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Volumn 47, Issue 4, 2004, Pages 935-946

Structural Basis for the Synthesis of Indirubins as Potent and Selective Inhibitors of Glycogen Synthase Kinase-3 and Cyclin-Dependent Kinases

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE; CYCLIN DEPENDENT KINASE; CYCLIN DEPENDENT KINASE 2; CYCLIN DEPENDENT KINASE 5; CYCLIN DEPENDENT KINASE INHIBITOR; GLYCOGEN SYNTHASE KINASE 3; GLYCOGEN SYNTHASE KINASE 3 INHIBITOR; GLYCOGEN SYNTHASE KINASE 3BETA; INDIRUBIN; INDIRUBIN DERIVATIVE; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 2442589341     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm031016d     Document Type: Article
Times cited : (362)

References (54)
  • 1
    • 0034797512 scopus 로고    scopus 로고
    • The role of protein phosphorylation in human health and disease
    • Cohen, P. The role of protein phosphorylation in human health and disease. Eur. J. Biochem. 2001, 268, 5001-5010.
    • (2001) Eur. J. Biochem. , vol.268 , pp. 5001-5010
    • Cohen, P.1
  • 2
    • 0036527429 scopus 로고    scopus 로고
    • Protein kinases - The major drug target of the twenty-first century?
    • Cohen, P. Protein kinases - the major drug target of the twenty-first century? Nat. Rev. Drug Discovery 2002, 1, 309-315.
    • (2002) Nat. Rev. Drug Discovery , vol.1 , pp. 309-315
    • Cohen, P.1
  • 3
    • 0011672458 scopus 로고    scopus 로고
    • ATP site-directed competitive and irreversible inhibitors of protein kinases
    • Garcia-Echeverria, C.; Traxler, P.; Evans, D. B. ATP site-directed competitive and irreversible inhibitors of protein kinases. Med. Res. Rev. 2000, 20, 28-57.
    • (2000) Med. Res. Rev. , vol.20 , pp. 28-57
    • Garcia-Echeverria, C.1    Traxler, P.2    Evans, D.B.3
  • 5
    • 0035117012 scopus 로고    scopus 로고
    • Protein kinase inhibitors: Emerging pharmacophores 1997-2000
    • Dumas, J. Protein kinase inhibitors: emerging pharmacophores 1997-2000. Exp. Opin. Ther. Pat. 2001, 11, 405-429.
    • (2001) Exp. Opin. Ther. Pat. , vol.11 , pp. 405-429
    • Dumas, J.1
  • 7
    • 0033790450 scopus 로고    scopus 로고
    • Genetic analysis of mammalian cyclin-dependent kinases and their inhibitors
    • Malumbres, M.; Ortega, S.; Barbacid, M. Genetic analysis of mammalian cyclin-dependent kinases and their inhibitors. Biol. Chem. 2000, 381, 827-838.
    • (2000) Biol. Chem. , vol.381 , pp. 827-838
    • Malumbres, M.1    Ortega, S.2    Barbacid, M.3
  • 8
    • 0035754080 scopus 로고    scopus 로고
    • To cycle or not to cycle: A critical decision in cancer
    • Malumbres, M.; Barbacid, M. To cycle or not to cycle: a critical decision in cancer. Nat. Rev. Cancer 2001, 1, 222-231.
    • (2001) Nat. Rev. Cancer , vol.1 , pp. 222-231
    • Malumbres, M.1    Barbacid, M.2
  • 9
    • 0037075887 scopus 로고    scopus 로고
    • Cyclin D -dependent kinases, INK4 inhibitors and cancer
    • Ortega, S.; Malumbres, M.; Barbacid, M. Cyclin D -dependent kinases, INK4 inhibitors and cancer. Biochim. Biophys. Acta 2002, 1602, 73-87.
    • (2002) Biochim. Biophys. Acta , vol.1602 , pp. 73-87
    • Ortega, S.1    Malumbres, M.2    Barbacid, M.3
  • 11
    • 0034831233 scopus 로고    scopus 로고
    • The protein kinase Cdk5. Structural aspects, roles in neurogenesis and involvement in Alzheimer's pathology
    • Maccioni, R. B.; Otth, C.; Concha, I. I.; Munoz, J. P. The protein kinase Cdk5. Structural aspects, roles in neurogenesis and involvement in Alzheimer's pathology. Eur. J. Biochem. 2001, 268, 1518-1527.
    • (2001) Eur. J. Biochem. , vol.268 , pp. 1518-1527
    • Maccioni, R.B.1    Otth, C.2    Concha, I.I.3    Munoz, J.P.4
  • 12
    • 0036169172 scopus 로고    scopus 로고
    • Cdk5 behind the wheel: A role in trafficking and transport?
    • Smith, D. S.; Tsai, L. H. Cdk5 behind the wheel: a role in trafficking and transport ? Trends Cell Biol. 2002, 12, 28-36.
    • (2002) Trends Cell Biol. , vol.12 , pp. 28-36
    • Smith, D.S.1    Tsai, L.H.2
  • 13
    • 0036302960 scopus 로고    scopus 로고
    • Inhibition of glycogen synthase kinase 3 improves insulin action and glucose metabolism in human skeletal muscle
    • Nikoulina, S. E.; Ciaraldi, T. P.; Mudaliar, S.; Carter, L.; Johnson, K. ; Henry, R. R. Inhibition of glycogen synthase kinase 3 improves insulin action and glucose metabolism in human skeletal muscle. Diabetes 2002, 51, 2190-2198.
    • (2002) Diabetes , vol.51 , pp. 2190-2198
    • Nikoulina, S.E.1    Ciaraldi, T.P.2    Mudaliar, S.3    Carter, L.4    Johnson, K.5    Henry, R.R.6
  • 14
    • 0036090823 scopus 로고    scopus 로고
    • Glycogen synthase kinase 3: An emerging therapeutic target
    • Eldar-Finkelman, H. Glycogen synthase kinase 3: an emerging therapeutic target. Trends Mol. Medic. 2002, 8, 126-132.
    • (2002) Trends Mol. Medic. , vol.8 , pp. 126-132
    • Eldar-Finkelman, H.1
  • 15
    • 0036606693 scopus 로고    scopus 로고
    • The GSK-3β signaling cascade and neurodegenerative disease
    • Kaytor, M. D.; Orr, H. T. The GSK-3β signaling cascade and neurodegenerative disease. Curr. Opinion Neurobiol. 2002, 12, 275-278.
    • (2002) Curr. Opinion Neurobiol. , vol.12 , pp. 275-278
    • Kaytor, M.D.1    Orr, H.T.2
  • 16
    • 0037809277 scopus 로고    scopus 로고
    • Mental plaque removal
    • De Strooper, B.; Woodgett, J. Mental plaque removal. Nature 2003, 423, 392-393.
    • (2003) Nature , vol.423 , pp. 392-393
    • De Strooper, B.1    Woodgett, J.2
  • 18
    • 0038187674 scopus 로고    scopus 로고
    • GSK-3alpha regulates production of Alzheimer's disease amyloid-beta peptides
    • Phiel, C. J.; Wilson, C. A.; Lee, V. M.; Klein, P. S. GSK-3alpha regulates production of Alzheimer's disease amyloid-beta peptides. Nature 2003, 423, 435-439.
    • (2003) Nature , vol.423 , pp. 435-439
    • Phiel, C.J.1    Wilson, C.A.2    Lee, V.M.3    Klein, P.S.4
  • 20
    • 0036710767 scopus 로고    scopus 로고
    • Pharmacological inhibitors of cyclin-dependent kinases
    • Knockaert, M.; Greengard, P.; Meijer, L. Pharmacological inhibitors of cyclin-dependent kinases. Trends Pharmacol. Sci. 2002, 23, 417-425.
    • (2002) Trends Pharmacol. Sci. , vol.23 , pp. 417-425
    • Knockaert, M.1    Greengard, P.2    Meijer, L.3
  • 21
    • 0036220822 scopus 로고    scopus 로고
    • Complexities in the development of cyclin-dependent kinase inhibitor drugs
    • Sausville, E. A. Complexities in the development of cyclin-dependent kinase inhibitor drugs. Trends Mol. Medic. 2002, 8, S32-S37.
    • (2002) Trends Mol. Medic. , vol.8
    • Sausville, E.A.1
  • 22
    • 0038440704 scopus 로고    scopus 로고
    • Cyclin-dependent kinase inhibitors
    • Meijer, L.; Jézéquel, A.; Roberge, M., Eds., Progress in Cell Cycle Research: Editions "Life in Progress", Station Biologique de Roscoff
    • Fischer, L.; Endicott, J.; Meijer, L. Cyclin-dependent kinase inhibitors. In Cell Cycle Regulators as Therapeutic Targets Meijer, L.; Jézéquel, A.; Roberge, M., Eds., Progress in Cell Cycle Research: Editions "Life in Progress", Station Biologique de Roscoff, 2003; Vol. 5, pp 235-248.
    • (2003) Cell Cycle Regulators as Therapeutic Targets , vol.5 , pp. 235-248
    • Fischer, L.1    Endicott, J.2    Meijer, L.3
  • 23
    • 0036799220 scopus 로고    scopus 로고
    • Inhibitors of glycogen synthase kinase-3: Future therapy for unmet medical needs?
    • Dorronsoro, I.; Castrob, A.; Martinez, A. Inhibitors of glycogen synthase kinase-3: future therapy for unmet medical needs? Expert Opin. Ther. Pat. 2002, 12, 1-10.
    • (2002) Expert Opin. Ther. Pat. , vol.12 , pp. 1-10
    • Dorronsoro, I.1    Castrob, A.2    Martinez, A.3
  • 24
    • 0036273020 scopus 로고    scopus 로고
    • Glycogen synthase kinase 3 (GSK-3) inhibitors as new promising drugs for diabetes, neurodegeneration, cancer, and inflammation
    • Martinez, A.; Castro, A.; Dorronsoro, I.; Alonso, M. Glycogen synthase kinase 3 (GSK-3) inhibitors as new promising drugs for diabetes, neurodegeneration, cancer, and inflammation. Medic. Res. Rev. 2002, 22, 373-384.
    • (2002) Medic. Res. Rev. , vol.22 , pp. 373-384
    • Martinez, A.1    Castro, A.2    Dorronsoro, I.3    Alonso, M.4
  • 25
    • 0035808457 scopus 로고    scopus 로고
    • Indirubins inhibit glycogen synthase kinase - 3β and CDK5/p25, two kinases involved in abnormal tau phosphorylation in Alzheimer's disease - A property common to most CDK inhibitors?
    • Leclerc, S.; Garnier, M.; Hoessel, R.; Marko, D.; Bibb, JA.; Snyder, GL. ; Greengard, P.; Biernat, J.; Mandelkow, E.-M.; Eisenbrand, G.; Meijer, L. Indirubins inhibit glycogen synthase kinase - 3β and CDK5/p25, two kinases involved in abnormal tau phosphorylation in Alzheimer's disease - A property common to most CDK inhibitors? J. Biol. Chem. 2001, 276, 251-260.
    • (2001) J. Biol. Chem. , vol.276 , pp. 251-260
    • Leclerc, S.1    Garnier, M.2    Hoessel, R.3    Marko, D.4    Bibb, J.A.5    Snyder, G.L.6    Greengard, P.7    Biernat, J.8    Mandelkow, E.-M.9    Eisenbrand, G.10    Meijer, L.11
  • 27
    • 0004249164 scopus 로고    scopus 로고
    • British Museum Press: London
    • Balfour-Paul, J. Indigo; British Museum Press: London, 1998; 1-264.
    • (1998) Indigo , pp. 1-264
    • Balfour-Paul, J.1
  • 28
    • 0042894451 scopus 로고    scopus 로고
    • Tyrian purple: 6,6′-Dibromoindigo and Related Compounds
    • Cooksey, C. J. Tyrian purple: 6,6′-Dibromoindigo and Related Compounds. Molecules 2001, 6, 736-769.
    • (2001) Molecules , vol.6 , pp. 736-769
    • Cooksey, C.J.1
  • 33
    • 0036332286 scopus 로고    scopus 로고
    • Indirubin and meisoindigo in the treatment of chronic myelogenous leukemia in China
    • Xiao, Z.; Hao, Y.; Liu, B.; Qian, L. Indirubin and meisoindigo in the treatment of chronic myelogenous leukemia in China. Leuk. Lymphoma 2002, 43, 1763-1768.
    • (2002) Leuk. Lymphoma , vol.43 , pp. 1763-1768
    • Xiao, Z.1    Hao, Y.2    Liu, B.3    Qian, L.4
  • 34
    • 0035963318 scopus 로고    scopus 로고
    • Anti-mitotic properties of indirubin-3′-oxime.; a CDK/GSK-3 inhibitor: Induction of endoreplication following prophase arrest
    • Damiens, E.; Baratte, B.; Marie, D.; Eisenbrand, G.; Meijer, L. Anti-mitotic properties of indirubin-3′-oxime.; a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest. Oncogene 2001, 20, 3786-3797.
    • (2001) Oncogene , vol.20 , pp. 3786-3797
    • Damiens, E.1    Baratte, B.2    Marie, D.3    Eisenbrand, G.4    Meijer, L.5
  • 36
    • 0642286536 scopus 로고    scopus 로고
    • Aryl hydrocarbon receptor-mediated cell cycle control
    • Meijer, L.; Jezequel, A.; Roberge, M. Eds; Progress in Cell Cycle Research: Editions "Life in Progress", Station Biologique de Roscoff
    • Elferink, C. J. Aryl hydrocarbon receptor-mediated cell cycle control. In Cell Cycle Regulators as Therapeutic Targets; Meijer, L.; Jezequel, A.; Roberge, M. Eds; Progress in Cell Cycle Research: Editions "Life in Progress", Station Biologique de Roscoff, 2003; Vol. 5, pp 261-267.
    • (2003) Cell Cycle Regulators as Therapeutic Targets , vol.5 , pp. 261-267
    • Elferink, C.J.1
  • 39
    • 0037026632 scopus 로고    scopus 로고
    • Increased aryl hydrocarbon receptor expression offers a potential therapeutic target for pancreatic cancer
    • Koliopanos, A.; Kleeff, J.; Xiao, Y.; Safe, S.; Zimmermann, A.; Buchler, M. W.; Friess, H. Increased aryl hydrocarbon receptor expression offers a potential therapeutic target for pancreatic cancer. Oncogene 2002, 21, 6059-6070.
    • (2002) Oncogene , vol.21 , pp. 6059-6070
    • Koliopanos, A.1    Kleeff, J.2    Xiao, Y.3    Safe, S.4    Zimmermann, A.5    Buchler, M.W.6    Friess, H.7
  • 40
    • 0036615860 scopus 로고    scopus 로고
    • Mechanism of action and development of selective aryl hydrocarbon receptor modulators for treatment of hormone-dependent cancers
    • Safe, S.; McDougal, A. Mechanism of action and development of selective aryl hydrocarbon receptor modulators for treatment of hormone-dependent cancers. Int. J. Oncol. 2002, 22, 1123-1128.
    • (2002) Int. J. Oncol. , vol.22 , pp. 1123-1128
    • Safe, S.1    McDougal, A.2
  • 41
    • 0034988970 scopus 로고    scopus 로고
    • Inhibitor binding to active and inactive CDK2. The crystal structure of a CDK2-cyclin A/indirubin-5-sulphonate
    • Davies, T. G.; Tunnah, P.; Meijer, L.; Marko, D.; Eisenbrand, G.; Endicott, J. A.; Noble, M. E. M. Inhibitor binding to active and inactive CDK2. The crystal structure of a CDK2-cyclin A/indirubin-5-sulphonate. Structure 2001, 9, 389-397.
    • (2001) Structure , vol.9 , pp. 389-397
    • Davies, T.G.1    Tunnah, P.2    Meijer, L.3    Marko, D.4    Eisenbrand, G.5    Endicott, J.A.6    Noble, M.E.M.7
  • 42
    • 0000097199 scopus 로고    scopus 로고
    • Bromoindirubins: The synthesis and properties of minor components of tyrian purple and the composition of the colorant from Nucella lapillus
    • Clark, R. J. H.; Cooksey, C. J. Bromoindirubins: the synthesis and properties of minor components of tyrian purple and the composition of the colorant from Nucella lapillus. J. Soc. Dyers Colour. 1997, 113, 316-321.
    • (1997) J. Soc. Dyers Colour. , vol.113 , pp. 316-321
    • Clark, R.J.H.1    Cooksey, C.J.2
  • 43
    • 0000290487 scopus 로고
    • New synthetic route to 6-nitroisatin via nitration of 3-indolealdehyde
    • Noland, W.; Rieke, R. New synthetic route to 6-nitroisatin via nitration of 3-indolealdehyde. J. Org. Chem. 1962, 27, 2250-2252.
    • (1962) J. Org. Chem. , vol.27 , pp. 2250-2252
    • Noland, W.1    Rieke, R.2
  • 44
    • 0029135744 scopus 로고
    • Pseudoreceptor Modeling: The Construction of Three-Dimensional Receptor Surrogates
    • Vedani, A.; Zbinden, P.; Snyder, J.; Greenidge, P. Pseudoreceptor Modeling: The Construction of Three-Dimensional Receptor Surrogates. J. Am. Chem. Soc. 1995, 117, 4987-4994.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4987-4994
    • Vedani, A.1    Zbinden, P.2    Snyder, J.3    Greenidge, P.4
  • 47
    • 0036709880 scopus 로고    scopus 로고
    • Identifying in vivo targets of cyclin-dependent kinase inhibitors by affinity chromatography
    • Knockaert, M.; Meijer, L. Identifying in vivo targets of cyclin-dependent kinase inhibitors by affinity chromatography. Biochem. Pharmacol. 2002, 64, 819-825.
    • (2002) Biochem. Pharmacol. , vol.64 , pp. 819-825
    • Knockaert, M.1    Meijer, L.2
  • 49
    • 0036697233 scopus 로고    scopus 로고
    • Protein kinases as drug targets of parasitic protozoa
    • Doerig, C.; Meijer, L.; Mottram, J. C. Protein kinases as drug targets of parasitic protozoa. Trends Parasitol. 2002, 18, 366-371.
    • (2002) Trends Parasitol. , vol.18 , pp. 366-371
    • Doerig, C.1    Meijer, L.2    Mottram, J.C.3
  • 51
    • 0029981099 scopus 로고    scopus 로고
    • cdc2 on its Thr-14 and Tyr-15 residues at the prophase/metaphase transition
    • cdc2 on its Thr-14 and Tyr-15 residues at the prophase/metaphase transition. J. Biol. Chem. 1996, 271, 27847-27854.
    • (1996) J. Biol. Chem. , vol.271 , pp. 27847-27854
    • Borgne, A.1    Meijer, L.2
  • 53
    • 0025390935 scopus 로고
    • MOPAC - A semiempirical molecular orbital program
    • Stewart, J. J. P. MOPAC-a semiempirical molecular orbital program. J. Comput.-Aided Mol. Des. 1990, 4, 1-105.
    • (1990) J. Comput.-Aided Mol. Des. , vol.4 , pp. 1-105
    • Stewart, J.J.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.