, L. Microtubules as a target for anticancer drugs. Nat. Rev. Cancer 2004, 4, 253-265.
    • (2004) Nat. Rev. Cancer , vol.4 , pp. 253-265
    • Jordan, M.A.1    Wilson, L.2
  • 5
    • 0031027531 scopus 로고    scopus 로고
    • Activities of the microtubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol)
    • (b) Kowalski, R. J.; Giannakakou, P.; Hamel, E. Activities of the microtubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol). J. Biol. Chem. 1997, 272, 2534-2541.
    • (1997) J. Biol. Chem , vol.272 , pp. 2534-2541
    • Kowalski, R.J.1    Giannakakou, P.2    Hamel, E.3
  • 6
    • 0029776766 scopus 로고    scopus 로고
    • Antibiotics from gliding bacteria. 77. Epothilone A and B - novel 16-membered macrolides with cytotoxic activity: Isolation, crystal structure, and conformation in solution
    • Höfle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Antibiotics from gliding bacteria. 77. Epothilone A and B - novel 16-membered macrolides with cytotoxic activity: Isolation, crystal structure, and conformation in solution. Angew. Chem., Int. Ed. 1996, 35, 1567-9.
    • (1996) Angew. Chem., Int. Ed , vol.35 , pp. 1567-1569
    • Höfle, G.1    Bedorf, N.2    Steinmetz, H.3    Schomburg, D.4    Gerth, K.5    Reichenbach, H.6
  • 9
    • 1542380040 scopus 로고    scopus 로고
    • Interaction of epothilone analogs with the paclitaxel binding site: Relationship between binding affinity, microtubule stabilization, and cytotoxicity
    • Buey, R. M.; Diaz, J. F.; Andreu, J. M.; O'Brate, A.; Giannakakou, P.; Nicolau, K. C.; Sasmal, P. K.; Ritzen, A.; Namoto, K. Interaction of epothilone analogs with the paclitaxel binding site: Relationship between binding affinity, microtubule stabilization, and cytotoxicity. Chem. Biol. 2004, 11, 225-236.
    • (2004) Chem. Biol , vol.11 , pp. 225-236
    • Buey, R.M.1    Diaz, J.F.2    Andreu, J.M.3    O'Brate, A.4    Giannakakou, P.5    Nicolau, K.C.6    Sasmal, P.K.7    Ritzen, A.8    Namoto, K.9
  • 10
    • 0033565018 scopus 로고    scopus 로고
    • A unified and quantitative receptor model for the microtubule binding of paclitaxel and epothilone
    • (a) Wang, M. M.; Xia, X. Y.; Kim, Y.; Hwang, D.; Jansen, J. M.; Botta, M.; Liotta, D. C.; Snyder, J. P. A unified and quantitative receptor model for the microtubule binding of paclitaxel and epothilone. Org. Lett. 1999, 1, 43-46.
    • (1999) Org. Lett , vol.1 , pp. 43-46
    • Wang, M.M.1    Xia, X.Y.2    Kim, Y.3    Hwang, D.4    Jansen, J.M.5    Botta, M.6    Liotta, D.C.7    Snyder, J.P.8
  • 13
    • 0037407830 scopus 로고    scopus 로고
    • 3D QSAR studies of the interaction between β-tubulin and microtubule stabilizing antimitotic agents (MSAA). A combined pharmacophore generation and pseudoreceptor modeling approach applied to taxanes and epothilones
    • (d) Manetti, F.; Forli, S.; Maccari, L.; Corelli, F.; Botta, M. 3D QSAR studies of the interaction between β-tubulin and microtubule stabilizing antimitotic agents (MSAA). A combined pharmacophore generation and pseudoreceptor modeling approach applied to taxanes and epothilones. Farmaco 2003, 58, 357-361.
    • (2003) Farmaco , vol.58 , pp. 357-361
    • Manetti, F.1    Forli, S.2    Maccari, L.3    Corelli, F.4    Botta, M.5
  • 14
    • 1542394399 scopus 로고    scopus 로고
    • 3D QSAR models of interactions between β-tubulin and microtubule stabilizing antimitotic agents (MSAA): A survey on taxanes and epothilones
    • (e) Manetti, F.; Maccari, L.; Corelli, F.; Botta, M. 3D QSAR models of interactions between β-tubulin and microtubule stabilizing antimitotic agents (MSAA): A survey on taxanes and epothilones. Curr. Top. Med. Chem. 2004, 4, 203-217.
    • (2004) Curr. Top. Med. Chem , vol.4 , pp. 203-217
    • Manetti, F.1    Maccari, L.2    Corelli, F.3    Botta, M.4
  • 15
    • 3843053396 scopus 로고    scopus 로고
    • The binding mode of epothilone A on α,β-tubulin by electron crystallography
    • Nettles, J. H.; Li, H.; Cornett, B.; Krahn, J. M.; Synder, J. P.; Downing, K. H. The binding mode of epothilone A on α,β-tubulin by electron crystallography. Science 2005, 305, 866-869.
    • (2005) Science , vol.305 , pp. 866-869
    • Nettles, J.H.1    Li, H.2    Cornett, B.3    Krahn, J.M.4    Synder, J.P.5    Downing, K.H.6
  • 16
    • 0037663864 scopus 로고    scopus 로고
    • Derivation of dihedral angles from CH-CH dipolar-dipolar cross-correlated relaxation rates: A C-C torsion involving a quaternary carbon atom in epothilone A bound to tubulin
    • Carlomagno, T.; Sanchez, V. M.; Blommers, M. J. J.; Griesinger, C. Derivation of dihedral angles from CH-CH dipolar-dipolar cross-correlated relaxation rates: A C-C torsion involving a quaternary carbon atom in epothilone A bound to tubulin. Angew. Chem., Int. Ed. 2003, 42, 2515-2517.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 2515-2517
    • Carlomagno, T.1    Sanchez, V.M.2    Blommers, M.J.J.3    Griesinger, C.4
  • 17
    • 0038339605 scopus 로고    scopus 로고
    • The high-resolution solution structure of epothilone A bound to tubulin: An understanding of the structure-activity relationships for a powerful class of antitumor agents
    • Carlomagno, T.; Blommers, M. J. J.; Meiler, J.; Jahnke, W.; Schupp, T.; Petersen, F.; Schinzer, D.; Altmann, K.-H.; Griesinger, C. The high-resolution solution structure of epothilone A bound to tubulin: An understanding of the structure-activity relationships for a powerful class of antitumor agents. Angew. Chem., Int. Ed. 2003, 42, 2511-2515.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 2511-2515
    • Carlomagno, T.1    Blommers, M.J.J.2    Meiler, J.3    Jahnke, W.4    Schupp, T.5    Petersen, F.6    Schinzer, D.7    Altmann, K.-H.8    Griesinger, C.9
  • 18
    • 41649116545 scopus 로고    scopus 로고
    • High-resolution solid-state NMR structure of an anticancer agent
    • Lange, A.; Schupp, T.; Petersen, F.; Carlomagno, T.; Baldus, M. High-resolution solid-state NMR structure of an anticancer agent. ChemMedChem 2007, 2, 522-527.
    • (2007) ChemMedChem , vol.2 , pp. 522-527
    • Lange, A.1    Schupp, T.2    Petersen, F.3    Carlomagno, T.4    Baldus, M.5
  • 19
    • 0033578846 scopus 로고    scopus 로고
    • Conformational properties of epothilone
    • Taylor, R. E.; Zajicek, J. Conformational properties of epothilone. J. Org. Chem. 1999, 64, 7224-7228.
    • (1999) J. Org. Chem , vol.64 , pp. 7224-7228
    • Taylor, R.E.1    Zajicek, J.2
  • 20
    • 0037425543 scopus 로고    scopus 로고
    • Conformation-activity relationships in polydetide natural products: A new perspective on the rational design of epothilone analogues
    • For additional work by the Taylor group on the conformation of epothilones, see a
    • For additional work by the Taylor group on the conformation of epothilones, see (a) Taylor, R. E.; Chen, Y.; Beatty, A. Conformation-activity relationships in polydetide natural products: A new perspective on the rational design of epothilone analogues. J. Am. Chem. Soc. 2003, 125, 26-27.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 26-27
    • Taylor, R.E.1    Chen, Y.2    Beatty, A.3
  • 21
    • 0038339582 scopus 로고    scopus 로고
    • Yoshimura, F.; Rivkin, A.; Gabarda, A. E.; Chou, T.-C.; Dong, H.; Sukenick, G.; Morel, F. F.; Taylor, R. E.; Danishefsky, S. J. Synthesis and conformational analysis of (E)-9,10-dehydroeepothilone B: A suggestive link between the chemistry and biology of epothilones. Angew. Chem., Int. Ed. 2003, 42, 2518-2521.
    • (b) Yoshimura, F.; Rivkin, A.; Gabarda, A. E.; Chou, T.-C.; Dong, H.; Sukenick, G.; Morel, F. F.; Taylor, R. E.; Danishefsky, S. J. Synthesis and conformational analysis of (E)-9,10-dehydroeepothilone B: A suggestive link between the chemistry and biology of epothilones. Angew. Chem., Int. Ed. 2003, 42, 2518-2521.
  • 22
    • 14844338576 scopus 로고    scopus 로고
    • Much anticipated - The bioactive conformation of epothilone and its binding to tubulin
    • Heinz, D.; Schubert, W.-D.; Höefle, G. Much anticipated - The bioactive conformation of epothilone and its binding to tubulin. Angew. Chem., Int. Ed. 2005, 44, 1298-1301.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 1298-1301
    • Heinz, D.1    Schubert, W.-D.2    Höefle, G.3
  • 23
    • 0026532051 scopus 로고
    • A conformation of cyclosporine A in aqueous environment revealed by the X-ray structure of a cyclosporin-fab complex
    • (a) Altschuh, D.; Vix, O.; Rees, B.; Thierry, J. C. A conformation of cyclosporine A in aqueous environment revealed by the X-ray structure of a cyclosporin-fab complex. Science 1992, 256, 92-94.
    • (1992) Science , vol.256 , pp. 92-94
    • Altschuh, D.1    Vix, O.2    Rees, B.3    Thierry, J.C.4
  • 24
    • 0028273057 scopus 로고
    • The 3D structure of a cyclosporine analogue in water is nearly identical to the cyclophilin-bound cyclosporine conformation
    • (b) Wenger, R. M.; France, J.; Bovermann, G.; Walliser, L.; Widmer, A.; Widmer, H. The 3D structure of a cyclosporine analogue in water is nearly identical to the cyclophilin-bound cyclosporine conformation. FEBS Lett. 1994, 340, 255-259.
    • (1994) FEBS Lett , vol.340 , pp. 255-259
    • Wenger, R.M.1    France, J.2    Bovermann, G.3    Walliser, L.4    Widmer, A.5    Widmer, H.6
  • 26
    • 33947427870 scopus 로고    scopus 로고
    • Relationship among ligand conformations in solution, in the solid state, and at the Hsp90 binding site. Geldanamycin and Radicicol
    • (d) Thepchatri, P.; Eliseo, T.; Cicero, D. O.; Myles, D.; Synder, J. P. Relationship among ligand conformations in solution, in the solid state, and at the Hsp90 binding site. Geldanamycin and Radicicol. J. Am. Chem. Soc. 2007, 129, 3127-3134.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 3127-3134
    • Thepchatri, P.1    Eliseo, T.2    Cicero, D.O.3    Myles, D.4    Synder, J.P.5
  • 30
    • 28044438972 scopus 로고    scopus 로고
    • Scaffolds for microtubule inhibition through extensive modification of the epothilone template
    • Cachoux, F.; Isarno, T.; Wartmann, M.; Altmann, K.-H. Scaffolds for microtubule inhibition through extensive modification of the epothilone template. Angew. Chem., Int. Ed. 2005, 44, 7469-7473.
    • (2005) Angew. Chem., Int. Ed , vol.44 , pp. 7469-7473
    • Cachoux, F.1    Isarno, T.2    Wartmann, M.3    Altmann, K.-H.4
  • 32
    • 0028793933 scopus 로고
    • NMR analysis of molecular flexibility in solution: A new method for the study of complex distributions of rapidly exchanging conformations. Application to a 13-residue peptide with an 8-residue loop
    • Cicero, D. O.; Barbato, G.; Bazzo, R. NMR analysis of molecular flexibility in solution: a new method for the study of complex distributions of rapidly exchanging conformations. Application to a 13-residue peptide with an 8-residue loop. J. Am. Chem. Soc. 1995, 117, 1027-1033.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 1027-1033
    • Cicero, D.O.1    Barbato, G.2    Bazzo, R.3
  • 35
    • 33744973034 scopus 로고    scopus 로고
    • Accurate measurement of long-range heteronuclear coupling constants from undistorted multiplets of an enhanced CPMG-HSQMBC experiment
    • Kövér, K. E.; Batta, G.; Feher, K. Accurate measurement of long-range heteronuclear coupling constants from undistorted multiplets of an enhanced CPMG-HSQMBC experiment. J. Magn. Reson. 2006, 181, 89-97.
    • (2006) J. Magn. Reson , vol.181 , pp. 89-97
    • Kövér, K.E.1    Batta, G.2    Feher, K.3
  • 36
    • 0034178731 scopus 로고    scopus 로고
    • Effect of oxygen substituents on two- and three-bond carbon-proton spin-spin coupling constants
    • Morvai, M.; Nagy, T.; Kocsis, A.; Szabo, L. F.; Podanyi, B. Effect of oxygen substituents on two- and three-bond carbon-proton spin-spin coupling constants. Magn. Reson. Chem. 2000, 38, 343-359.
    • (2000) Magn. Reson. Chem , vol.38 , pp. 343-359
    • Morvai, M.1    Nagy, T.2    Kocsis, A.3    Szabo, L.F.4    Podanyi, B.5
  • 38
    • 0344778061 scopus 로고
    • Semi-analytical treatment of solvation for molecular mechanics and dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semi-analytical treatment of solvation for molecular mechanics and dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6179.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 6127-6179
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 39
    • 0020537657 scopus 로고
    • Modulation of tubulin-nucleotide interactions by microtubule-associated proteins: Polymerization with ribose-modified analogues of guanosine 5′- triphosphate
    • Hamel, E.; del Campo, A. A.; Lustbader, J.; Lin, C. M. Modulation of tubulin-nucleotide interactions by microtubule-associated proteins: Polymerization with ribose-modified analogues of guanosine 5′- triphosphate. Biochemistry 1983, 22, 1271-1279.
    • (1983) Biochemistry , vol.22 , pp. 1271-1279
    • Hamel, E.1    del Campo, A.A.2    Lustbader, J.3    Lin, C.M.4
  • 40
    • 0024379951 scopus 로고
    • A derivative of staurosporine (CGP 41 251) shows selectivity for protein kinase C inhibition and in vitro anti-proliferative as well as in vivo anti-tumor activity
    • Meyer, T.; Regenass, U.; Fabbro, D.; Alteri, E.; Rösel, J.; Müller, M.; Caravatti, G.; Matter, A. A derivative of staurosporine (CGP 41 251) shows selectivity for protein kinase C inhibition and in vitro anti-proliferative as well as in vivo anti-tumor activity. Int. J. Cancer 1989, 43, 851-856.
    • (1989) Int. J. Cancer , vol.43 , pp. 851-856
    • Meyer, T.1    Regenass, U.2    Fabbro, D.3    Alteri, E.4    Rösel, J.5    Müller, M.6    Caravatti, G.7    Matter, A.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.