Olomoucine II | CAS#500735-47-7 | CDK inhibitor

MedKoo Cat#: 464409 | Name: Olomoucine II

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Olomoucine II is an inhibitor of cyclin-dependent kinases (CDKs; IC50s = 7.6, 0.1, 19.8, 0.45, and 0.06 µM for Cdk1, -2, -4, -7, and -9, respectively). It is selective for CDKs over 10 additional kinases (IC50s = >100 µM for all) but does inhibit ERK2 (IC50 = 32 µM) and the ATP-binding cassette transporter B1 (ABCB1; IC50 = 6.4 µM). Olomoucine II inhibits proliferation of a variety of cancer cells, including those expressing wild-type p53 or mutant p53 (mean IC50s = 7.4 and 10.1 µM, respectively), and it acts synergistically with daunorubicin to inhibit proliferation of HCT-8 cells that endogenously express ABCB1. Olomoucine also inhibits replication of herpes simplex virus 1 (HSV-1), HSV-2, vaccinia virus, human adenovirus type 4 (Ad4), and human CMV (IC50s = 5, 4.7, 3.8, 2.4, and 3.2 µM, respectively) but not measles virus or influenza virus (IC50s = >20 µM for both).

Chemical Structure

Olomoucine II

CAS#500735-47-7

Theoretical Analysis

MedKoo Cat#: 464409

Name: Olomoucine II

CAS#: 500735-47-7

Chemical Formula: C19H26N6O2

Exact Mass: 370.2117

Molecular Weight: 370.46

Elemental Analysis: C, 61.60; H, 7.07; N, 22.69; O, 8.64

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 500.00	2 Weeks
5mg	USD 800.00	2 Weeks

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Synonym

Olomoucine II; Olomoucine-II;

IUPAC/Chemical Name

(S)-2-(((2-((1-hydroxybutan-2-yl)amino)-9-isopropyl-9H-purin-6-yl)amino)methyl)phenol

InChi Key

NDUVSANREQEDRE-AWEZNQCLSA-N

InChi Code

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

SMILES Code

OC[C@H](CC)NC1=NC(NCC2=C(C=CC=C2)O)=C3N=CN(C3=N1)C(C)C

Appearance

Solid powder

Purity

>95% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Olomoucine II is an inhibitor of cyclin-dependent kinases.

In vitro activity:

This follow up study investigated whether olomoucine II and purvalanol A are transported by ABCG2 and ABCB1 (P-glycoprotein). Using monolayers of MDCKII cells stably expressing human ABCB1 or ABCG2, this study demonstrated that olomoucine II, but not purvalanol A, is a dual substrate of both ABCG2 and ABCB1. Reference: PLoS One. 2013 Oct 8;8(10):e75520. https://pubmed.ncbi.nlm.nih.gov/24116053/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 370.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. 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. 2. 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.

In vitro protocol:

In vivo protocol:

TBD

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.