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Volumn 47, Issue 14, 2004, Pages 3697-3699

Total synthesis and anti-tubulin activity of epi-C3 analogues of cryptophycin-24

Author keywords

[No Author keywords available]

Indexed keywords

ARENASTATIN A; CRYPTOPHYCIN DERIVATIVE; EPI C3 1,3 CHLOROBENZYLCRYPTOPHYCIN 24; EPI C3 CRYPTOPHYCIN 24; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 3042594461     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030555f     Document Type: Article
Times cited : (17)

References (22)
  • 1
    • 0036181751 scopus 로고    scopus 로고
    • The cryptophycins: Their synthesis and anticancer activity
    • and references therein
    • Eggen, M.; Georg, G. I. The Cryptophycins: Their Synthesis and Anticancer Activity. Med. Res. Rev. 2002, 22, 85-101 and references therein.
    • (2002) Med. Res. Rev. , vol.22 , pp. 85-101
    • Eggen, M.1    Georg, G.I.2
  • 2
    • 0028962299 scopus 로고
    • Total synthesis of cryptophycins. Revision of the structures of cryptophycin A and C
    • Barrow, R. A.; Hemscheidt, T.; Liang, J.; Paik, S.; Moore, R. E.; Tius, M. A. Total Synthesis of Cryptophycins. Revision of the Structures of Cryptophycin A and C. J. Am. Chem. Soc. 1995, 117, 2479-2490.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2479-2490
    • Barrow, R.A.1    Hemscheidt, T.2    Liang, J.3    Paik, S.4    Moore, R.E.5    Tius, M.A.6
  • 3
    • 0028141462 scopus 로고
    • Cryptophycin: A new antimicrotubule agent active against drug-resistant cells
    • Smith, C. D.; Zhang, X.; Mooberry, S. L.; Patterson, G. M. L.; Moore, R. E. Cryptophycin: A New Antimicrotubule Agent Active against Drug-Resistant Cells. Cancer Res. 1994, 54, 3779-3784.
    • (1994) Cancer Res. , vol.54 , pp. 3779-3784
    • Smith, C.D.1    Zhang, X.2    Mooberry, S.L.3    Patterson, G.M.L.4    Moore, R.E.5
  • 4
    • 0028117690 scopus 로고
    • Arenastatin A a potent cytotoxic depsipeptide from the Okinawa marine sponge Dysidea Arenaria
    • Kobayashi, M.; Aoki, S.; Ohyabu, N.; Kuroso, M.; Wang, W.; Kitigawa, I. Arenastatin A, a Potent Cytotoxic Depsipeptide from the Okinawa Marine Sponge Dysidea Arenaria. Tetrahedron Lett. 1994, 35, 7969-7972.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7969-7972
    • Kobayashi, M.1    Aoki, S.2    Ohyabu, N.3    Kuroso, M.4    Wang, W.5    Kitigawa, I.6
  • 6
    • 0029874514 scopus 로고    scopus 로고
    • Mechanism of action of cryptophycin
    • Smith, C. D.; Zhang, X. Mechanism of Action of Cryptophycin. J. Biol. Chem. 1996, 271, 6192-6198.
    • (1996) J. Biol. Chem. , vol.271 , pp. 6192-6198
    • Smith, C.D.1    Zhang, X.2
  • 7
    • 0029759374 scopus 로고    scopus 로고
    • Characterization of the interaction of cryptophycin 1 with tubulin: Binding in the vinca domain, competitive inhibition of dolastatin 10 binding, and an unusual aggregation reaction
    • Bai, R.; Schwartz, R. E.; Kepler, J. A.; Pettit, G. R.; Hamel, E. Characterization of the Interaction of Cryptophycin 1 with Tubulin: Binding in the Vinca Domain, Competitive Inhibition of Dolastatin 10 Binding, and an Unusual Aggregation Reaction. Cancer Res. 1996, 56, 4398-4406.
    • (1996) Cancer Res. , vol.56 , pp. 4398-4406
    • Bai, R.1    Schwartz, R.E.2    Kepler, J.A.3    Pettit, G.R.4    Hamel, E.5
  • 9
    • 0030721014 scopus 로고    scopus 로고
    • Mechanism of action of the unusually potent microtubule inhibitor cryptophycin 1
    • Panda, D.; Himes, R. H.; Moore, R. E.; Wilson, L.; Jordan, M. A. Mechanism of Action of the Unusually Potent Microtubule Inhibitor Cryptophycin 1. Biochemistry 1997, 36, 12948-12953.
    • (1997) Biochemistry , vol.36 , pp. 12948-12953
    • Panda, D.1    Himes, R.H.2    Moore, R.E.3    Wilson, L.4    Jordan, M.A.5
  • 10
    • 0032482920 scopus 로고
    • Antiproliferative mechanism of action of cryptophycin-52: Kinetic stabilization of microtubule dynamics of high-affinity binding to microtubule ends
    • Panda, D.; DeLuca, K.; Williams, D.; Jordan, M. A.; Wilson, L. Antiproliferative Mechanism of Action of Cryptophycin-52: Kinetic Stabilization of Microtubule Dynamics of High-Affinity Binding to Microtubule Ends. Proc. Natl. Acad. Sci. U.S.A. 1988, 95, 9313-9318.
    • (1988) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 9313-9318
    • Panda, D.1    DeLuca, K.2    Williams, D.3    Jordan, M.A.4    Wilson, L.5
  • 11
    • 0037159216 scopus 로고    scopus 로고
    • The cryptophycin-tubulin ring structure indicates two points of curvature in the tubulin dimer
    • Watts, N. R.; Cheng, N.; West, W.; Steven, A. C.; Sackett, D. L. The Cryptophycin-Tubulin Ring Structure Indicates Two Points of Curvature in the Tubulin Dimer. Biochemistry 2002, 41, 12662-12669.
    • (2002) Biochemistry , vol.41 , pp. 12662-12669
    • Watts, N.R.1    Cheng, N.2    West, W.3    Steven, A.C.4    Sackett, D.L.5
  • 12
    • 0035856541 scopus 로고    scopus 로고
    • In vitro effect of cryptophycin 52 on microtubule assembly and tubulin: Molecular modeling of the mechanism of action of a new antimitotic drug
    • Barbier, P.; Gregoire, C.; Devred, F.; Sarrazin, M.; Peyrot, V. In Vitro Effect of Cryptophycin 52 on Microtubule Assembly and Tubulin: Molecular Modeling of the Mechanism of Action of a New Antimitotic Drug. Biochemistry 2001, 40, 13510-13519.
    • (2001) Biochemistry , vol.40 , pp. 13510-13519
    • Barbier, P.1    Gregoire, C.2    Devred, F.3    Sarrazin, M.4    Peyrot, V.5
  • 13
    • 0030670103 scopus 로고    scopus 로고
    • Induction of apoptosis by cryptophycin 1, a new antimicrotubule agent
    • Mooberry, S. L.; Busquets, L.; Tien, G. Induction of Apoptosis by Cryptophycin 1, a New Antimicrotubule Agent. Int. J. Cancer 1997, 73, 440-448.
    • (1997) Int. J. Cancer , vol.73 , pp. 440-448
    • Mooberry, S.L.1    Busquets, L.2    Tien, G.3
  • 14
    • 0034913052 scopus 로고    scopus 로고
    • Cryptophycin-induced hyperphosphorylation of Bcl-2, cell cycle arrest and growth inhibition in human H460 NSCLC cells
    • Lu, K.; Dempsey, J.; Schultz, R. M.; Shih, C.; Teicher, B. A. Cryptophycin-Induced Hyperphosphorylation of Bcl-2, Cell Cycle Arrest and Growth Inhibition in Human H460 NSCLC Cells. Cancer Chemother. Pharmacol. 2001, 47, 170-178.
    • (2001) Cancer Chemother. Pharmacol. , vol.47 , pp. 170-178
    • Lu, K.1    Dempsey, J.2    Schultz, R.M.3    Shih, C.4    Teicher, B.A.5
  • 15
    • 0030272586 scopus 로고    scopus 로고
    • Cryptophycin 1 binds to tubulin at a site distinct from the colchicine binding site and at a site that may overlap the vinca binding site
    • Mooberry, S. L.; Taoka, C. R.; Busquets, L. Cryptophycin 1 Binds to Tubulin at a Site Distinct from the Colchicine Binding Site and at a Site That May Overlap the Vinca Binding Site. Cancer Lett. 1996, 107, 53-57.
    • (1996) Cancer Lett. , vol.107 , pp. 53-57
    • Mooberry, S.L.1    Taoka, C.R.2    Busquets, L.3
  • 17
    • 0012340591 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationship studies of cryptophycins: A novel class of potent antimitotic antitumor depsipeptides
    • Ojima, I., Vite, G. D., Altmann, K.-H., Eds.; American Chemical Society: Washington, DC
    • Shih, C.; Al-Awar, R. S.; Fray, A. H.; Martinelli, M. J.; Moher, E. D.; Norman, B. H.; Patel, V. F.; Schultz, R. M.; Toth, J. E.; Varie, D. L.; Corbett, T. H.; Moore, R. E. Synthesis and Structure-Activity Relationship Studies of Cryptophycins: A Novel Class of Potent Antimitotic Antitumor Depsipeptides. In Anticancer Agents; Ojima, I., Vite, G. D., Altmann, K.-H., Eds.; American Chemical Society: Washington, DC, 2001; pp 171-189.
    • (2001) Anticancer Agents , pp. 171-189
    • Shih, C.1    Al-Awar, R.S.2    Fray, A.H.3    Martinelli, M.J.4    Moher, E.D.5    Norman, B.H.6    Patel, V.F.7    Schultz, R.M.8    Toth, J.E.9    Varie, D.L.10    Corbett, T.H.11    Moore, R.E.12
  • 18
    • 0034680612 scopus 로고    scopus 로고
    • Total synthesis of cryptophycin-24 (Arenastatin A) amenable to structural modifications in the C16 side chain
    • and references therein
    • Eggen, M.; Mossman, C. J.; Buck, S. B.; Nair, S. K.; Bhat, L.; Ali, S. M.; Reiff, E. A.; Boge, T. C.; Georg, G. I. Total Synthesis of Cryptophycin-24 (Arenastatin A) Amenable to Structural Modifications in the C16 Side Chain. J. Org. Chem. 2000, 65, 7792-7799 and references therein.
    • (2000) J. Org. Chem. , vol.65 , pp. 7792-7799
    • Eggen, M.1    Mossman, C.J.2    Buck, S.B.3    Nair, S.K.4    Bhat, L.5    Ali, S.M.6    Reiff, E.A.7    Boge, T.C.8    Georg, G.I.9
  • 19
    • 0017136359 scopus 로고
    • Synthesis of optically active forms of ipsenol, the pheromone of IPS bark beetles
    • Mori, K. Synthesis of Optically Active Forms of Ipsenol, the Pheromone of IPS Bark Beetles. Tetrahedron 1976, 32, 1101-1106.
    • (1976) Tetrahedron , vol.32 , pp. 1101-1106
    • Mori, K.1
  • 20
    • 84985666791 scopus 로고
    • Convenient preparation of acetone solutions of dimethyldioxirane
    • Adam, W.; Bialas, J.; Hadjiarapoglou, L. A. Convenient Preparation of Acetone Solutions of Dimethyldioxirane. Chem. Ber. 1991, 124, 2377.
    • (1991) Chem. Ber. , vol.124 , pp. 2377
    • Adam, W.1    Bialas, J.2    Hadjiarapoglou, L.A.3
  • 21
    • 0033566133 scopus 로고    scopus 로고
    • Novel cryptophycin antitumor agents: Synthesis and cytotoxicity of fragment "B" analogues
    • Patel, V. F.; Andis, S. L.; Kennedy, J. H.; Ray, J. E.; Schultz, R. M. Novel Cryptophycin Antitumor Agents: Synthesis and Cytotoxicity of Fragment "B" Analogues. J. Med. Chem. 1999, 42, 2588-2603.
    • (1999) J. Med. Chem. , vol.42 , pp. 2588-2603
    • Patel, V.F.1    Andis, S.L.2    Kennedy, J.H.3    Ray, J.E.4    Schultz, R.M.5
  • 22
    • 1642540539 scopus 로고    scopus 로고
    • Total synthesis and anti-tubulin activity of C10 analogues of cryptophycin-24
    • and references therein
    • Buck, S. B.; Huff, J. K.; Himes, R. H.; Georg, G. I. Total Synthesis and Anti-Tubulin Activity of C10 Analogues of Cryptophycin-24. J. Med. Chem. 2004, 47, 696-702 and references therein.
    • (2004) J. Med. Chem. , vol.47 , pp. 696-702
    • Buck, S.B.1    Huff, J.K.2    Himes, R.H.3    Georg, G.I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.