A novel roscovitine derivative potently induces G1-phase arrest in platelet-derived growth factor-BB-activated vascular smooth muscle cells

Molecular Pharmacology

Volumn 77, Issue 2, 2010, Pages 255-261

  Sroka, Irene M ^a   Heiss, Elke H ^a   Havlicek, Libor ^b   Totzke, Frank ^c   Aristei, Yasmin ^e   Pechan, Paul ^d   Kubbutat, Michael H G ^c   Strnad, Miroslav ^b   Dirsch, Verena M ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b INSTITUTE OF EXPERIMENTAL BOTANY   (Czech Republic)

^c PROQINASE GMBH   (Germany)

^d C3 BIO GmbH   (Germany)

^e UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BROXURIDINE; CYCLIN A; CYCLIN DEPENDENT KINASE 1; CYCLIN DEPENDENT KINASE 2; CYCLIN DEPENDENT KINASE 4; CYCLIN E; DNA; LGR 1406; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; MITOGEN ACTIVATED PROTEIN KINASE P38; N 5 (2 AMINOCYCLOHEXYL) N 7 BENZYL 3 ISOPROPYL 1(2)H PYRAZOLO[4,3 D]PYRIMIDINE 5,7 DI AMINE; PHOSPHOTRANSFERASE; PLATELET DERIVED GROWTH FACTOR BB; PROPIDIUM IODIDE; PROTEIN KINASE B; PROTEIN P107; RETINOBLASTOMA PROTEIN; ROSCOVITINE; STAT3 PROTEIN; STRESS ACTIVATED PROTEIN KINASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL CYCLE ARREST; CELL CYCLE G1 PHASE; CELL CYCLE PROGRESSION; CELL NUCLEUS; CELL PROLIFERATION; COMPUTER MODEL; CONTROLLED STUDY; DNA SYNTHESIS; DRUG INHIBITION; DRUG METABOLISM; DRUG POTENCY; DRUG STABILITY; FLOW CYTOMETRY; GENE EXPRESSION REGULATION; IC 50; IN VITRO STUDY; NONHUMAN; PHOSPHORYLATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RAT; SIGNAL TRANSDUCTION; STAINING; VASCULAR SMOOTH MUSCLE; WESTERN BLOTTING;

ANIMALS; CELL LINE; DOSE-RESPONSE RELATIONSHIP, DRUG; G1 PHASE; HUMANS; MUSCLE, SMOOTH, VASCULAR; MYOCYTES, SMOOTH MUSCLE; PLATELET-DERIVED GROWTH FACTOR; PURINES; RATS; RATS, SPRAGUE-DAWLEY; SPODOPTERA;

EID: 74549214867     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.109.060327     Document Type: Article

References (34)

1. Alessi F, Quarta S, Savio M, Riva F, Rossi L, Stivala LA, Scovassi AI, Meijer L, and Prosperi E (1998) The cyclin-dependent kinase inhibitors olomoucine and roscovitine arrest human fibroblasts in G1 phase by specific inhibition of CDK2 kinase activity. Exp Cell Res 245:8-18.
2. Allen TR, Krueger KD, Hunter WJ 3rd, and Agrawal DK (2005) Evidence that insulin-like growth factor-1 requires protein kinase C-epsilon, PI3-kinase and mitogen-activated protein kinase pathways to protect human vascular smooth muscle cells from apoptosis. Immunol Cell Biol 83:651-667.
3. Atanasova G, Jans R, Zhelev N, Mitev V, and Poumay Y (2005) Effects of the cyclin-dependent kinase inhibitor CYC202 (R-roscovitine) on the physiology of cultured human keratinocytes. Biochem Pharmacol 70:824-836.
4. Bach S, Knockaert M, Reinhardt J, Lozach O, Schmitt S, Baratte B, Koken M, Coburn SP, Tang L, Jiang T, et al. (2005) Roscovitine targets, protein kinases and pyridoxal kinase. J Biol Chem 280:31208-31219.
5. Benson C, White J, De Bono J, O'Donnell A, Raynaud F, Cruickshank C, McGrath H, Walton M, Workman P, Kaye S, et al. (2007) A phase I trial of the selective oral cyclin-dependent kinase inhibitor seliciclib (CYC202; R-Roscovitine), administered twice daily for 7 days every 21 days. Br J Cancer 96:29-37.
6. Berellini G, Cruciani G, and Mannhold R (2005) Pharmacophore, drug metabolism, and pharmacokinetics models on non-peptide AT1, AT2, and AT1/AT2 angiotensin II receptor antagonists. J Med Chem 48:4389-4399.
7. Bettayeb K, Oumata N, Echalier A, Ferandin Y, Endicott JA, Galons H, and Meijer L (2008) CR8, a potent and selective, roscovitine-derived inhibitor of cyclindependent kinases. Oncogene 27:5797-5807.
8. Cianchetta G, Mannhold R, Cruciani G, Baroni M, and Cecchetti V (2004) Chemometric studies on the bactericidal activity of quinolones via an extended VolSurf approach. J Med Chem 47:3193-3201.
9. Crivori P, Cruciani G, Carrupt PA, and Testa B (2000) Predicting blood-brain barrier permeation from three-dimensional molecular structure. J Med Chem 43:2204-2216.
10. Crivori P, Zamora I, Speed B, Orrenius C, and Poggesi I (2004) Model based on GRID-derived descriptors for estimating CYP3A4 enzyme stability of potential drug candidates. J Comput Aided Mol Des 18:155-166.
11. Cruciani G, Crivori P, Carrupt PA, and Testa B (2000) Molecular fields in quantitative structure-permeation relationships: the VolSurf approach. Theochem 503: 17-30.
12. Gautschi O, Heighway J, Mack PC, Purnell PR, Lara PN Jr, and Gandara DR (2008) Aurora kinases as anticancer drug targets. Clin Cancer Res 14:1639-1648.
13. Heldin CH and Westermark B (1990) Platelet-derived growth factor: mechanism of action and possible in vivo function. Cell Regul 1:555-566.
14. Krystof V, Moravcová D, Paprskárová M, Barbier P, Peyrot V, Hlobilková A, Havlícek L, and Strnad M (2006) Synthesis and biological activity of 8-azapurine and pyrazolo[4,3-d]pyrimidine analogues of myoseverin. Eur J Med Chem 41:1405-1411.
15. Kukreja N, Onuma Y, Daemen J, and Serruys PW (2008) The future of drug-eluting stents. Pharmacol Res 57:171-180.
16. Li AY, Han M, Zheng B, and Wen JK (2008) Roscovitine inhibits ERK1/2 activation induced by angiotensin II in vascular smooth muscle cells. FEBS Lett 582:243-248.
17. Mannhold R, Cruciani G, Weber H, Lemoine H, Derix A, Weichel C, and Clementi M (1999) 6-Substituted benzopyrans as potassium channel activators: synthesis, vasodilator properties, and multivariate analysis. J Med Chem 42:981-991.
18. McClue SJ and Stuart I (2008) Metabolism of the trisubstituted purine cyclindependent kinase inhibitor seliciclib (R-roscovitine) in vitro and in vivo. Drug Metab Dispos 36:561-570.
19. Meijer L, Borgne A, Mulner O, Chong JP, Blow JJ, Inagaki N, Inagaki M, Delcros JG, and Moulinoux JP (1997) 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.
20. Meijer L and Raymond E (2003) Roscovitine and other purines as kinase inhibitors. From starfish oocytes to clinical trials. Acc Chem Res 36:417-425.
21. Mgbonyebi OP, Russo J, and Russo IH (1999) Roscovitine induces cell death and morphological changes indicative of apoptosis in MDA-MB-231 breast cancer cells. Cancer Res 59:1903-1910.
22. Nutley BP, Raynaud FI, Wilson SC, Fischer PM, Hayes A, Goddard PM, McClue SJ, Jarman M, Lane DP, and Workman P (2005) Metabolism and pharmacokinetics of the cyclin-dependent kinase inhibitor R-roscovitine in the mouse. Mol Cancer Ther 4:125-139.
23. O'Sullivan M, Scott SD, McCarthy N, Figg N, Shapiro LM, Kirkpatrick P, and Bennett MR (2003) Differential cyclin E expression in human in-stent stenosis smooth muscle cells identifies targets for selective anti-restenosis therapy. Cardiovasc Res 60:673-683.
24. Oumata N, Bettayeb K, Ferandin Y, Demange L, Lopez-Giral A, Goddard ML, Myrianthopoulos V, Mikros E, Flajolet M, Greengard P, et al. (2008) Roscovitine-derived, dual-specificity inhibitors of cyclin-dependent kinases and casein kinases 1. J Med Chem 51:5229-5242.
25. Pollard JR and Mortimore M (2009) Discovery and development of aurora kinase inhibitors as anticancer agents. J Med Chem 52:2629-2651.
26. Ravenhall C, Guida E, Harris T, Koutsoubos V, and Stewart A (2000) The importance of ERK activity in the regulation of cyclin D1 levels and DNA synthesis in human cultured airway smooth muscle. Br J Pharmacol 131:17-28.
27. Raynaud FI, Whittaker SR, Fischer PM, McClue S, Walton MI, Barrie SE, Garrett MD, Rogers P, Clarke SJ, Kelland LR, et al. (2005) In vitro and in vivo pharmacokinetic-pharmacodynamic relationships for the trisubstituted aminopurine cyclin-dependent kinase inhibitors olomoucine, bohemine and CYC202. Clin Cancer Res 11:4875-4887.
28. Riccardi C and Nicoletti I (2006) Analysis of apoptosis by propidium iodide staining and flow cytometry. Nat Protoc 1:1458-1461.
29. Steffel J, Eberli FR, Lüscher TF, and Tanner FC (2008) Drug-eluting stents - should be improved? Ann Med 40:242-252.
30. Vita M, Abdel-Rehim M, Nilsson C, Hassan Z, Skansen P, Wan H, Meurling L, and Hassan M (2005a) Stability, pKa and plasma protein binding of roscovitine. J Chromatogr B Analyt Technol Biomed Life Sci 821:75-80.
31. Vita M, Abdel-Rehim M, Olofsson S, Hassan Z, Meurling L, Sidén A, Sidén M, Pettersson T, and Hassan M (2005b) Tissue distribution, pharmacokinetics and identification of roscovitine metabolites in rat. Eur J Pharm Sci 25:91-103.
32. Whittaker SR, Walton MI, Garrett MD, and Workman P (2004) The cyclindependent kinase inhibitor CYC202 (R-roscovitine) inhibits retinoblastoma protein phosphorylation, causes loss of Cyclin D1, and activates the mitogen-activated protein kinase pathway. Cancer Res 64:262-272.
33. Windecker S and Jüni P (2008) Safety of drug-eluting stents. Nat Clin Pract Cardiovasc Med 5:316-328.
34. Zhou H, Kuang J, Zhong L, Kuo WL, Gray JW, Sahin A, Brinkley BR, and Sen S (1998) Tumour amplified kinase STK15/BTAK induces centrosome amplification, aneuploidy and transformation. Nat Genet 20:189-193.