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Volumn 55, Issue 15, 2012, Pages 6724-6737

Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins

Author keywords

[No Author keywords available]

Indexed keywords

7 ALPHA (1 HYDROXY 1,1 DIPHENYLMETHYL) EPIPODOPHYLLOTOXIN; 7 ALPHA (2 HYDROXYPROP 2 YL) EPIPODOPHYLLOTOXIN; 7 ALPHA (2 HYDROXYPROP 2 YL) PODOPHYLLOTOXIN; 7 ALPHA [(1R)1 CYCLOHEX 3 ENYL 1 HYDROXYMETHYL] PIPODOPHYLLOTOXIN; 7 ALPHA [(1R)1 HYDROXY 1(3,4 DIMETHOXYPHENYL) ETHYL] EPIPODOPHYLLOTOXIN; 7 ALPHA [(1R)1 HYDROXY 2 METHYL 1 PHENYLPROPYL] EPIPODOPHYLLOTOXIN; 7 ALPHA [(1R)1 HYDROXYBUTYL] EPIPODOPHYLLOTOXIN; 7 ALPHA [(1R)1 HYDROXYETHYL] 2,2,5 TRIMETHYL 1,3 DIOXOLAN 4 YL EPIPODOPHYLLOTOXIN ACETONIDE; 7 ALPHA [(1S)1 CYCLOHEX 3 ENYL 1 HYDROXYMETHYL] EPIPODOPHYLLOTOXIN; 7 ALPHA [(1S)1 HYDROXYBUTYL] EPIPODOPHYLLOTOXIN; 7 ALPHA [(1S)1 HYDROXYETHYL] 2,2,5 TRIMETHYL 1,3 DIOXOLAN 4 YL EPIPODOPHYLLOTOXIN ACETONIDE; 7 ALPHA [(2R)2 HYDROXY 3 METHYLBUT 2 YL] EPIPODOPHYLLOTOXIN; 7 ALPHA [(2S)2 HYDROXY 3 METHYLBUT 2 YL] EPIPODOPHYLLOTOXIN; 7 ALPHA ISOPROPYL 7 DEOXYPODOPHYLLOTOXIN; 7 BETA (1 HYDROXY 1,1 DIPHENYLMETHYL) PODOPHYLLOTOXIN; 7(2 METHYL 1 PHENYL 1 PROPYLIDENE) DEOXYPODOPHYLLOTOXIN; 7(3 METHYL 2 BUTYLIDENE) DEOXYPODOPHYLLOTOXIN; ALDEHYDE; ALKYLIDENE; ANTIMITOTIC AGENT; ANTINEOPLASTIC AGENT; COLCHICINE; DOXORUBICIN; EPIPODOPINACOL; HYDROXYL GROUP; KETONE; PINACOL DERIVATIVE; PODOPHYLLOTOXIN DERIVATIVE; TUBULIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84864910183     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2017573     Document Type: Article
Times cited : (81)

References (60)
  • 1
    • 0042844744 scopus 로고    scopus 로고
    • Natural products as sources of new drugs over the period 1981-2002
    • Newman, D. J.; Cragg, G. M.; Snader, K. M. Natural products as sources of new drugs over the period 1981-2002 J. Nat. Prod. 2003, 66, 1022-1037
    • (2003) J. Nat. Prod. , vol.66 , pp. 1022-1037
    • Newman, D.J.1    Cragg, G.M.2    Snader, K.M.3
  • 2
    • 42949160050 scopus 로고    scopus 로고
    • Natural products as leads to potential drugs: An old process or the new hope for drug discovery
    • Newman, D. J. Natural products as leads to potential drugs: an old process or the new hope for drug discovery J. Med. Chem. 2008, 51, 2589-2599
    • (2008) J. Med. Chem. , vol.51 , pp. 2589-2599
    • Newman, D.J.1
  • 3
    • 17844399025 scopus 로고    scopus 로고
    • Natural products to drugs: Natural product derived compounds in clinical trials
    • Butler, M. S. Natural products to drugs: natural product derived compounds in clinical trials Nat. Prod. Rep. 2005, 22, 162-195
    • (2005) Nat. Prod. Rep. , vol.22 , pp. 162-195
    • Butler, M.S.1
  • 4
    • 44249098800 scopus 로고    scopus 로고
    • Natural products to drugs: Natural product-derived compounds in clinical trials
    • Butler, M. S. Natural products to drugs: natural product-derived compounds in clinical trials Nat. Prod. Rep. 2008, 25, 475-516
    • (2008) Nat. Prod. Rep. , vol.25 , pp. 475-516
    • Butler, M.S.1
  • 5
    • 79959723884 scopus 로고    scopus 로고
    • A Snapshot of Natural Product-Derived Compounds in Late Stage Clinical Development at the End of 2008
    • Buss, A. D. Butler, M. S. Eds; RSC: Cambridge, U.K.
    • Butler, M. S. A Snapshot of Natural Product-Derived Compounds in Late Stage Clinical Development at the End of 2008. In Natural Product Chemistry for Drug Discovery; Buss, A. D.; Butler, M. S., Eds; RSC: Cambridge, U.K., 2010; pp 321-354.
    • (2010) Natural Product Chemistry for Drug Discovery , pp. 321-354
    • Butler, M.S.1
  • 7
    • 0032033637 scopus 로고    scopus 로고
    • Discovery of podophyllotoxins
    • Imbert, T. F. Discovery of podophyllotoxins Biochimie 1998, 80, 207-222
    • (1998) Biochimie , vol.80 , pp. 207-222
    • Imbert, T.F.1
  • 8
    • 0030477322 scopus 로고    scopus 로고
    • Etoposide phosphate: What, why, where, and how?
    • Schacter, L. Etoposide phosphate: what, why, where, and how? Semin. Oncol 1996, 23, 23-7
    • (1996) Semin. Oncol , vol.23 , pp. 23-27
    • Schacter, L.1
  • 9
    • 0024404351 scopus 로고
    • From podophyllotoxin glucoside to etoposide
    • Stahelin, H.; von Wartburg, A. From podophyllotoxin glucoside to etoposide Prog. Drug Res. 1989, 33, 169-266
    • (1989) Prog. Drug Res. , vol.33 , pp. 169-266
    • Stahelin, H.1    Von Wartburg, A.2
  • 10
    • 0026011121 scopus 로고
    • The chemical and biological route from podophyllotoxin glucoside to etoposide: Ninth Cain Memorial Award Lecture
    • Stahelin, H. F.; von Wartburg, A. The chemical and biological route from podophyllotoxin glucoside to etoposide: Ninth Cain Memorial Award Lecture Cancer Res. 1991, 51, 5-15
    • (1991) Cancer Res. , vol.51 , pp. 5-15
    • Stahelin, H.F.1    Von Wartburg, A.2
  • 11
    • 33646259246 scopus 로고    scopus 로고
    • Relationships between DNA strand breakage and apoptotic progression upon treatment of HL-60 leukemia cells with tafluposide or etoposide
    • Kluza, J.; Mazinghien, R.; Irwin, H.; Hartley, J. A.; Bailly, C. Relationships between DNA strand breakage and apoptotic progression upon treatment of HL-60 leukemia cells with tafluposide or etoposide Anti-Cancer Drugs 2006, 17, 155-164
    • (2006) Anti-Cancer Drugs , vol.17 , pp. 155-164
    • Kluza, J.1    Mazinghien, R.2    Irwin, H.3    Hartley, J.A.4    Bailly, C.5
  • 12
    • 0035953324 scopus 로고    scopus 로고
    • Antitumor agents. 207. Design, synthesis, and biological testing of 4beta-anilino-2-fluoro-4′-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents
    • VanVliet, D. S.; Tachibana, Y.; Bastow, K. F.; Huang, E. S.; Lee, K. H. Antitumor agents. 207. Design, synthesis, and biological testing of 4beta-anilino-2-fluoro-4′-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents J. Med. Chem. 2001, 44, 1422-1428
    • (2001) J. Med. Chem. , vol.44 , pp. 1422-1428
    • Vanvliet, D.S.1    Tachibana, Y.2    Bastow, K.F.3    Huang, E.S.4    Lee, K.H.5
  • 13
    • 84864950788 scopus 로고    scopus 로고
    • 893 study references found by May 2
    • Clinical Trials. http://clinicaltrials.gov/ct2/results?term=etoposide (893 study references found by May 2, 2011).
    • (2011)
  • 15
    • 0034583327 scopus 로고    scopus 로고
    • Nomenclature of lignans and neolignans
    • Moss, G. P. Nomenclature of lignans and neolignans Pure Appl. Chem. 2000, 72, 1493-1523
    • (2000) Pure Appl. Chem. , vol.72 , pp. 1493-1523
    • Moss, G.P.1
  • 17
    • 0033168569 scopus 로고    scopus 로고
    • Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4′- O -demethyl- podophyllotoxin and related compounds with improved pharmacological profiles
    • Zhu, X. K.; Guan, J.; Tachibana, Y.; Bastow, K. F.; Cho, S. J.; Cheng, H. H.; Cheng, Y. C.; Gurwith, M.; Lee, K. H. Antitumor agents. 194. Synthesis and biological evaluations of 4-beta-mono-, -di-, and -trisubstituted aniline-4′- O -demethyl-podophyllotoxin and related compounds with improved pharmacological profiles J. Med. Chem. 1999, 42, 2441-2446
    • (1999) J. Med. Chem. , vol.42 , pp. 2441-2446
    • Zhu, X.K.1    Guan, J.2    Tachibana, Y.3    Bastow, K.F.4    Cho, S.J.5    Cheng, H.H.6    Cheng, Y.C.7    Gurwith, M.8    Lee, K.H.9
  • 18
    • 0032784679 scopus 로고    scopus 로고
    • A novel podophyllotoxin-derived compound GL331 is more potent than its congener VP-16 in killing refractory cancer cells
    • Huang, T. S.; Lee, C. C.; Chao, Y.; Shu, C. H.; Chen, L. T.; Chen, L. L.; Chen, M. H.; Yuan, C. C.; Whang-Peng, J. A novel podophyllotoxin-derived compound GL331 is more potent than its congener VP-16 in killing refractory cancer cells Pharm. Res. 1999, 16, 997-1002
    • (1999) Pharm. Res. , vol.16 , pp. 997-1002
    • Huang, T.S.1    Lee, C.C.2    Chao, Y.3    Shu, C.H.4    Chen, L.T.5    Chen, L.L.6    Chen, M.H.7    Yuan, C.C.8    Whang-Peng, J.9
  • 19
    • 34248221211 scopus 로고    scopus 로고
    • Podophyllotoxin: Current perspectives
    • Liu, Y. Q.; Yang, L.; Tian, X. Podophyllotoxin: current perspectives Curr. Bioact. Compd. 2007, 3, 37-66
    • (2007) Curr. Bioact. Compd. , vol.3 , pp. 37-66
    • Liu, Y.Q.1    Yang, L.2    Tian, X.3
  • 20
    • 3042747893 scopus 로고    scopus 로고
    • Anti-AIDS agents. Part 61: Anti-HIV activity of new podophyllotoxin derivatives
    • Zhu, X. K.; Guan, J.; Xiao, Z.; Cosentino, L. M.; Lee, K. H. Anti-AIDS agents. Part 61: anti-HIV activity of new podophyllotoxin derivatives Bioorg. Med. Chem. 2004, 12, 4267-4273
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 4267-4273
    • Zhu, X.K.1    Guan, J.2    Xiao, Z.3    Cosentino, L.M.4    Lee, K.H.5
  • 22
    • 77957374075 scopus 로고    scopus 로고
    • Microtubule-binding agents: A dynamic field of cancer therapeutics
    • Dumontet, C.; Jordan, M. A. Microtubule-binding agents: a dynamic field of cancer therapeutics Nat. Rev. Drug Discovery 2010, 9, 790-803
    • (2010) Nat. Rev. Drug Discovery , vol.9 , pp. 790-803
    • Dumontet, C.1    Jordan, M.A.2
  • 23
    • 0031872051 scopus 로고    scopus 로고
    • Tubulin as a target for anticancer drugs: Agents which interact with the mitotic spindle
    • Jordan, A.; Hadfield, J. A.; Lawrence, N. J.; McGown, A. T. Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle Med. Res. Rev. 1998, 18, 259-296
    • (1998) Med. Res. Rev. , vol.18 , pp. 259-296
    • Jordan, A.1    Hadfield, J.A.2    Lawrence, N.J.3    McGown, A.T.4
  • 24
    • 0032168167 scopus 로고    scopus 로고
    • Etoposide: Four decades of development of a topoisomerase II inhibitor
    • Hande, K. R. Etoposide: four decades of development of a topoisomerase II inhibitor Eur. J. Cancer 1998, 34, 1514-1521
    • (1998) Eur. J. Cancer , vol.34 , pp. 1514-1521
    • Hande, K.R.1
  • 26
    • 18744373344 scopus 로고    scopus 로고
    • Podophyllotoxin derivatives: Current synthetic approaches for new anticancer agents
    • You, Y. Podophyllotoxin derivatives: current synthetic approaches for new anticancer agents Curr. Pharm. Des. 2005, 11, 1695-1717
    • (2005) Curr. Pharm. Des. , vol.11 , pp. 1695-1717
    • You, Y.1
  • 28
    • 0034831086 scopus 로고    scopus 로고
    • Advances in cancer therapy with plant based natural products
    • Mukherjee, A. K.; Basu, S.; Sarkar, N.; Ghosh, A. C. Advances in cancer therapy with plant based natural products Curr. Med. Chem. 2001, 8, 1467-1486
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1467-1486
    • Mukherjee, A.K.1    Basu, S.2    Sarkar, N.3    Ghosh, A.C.4
  • 29
    • 33646856607 scopus 로고    scopus 로고
    • Oxalone and lactone moieties of podophyllotoxin exhibit properties of both the B and C rings of colchicine in its binding with tubulin
    • Gupta, S.; Das, L.; Datta, A. B.; Poddar, A.; Janik, M. E.; Bhattacharyya, B. Oxalone and lactone moieties of podophyllotoxin exhibit properties of both the B and C rings of colchicine in its binding with tubulin Biochemistry 2006, 45, 6467-6475
    • (2006) Biochemistry , vol.45 , pp. 6467-6475
    • Gupta, S.1    Das, L.2    Datta, A.B.3    Poddar, A.4    Janik, M.E.5    Bhattacharyya, B.6
  • 30
    • 33748876011 scopus 로고    scopus 로고
    • Design and biological evaluation of novel tubulin inhibitors as antimitotic agents using a pharmacophore binding model with tubulin
    • Kim do, Y.; Kim, K. H.; Kim, N. D.; Lee, K. Y.; Han, C. K.; Yoon, J. H.; Moon, S. K.; Lee, S. S.; Seong, B. L. Design and biological evaluation of novel tubulin inhibitors as antimitotic agents using a pharmacophore binding model with tubulin J. Med. Chem. 2006, 49, 5664-5670
    • (2006) J. Med. Chem. , vol.49 , pp. 5664-5670
    • Kim Do, Y.1    Kim, K.H.2    Kim, N.D.3    Lee, K.Y.4    Han, C.K.5    Yoon, J.H.6    Moon, S.K.7    Lee, S.S.8    Seong, B.L.9
  • 31
    • 2542478114 scopus 로고    scopus 로고
    • Antitumor agents. Part 227: Studies on novel 4′- O -demethyl-epipodophyllotoxins as antitumor agents targeting topoisomerase II
    • Xiao, Z.; Bastow, K. F.; Vance, J. R.; Lee, K. H. Antitumor agents. Part 227: studies on novel 4′- O -demethyl-epipodophyllotoxins as antitumor agents targeting topoisomerase II Bioorg. Med. Chem. 2004, 12, 3339-3344
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 3339-3344
    • Xiao, Z.1    Bastow, K.F.2    Vance, J.R.3    Lee, K.H.4
  • 32
    • 0037161603 scopus 로고    scopus 로고
    • Antitumor agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR method
    • Xiao, Z.; Xiao, Y. D.; Feng, J.; Golbraikh, A.; Tropsha, A.; Lee, K. H. Antitumor agents. 213. Modeling of epipodophyllotoxin derivatives using variable selection k nearest neighbor QSAR method J. Med. Chem. 2002, 45, 2294-2309
    • (2002) J. Med. Chem. , vol.45 , pp. 2294-2309
    • Xiao, Z.1    Xiao, Y.D.2    Feng, J.3    Golbraikh, A.4    Tropsha, A.5    Lee, K.H.6
  • 33
    • 33751065347 scopus 로고    scopus 로고
    • Evolution of the stereoselective pinacol coupling reaction
    • Chatterjee, A.; Joshi, N. N. Evolution of the stereoselective pinacol coupling reaction Tetrahedron 2006, 62, 12137-12158
    • (2006) Tetrahedron , vol.62 , pp. 12137-12158
    • Chatterjee, A.1    Joshi, N.N.2
  • 34
    • 32444446275 scopus 로고    scopus 로고
    • Correct structures of Diels-Alder adducts from the natural cyclolignan thuriferic acid and its 8-epimer
    • López-Pérez, J. L.; Abad, A.; del Olmo, E.; San Feliciano, A. Correct structures of Diels-Alder adducts from the natural cyclolignan thuriferic acid and its 8-epimer Tetrahedron 2006, 62, 2370-2379
    • (2006) Tetrahedron , vol.62 , pp. 2370-2379
    • López-Pérez, J.L.1    Abad, A.2    Del Olmo, E.3    San Feliciano, A.4
  • 35
    • 4243973410 scopus 로고
    • Carbonyl-coupling reactions using low-valent titanium
    • McMurry, J. E. Carbonyl-coupling reactions using low-valent titanium Chem. Rev. 1989, 89, 1513-1524
    • (1989) Chem. Rev. , vol.89 , pp. 1513-1524
    • McMurry, J.E.1
  • 36
    • 0032495089 scopus 로고    scopus 로고
    • A new look at the McMurry reaction
    • Ephritikhine, M. A new look at the McMurry reaction Chem. Commun. 1998, 2549-2554
    • (1998) Chem. Commun. , pp. 2549-2554
    • Ephritikhine, M.1
  • 37
    • 2842538120 scopus 로고    scopus 로고
    • Synthesis and photocyclization of macrocyclic stilbene derivatives
    • Dyker, G.; Korning, J.; Stirner, W. Synthesis and photocyclization of macrocyclic stilbene derivatives Eur. J. Org. Chem. 1998, 149-154
    • (1998) Eur. J. Org. Chem. , pp. 149-154
    • Dyker, G.1    Korning, J.2    Stirner, W.3
  • 38
    • 0028346358 scopus 로고
    • A novel rearrangement product of podophyllotoxone-ester derivates and in vitro cytotoxicity studies
    • Höfert, P. H.; Matusch, R. A novel rearrangement product of podophyllotoxone-ester derivates and in vitro cytotoxicity studies Helv. Chim. Acta 1994, 77, 771-777
    • (1994) Helv. Chim. Acta , vol.77 , pp. 771-777
    • Höfert, P.H.1    Matusch, R.2
  • 40
    • 36549043394 scopus 로고    scopus 로고
    • NAPROC-13: A database for the dereplication of natural product mixtures in bioassay-guided protocols
    • López-Pérez, J. L.; Theron, R.; del Olmo, E.; Díaz, D. NAPROC-13: a database for the dereplication of natural product mixtures in bioassay-guided protocols Bioinformatics 2007, 23, 3256-3257
    • (2007) Bioinformatics , vol.23 , pp. 3256-3257
    • López-Pérez, J.L.1    Theron, R.2    Del Olmo, E.3    Díaz, D.4
  • 41
    • 34347230544 scopus 로고    scopus 로고
    • Sulforhodamine B colorimetric assay for cytotoxicity screening
    • Vichai, V.; Kirtikara, K. Sulforhodamine B colorimetric assay for cytotoxicity screening Nat. Protoc. 2006, 1, 1112-1116
    • (2006) Nat. Protoc. , vol.1 , pp. 1112-1116
    • Vichai, V.1    Kirtikara, K.2
  • 42
    • 0028906786 scopus 로고
    • Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen
    • Boyd, M. R.; Paull, K. D. Some practical considerations and applications of the National Cancer Institute in vitro anticancer drug discovery screen Drug Dev. Res. 1995, 34, 91-109
    • (1995) Drug Dev. Res. , vol.34 , pp. 91-109
    • Boyd, M.R.1    Paull, K.D.2
  • 43
    • 0027330403 scopus 로고
    • Podophyllotoxin, steganacin and combretastatin: Natural products that bind at the colchicine site of tubulin
    • Sackett, D. L. Podophyllotoxin, steganacin and combretastatin: natural products that bind at the colchicine site of tubulin Pharmacol. Ther. 1993, 59, 163-228
    • (1993) Pharmacol. Ther. , vol.59 , pp. 163-228
    • Sackett, D.L.1
  • 45
    • 0026643589 scopus 로고
    • Effects of vinblastine, podophyllotoxin and nocodazole on mitotic spindles. Implications for the role of microtubule dynamics in mitosis
    • Jordan, M. A.; Thrower, D.; Wilson, L. Effects of vinblastine, podophyllotoxin and nocodazole on mitotic spindles. Implications for the role of microtubule dynamics in mitosis J. Cell Sci. 1992, 102, 401-416
    • (1992) J. Cell Sci. , vol.102 , pp. 401-416
    • Jordan, M.A.1    Thrower, D.2    Wilson, L.3
  • 46
    • 0017112021 scopus 로고
    • Molecular features of colchicine associated with antimitotic activity and inhibition of tubulin polymerization
    • Fitzgerald, T. J. Molecular features of colchicine associated with antimitotic activity and inhibition of tubulin polymerization Biochem. Pharmacol. 1976, 25, 1383-1387
    • (1976) Biochem. Pharmacol. , vol.25 , pp. 1383-1387
    • Fitzgerald, T.J.1
  • 47
    • 0025823564 scopus 로고
    • Roles of ring C oxygens in the binding of colchicine to tubulin
    • Medrano, F. J.; Andreu, J. M.; Gorbunoff, M. J.; Timasheff, S. N. Roles of ring C oxygens in the binding of colchicine to tubulin Biochemistry 1991, 30, 3770-3777
    • (1991) Biochemistry , vol.30 , pp. 3770-3777
    • Medrano, F.J.1    Andreu, J.M.2    Gorbunoff, M.J.3    Timasheff, S.N.4
  • 48
    • 44449096594 scopus 로고    scopus 로고
    • Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization
    • álvarez, C.; álvarez, R.; Corchete, P.; López, J. L.; Pérez-Melero, C.; Peláez, R.; Medarde, M. Diarylmethyloxime and hydrazone derivatives with 5-indolyl moieties as potent inhibitors of tubulin polymerization Bioorg. Med. Chem. 2008, 16, 5952-5961
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 5952-5961
    • Álvarez, C.1    Álvarez, R.2    Corchete, P.3    López, J.L.4    Pérez-Melero, C.5    Peláez, R.6    Medarde, M.7
  • 49
    • 1642401199 scopus 로고    scopus 로고
    • Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain
    • Ravelli, R. B.; Gigant, B.; Curmi, P. A.; Jourdain, I.; Lachkar, S.; Sobel, A.; Knossow, M. Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain Nature 2004, 428, 198-202
    • (2004) Nature , vol.428 , pp. 198-202
    • Ravelli, R.B.1    Gigant, B.2    Curmi, P.A.3    Jourdain, I.4    Lachkar, S.5    Sobel, A.6    Knossow, M.7
  • 50
    • 77049092824 scopus 로고    scopus 로고
    • Wavefunction, Inc. Irvine, CA.
    • Spartan 08; Wavefunction, Inc.: Irvine, CA.
    • Spartan 08
  • 52
    • 33947716119 scopus 로고    scopus 로고
    • A semiempirical free energy force field with charge-based desolvation
    • 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
  • 53
    • 0035834034 scopus 로고    scopus 로고
    • The interaction of baccatin III with the Taxol binding site of microtubules determined by a homogeneous assay with fluorescent taxoid
    • Andreu, J. M.; Barasoain, I. The interaction of baccatin III with the Taxol binding site of microtubules determined by a homogeneous assay with fluorescent taxoid Biochemistry 2001, 40, 11975-11984
    • (2001) Biochemistry , vol.40 , pp. 11975-11984
    • Andreu, J.M.1    Barasoain, I.2
  • 54
    • 0027467778 scopus 로고
    • Assembly of purified GDP-tubulin into microtubules induced by Taxol and Taxotere: Reversibility, ligand stoichiometry, and competition
    • Diaz, J. F.; Andreu, J. M. Assembly of purified GDP-tubulin into microtubules induced by Taxol and Taxotere: reversibility, ligand stoichiometry, and competition Biochemistry 1993, 32, 2747-2755
    • (1993) Biochemistry , vol.32 , pp. 2747-2755
    • Diaz, J.F.1    Andreu, J.M.2
  • 55
    • 38449116238 scopus 로고    scopus 로고
    • Large Scale Purification of Tubulin from Brain Employing the Modified Weisengerg Procedure
    • Zhou, J. Methods in Molecular Medicine, Humana Press Inc. Totowa, NJ
    • Andreu, J. M. Large Scale Purification of Tubulin from Brain Employing the Modified Weisengerg Procedure. In Microtubule Protocols; Zhou, J., Ed.; Methods in Molecular Medicine, Vol. 137; Humana Press Inc.: Totowa, NJ, 2007; pp 17-28.
    • (2007) Microtubule Protocols , vol.137 , pp. 17-28
    • Andreu, J.M.1
  • 56
    • 0021348322 scopus 로고
    • Interaction of tubulin with bifunctional colchicine analogues: An equilibrium study
    • Andreu, J. M.; Gorbunoff, M. J.; Lee, J. C.; Timasheff, S. N. Interaction of tubulin with bifunctional colchicine analogues: an equilibrium study Biochemistry 1984, 23, 1742-1752
    • (1984) Biochemistry , vol.23 , pp. 1742-1752
    • Andreu, J.M.1    Gorbunoff, M.J.2    Lee, J.C.3    Timasheff, S.N.4
  • 57
    • 0017112021 scopus 로고
    • Molecular features of colchicine associated with antimitotic activity and inhibition of tubulin polymerization
    • Fitzgerald, T. J. Molecular features of colchicine associated with antimitotic activity and inhibition of tubulin polymerization Biochem. Pharmacol. 1976, 25, 1383-1387
    • (1976) Biochem. Pharmacol. , vol.25 , pp. 1383-1387
    • Fitzgerald, T.J.1
  • 58
    • 0032499648 scopus 로고    scopus 로고
    • Role of the colchicine ring A and its methoxy groups in the binding to tubulin and microtubule inhibition
    • Andreu, J. M.; Pérez-Ramírez, B.; Gorbunoff, M. J.; Ayala, D.; Timasheff, S. N. Role of the colchicine ring A and its methoxy groups in the binding to tubulin and microtubule inhibition Biochemistry 1998, 37, 8356-8368
    • (1998) Biochemistry , vol.37 , pp. 8356-8368
    • Andreu, J.M.1    Pérez-Ramírez, B.2    Gorbunoff, M.J.3    Ayala, D.4    Timasheff, S.N.5
  • 60
    • 0028044792 scopus 로고
    • Inhibition of microtubules and cell cycle arrest by a new 1-deaza-7,8-dihydropteridine antitumor drug, CI 980, and by its chiral isomer, NSC 613863
    • De Ines, C.; Leynadier, D.; Barasoain, I.; Peyrot, V.; Garcia, P.; Briand, C.; Rener, G. A.; Temple, C., Jr. Inhibition of microtubules and cell cycle arrest by a new 1-deaza-7,8-dihydropteridine antitumor drug, CI 980, and by its chiral isomer, NSC 613863 Cancer Res. 1994, 54, 75-84
    • (1994) Cancer Res. , vol.54 , pp. 75-84
    • De Ines, C.1    Leynadier, D.2    Barasoain, I.3    Peyrot, V.4    Garcia, P.5    Briand, C.6    Rener, G.A.7    Temple Jr., C.8


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