Olomoucine II

• CAT Number: I033858
• CAS Number: 500735-47-7
• Molecular Formula: C19H26N6O2
• Molecular Weight: 370.457
• Purity: 98%
• Solubility: To be determined
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (S)-2-(((2-((1-hydroxybutan-2-yl)amino)-9-isopropyl-9H-purin-6-yl)amino)methyl)phenol
• InChI: InChI=1S/C19H26N6O2/c1-4-14(10-26)22-19-23-17(20-9-13-7-5-6-8-15(13)27)16-18(24-19)25(11-21-16)12(2)3/h5-8,11-12,14,26-27H,4,9-10H2,1-3H3,(H2,20,22,23,24)/t14-/m0/s1
• InChIKey: NDUVSANREQEDRE-AWEZNQCLSA-N
• SMILES: OC[C@H](CC)NC1=NC(NCC2=C(C=CC=C2)O)=C3N=CN(C3=N1)C(C)C

Olomoucine II (CAT: I033858) is a potent and selective inhibitor of cyclin-dependent kinases (CDKs). It specifically targets CDK1, CDK2, CDK5, and CDK7, which are involved in cell cycle regulation and other cellular processes. Olomoucine II inhibits the activity of CDKs by competing with ATP binding, leading to cell cycle arrest and inhibition of cell proliferation. This compound has been extensively used as a research tool to study cell cycle progression, cell growth, and CDK-related signaling pathways. It has also shown potential in anti-cancer research due to its ability to selectively target and inhibit CDKs involved in aberrant cell proliferation observed in cancer cells.

Reference

1: Hofman J, Kučera R, Neumanova Z, Klimes J, Ceckova M, Staud F. Placental passage of olomoucine II, but not purvalanol A, is affected by p-glycoprotein (ABCB1), breast cancer resistance protein (ABCG2) and multidrug resistance- associated proteins (ABCCs). Xenobiotica. 2016;46(5):416-23. doi: 10.3109/00498254.2015.1086039. Epub 2015 Sep 12. PMID: 26364927.
2: Holcakova J, Muller P, Tomasec P, Hrstka R, Nekulova M, Krystof V, Strnad M, Wilkinson GW, Vojtesek B. Inhibition of post-transcriptional RNA processing by CDK inhibitors and its implication in anti-viral therapy. PLoS One. 2014 Feb 21;9(2):e89228. doi: 10.1371/journal.pone.0089228. PMID: 24586613; PMCID: PMC3931720.
3: Cihalova D, Hofman J, Ceckova M, Staud F. Purvalanol A, olomoucine II and roscovitine inhibit ABCB1 transporter and synergistically potentiate cytotoxic effects of daunorubicin in vitro. PLoS One. 2013 Dec 23;8(12):e83467. doi: 10.1371/journal.pone.0083467. PMID: 24376706; PMCID: PMC3871618.
4: Hofman J, Kučera R, Cihalova D, Klimes J, Ceckova M, Staud F. Olomoucine II, but not purvalanol A, is transported by breast cancer resistance protein (ABCG2) and P-glycoprotein (ABCB1). PLoS One. 2013 Oct 8;8(10):e75520. doi: 10.1371/journal.pone.0075520. PMID: 24116053; PMCID: PMC3792958.
5: Wang R, Guo YL. Transient inhibition of cell proliferation does not compromise self-renewal of mouse embryonic stem cells. Exp Cell Res. 2012 Oct 1;318(16):2094-104. doi: 10.1016/j.yexcr.2012.05.017. Epub 2012 Jun 13. PMID: 22705123; PMCID: PMC3408772.
6: Hofman J, Ahmadimoghaddam D, Hahnova L, Pavek P, Ceckova M, Staud F. Olomoucine II and purvalanol A inhibit ABCG2 transporter in vitro and in situ and synergistically potentiate cytostatic effect of mitoxantrone. Pharmacol Res. 2012 Mar;65(3):312-9. doi: 10.1016/j.phrs.2011.11.017. Epub 2011 Dec 6. PMID: 22173067.
7: Siller M, Anzenbacher P, Anzenbacherová E, Doležal K, Strnad M. In vitro interaction of a novel neutrophil growth factor with human liver microsomal cytochromes P450 and the contribution of UDP-glucuronosyltransferases to its metabolism. Xenobiotica. 2011 Nov;41(11):934-44. doi: 10.3109/00498254.2011.593209. Epub 2011 Jul 11. PMID: 21745145.
8: Smejkal K, Svacinová J, Slapetová T, Schneiderová K, Dall’acqua S, Innocenti G, Závalová V, Kollár P, Chudík S, Marek R, Julínek O, Urbanová M, Kartal M, Csöllei M, Dolezal K. Cytotoxic activities of several geranyl-substituted flavanones. J Nat Prod. 2010 Apr 23;73(4):568-72. doi: 10.1021/np900681y. PMID: 20192247.
9: Holcakova J, Tomasec P, Bugert JJ, Wang EC, Wilkinson GW, Hrstka R, Krystof V, Strnad M, Vojtesek B. The inhibitor of cyclin-dependent kinases, olomoucine II, exhibits potent antiviral properties. Antivir Chem Chemother. 2010 Jan 5;20(3):133-42. doi: 10.3851/IMP1460. PMID: 20054100; PMCID: PMC2948526.
10: Koledova Z, Kafkova LR, Calabkova L, Krystof V, Dolezel P, Divoky V. Cdk2 inhibition prolongs G1 phase progression in mouse embryonic stem cells. Stem Cells Dev. 2010 Feb;19(2):181-94. doi: 10.1089/scd.2009.0065. PMID: 19737069.
11: Paprskárová M, Krystof V, Jorda R, Dzubák P, Hajdúch M, Wesierska-Gadek J, Strnad M. Functional p53 in cells contributes to the anticancer effect of the cyclin-dependent kinase inhibitor roscovitine. J Cell Biochem. 2009 Jun 1;107(3):428-37. doi: 10.1002/jcb.22139. PMID: 19308936.
12: Siller M, Anzenbacher P, Anzenbacherova E, Dolezal K, Popa I, Strnad M. Interactions of olomoucine II with human liver microsomal cytochromes P450. Drug Metab Dispos. 2009 Jun;37(6):1198-202. doi: 10.1124/dmd.108.025502. Epub 2009 Feb 27. PMID: 19251823.
13: Krystof V, McNae IW, Walkinshaw MD, Fischer PM, Müller P, Vojtesek B, Orság M, Havlícek L, Strnad M. Antiproliferative activity of olomoucine II, a novel 2,6,9-trisubstituted purine cyclin-dependent kinase inhibitor. Cell Mol Life Sci. 2005 Aug;62(15):1763-71. doi: 10.1007/s00018-005-5185-1. PMID: 16003486.
14: Krystof V, Lenobel R, Havlícek L, Kuzma M, Strnad M. Synthesis and biological activity of olomoucine II. Bioorg Med Chem Lett. 2002 Nov 18;12(22):3283-6. doi: 10.1016/s0960-894x(02)00693-5. PMID: 12392733.
15: Lenobel R, Havli L, Kryscaron PV, Otyepka M, Strnad M. Olomoucine II, New Effective CDK Inhibitor with Strong Cytotoxic Properties. ScientificWorldJournal. 2001 Oct 17;1:128. doi: 10.1100/tsw.2001.227. PMID: 30147607; PMCID: PMC6084208.