From the insoluble dye indirubin towards highly active, soluble CDK2-inhibitors

ChemBioChem

Volumn 6, Issue 3, 2005, Pages 531-540

  Jautelat, Rolf ^a   Brumby, Thomas ^a   Schäfer, Martina ^a   Briem, Hans ^a   Eisenbrand, Gerhard ^b   Schwahn, Stefan ^b   Krüger, Martin ^a   Lücking, Ulrich ^a   Prien, Olaf ^a   Siemeister, Gerhard ^a  

^a BAYER PHARMA AG   (Germany)

^b Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Biological activity; Enzymes; Medicinal chemistry; Natural products; Structure activity relationships

Indexed keywords

CYCLIN DEPENDENT KINASE INHIBITOR; INDIRUBIN; INDIRUBIN 5 SULFONYL CHLORIDE; SULFONAMIDE; UNCLASSIFIED DRUG; ADENOSINE TRIPHOSPHATE; CELL CYCLE PROTEIN; COLORING AGENT; CYCLIN DEPENDENT KINASE INHIBITOR 1A; INDOLE DERIVATIVE; PROTEIN KINASE INHIBITOR;

ANIMAL CELL; ARTICLE; DEPOLARIZATION; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; PROTEIN TERTIARY STRUCTURE; SOLUBILITY; SYNTHESIS;

ADENOSINE TRIPHOSPHATE; BINDING SITES; CELL CYCLE PROTEINS; COLORING AGENTS; CYCLIN-DEPENDENT KINASE INHIBITOR P21; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PROTEIN STRUCTURE, TERTIARY; SOLUBILITY; SULFONAMIDES;

EID: 20444445904     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200400108     Document Type: Article

References (30)

1. J. Balfour-Paul, Indigo, British Museum Press, London, 1998.
2. A. von Bayer, P. Emmerling, Ber. Dtsch. Chem. Ges. 1870, S1S.
3. L. M. Wu, Y. P. Yang, Z. H. Zhu, Comm. Chin. Herb. Med. 1979, 9, 6.
4. K.-M. Wu, M.-Y. Zhang, Z. Fang, L. Hunag, Yaoxue Xuebao 1985, 20, 821.
5. Y. C. Gu, G. L. Li, Y. P. Yang, J. P. Fu, C. Z. Li, Yaoxue Xuebao 1989, 24, 629.
6. R. Han, Stem Cells 1994, 12, 53.
7. R. Hoessel, S. Leclerc, J. A. Endicott, M. E. M. Nobel, A. Lawrie, P. Tunnah, M. Leost, E. Damiens, D. Marie, D. Marko, E. Niederberger, W. Tang, G. Eisenbrand, L. Meijer, Nat. Cell Biol. 1999, 1, 60.
8. A. Huwe, R. Mazitschek, A. Giannis, Angew. Chem. 2003, 115, 2170;
9. Angew. Chem. Int. Ed. 2003, 42, 2122.
10. W. Grell, R. Walter, A. Heckel, F. Himmelsbach, H. Wittneben, J. v. Meel, N. Redemann, R. Haigh, in PCT WO99S1S90, 1999.
11. S. C. Conway, G. W. Gribble, Heterocycles 1990, 30, 627.
12. T. G. Davies, P. Tunnah, L. Meijer, D. Marko, G. Eisenbrand, J. A. Endicott, M. E. M. Noble, Structure 2001, 9, 389.
13. S. H. Yalkowski, S. C. Valvani, J. Pharm. Sci. 1980, 69, 912
14. H. van de Waterbeemd, D. A. Smith, K. Beaumont, D. K. Walker, J. Med. Chem. 2001, 44, 1313
15. M. Y. Tesconi, H. Samuel in Handbook of Property Estimation Methods for Chemicals (Ed.: R. S. M. Boethling, D. C. Donald), Lewis, Boca Raton, FA, 2000, p. 3.
16. S. J. Danishefsky, M. J. O. Grandi, C. A. Coburn, R. C. A. Isaacs, J. Org. Chem. 1993, 58, 7728.
17. S. Lederc, M. Garnier, R. Hoessel, D. Marko, J. A. Bibb, G. L. Snyder, P. Greengard, J. Biernat, Y.-Z. Wu, E.-M. Mandelkow, G. Eisenbrand, L. Meijer, J. Biol. Chem. 2001, 276, 251.
18. L. Meijer, A.-L. Skaitsounis, P. Magiatis, P. Polychronopoulos, M. Knockaert, M. Leost, X. P. Ryan, C. A. Vonica, A. Brivanlou, R. Dajani, Chem. Biol. 2003, 10, 1255.
19. J. Adachi, Y. Mori, S. Matsui, H. Takigami, J. Fujino, H. Kitagawa, C. A. Miller III, T. Kato, K. Saeki, T. Matsuda, J. Biol. Chem. 2001, 276, 31475.
20. F. P. Guengerich, M. V. Martin, W. A. McCormick, L. P. Nguyen, E. Glover, C. A. Bradfield, Arch. Biochem. Biophys. 2004, 423, 309.
21. K. Sugihara, S. Kitamura, T. Yamada, T. Okayama, S. Ohta, K. Yamashita, M. Yasuda, Y. Fujii-Kuriyama, K. Saeki, S. Matsui, T. Matsuda, Biochem. Biophys. Res. Commun. 2004, 318, 571.
22. M. Knockaert, M. Blondel, S. Bach, M. Leost, C. Elbi, G. L. Hager, S. R. Nagy, D. Han, M. Denison, M. Ffrench, X. P. Ryan, P. Magiatis, P. Polychronopolous, P. Greengard, L. Skaltsounis, L. Meijer, Oncogens 2004, 23, 4400.
23. T. D. Bradshaw, V. Trapani, D. A. Vasselin, A. D. Westwell, Current Pharmaceutical Design 2002, 8, 2475.
24. S. Safe, A. McDougal, Int. J. Oncol. 2002, 20, 1123.
25. S. L. McGovern, B. K. Shoichet, J. Med. Chem. 2003, 46, 1478
26. J. Seidler, S. L. McGovern, T. N. Doman, B. K. Shoichet, J. Med. Chem. 2003, 46, 4477.
27. For a recent related work on indirubins that acknowledges the importance of solubility but does not address this aspect, see: P. Polychronopoulos, P. Magiatis, A.-L. Skaltsounis, V. Myrianthopoulos, E. Mikros, A. Tarricone, A. Musacchio, S. M. Roe, L. Pearl, M. Leost, P. Greengard, L. Meijer, J. Med. Chem. 2004, 47, 935.
28. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307.
29. J. Navaza, Acta Crystallogr. A 1994, 50, 157.
30. G. M. Sheldrick, T. R. Schneider, Methods Enzymol. 1997, 277, 319.