Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases

Nature Cell Biology

Volumn 1, Issue 1, 1999, Pages 60-67

  Hoessel, Ralph ^a   Leclerc, Sophie ^b   Endicott, Jane A ^c   Nobel, Martin E M ^c   Lawrie, Alison ^c   Tunnah, Paul ^c   Leost, Maryse ^b   Damiens, Eve ^b,d   Marie, Dominique ^b   Marko, Doris ^a   Niederberger, Ellen ^a   Tang, Weici ^a   Eisenbrand, Gerhard ^a   Meijer, Laurent ^b  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

^b STATION BIOLOGIQUE   (France)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; CDK2 PROTEIN, HUMAN; CDK2 PROTEIN, MOUSE; CYCLIN DEPENDENT KINASE; CYCLIN DEPENDENT KINASE 2; ENZYME INHIBITOR; INDIGO; INDIRUBIN; INDOLE DERIVATIVE; ISATIN; PROTEIN SERINE THREONINE KINASE; RECOMBINANT PROTEIN;

ANIMAL; APOPTOSIS; ARMYWORM; ARTICLE; CELL CYCLE; CELL DIVISION; CELL LINE; CELL STRAIN HL 60; CELL STRAIN K 562; CHEMICAL STRUCTURE; CHEMISTRY; CHINESE MEDICINE; CONFORMATION; DRUG ANTAGONISM; DRUG EFFECT; GENETIC TRANSFECTION; HUMAN; LEUKEMIA CELL LINE; LEUKEMIA L 1210; MOUSE; PROTEIN CONFORMATION;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; APOPTOSIS; CDC2-CDC28 KINASES; CELL CYCLE; CELL DIVISION; CELL LINE; CYCLIN-DEPENDENT KINASE 2; CYCLIN-DEPENDENT KINASES; ENZYME INHIBITORS; HL-60 CELLS; HUMANS; INDOLES; ISATIN; JURKAT CELLS; K562 CELLS; LEUKEMIA L1210; MEDICINE, CHINESE TRADITIONAL; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEIN CONFORMATION; PROTEIN-SERINE-THREONINE KINASES; RECOMBINANT PROTEINS; SPODOPTERA; TRANSFECTION;

EID: 0033128165     PISSN: 14657392     EISSN: None     Source Type: Journal    
DOI: 10.1038/9035     Document Type: Article

References (48)

1. Zhu, Y.-P. & Woerdenbag, H. J. Traditional Chinese herbal medicine. Pharm. World Sci. 17, 103-112 (1995).
2. Tang, W. & Eisenbrand, G. Chinese Drugs of Plant Origin: Chemistry, Pharmacology, and Use in Traditional and Modern Medicine (Springer, Heidelberg, 1992).
3. Han, R. Highlight on the studies of anticancer drugs derived from plants in China. Stem Cells 12, 53-63 (1994).
4. Chinese Pharmacopoeia Vol. 1 (People's Health Publisher, Beijing, 1995).
5. Institute of Haematology, Chinese Academy of Medical Sciences. Clinical studies of Dang Gui Lu Hui Wan in the treatment of CML. Chinese J. Intern. Med. 15, 86-88 (1979).
6. Wu, L. M., Yang, Y. P. & Zhu, Z. H. Studies on the active principles of indigofera tinctoria in the treatment of CML. Comm. Chinese Herb. Med. 9, 6-8 (1979).
7. Wu, G. Y., Fang, F. D., Liu, J. Z., Chang, A. & Ho, Y. H. Studies on the mechanism of action of indirubin in the treatment of chronic granulocytic leukemia. I. Effects on nucleic acid and protein synthesis in human leukemic cells. Chinese Med. J. 60, 451-454 (1980).
8. Zheng, Q. T., Lu, D. J. & Yang, S. L. Pharmacological studies of indirubin. I. Antitumor effect. Comm. Chinese Herb. Med. 10, 35-39 (1979).
9. 3H-indirubin. Comm. Chinese Herb. Med. 10, 19-21 (1979).
10. Zhang, S. X. Studies on the chemical constituents of Isatis indigotica root. Chinese Trad. Herb. Drugs 14, 247-248 (1983).
11. Chen, D. H. & Xie, J. X. Chemical constituents of traditional Chinese medicine Qing Dai. Chinese Trad. Herb. Drugs 15, 6-8 (1984).
12. Hurry, J. B. The Wood Plant and its Dye (Oxford Univ. Press, Oxford, 1930).
13. Balfour-Paul, J. Indigo (British Mus. Press, London, 1998).
14. Chang, H. M. & But, P. P. H. Pharmacology and Applications of Chinese Materia Medica Vol. 2 (ed. Teaneck, N.J.) (World Scientific Pub. Co., Singapore, 1987).
15. Zhang, L., Wu, G. Y. & Qiu, C. C. Effect of indirubin on DNA synthesis in vitro. Acta Acad. Med. Sin. 7, 112-116 (1985).
16. Du, D. J. & Ceng, Q. T. Effect of indirubin on the incorporation of isotope labeled precursors into nucleic acid and protein of tumor tissues. Chinese Trad. Herb Drugs 12, 406-409 (1981).
17. Wu, G. Y., Liu, J. Z., Fang, F. D. & Zuo, J. Studies on the mechanism of indirubin action in the treatment of chronic granulocytic leukemia. V. Binding between indirubin and DNA and identification of the type of binding. Sci. Sin. 25, 1071-1079 (1982).
18. Lee, K. et al. Ultrastructural study on the mechanism of the therapeutic effect of indirubin for human chronic granulocytic leukemia. Natl Med. J. China 59, 129-132 (1979).
19. Ji, X. J., Zhang, F. R., Lei, J. L. & Xu, Y. T. Studies on the antineoplastic effect and toxicity of synthetic indirubin. Acta Pharma. Sin. 16, 146-148 (1981).
20. Wang, J. H., You, Y. C., Mi, J. X. & Ying, H. G. Effect of indirubin on hematopoietic cell production. Acta Pharmacol. Sin. 2, 241-244 (1981).
21. Sichuan Institute of Traditional Chinese Medicine. Subacute toxicity of indirubin in dogs. Chinese Trad. Herb Drugs 12, 27-29 (1981).
22. Ji, X. J. & Zhang, F. R. Antineoplastic effect of indirubin derivatives and their structure-activity relationship. Acta Pharm. Sin. 20, 137-139 (1985).
23. Gu, Y. C., Li, G. L., Yang, Y. P., Fu, J. P. & Li, C. Z. Synthesis of some halogenated indirubin derivatives. Acta Pharm. Sin. 24, 629-632 (1989).
24. Ji, X. J., Liu, X. M., Li, K., Chen, R. H. & Wang, L. G. Pharmacological studies of meisoindigo: absorption and mechanism of action. Biomed. Environm. Sci. 4, 332-337 (1991).
25. Li, C. et al. The synthesis, antileukemic activity, and crystal structures of indirubin derivatives. Bull. Chem. Soc. Jpn 69, 1621-1627 (1996).
26. Wu, K. M., Zhang, M. Y., Fang, Z. & Huang, L. Potential antileukemic agents, synthesis of derivatives of indirubin, indigo and isoindigotin. Acta Pharm. Sin. 20, 821-826 (1985).
27. Chang, C. N. in Advances in Chinese Medicinal Materials Research (eds Chang, H. M., Yeung, H. W., Tso, W., Koo, A.) 369-376 (World Scientific Pub. Co., Singapore, 1985).
28. Wan, J. H., You, Y. C., Mi, J. X. & Ying, H. G. Effect of indirubin on hematopoietic cell production. Acta Pharmacol. Sin. 2, 241-244 (1981).
29. Institute of Haematology, Chinese Academy of Medical Sciences. Experimental and clinical studies of indirubin in the treatment of CML. Chinese J. Intern. Med. 18, 83-88 (1979).
30. Cooperative Group of Clinical Therapy of Indirubin. Clinical studies of 314 cases of CML treated with indirubin. Chinese J. Intern. Med. 1, 132-135 (1980).
31. Gan, W. J. et al. Studies on the mechanism of indirubin action in treatment of chronic myelocytic leukemia (CML). II. 5′-Nucleotidase in the peripheral white blood cells of CML. Chinese J. Hematol. 6, 611-613 (1985).
32. Zhang, Z. N. et al. Treatment of chronic myelocytic leukemia (CML) by traditional Chinese medicine and Western medicine alternatively. J. Trad. Chinese Med. 5, 246-248 (1985).
33. Ma, M. & Yao, B. Progress in indirubin treatment of chronic myelocytic leukaemia. J. Trad. Chinese Med. 3, 245-248 (1983).
34. Jiang, S.Z. et al. Adverse effects of indirubin on cardiovascular system. Chinese J. Hematol. 7, 30 (1986).
35. Morgan, D. Cyclin-dependent kinases: engines, clocks, and microprocessors. Annu. Rev. Cell Dev. Biol. 13, 261-291 (1997).
36. Meijer, L. & Kim, S. H. Chemical inhibitors of cyclin-dependent kinases. Methods Enzymol. 283, 113-128 (1997).
37. Meijer, L. et al. Biochemical and cellular effects of roscovitine, a potent and selective inhibitor of the cyclin-dependent kinases cdc2, cdk2 and cdk5. Eur. J. Biochem. 243, 527-536 (1997).
38. Schulze-Gahmen, U. et al. Multiple modes of ligand recognition: crystal structures of cyclin-dependent protein kinase 2 in complex with ATP and two inhibitors, olomoucine and isopentenyladenine. Proteins Struct. Funct. Genet. 22, 378-391 (1995).
39. De Azevedo, W. F. et al. Structural basis for specificity and potency of a flavonoid inhibitor of human CDK2, a cell cycle kinase. Proc. Natl Acad. Sci. USA 93, 2735-2740 (1996).
40. De Azevedo, W. F. et al. Inhibition of cyclin-dependent kinases by purine analogues: crystal structure of human cdk2 complexed with roscovitine. Eur. J. Biochem. 243, 518-526 (1997).
41. Gray, N. et al. Exploiting chemical libraries, structure, and genomics in the search for new kinase inhibitors. Science 281, 533-538 (1998).
42. Lawrie, A. M. et al. Protein kinase inhibition by staurosporine revealed in details of the molecular interaction with CDK2. Nature Struct. Biol. 4, 796-800 (1997).
43. De Bondt, H.L. et al. Crystal structure of cyclin-dependent kinase 2. Nature 363, 595-602 (1993).
44. Russo, A., Jeffrey, P. D. & Pavletich, N. P. Structural basis of cyclin-dependent kinase activation by phosphorylation. Nature Struct. Biol. 3, 696-700 (1996).
45. Knighton, D.R. et al. Structure of a peptide inhibitor bound to the catalytic subunit of cyclic adenosine monophosphate-dependent protein kinase. Science 253, 414-420 (1991).
46. Brown, N. R. et al. Effects of phosphorylation of threonine 160 on CDK2 structure and activity. J. Biol. Chem. (in the press).
47. Otwinowski, Z. in Oscillation Data Reduction Program (eds Sawyer, L., Isaacs, N. & Bailey, S.) 56-62 (SERC Lab., Daresbury, Warrington, UK, 1993).
48. Collaborative Computional Project No. 4. The CCP4 suite: programs for protein crystallography. Acta Crystallogr. D 50, 760-763 (1994).