HR22C16: A potent small-molecule probe for the dynamics of cell division

Angewandte Chemie - International Edition

Volumn 42, Issue 21, 2003, Pages 2379-2382

  Hotha, Srinivas ^a   Yarrow, Justin C ^b   Yang, Janet G ^a   Garrett, Sarah ^a   Renduchintala, Kishore V ^a   Mayer, Thomas U ^c   Kapoor, Tarun M ^a  

^a ROCKEFELLER UNIVERSITY   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

^c MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

Author keywords

Antimitotics; Inhibitors; Molecular motors; Photolysis; Solid phase synthesis

Indexed keywords

GENES; MICROSCOPIC EXAMINATION; PROTEINS; SYNTHESIS (CHEMICAL);

BIOLOGICAL ASSAYS;

CELLS;

PROTEIN; PROTEIN EG5; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL DIVISION; CELL MEMBRANE PERMEABILITY; CYTOSKELETON; DIASTEREOISOMER; FLUORESCENCE MICROSCOPY; GENETIC SCREENING; MICROTUBULE; NONHUMAN; PHENOTYPE; PROTEIN TARGETING; SOLID; SYNTHESIS;

CELL DIVISION; INDOLES; MOLECULAR PROBES; PHENOLS;

EID: 0038343601     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351173     Document Type: Article

References (30)

1. For a review, see: T. J. Mitchison, E. D. Salmon, Nat. Cell Biol. 2001, 3, E17-E21.
2. a) R. Micura, Angew. Chem. 2002, 114, 2369-2373; Angew. Chem. Int. Ed. 2002, 41, 2265-2269;
3. a) R. Micura, Angew. Chem. 2002, 114, 2369-2373; Angew. Chem. Int. Ed. 2002, 41, 2265-2269;
4. b) C. M. Crews, R. Mohan, Curr. Opin. Chem. Biol. 2000, 4, 47-53;
5. c) J. R. Peterson, T. J. Mitchison, Chem. Biol. 2002, 9, 1275-1285.
6. S. L. Schreiber, Bioorg. Med. Chem. 1998, 6, 1127-1152.
7. For a review, see: C. E. Walczak, T. J. Mitchison, Cell 1996, 85, 943-946;
8. T. U. Mayer, T. M. Kapoor, S. J. Haggarty, R. W. King, S. L. Schreiber, T. J. Mitchison, Science 1999, 286, 971-974.
9. 1H NMR spectroscopic data of solid-phase Pictet-Spengler-reaction products revealed the diastereoselectivity for each aldehyde to be (trans/cis): m-hydroxybenzaldehyde (9.0:1), benzaldehyde (7.6:1), m-nitrobenzaldehyde (8.5:1), cyclohexanecarboxaldehyde (10.5:1), 2-ethylbutyraldehyde (7.8:1), 4-pyridinecarboxaldehyde (9.6:1).
10. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
11. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
12. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
13. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
14. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
15. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
16. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
17. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
18. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
19. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
20. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
21. Nondiastereoselective solid-phase Pictet-Spengler reactions: a) D. Bonnet, A. Ganesan, J. Comb. Chem. 2002, 4, 546-548; b) R. V. Connors, A. J. Zhang, S. J. Shuttleworth, Tetrahedron Lett. 2002, 43, 6661-6663; b) X. Li, L. Zhang, W. Zhang, S. E. Hall, J. P. Tam, Org. Lett. 2000, 2, 3075-3078; c) S. Vendeville, L. Bourel, E. Davioud-Charvet, P. Grellier, B. Deprez, C. Sergheraert, Bioorg. Med. Chem. Lett. 1999, 9, 437-442; d) H. Wang, A. Ganesan, Org. Lett. 1999, 1, 1647-1649; e) P. P. Fantauzzi, K. M. Yager, Tetrahedron Lett. 1998, 39, 1291-1294; f) J. P. Mayer, D. Bankaitis-Davis, J. Zhang, G. Beaton, K. Bjergarde, C. M. Andersen, B. A. Goodman, C. J. Herrera, Tetrahedron Lett. 1996, 37, 5633-5636; g) R. Mohan, Y.-L. Chou, M. M. Morrissey, Tetrahedron Lett. 1996, 37, 3963-3966; h) L. Yang, L. Guo, Tetrahedron Lett. 1996, 37, 5041-5044; i) K. Kalijuste, A. Undén, Tetrahedron Lett. 1995, 36, 9211-9214; k) B. Sauerbrei, V. Jungmann, H. Waldmann, Angew. Chem. 1998, 110, 1187-1190; Angew. Chem. Int. Ed. 1998, 37, 1143-1146.
22. a) J. Li, T. Wang, P. Yu, A. Peterson, R. Weber, D. Soerens, D. Grubisha, D. Bennett, J. M. Cook, J. Am. Chem. Soc. 1999, 121, 6998-7010;
23. b) E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797-1842.
24. For the synthesis of 5-oxo-2,2-bis(phenylthio)pentanoic acid methyl ester, see: G. Massiot, T. Mulamba, J. Chem. Soc. Chem. Commun. 1983, 1147-1149; an α,β-unsaturated ester can be unmasked and cyclized.
25. a) S. Yu, O. M. Berner, J. M. Cook, J. Am. Chem. Soc. 2000, 122, 7827-7828;
26. b) L. E. Overman, A. J. Robichaud, J. Am. Chem. Soc. 1989, 111, 300-308;
27. c) V. H. Rawal, C. Michoud, R. Monested, J. Am. Chem. Soc. 1993, 115, 3030-3031.
28. S. Faruki, R. W. Cole, C. L. Rieder, Cell Motil. Cytoskeleton 2002, 52, 107-121.
29. a) T. Furuta, S. S.-H. Wang, J. L. Dantzker, T. M. Dore, W. J. Bybee, E. M. Callaway, W. Denk, Proc. Natl. Acad. Sci. USA 1999, 96, 1193-1200;
30. b) S. R. Adams, R. Y. Tsien, Annu. Rev. Physiol. 1993, 55, 755-784.