In-vitro antiproliferative activities and kinase inhibitory potencies of glycosyl-isoindigo derivatives

Anti-Cancer Drugs

Volumn 18, Issue 9, 2007, Pages 1069-1074

  Sassatelli, Mathieu ^a   Bouchikhi, Fadoua ^a   Aboab, Bettina ^a   Anizon, Fabrice ^a   Fabbro, Doriano ^b   Prudhomme, Michelle ^a   Moreau, Pascale ^a  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Antiproliferative activities; Isoindigos; Kinase inhibitory activities

Indexed keywords

CYCLIN A; CYCLIN DEPENDENT KINASE 2; GLYCOSYL ISOINDIGO DERIVATIVE; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CARBOHYDRATE ANALYSIS; CELL PROLIFERATION; CONTROLLED STUDY; DRUG BINDING; DRUG INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; PROTEIN INTERACTION;

ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; GLYCOSYLATION; HUMANS; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; PROTEIN KINASE INHIBITORS; PROTEIN KINASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34548059152     PISSN: 09594973     EISSN: None     Source Type: Journal    
DOI: 10.1097/CAD.0b013e328182d281     Document Type: Article

References (18)

1. Messaoudi S, Sancelme M, Polard-Housset V, Aboab B, Moreau P, Prudhomme M. Synthesis and biological evaluation of oxindoles and benzimidazolinones derivatives. Eur J Med Chem 2004; 39:453-458.
2. Sassatelli M, Saab E, Anizon F, Prudhomme M, Moreau P. Synthesis of glycosyl-isoindigo derivatives. Tetrahedron Lett 2004; 45:4827-4830.
3. Sassatelli M, Bouchikhi F, Messaoudi S, Anizon F, Debiton E, Barthomeuf C, et al. Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives. Eur J Med Chem 2006; 41:88-100.
4. Sassatelli M, Debiton E, Aboab B, Prudhomme M, Moreau P. Synthesis and antiproliferative activities of indolin-2-one derivatives bearing amino acid moieties. Eur J Med Chem 2006; 41:709-716.
5. Leclerc S, Garnier M, Hoessel R, Marko D, Bibb JA, Snyder GL, et al. Indirubins inhibit glycogen synthase kinase-3β and CDK5/P25, two protein kinases involved in abnormal Tau phosphorylation in Alzheimer's disease. J Biol Chem 2001; 276:251-260.
6. Hoessel R, Leclerc S, Endicott JA, Nobel MEM, Lawrie A, Tunnah P et al. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nat Cell Biol 1999; 1:60-67.
7. Adachi J, Mori Y, Takigami H, Fujino J, Kitagawa H, Miller CA III, et al. Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine. J Biol Chem 2001; 276:31475-31478.
8. Knockaert M, Blondel M, Bach S, Leost M, Elbi C, Hager G, et al. Independent actions on cyclin-dependent kinases and aryl hydrocarbon receptor mediate the antiproliferative effects of indirubins. Oncogene 2004; 23:4400-4412.
9. Laird AD, Cherrington JM. Small molecule tyrosine kinase inhibitors: clinical development of anticancer agents. Exp Opin Invest Drugs 2003; 12:51-64.
10. Sun L, Liang C, Shirazian S, Zhou Y, Miller T, Cui J, et al. Discovery of 5-[5-fluoro-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl]-2, 4dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide, a novel tyrosine kinase inhibitor targeting vascular endothelial and platelet-derived growth factor receptor tyrosine kinase. J Med Chem 2003; 46:1116-1119.
11. Andreani A, Cavalli A, Granaiola M, Leoni A, Locatelli A, Morigi R, et al. Imadazo[2,1-b]thiazolylmethylene and indolylmethylene-2- indolinones: a new class of cyclin-dependent kinase inhibitors. Design, synthesis, and CDK1/cyclin B inhibition. Anticancer drug Des 2000; 15:447-452.
12. Moshinsky DJ, Bellamacina CR, Boisvert DC, Huang P, Hui T, Jancarik J, et al. SU9516: biochemical analysis of cdk inhibition and crystal structure in complex with cdk2. Biochem Biophys Res Commun 2003; 310:1026-1031.
13. Wood JM, Bold G, Buchdunger E, Cozens R, Ferrari S, Frei J, et al. PTK787/ZK 222584, a novel and potent inhibitor of vascular endothelial growth factor receptor tyrosine kinases, impairs vascular endothelial growth factor-induced responses and tumor growth after oral administration. Cancer Res 2000; 60:2178-2189.
14. Bold G, Altmann K-H, Frei J, Lang M, Manley PW, Traxler P, et al. New anilinophtalazines as potent and orally well absorbed inhibitors of the VEGF receptor tyrosine kinases useful as antagonists of tumor-driven angiogenesis. J Med Chem 2000; 43: 2310-2323. Erratum in: J Med Chem 2000; 43:3200.
15. Soni R, Fretz H, Muller L, Schoepfer J, Chaudhuri B. Novel CDK inhibitors restore TGF-β sensitivity in CDK4 overexpressing epithelial cells. Biochem Biophys Res Commun 2000; 272:794-800.
16. Neal Bramson H, Corona J, Davis ST, Dickerson SH, Edelstein M, Frye SV, et al. Oxindole-based inhibitors of cyclin-dependent kinase 2 (CDK2): design, synthesis, enzymatic activities and X-ray crystallographic analysis. J Med Chem 2001; 44:4339-4358.
17. Weiner SJ, Kollman PA, Case DA, Singh UC, Ghio C, Alagona G, et al. A new force field for molecular mechanical simulation of nucleic acids and proteins. J Am Chem Soc 1984; 106:765-784.
18. Cornell WD, Cieplak P, Bayly CI, Gould IR, Merz KM, Ferguson DM, et al. A second generation force field for the simulation of proteins, nucleic acids, and organic molecules. J Am Chem Soc 1995; 117:5179-5197.