Molecular mechanisms of indirubin and its derivatives: Novel anticancer molecules with their origin in traditional Chinese phytomedicine

Journal of Cancer Research and Clinical Oncology

Volumn 130, Issue 11, 2004, Pages 627-635

  Eisenbrand, Gerhard ^a   Hippe, Frankie ^a   Jakobs, Sandra ^a   Muehlbeyer, Stephan ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Antileukaemic; Cyclin dependent kinases; Indirubin; Molecular mechanisms; Traditional Chinese phytomedicine

Indexed keywords

7 HYDROXYSTAUROSPORINE; ANTINEOPLASTIC AGENT; AZEPINE DERIVATIVE; CYCLIN DEPENDENT KINASE INHIBITOR; FLAVOPIRIDOL; INDIRUBIN; INDIRUBIN DERIVATIVE; KENPAULLONE; OLOMOUCINE; PURINE DERIVATIVE; ROSCOVITINE; STAUROSPORINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CHRONIC GRANULOCYTIC LEUKEMIA; CHRONIC MYELOID LEUKEMIA; CONTROLLED STUDY; DRUG STRUCTURE; HUMAN; HUMAN CELL; PRIORITY JOURNAL; REVIEW; SIDE EFFECT; STRUCTURE ACTIVITY RELATION;

ADENOSINE TRIPHOSPHATE; ALZHEIMER DISEASE; ANTIBIOTICS, ANTINEOPLASTIC; CELL CYCLE; CYCLIN-DEPENDENT KINASES; DIABETES MELLITUS; ENZYME INHIBITORS; HUMANS; INDOLES; LEUKEMIA, MYELOID, CHRONIC; MEDICINE, CHINESE TRADITIONAL; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 8644224855     PISSN: 01715216     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00432-004-0579-2     Document Type: Review

References (57)

1. Bernards R (1997) E2F: a nodal point in cell cycle regulation. Biochim Biophys Acta 1333:M33-M40
2. Carnero A and Hannon GJ (1997) The INK4 family of CDK inhibitors. In: Vogt PK and Reed SI (eds) Cyclin-dependent kinase (CDK) inhibitors, 1st edn. Springer, Berlin Hidleberg New York, pp 43-56
3. Chang HM, But PPH (1996) Pharmacology and applications of Chinese materia medica, vol. 2. World Scientific, Singapore
4. Cheng MP, Olivier P, Diehl JA, Fero M, Roussel MF, Roberts JM, Sherr CJ (1999) The p21(Cip1) and p27(Kip1) CDK 'inhibitors' are essential activators of cyclinD-dependent kinases in murine fibroblasts. EMBO J 18:1571-1583
5. Cohen P (1999) The Croonian Lecture 1998. Identification of a protein kinase cascade of major importance in insulin signal transduction. Philos Trans R Soc Lond B Biol Sci 354:485-495
6. Coleman KG, Lyssikatos JP, Yang BV (1997) Chemical inhibitors of cyclin-dependent kinases. Ann Rep Med Chem 32:171-179
7. Connell-Crowley L, Harper JW, Goodrich DW (1997) CycinD1/ CDK4 regulates retinoblastoma protein mediated cell cycle arrest by specific phosphorylation. Mol Biol Cell 8:287-301
8. Damiens E, Baratte B, Marie D, Eisenbrand G, Meijer L (2001) Anti-mitotic properties of indirubin-3′-monoxime, a CDK/ GSK-3 inhibitor: induction of endoreplication following prophase arrest. Oncogene 20:3786-3797
9. Davies TG, Tunnah P, Meijer L, Marko D, Eisenbrand G, Endicott JA, Noble ME (2001) Inhibitor binding to active and inactive CDK2: the crystal structure of CDK2-cyclin A/Indirubin-5-sulphonate. Structure, 9:389-397
10. Diehl JA, Cheng M, Roussel MF, Sherr CJ (1998) Glycogen synthase kinase-3beta regulates cyclin D1 proteolysis and subcellular localization. Genes Dev 12:3499-3511
11. Draetta G, Pagano M (1996) Cell cycle control and cancer. Ann Rep Med Chem 31:241-248
12. Du D, Ceng Q (1981) Effect of indirubin on the incorporation of isotope labeled precursors into nucleic acid and protein of tumour tissues. Zhongcaoya 12:406-409
13. Edamatsu H, Gau CL, Nemoto T, Guo L, Tamanoi F (2000) CDK inhibitors, roscovitine and olomoucine, synergize with farnesyl transferase inhibitor (FTI) to induce efficient apoptosis of human cancer cell lines. Oncogene 19:3059-3068
14. Eisenbrand G, Muehlbeyer S, Hippe F, Jakobs S (2004) Novel indirubin derivatives, promising anti-tumor agents. AACR, 95th annual meeting, Orlando, FL, USA
15. Emily-Fenouil F, Ghiglione C, Lhomond G, Lepage T, Gache C (1998) GSK3beta/shaggy mediates patterning along the animal-vegetal axis of the sea urchin embryo. Development 125:89-98
16. Fiebig HH, Marko D, Eisenbrand G (2001) Indirubins, novel potent inhibitors of cyclin-dependent kinases, inhibit the growth of human xenograft tumours. AACR, 92nd annual meeting, New Orleans, LA, USA
17. Gan WJ, Yang T, Wen S, Liu Y, Tan Z, Deng C, Wu J, Liu M (1985) Studies on the mechanism of indirubin action in the treatment of chronic myelocytic leukemia (CML). II. 5′-Nucleotidase in the peripheral white blood cells of CML. Chin Acad Med Sci Beijing 6:611-613
18. Garrett MD, Fattaey A (1999) CDK inhibition and cancer therapy. Curr Opin Genet Dev 9:104-111
19. Gray N, Detivaud L, Doerig C, Meijer L (1999) ATP-site directed inhibitors of cyclin-dependent kinases. Curr Med Chem 6:859-875
20. Han R (1994) Highlight on the studies of anticancer drugs derived from plants in China. Stem Cells 12:53-63
21. Harbour JW, Dean DC (2000) Rb function in cell-cycle regulation and apoptosis. Nature Cell Biol 2:E65-E67
22. He X, Saint-Jeannet JP, Woodgett HE, Varmus HE, Dawid IB (1995) Glycogen synthase kinase-3 and dorsoventral patterning in Xenopus embryos. Nature 374:617-22
23. Hoessel R, Leclerc S, Endicott JA, Nobel ME, Lawrie A, Tunnah P, Leost M, Damiens E, Marie D, Marko D, Niederberger E, Tang W, Eisenbrand G, Meijer L (1999) Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nat Cell Biol 1:60-67
24. Imahori K, Uchida T (1997) Physiology and pathology of tau protein kinases in relation to Alzheimer's disease. J Biochem (Tokyo) 121:179-88
25. Ji XJ, Zhang FR, Lei JL, Xu YT (1981) Studies on the antineoplastic effect and toxicity of synthetic indirubin. Yaoxue Xuebao 16:146-148
26. LaBaer MD, Garrett MD, Stevenson LF, Slingerland JM, Sandhu C, Chou HS, Fattaey A, Harlow E (1997) New functional activities for the p21 family of CDK inhibitors. Genes Dev 11:847-862
27. Leclerc S, Garnier M, Hoessel R, Marko D, Bibb JA, Snyder GL, Greengard P, Biernat J, Wu YZ, Mandelkow E-M, Eisenbrand G, Meijer L (2001) Indirubins inhibit glycogen synthase kinase-3β and CDK5/P25, two protein kinases involved in abnormal tau phosphorylation in alzheimer's disease. J Biol Chem 276:251-260
28. Lee JC, Adams JL (1995) Inhibitors of serine/threonine kinases. Curr Opin Biotech 6:657-661
29. Lee K, Shih CY, Yang TY, Chien LS, Chao WM, Sun CS, Wang TC, Pien SK, Sung KH (1979) Ultrastructural study on the mechanism of the therapeutic effect of indirubin for human chronic granulocytic leukemia. Zhinghua Yixue Zazhi 59:129-132
30. Li Q (1987) The chemical constituents of Qing Dai. Zhiwu Xuebao 29:67-72
31. Malumbres M, Barbacid M (2001) To cycle or not to cycle: a critical decision in cancer. Nat Rev Cancer 1:222-231
32. Mandelkow EM, Mandelkow E (1998) Tau in Alzheimer's disease. Trends Cell Biol 8:425-427
33. Marko D, Schätzle S, Friedel A, Genzlinger A, Zankl H, Meijer L, Eisenbrand G (2001) Inhibition of cyclin-dependent kinase 1 (CDK1) by indirubin derivatives in human tumour cells. Br J Cancer 84:283-289
34. Meijer L (1996) Chemical inhibitors of cyclin-dependent kinases. Trends Cell Biol 6:393-397
35. Morgan DO (1997) Cyclin- dependent kinases: engines, clocks, and microprocessors. Annu Rev Cell Dev Biol 13:261-291
36. Mueller H, Helin K (2000) The E2F transcription factors: key regulators of cell proliferation. Biochim Biophys Acta 1470:M1-M12
37. Senderowicz AM, Sausville EA (2000) Preclinical and clinical development of CDK modulators. J Natl Cancer Inst 92:376-387
38. Sherr CJ, Roberts JM (1995) Inhibitors of mammalian G1 cyclin-dependent kinases. Genes Dev 9:1149-1163
39. Sherr CJ, Roberts JM (1999) CDK inhibitors: positive and negative regulators of G1-phase progression. Genes Dev 13:1501-1512
40. Sielecki TM, Boylan JF, Benfield PA, Trainor GL (2000) Cyclin-dependent kinase inhibitors: useful targets in cell cycle regulation. J Med Chem 43:1-18
41. Soni R, O'Reilly T, Furet P, Muller L, Stephan C, Zumstein-Mecker S, Fretz H, Fabbro D, Chaudhuri B (2001) Selective in vivo and in vitro effects of a small molecule inhibitor of cyclin-dependent kinase 4. J Natl Cancer Inst 93:436-446
42. Summers SA, Kao AW, Kohn AD, Backus GS, Roth RA, Pessin JE, Birmbaum MJ (1999) The role of glycogen synthase kinase 3beta in insulin-stimulated glucose metabolism. J Biol Chem 274:17934-17940
43. Tamrakar S, Rubin E, Ludlow JW (2000) Role of pRb dephosphorylation in cell cycle regulation. Front Biosci 5:121-137
44. Tang W, Eisenbrand G (1992) Chinese drugs of plant origin: chemistry, pharmacology, and use in traditional and modern medicine. Springer, Berlin Heidelberg New York
45. Toledo LM, Lydon NB, Elbaum D (1999) Structure-based design of ATP-site directed protein kinase inhibitors. Curr Med Chem 6:775-805
46. Toogood PL (2001) Cyclin-dependent kinase inhibitors for treating cancer. Med Res Rev 21:487-498
47. Van den Heuvel S, Harlow E (1993) Distinct roles for cyclin-dependent kinases in cell cycle control. Science 262:2050-2054
48. Walker DH (1998) Small molecule inhibitors of cyclin-dependent kinases: molecular tools and potential therapeutics. Curr Top Microbiol Immunol 227:149-165
49. Wan JH, You YC, Mi JX, Ying HG (1981) Effect of indirubin on hematopoietic cell production. Acta Pharmacol Sin 2:241-244
50. Weinberg RA (1995) The retinoblastoma protein and cell cycle control. Cell 81:323-330
51. Willert K, Nusse R (1998) Beta-catenin: a key mediator of Wnt signaling. Curr Opin Genet Dev 8:95-102
52. Wu GY, Fang FD, Liu JZ, Chang A, Ho YH (1980) 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
53. Yost C, Torres M, Miller JR, Huang E, Kimelman D, Moon RT (1996) The axis-inducing activity, stability, and subcellular distribution of beta-catenin is regulated in Xenopus embryos by glycogen synthase kinase 3. Genes Dev 10:1443-1454
54. Zhang S (1983) Studies on the chemical constituents of Isatis indigotica root. Chinese Trad Herb Drugs 14:247-248
55. Zhang ZN, Liu EK, Zheng TL, Li DG (1985) Treatment of chronic myelocytic leukemia (CML) by traditional Chinese medicine and Western medicine alternatively. J Trad Chinese Med 5:246-248
56. Zheng QT, Lu DJ, Yang SL (1979a) Pharmalogical studies of indirubin. I. Antitumor effect. Comm Chinese Herb Med 10:35-39
57. 3H-indirubin. Comm Chinese Herb Med 10:19-21