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Volumn 53, Issue 1, 2010, Pages 155-165

The discodermolide hairpin structure flows from conformationally stable modular motifs

Author keywords

[No Author keywords available]

Indexed keywords

BETA TUBULIN; DISCODERMOLIDE;

EID: 74849140127     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9015284     Document Type: Article
Times cited : (18)

References (75)
  • 1
    • 0025160288 scopus 로고    scopus 로고
    • Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. Discoderolide: A New Bioactive Polyhydroxylated Lactone from the Marine Sponge Discodermia dissoluta. J. Org. Chem. 1990, 55, 4912-4915.
    • Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. Discoderolide: A New Bioactive Polyhydroxylated Lactone from the Marine Sponge Discodermia dissoluta. J. Org. Chem. 1990, 55, 4912-4915.
  • 2
    • 28844499921 scopus 로고    scopus 로고
    • Microtubule Interactions with Chemically Diverse Stabilizing Agents: Thermodynamics of Binding to the Paclitaxel Site Predicts Cytotoxicity
    • Buey, R. M.; Barasoain, I.; Jackson, E.; Meyer, A.; Giannakakou, P.; Paterson, I.; Mooberry, S.; Andreu, J. M.; Diaz, J. F. Microtubule Interactions with Chemically Diverse Stabilizing Agents: Thermodynamics of Binding to the Paclitaxel Site Predicts Cytotoxicity. Chem. Biol. 2005, 12, 1269-1279.
    • (2005) Chem. Biol , vol.12 , pp. 1269-1279
    • Buey, R.M.1    Barasoain, I.2    Jackson, E.3    Meyer, A.4    Giannakakou, P.5    Paterson, I.6    Mooberry, S.7    Andreu, J.M.8    Diaz, J.F.9
  • 3
    • 31544473618 scopus 로고    scopus 로고
    • A phase I pharmacokinetic (PK) of AAA296A (discodermolide) administered every 3 weeks in adult patients with advanced solid tumors
    • 133Abstr 2025
    • Mita, A.; Lockhart, A.; Chen, T. A phase I pharmacokinetic (PK) of AAA296A (discodermolide) administered every 3 weeks in adult patients with advanced solid tumors. Proc. Am. Soc. Clin. Oncol. 2004, 23, 133(Abstr 2025) .
    • (2004) Proc. Am. Soc. Clin. Oncol , vol.23
    • Mita, A.1    Lockhart, A.2    Chen, T.3
  • 4
    • 60849103522 scopus 로고    scopus 로고
    • Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates
    • (a) Mollat du Jourdin, X.; Noshi, M.; Fuchs, P. L. Designer Discodermolide Segments via Ozonolysis of Vinyl Phosphonates. Org. Lett. 2009, 11, 543-346.
    • (2009) Org. Lett , vol.11 , pp. 543-346
    • Mollat du Jourdin, X.1    Noshi, M.2    Fuchs, P.L.3
  • 6
    • 36549038147 scopus 로고    scopus 로고
    • (+)-Discodermalide: Total Syntheses, Construction of Novel Analogues, and Biological Evaluation: An Overview
    • (c) Smith, A. B.; Freeze, B. S. (+)-Discodermalide: Total Syntheses, Construction of Novel Analogues, and Biological Evaluation: An Overview. Tetrahedron 2008, 64 (2), 261-298.
    • (2008) Tetrahedron , vol.64 , Issue.2 , pp. 261-298
    • Smith, A.B.1    Freeze, B.S.2
  • 7
    • 52649167707 scopus 로고    scopus 로고
    • Total synthesis of a potent hybrid of the anticancer natural products dictyostatin and discodermolide
    • (d) Paterson, I.; Naylor, G. J.; Wright, A. E. Total synthesis of a potent hybrid of the anticancer natural products dictyostatin and discodermolide. Chem. Commun. 2008, 38, 4628-4630.
    • (2008) Chem. Commun , vol.38 , pp. 4628-4630
    • Paterson, I.1    Naylor, G.J.2    Wright, A.E.3
  • 8
    • 41749125906 scopus 로고    scopus 로고
    • Development of practical syntheses of the marine anticancer agents discodermolide and dictyostatin
    • (e) Florence, G. J.; Gardner, N. M.; Paterson, I. Development of practical syntheses of the marine anticancer agents discodermolide and dictyostatin. Nat. Prod. Rep. 2008, 25, 342-375.
    • (2008) Nat. Prod. Rep , vol.25 , pp. 342-375
    • Florence, G.J.1    Gardner, N.M.2    Paterson, I.3
  • 9
    • 45849086601 scopus 로고    scopus 로고
    • Short Synthesis of the C1-C14 Stretch of Discodermolide from Building Blocks Prepared by Asymmetric Catalysis
    • (f) Cao, H.; Parker, K. A. Short Synthesis of the C1-C14 Stretch of Discodermolide from Building Blocks Prepared by Asymmetric Catalysis. Org. Lett. 2008, 10, 1353-1356.
    • (2008) Org. Lett , vol.10 , pp. 1353-1356
    • Cao, H.1    Parker, K.A.2
  • 10
    • 42449120174 scopus 로고    scopus 로고
    • The Structure - Activity Relationship of Discodermolide Analogues
    • (g) Shaw, S. J. The Structure - Activity Relationship of Discodermolide Analogues. Mini-Rev. Med. Chem. 2008, 8, 276-284.
    • (2008) Mini-Rev. Med. Chem , vol.8 , pp. 276-284
    • Shaw, S.J.1
  • 11
    • 33751204460 scopus 로고    scopus 로고
    • The Tubulin-Bound Conformation of Discodermolide Derived by NMR Studies in Solution Supports a Common Pharmacophore Model for Epothilone and Discodermolide
    • Sanchez-Pedregal, V. S.; Kubicek, K.; Meiler, J.; Lyothier, I.; Paterson, I.; Carlomagno, T. The Tubulin-Bound Conformation of Discodermolide Derived by NMR Studies in Solution Supports a Common Pharmacophore Model for Epothilone and Discodermolide. Angew. Chem., Int. Ed. 2006, 45, 7388-7394.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 7388-7394
    • Sanchez-Pedregal, V.S.1    Kubicek, K.2    Meiler, J.3    Lyothier, I.4    Paterson, I.5    Carlomagno, T.6
  • 12
    • 53849091740 scopus 로고    scopus 로고
    • The Bound Conformation of Microtubule-Stabilizing Agents: NMR Insights into the Bioactive 3D Structure of Discodermolide and Dictyostatin
    • Canales, A.; Matesanz, R.; Gardner, N. M.; Andreu, J. M.; Paterson, I.; Diaz, J. F.; Jiménez-Barbero, J. The Bound Conformation of Microtubule-Stabilizing Agents: NMR Insights into the Bioactive 3D Structure of Discodermolide and Dictyostatin. Chem. - Eur. J. 2008, 14, 7557-7569.
    • (2008) Chem. - Eur. J , vol.14 , pp. 7557-7569
    • Canales, A.1    Matesanz, R.2    Gardner, N.M.3    Andreu, J.M.4    Paterson, I.5    Diaz, J.F.6    Jiménez-Barbero, J.7
  • 15
    • 0028793933 scopus 로고
    • NMRAnalysis 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.NMRAnalysis 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
  • 16
    • 0033612194 scopus 로고    scopus 로고
    • A Test of the Single-Conformation Hypothesis in the Analysis ofNMRData for Small Polar Molecules: A Force Field Comparison
    • Nevins, N.; Cicero, D. O.; Snyder, J. P. A Test of the Single-Conformation Hypothesis in the Analysis ofNMRData for Small Polar Molecules: A Force Field Comparison. J. Org. Chem. 1999, 64, 3979-3986.
    • (1999) J. Org. Chem , vol.64 , pp. 3979-3986
    • Nevins, N.1    Cicero, D.O.2    Snyder, J.P.3
  • 17
    • 0842306927 scopus 로고    scopus 로고
    • 7-24 and Finale. Org. Process Res. Dev. 2004, 8, 122-130and cited references. .
    • 7-24 and Finale. Org. Process Res. Dev. 2004, 8, 122-130and cited references. .
  • 18
    • 0031833483 scopus 로고    scopus 로고
    • Conformation Design of Hydrocarbon Backbones: A Modular Approach
    • Hoffmann,R.W.; Stahl,M.; Shopfer,U.; Frenking,G.Conformation Design of Hydrocarbon Backbones: A Modular Approach. Chem. - Eur. J. 1998, 4, 559-566.
    • (1998) Chem. - Eur. J , vol.4 , pp. 559-566
    • Hoffmann, R.W.1    Stahl, M.2    Shopfer, U.3    Frenking, G.4
  • 19
    • 0032698882 scopus 로고    scopus 로고
    • Flexible Molecules with Defined Shape XI Conformer Equilibria in 2,4-Disubstituted Pentane Derivatives
    • Hoffmann, R. W.; Stenkamp, D.; Trieselmann, T.; Gottlich, R. Flexible Molecules with Defined Shape XI Conformer Equilibria in 2,4-Disubstituted Pentane Derivatives. Eur. J. Org. Chem. 1999, 2915-2917.
    • (1999) Eur. J. Org. Chem , pp. 2915-2917
    • Hoffmann, R.W.1    Stenkamp, D.2    Trieselmann, T.3    Gottlich, R.4
  • 20
    • 0042891852 scopus 로고    scopus 로고
    • Calculated Conformer Energies for Organic Molecules with Multiple Polar Functionalities are Method Dependent: Taxol Case Study
    • Lakdawala, A.; Wang, M.; Nevins, N.; Liotta, D. C.; Rusinska-Rosak, D.; Lozynski, M.; Snyder, J. P. Calculated Conformer Energies for Organic Molecules with Multiple Polar Functionalities are Method Dependent: Taxol Case Study. BMC Biology 2001, 1, 2.
    • (2001) BMC Biology , vol.1 , pp. 2
    • Lakdawala, A.1    Wang, M.2    Nevins, N.3    Liotta, D.C.4    Rusinska-Rosak, D.5    Lozynski, M.6    Snyder, J.P.7
  • 21
    • 74849089512 scopus 로고    scopus 로고
    • As pointed out by Martello et al. (ref 16), the distributed X-ray coordinates of (+)-discodermolide require mirror-image inversion to correspond to the absolute configuration of the natural product.
    • As pointed out by Martello et al. (ref 16), the distributed X-ray coordinates of (+)-discodermolide require mirror-image inversion to correspond to the absolute configuration of the natural product.
  • 22
    • 0034826406 scopus 로고    scopus 로고
    • The relationship between Taxol and (+)-discodermolide: Synthetic analogs and modeling studies
    • Martello, L. A.; LaMarche, M. J.; He, L.; Beauchamp, T. J.; Smith, A. B., III; Horwitz, S. B. The relationship between Taxol and (+)-discodermolide: synthetic analogs and modeling studies. Chem. Biol. 2001, 8, 843-855.
    • (2001) Chem. Biol , vol.8 , pp. 843-855
    • Martello, L.A.1    LaMarche, M.J.2    He, L.3    Beauchamp, T.J.4    Smith III, A.B.5    Horwitz, S.B.6
  • 23
    • 2342586724 scopus 로고    scopus 로고
    • Conformational Analysis of Drug-Like Molecules Bound to Proteins: An Extensive Study of Ligand Reorganization upon Binding
    • Perola, E.; Charifson, P. S. Conformational Analysis of Drug-Like Molecules Bound to Proteins: An Extensive Study of Ligand Reorganization upon Binding. J. Med. Chem. 2004, 47, 2499-2510.
    • (2004) J. Med. Chem , vol.47 , pp. 2499-2510
    • Perola, E.1    Charifson, P.S.2
  • 25
    • 74849119623 scopus 로고    scopus 로고
    • H-H. The smaller the value, the better the fitting. Good to excellent fits between data and structure ordinarily fall at SSD < 100. For the analytical expression used to evaluate the latter, see refs 9 and 10.
    • H-H. The smaller the value, the better the fitting. Good to excellent fits between data and structure ordinarily fall at SSD < 100. For the analytical expression used to evaluate the latter, see refs 9 and 10.
  • 26
    • 0039432412 scopus 로고
    • Spectroscopic Studies of Solvent Effects on Intramolecular Hydrogen Bonding in N-Substituted Salicylamides
    • (a) Kondo, M. Spectroscopic Studies of Solvent Effects on Intramolecular Hydrogen Bonding in N-Substituted Salicylamides. Bull. Chem. Soc. Jpn. 1979, 52, 521-523.
    • (1979) Bull. Chem. Soc. Jpn , vol.52 , pp. 521-523
    • Kondo, M.1
  • 27
    • 0034643911 scopus 로고    scopus 로고
    • Intramolecular hydrogen bonding and tautomerism in Schiff bases. Structure of N-(2-pyridil)-2-oxo-1-naphthylidenemethylamine
    • (b) Nazir, H.; Yildiz, M.; Tahir,M. N.; Uikü, D. Intramolecular hydrogen bonding and tautomerism in Schiff bases. Structure of N-(2-pyridil)-2-oxo-1-naphthylidenemethylamine. J. Mol. Struct. 2000, 524, 241-250.
    • (2000) J. Mol. Struct , vol.524 , pp. 241-250
    • Nazir, H.1    Yildiz, M.2    Tahir, M.N.3    Uikü, D.4
  • 28
    • 3242724340 scopus 로고    scopus 로고
    • Intramolecular hydrogen bonding of (+)-biotin and biotin derivatives in organic solvents (DC-178BP)
    • (c) Crisp, G. T.; Jiang, Y.-L. Intramolecular hydrogen bonding of (+)-biotin and biotin derivatives in organic solvents (DC-178BP). ARKIVOC 2001, vii, 77-87.
    • (2001) ARKIVOC , vol.7 , pp. 77-87
    • Crisp, G.T.1    Jiang, Y.-L.2
  • 29
    • 31744435050 scopus 로고    scopus 로고
    • Evidences that β-Lactose Forms Hydrogen Bonds in DMSO
    • (d) Ko, H.; Shim, G.; Kim, Y. Evidences that β-Lactose Forms Hydrogen Bonds in DMSO. Bull. Korean Chem. Soc. 2005, 26, 2001-2006.
    • (2005) Bull. Korean Chem. Soc , vol.26 , pp. 2001-2006
    • Ko, H.1    Shim, G.2    Kim, Y.3
  • 30
    • 25144481876 scopus 로고    scopus 로고
    • Relationship Among Ligand Conformations in Solution, in the Solid State, and at the Hsp90 Binding Site: Geldanamycin and Radicicol
    • Thepchatri, P.; Cicero, D. O.; Monteagudo, E.; Ghosh, A. K.; Cornett, B.; Liotta, D. C.; Snyder, 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. 2005, 127, 12838-12846.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 12838-12846
    • Thepchatri, P.1    Cicero, D.O.2    Monteagudo, E.3    Ghosh, A.K.4    Cornett, B.5    Liotta, D.C.6    Snyder, J.P.7
  • 32
    • 0033578846 scopus 로고    scopus 로고
    • Conformational Properties of Epothilone
    • (a) Taylor, R. E.; Zajicek, J. Conformational Properties of Epothilone. J. Org. Chem. 2000, 64, 7224-7228.
    • (2000) J. Org. Chem , vol.64 , pp. 7224-7228
    • Taylor, R.E.1    Zajicek, J.2
  • 35
    • 74849100839 scopus 로고    scopus 로고
    • The maximum average heavy atom rmsd for conformations in any one cluster is 0.6 Å.
    • The maximum average heavy atom rmsd for conformations in any one cluster is 0.6 Å.
  • 36
    • 1642420641 scopus 로고    scopus 로고
    • Conformation - activity relationships in polyketide natural products. Towards the biologically active conformation of epothilone
    • Taylor, R. E.; Chen, Y.; Galvin, G. M.; Pabba, P. K. Conformation - activity relationships in polyketide natural products. Towards the biologically active conformation of epothilone. Org. Biomol. Chem. 2004, 2, 127-132.
    • (2004) Org. Biomol. Chem , vol.2 , pp. 127-132
    • Taylor, R.E.1    Chen, Y.2    Galvin, G.M.3    Pabba, P.K.4
  • 37
    • 74849130686 scopus 로고    scopus 로고
    • ref 18, Supporting Information.
    • ref 18, Supporting Information.
  • 38
    • 74849127570 scopus 로고    scopus 로고
    • 6 we consider this result to be only an approximation to the unpublished NMR data.
    • 6 we consider this result to be only an approximation to the unpublished NMR data.
  • 39
    • 12144289984 scopus 로고    scopus 로고
    • Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shaw, D. E.; Shelley, M.; Perry, J. K.; Sander, L. C.; Shenkin, P. S. Glide: A New Approach for Rapid, Accurate Docking and Scoring. 1. Method and Assessment of Docking Accuracy. J. Med. Chem. 2004, 47, 1739-1749.
    • (a) Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shaw, D. E.; Shelley, M.; Perry, J. K.; Sander, L. C.; Shenkin, P. S. Glide: A New Approach for Rapid, Accurate Docking and Scoring. 1. Method and Assessment of Docking Accuracy. J. Med. Chem. 2004, 47, 1739-1749.
  • 40
    • 1642310340 scopus 로고    scopus 로고
    • Halgren, T. A.; Murphy,R. B.; Friesner,R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; Banks, J. L. Glide: A New Approach for Rapid, Accurate Docking and Scoring. 2. Enrichment Factors in Database Screening. J. Med. Chem. 2004, 47, 1750-1759.
    • (b) Halgren, T. A.; Murphy,R. B.; Friesner,R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; Banks, J. L. Glide: A New Approach for Rapid, Accurate Docking and Scoring. 2. Enrichment Factors in Database Screening. J. Med. Chem. 2004, 47, 1750-1759.
  • 41
    • 58149094776 scopus 로고    scopus 로고
    • ROSETTALIGAND Docking with Full Ligand and Receptor Flexibility
    • Davis, I. W.; Baker, D. ROSETTALIGAND Docking with Full Ligand and Receptor Flexibility. J. Mol. Biol. 2009, 385, 381-392.
    • (2009) J. Mol. Biol , vol.385 , pp. 381-392
    • Davis, I.W.1    Baker, D.2
  • 42
    • 11644261806 scopus 로고    scopus 로고
    • Automated Docking Using a Lamarckian Genetic Algorithm and and Empirical Binding Free Energy Function
    • (a) Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated Docking Using a Lamarckian Genetic Algorithm and and Empirical Binding Free Energy Function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 43
    • 33947716119 scopus 로고    scopus 로고
    • A Semiempirical Free Energy Force Field with Charge-Based Desolvation
    • (b) Huey, R.; Morris, G. M.; Olson, A. J.; Goodsell, D. S. A Semiempirical Free Energy Force Field with Charge-Based Desolvation. J. Comput. Chem. 2007, 28, 1145-1152.
    • (2007) J. Comput. Chem , vol.28 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4
  • 44
    • 33244490820 scopus 로고    scopus 로고
    • Physics-Based Scoring of Protein - Ligand Complexes: Enrichment of Known Inhibitors in Large-Scale Virtual Screening
    • (a) Niu, H.; Kalyanaraman, C.; Irwin, J. J.; Jacobson, M. P. Physics-Based Scoring of Protein - Ligand Complexes: Enrichment of Known Inhibitors in Large-Scale Virtual Screening. J. Chem. Inf. Model. 2006, 46, 243-253.
    • (2006) J. Chem. Inf. Model , vol.46 , pp. 243-253
    • Niu, H.1    Kalyanaraman, C.2    Irwin, J.J.3    Jacobson, M.P.4
  • 45
    • 33746872935 scopus 로고    scopus 로고
    • Accurate Prediction of the Relative Potencies of Members of a Series of Kinase Inhibitors Using Molecular Docking and MM-GBSA
    • (b) Lyne, P. D.; Lamb, M. L.; Saeh, J. C. Accurate Prediction of the Relative Potencies of Members of a Series of Kinase Inhibitors Using Molecular Docking and MM-GBSA. J. Med. Chem. 2006, 49, 4805-4808.
    • (2006) J. Med. Chem , vol.49 , pp. 4805-4808
    • Lyne, P.D.1    Lamb, M.L.2    Saeh, J.C.3
  • 46
    • 85120283858 scopus 로고    scopus 로고
    • Graves, A. P.; Shivakumar, D. M.; Boyce1, S. E.; Jacobson, M. P.; Case, D. A.; Shoichet, B. K. Rescoring Docking Hit Lists for Model Cavity Sites: Predictions and Experimental Testing. J. Mol. Biol. 2008, 377, 914-934.
    • (c) Graves, A. P.; Shivakumar, D. M.; Boyce1, S. E.; Jacobson, M. P.; Case, D. A.; Shoichet, B. K. Rescoring Docking Hit Lists for Model Cavity Sites: Predictions and Experimental Testing. J. Mol. Biol. 2008, 377, 914-934.
  • 47
    • 0030761586 scopus 로고    scopus 로고
    • The microtubule-stabilizing agent discodermolide competitively inhibits the binding of paclitaxel (Taxol) to tubulin polymers, enhances tubulin nucleation reactions more potently than paclitaxel, and inhibits the growth of paclitaxel-resistant cells
    • Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. The microtubule-stabilizing agent discodermolide competitively inhibits the binding of paclitaxel (Taxol) to tubulin polymers, enhances tubulin nucleation reactions more potently than paclitaxel, and inhibits the growth of paclitaxel-resistant cells. Mol. Pharmacol. 1997, 52, 613-622.
    • (1997) Mol. Pharmacol , vol.52 , pp. 613-622
    • Kowalski, R.J.1    Giannakakou, P.2    Gunasekera, S.P.3    Longley, R.E.4    Day, B.W.5    Hamel, E.6
  • 50
    • 0034681179 scopus 로고    scopus 로고
    • Li, Y.; Poliks, B.; Cegelski, L.; Poliks, M.; Gryczynski, Z.; Piszczek, G.; Jagtap, P. G.; Studelska, D. R.; Kingston, D. G. I.; Schaefer, J.; Bane, S. REDOR NMR Distance Measurements for the Tubulin-Bound Paclitaxel Conformation. Biochemistry 2000, 39, 281-291.
    • Li, Y.; Poliks, B.; Cegelski, L.; Poliks, M.; Gryczynski, Z.; Piszczek, G.; Jagtap, P. G.; Studelska, D. R.; Kingston, D. G. I.; Schaefer, J.; Bane, S. REDOR NMR Distance Measurements for the Tubulin-Bound Paclitaxel Conformation. Biochemistry 2000, 39, 281-291.
  • 51
    • 0035942226 scopus 로고    scopus 로고
    • The binding conformation of Taxol in β-tubulin: A model based on electron crystallographic density
    • (a) Snyder, J. P.; Nettles, J. H.; Cornett, B.; Downing, K. H.; Nogales, E. The binding conformation of Taxol in β-tubulin: A model based on electron crystallographic density. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 5312-5316.
    • (2001) Proc. Natl. Acad. Sci. U.S.A , vol.98 , pp. 5312-5316
    • Snyder, J.P.1    Nettles, J.H.2    Cornett, B.3    Downing, K.H.4    Nogales, E.5
  • 52
    • 33846201709 scopus 로고    scopus 로고
    • Paik, Y.; Yang, C.; Metaferia, B.; Tang, S.; Bane, S.; Ravindra, R.; Shanker, N.; Alcaraz, A. A.; Snyder, J. P.; Cegelski, L.; Kingston, D. G. I. Rotational-Echo Double-Resonance NMR Distance Measurements for the Tubulin-Bound Paclitaxel Conformation. J. Am. Chem. Soc. 2007, 129, 361-370.
    • (b) Paik, Y.; Yang, C.; Metaferia, B.; Tang, S.; Bane, S.; Ravindra, R.; Shanker, N.; Alcaraz, A. A.; Snyder, J. P.; Cegelski, L.; Kingston, D. G. I. Rotational-Echo Double-Resonance NMR Distance Measurements for the Tubulin-Bound Paclitaxel Conformation. J. Am. Chem. Soc. 2007, 129, 361-370.
  • 55
    • 0029860912 scopus 로고    scopus 로고
    • Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization
    • Hung, D. T.; Nerenberg, J. B.; Schreiber, S. L. Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization. J. Am. Chem. Soc. 1996, 118, 11054-11080.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 11054-11080
    • Hung, D.T.1    Nerenberg, J.B.2    Schreiber, S.L.3
  • 56
    • 74849110465 scopus 로고    scopus 로고
    • Kinder, F. R., Jr.; Bair, K. W.; Chen, W.; Florence, G. J.; Francavilla, C.; Geng, P.; Gunasekera, S.; Lassota, P. T.; Longley, R.; Palermo, M.; Paterson, I.; Pomponi, S.; Ramsey, T. M.; Rogers, L.; Sabio, M.; Sereinig, N.; Sorensen, E.; Wang, R.; Wright, A. Global SAR study of the novel microtubule stabilizing agent discodermolide. Proc. AACR 2002, 43, 3650; Presented at American Association for Cancer Research 93rd Annual Meeting, San Francisco, CA, 2002. Poster no. 3650. .
    • Kinder, F. R., Jr.; Bair, K. W.; Chen, W.; Florence, G. J.; Francavilla, C.; Geng, P.; Gunasekera, S.; Lassota, P. T.; Longley, R.; Palermo, M.; Paterson, I.; Pomponi, S.; Ramsey, T. M.; Rogers, L.; Sabio, M.; Sereinig, N.; Sorensen, E.; Wang, R.; Wright, A. Global SAR study of the novel microtubule stabilizing agent discodermolide. Proc. AACR 2002, 43, 3650; Presented at American Association for Cancer Research 93rd Annual Meeting, San Francisco, CA, 2002. Poster no. 3650. .
  • 58
    • 74849138612 scopus 로고    scopus 로고
    • Process For Preparing Discodermolide And Analogues Thereof
    • Patent WO 2,002,012,220, 2002;
    • (a) Kinder, F. R. Process For Preparing Discodermolide And Analogues Thereof. Patent WO 2,002,012,220, 2002;
    • Kinder, F.R.1
  • 59
    • 74849115974 scopus 로고    scopus 로고
    • Kinder, F. R., Jr.; Kapa, P. K.; Loeser, E. M. Certain Salts Of Discodermolide Acid, Pharmaceutical Compositions Containing Them and Their Use In Treating Tumors. Patent WO 2,002,098,843, 2002;
    • (b) Kinder, F. R., Jr.; Kapa, P. K.; Loeser, E. M. Certain Salts Of Discodermolide Acid, Pharmaceutical Compositions Containing Them and Their Use In Treating Tumors. Patent WO 2,002,098,843, 2002;
  • 60
    • 74849104200 scopus 로고    scopus 로고
    • Kinder, F. R., Jr.; Bair, K. W.; Ramsey, T. M.; Sabio, M. L. Certain Substituted Polyketides, Pharmaceutical Compositions Containing Them And Their Use In Treating Tumors. Patent WO 2,003,014,102, 2003.
    • (c) Kinder, F. R., Jr.; Bair, K. W.; Ramsey, T. M.; Sabio, M. L. Certain Substituted Polyketides, Pharmaceutical Compositions Containing Them And Their Use In Treating Tumors. Patent WO 2,003,014,102, 2003.
  • 63
    • 34547869791 scopus 로고    scopus 로고
    • Coumarin-derived discodermolide analogues possessing equivalent antiproliferative activity to the natural product - a further simplification of the lactone region
    • (c) Shaw, S. J.; Menzella, H. G.; Myles, D. C.; Xian, M.; Smith, A. B., III. Coumarin-derived discodermolide analogues possessing equivalent antiproliferative activity to the natural product - a further simplification of the lactone region. Org. Biomol. Chem. 2007, 5, 2753-2755.
    • (2007) Org. Biomol. Chem , vol.5 , pp. 2753-2755
    • Shaw, S.J.1    Menzella, H.G.2    Myles, D.C.3    Xian, M.4    Smith III, A.B.5
  • 64
    • 0036932485 scopus 로고    scopus 로고
    • Semisynthetic Analogues of the Microtubule-Stabilizing Agent Discodermolide: Preparation and Biological Activity
    • Gunasekera, S. P.; Longley, R. E.; Isbrucker, R. A. Semisynthetic Analogues of the Microtubule-Stabilizing Agent Discodermolide: Preparation and Biological Activity. J. Nat. Prod. 2002, 65, 1830-1837.
    • (2002) J. Nat. Prod , vol.65 , pp. 1830-1837
    • Gunasekera, S.P.1    Longley, R.E.2    Isbrucker, R.A.3
  • 66
    • 28244450355 scopus 로고    scopus 로고
    • Design, Synthesis, and Biological Evaluation of Potent Discodermolide Fluorescent and Photoaffinity Molecular Probes
    • Smith, A. B., III; Rucker, P. V.; Brouard, I.; Freeze, B. S.; Xia, S.; Horwitz, S. B. Design, Synthesis, and Biological Evaluation of Potent Discodermolide Fluorescent and Photoaffinity Molecular Probes. Org. Lett. 2005, 7, 5199-5202.
    • (2005) Org. Lett , vol.7 , pp. 5199-5202
    • Smith III, A.B.1    Rucker, P.V.2    Brouard, I.3    Freeze, B.S.4    Xia, S.5    Horwitz, S.B.6
  • 68
    • 3843053396 scopus 로고    scopus 로고
    • The Binding Mode of Epothilone A on R, β-Tubulin by Electron Crystallography
    • Nettles, J. H.; Li, H.; Cornett, B.; Krahn, J. M.; Snyder, J. P.; Downing, K. H. The Binding Mode of Epothilone A on R, β-Tubulin by Electron Crystallography. Science 2004, 305, 866-869.
    • (2004) Science , vol.305 , pp. 866-869
    • Nettles, J.H.1    Li, H.2    Cornett, B.3    Krahn, J.M.4    Snyder, J.P.5    Downing, K.H.6
  • 69
    • 74849122221 scopus 로고    scopus 로고
    • Atomic coordinates for Pose-1 are available from Professor Jesús Jiménez-Barbero (ref 6); Pose-2, from the present authors upon request.
    • Atomic coordinates for Pose-1 are available from Professor Jesús Jiménez-Barbero (ref 6); Pose-2, from the present authors upon request.
  • 71
    • 74849085694 scopus 로고    scopus 로고
    • 120 West 45th Street
    • Schrödinger, Inc
    • Schrödinger, Inc., 120 West 45th Street, 29th Floor, New York, NY 10036-4041, +1 (646) 366-9555, http://www.schrodinger.com/.
    • 29th Floor, New York, NY 10036-4041, +1 (646) , pp. 366-9555
  • 72
    • 0344778061 scopus 로고
    • Semi-analytical treatment of solvation for molecular mechanics and dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R.; Hendrickson, T. Semi-analytical treatment of solvation for molecular mechanics and dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6129.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.3    Hendrickson, T.4
  • 73
    • 0142236572 scopus 로고    scopus 로고
    • Low Mode Search. An Efficient, Automated Computational Method for Conformational Analysis: Application to Cyclic and Acyclic Alkanes and Cyclic Peptides
    • Kolossvary, I.; Guida, W. C. Low Mode Search. An Efficient, Automated Computational Method for Conformational Analysis: Application to Cyclic and Acyclic Alkanes and Cyclic Peptides. J. Am. Chem. Soc. 1996, 118, 5011-5019.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 5011-5019
    • Kolossvary, I.1    Guida, W.C.2
  • 74
    • 0043162336 scopus 로고
    • An internal-coordinate Monte Carlo method for searching conformational space. MCMM
    • Chang, G.; Guida, W. C.; Still, W. C. An internal-coordinate Monte Carlo method for searching conformational space. MCMM. J. Am. Chem. Soc. 1989, 111, 4379-4386.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 4379-4386
    • Chang, G.1    Guida, W.C.2    Still, W.C.3


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