Solid-phase total synthesis of (-)-apratoxin a and its analogues and their biological evaluation

Chemistry - An Asian Journal

Volumn 6, Issue 1, 2011, Pages 180-188

  Doi, Takayuki ^a,b   Numajiri, Yoshitaka ^b   Takahashi, Takashi ^b   Takagi, Motoki ^c   Shin Ya, Kazuo ^d  

^a TOHOKU UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c Koto ku   (Japan)

^d NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

cytotoxicity; peptides; solid phase synthesis; structure activity relationships; total synthesis

Indexed keywords

APRATOXIN A; BIOLOGICAL ACTIVITIES; BIOLOGICAL EVALUATION; CHEMO-SELECTIVITY; COPPER CATALYST; CYTOTOXIC ACTIVITIES; DIPOLAR CYCLOADDITIONS; LOW-YIELD; PHENYLACETYLENES; SEQUENTIAL COUPLING; SOLID PHASE PEPTIDE SYNTHESIS; SOLID-PHASE; SOLID-PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATIONSHIPS; SYNTHETIC ROUTES; THIAZOLINE; TOTAL SYNTHESIS;

ACETYLENE; AMINO ACIDS; AROMATIC HYDROCARBONS; CATALYSTS; CHLORINE COMPOUNDS; CYCLOADDITION; CYTOTOXICITY; ORGANIC POLYMERS; PEPTIDES;

CYCLIZATION;

ANTINEOPLASTIC AGENT; APRATOXIN A; DEPSIPEPTIDE;

ARTICLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; IC 50; NEOPLASM; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DEPSIPEPTIDES; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NEOPLASMS;

EID: 78650781428     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000549     Document Type: Article

References (41)

1. H. Luesch, W. Y. Yoshida, R. E. Moore, V. J. Paul, T. H. Corbett, J. Am. Chem. Soc. 2001, 123, 5418-5423.
2. H. Luesch, W. Y. Yoshida, R. E. Moore, V. J. Paul, Bioorg. Med. Chem. 2002, 10, 1973-1978.
3. S. Matthew, P. J. Schupp, H. Luesch, J. Nat. Prod. 2008, 71, 1113-1116.
4. M. Gutiérrez, T. L. Suyama, N. Engene, J. S. Wingerd, T. Matainaho, W. H. Gerwick, J. Nat. Prod. 2008, 71, 1099-1103.
5. K. Tidgewell, N. Engene, T. Byrum, J. Media, T. Doi, F. A. Valeriote, W. H. Gerwick, ChemBioChem 2010, 11, 1458-1466.
6. J. Chen, C. J. Forsyth, J. Am. Chem. Soc. 2003, 125, 8734-8735
7. J. Chen, C. J. Forsyth, Proc. Natl. Acad. Sci. USA 2004, 101, 12067-12072
8. J. Chen, C. J. Forsyth, Org. Lett. 2003, 5, 1281-1283.
9. T. Doi, Y. Numajiri, A. Munakata, T. Takahashi, Org. Lett. 2006, 8, 531-534
10. Y. Numajiri, T. Takahashi, T. Doi, Chem. Asian J. 2009, 4, 111-125.
11. D. Ma, B. Zou, G. Cai, X. Hu, J. O. Liu, Chem. Eur. J. 2006, 12, 7615-7626
12. B. Zou, J. Wei, G. Cai, D. Ma, Org. Lett. 2003, 5, 3503-3506.
13. A. Gilles, J. Martinez, F. Cavelier, J. Org. Chem. 2009, 74, 4298-4304.
14. H. Luesch, S. K. Chanda, R. M. Raya, P. D. Dejesus, A. P. Orth, J. R. Walker, J. C. I. Belmonte, P. G. Schultz, Nat. Chem. Biol. 2006, 2, 158-167
15. Y. Liu, B. K. Law, H. Luesch, Mol. Pharmacol. 2009, 76, 91-104.
16. S. Shen, P. Zhang, M. A. Lovchik, Y. Li, L. Tang, Z. Chen, R. Zeng, D. Ma, J. Yuan, Q. Yu, J. Cell Biol. 2009, 185, 629-639.
17. Trityl alcohol SynPhase Lanterns were purchased from Mimotopes Pty. Ltd. Clayton, Vic 3168 Australia. See:, F. Rasoul, F. Ercole, Y. Pham, C. T. Bui, Z. Wu, S. N. James, R. W. Trainor, G. Wickham, N. J. Maeji, Biopolymers 2000, 55, 207-216.
18. PyBroP=bromo-tris-pyrrolidino-phosphonium hexafluorophosphate
19. J. Coste, M.-N. Dufour, A. Pantaloni, B. Castro, Tetrahedron Lett. 1990, 31, 669-672
20. J. Coste, E. Frérot, P. Jouin, B. Castro, Tetrahedron Lett. 1991, 32, 1967-1970.
21. HATU=2-(1-oxy-7-azabenzotriazol-3-yl)-1,1,3,3-tetramethylguanidium hexafluorophosphate, L. A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397-4398.
22. J. D. Wade, J. Bedford, R. C. Sheppard, G. W. Tregear, Pept. Res. 1991, 4, 194-199.
23. Acid lability of some N-methylated peptides has been reported. See
24. M. J. O. Anteunis, C. vanderAuwera, Int. J. Pept. Prot. Res. 1988, 31, 301-310
25. T. Takahashi, H. Nagamiya, T. Doi, P. G. Griffiths, A. M. Bray, J. Comb. Chem. 2003, 5, 414-428.
26. E. Kaiser, Anal. Biochem. 1970, 34, 595-598.
27. K. Arimitsu, K. Ichimura, J. Mater. Chem. 2004, 14, 336-343.
28. S. You, H. Razavi, J. W. Kelly, Angew. Chem. 2003, 115, 87-89
29. Angew. Chem. Int. Ed. 2003, 42, 83-85.
30. PyAOP=7-azabenzotriazol-1-yloxytris(pyrrolidino)phosphonium hexafluorophosphate, F. Albericio, M. Cases, J. Alsina, S. A. Triolo, L. A. Carpino, S. A. Kates, Tetrahedron Lett. 1997, 38, 4853-4856.
31. R. Huisgen, Angew. Chem. 1963, 75, 604-637
32. Angew. Chem. Int. Ed. Engl. 1963, 2, 565-598.
33. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075
34. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
35. X. Li, Y. Hu, Curr. Med. Chem. 2010, 17, 3030-3044
36. A. M. Piggott, P. Karuso, Comb. Chem. High Throughput Screening 2004, 7, 607-630.
37. 50 value of synthetic apratoxinA measured in our hands was not as small as that previously reported. In our collaborative study with Professor Gerwick's group, however, it was found that synthetic apratoxinA exhibited the same potency as the natural product in vitro. Furthermore, the synthetic one had a significant in vivo antitumor effect in conventional mice bearing syngeneic solid tumors. See Ref.5.
38. Pull down assay has been performed utilizing the biotin probe of a tyrosine modified oxoapratoxin derivative. See Ref.11.
39. C. W. Tornàe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
40. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
41. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.