Olomoucine
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MedKoo CAT#: 406180

CAS#: 101622-51-9

Description: Olomoucine is a CDK inhibitor that competes for the ATP binding site of the kinase. Olomoucine was shown to reversibly arrest differentiated Petunia cells induced to divide at G1 phase and cycling Arabidopsis cells in late G1 and G2.


Chemical Structure

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Olomoucine
CAS# 101622-51-9

Theoretical Analysis

MedKoo Cat#: 406180
Name: Olomoucine
CAS#: 101622-51-9
Chemical Formula: C15H18N6O
Exact Mass: 298.15
Molecular Weight: 298.350
Elemental Analysis: C, 60.39; H, 6.08; N, 28.17; O, 5.36

Price and Availability

Size Price Availability Quantity
5mg USD 285 2 Weeks
10mg USD 520 2 Weeks
25mg USD 950 2 Weeks
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Synonym: Olomoucine

IUPAC/Chemical Name: 6-(Benzylamino)-2-(2-hydroxyethylamino)-9-methylpurine

InChi Key: GTVPOLSIJWJJNY-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H18N6O/c1-21-10-18-12-13(17-9-11-5-3-2-4-6-11)19-15(16-7-8-22)20-14(12)21/h2-6,10,22H,7-9H2,1H3,(H2,16,17,19,20)

SMILES Code: CN1C=NC2=C(NCC3=CC=CC=C3)N=C(NCCO)N=C12

Appearance: Solid powder

Purity: >98% (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: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:
Biological target: Olomoucine is an ATP competitive inhibitor of CDKs. Olomoucine is a purine (HY-34431) derivative and inhibits CDC2/cyclin B, Cdk2/cyclin A, Cdk2/cyclin E (both IC50=7 µM), CDK/p35 kinase (IC50=3 µM) and ERK1/p44 MAP kinase (IC50=25 µM).
In vitro activity: Kinetic analysis of kinase inhibition reveals that olomoucine behaves as a competitive inhibitor for ATP and as a non-competitive inhibitor for histone H1 (linear inhibition for both substrates). Olomoucine inhibits in vitro M-phase-promoting factor activity in metaphase-arrested Xenopus egg extracts, inhibits in vitro DNA synthesis in Xenopus interphase egg extracts and inhibits the licensing factor, an essential replication factor ensuring that DNA is replicated only once in each cell cycle. Reference: Eur J Biochem. 1994 Sep 1;224(2):771-86. https://pubmed.ncbi.nlm.nih.gov/7925396/
In vivo activity: Corneal debridement wounds of 1.5 mm were made on the ocular surface of CD-1 mice. A 20 microl drop of 15 microM olomoucine in 1% DMSO was applied to the wound area immediately after wounding and again after 6 h. Olomoucine treatment significantly enhanced corneal wound closure without increasing inflammation or infiltration of polymorphonuclear leukocytes 18 h after wounding (p<0.05). The increased localization of MMP-9 within epithelial cells at the wound edge was further enhanced by olomoucine while the expression of MMP-2 was reduced. Olomoucine treatment of scratch wounded HCLE cells produced similar changes in MMP-9 and MMP-2 expression. Reference: Mol Vis. 2008 Mar 17;14:542-9. https://pubmed.ncbi.nlm.nih.gov/18385789/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 66.7 223.46

Preparing Stock Solutions

The following data is based on the product molecular weight 298.35 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.

Recalculate based on batch purity %
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. Abraham RT, Acquarone M, Andersen A, Asensi A, Bellé R, Berger F, Bergounioux C, Brunn G, Buquet-Fagot C, Fagot D, et al. Cellular effects of olomoucine, an inhibitor of cyclin-dependent kinases. Biol Cell. 1995;83(2-3):105-20. doi: 10.1016/0248-4900(96)81298-6. PMID: 7549905. 2. Veselý J, Havlicek L, Strnad M, Blow JJ, Donella-Deana A, Pinna L, Letham DS, Kato J, Detivaud L, Leclerc S, et al. Inhibition of cyclin-dependent kinases by purine analogues. Eur J Biochem. 1994 Sep 1;224(2):771-86. doi: 10.1111/j.1432-1033.1994.00771.x. PMID: 7925396. 3. Tripathi BK, Stepp MA, Gao CY, Zelenka PS. The Cdk5 inhibitor olomoucine promotes corneal debridement wound closure in vivo. Mol Vis. 2008 Mar 17;14:542-9. PMID: 18385789; PMCID: PMC2274924. 4. Tian DS, Dong Q, Pan DJ, He Y, Yu ZY, Xie MJ, Wang W. Attenuation of astrogliosis by suppressing of microglial proliferation with the cell cycle inhibitor olomoucine in rat spinal cord injury model. Brain Res. 2007 Jun 18;1154:206-14. doi: 10.1016/j.brainres.2007.04.005. Epub 2007 Apr 6. PMID: 17482149.
In vitro protocol: 1. Abraham RT, Acquarone M, Andersen A, Asensi A, Bellé R, Berger F, Bergounioux C, Brunn G, Buquet-Fagot C, Fagot D, et al. Cellular effects of olomoucine, an inhibitor of cyclin-dependent kinases. Biol Cell. 1995;83(2-3):105-20. doi: 10.1016/0248-4900(96)81298-6. PMID: 7549905. 2. Veselý J, Havlicek L, Strnad M, Blow JJ, Donella-Deana A, Pinna L, Letham DS, Kato J, Detivaud L, Leclerc S, et al. Inhibition of cyclin-dependent kinases by purine analogues. Eur J Biochem. 1994 Sep 1;224(2):771-86. doi: 10.1111/j.1432-1033.1994.00771.x. PMID: 7925396.
In vivo protocol: 1. Tripathi BK, Stepp MA, Gao CY, Zelenka PS. The Cdk5 inhibitor olomoucine promotes corneal debridement wound closure in vivo. Mol Vis. 2008 Mar 17;14:542-9. PMID: 18385789; PMCID: PMC2274924. 2. Tian DS, Dong Q, Pan DJ, He Y, Yu ZY, Xie MJ, Wang W. Attenuation of astrogliosis by suppressing of microglial proliferation with the cell cycle inhibitor olomoucine in rat spinal cord injury model. Brain Res. 2007 Jun 18;1154:206-14. doi: 10.1016/j.brainres.2007.04.005. Epub 2007 Apr 6. PMID: 17482149.

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1: 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. PubMed PMID: 22173067.

2: Korinkova G, Cwiertka K, Paprskarova M, Dzubak P, Hajduch M. The radiosensitising effect of olomoucine derived synthetic cyclin-dependent kinase inhibitors. Neoplasma. 2010;57(2):161-9. PubMed PMID: 20099981.

3: 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. PubMed PMID: 20054100; PubMed Central PMCID: PMC2948526.

4: Małecki JM, Bentke A, Ostrowska B, Laidler P. Cytochalasin D, LY294002 and olomoucine synergize in promoting death of melanoma cells through activation of caspase-3 and apoptosis. Melanoma Res. 2010 Feb;20(1):52-8. doi: 10.1097/CMR.0b013e328332f1e6. PubMed PMID: 20010439.

5: Wandl S, Wesierska-Gadek J. Is olomoucine, a weak CDK2 inhibitor, able to induce apoptosis in cancer cells? Ann N Y Acad Sci. 2009 Aug;1171:242-9. doi: 10.1111/j.1749-6632.2009.04700.x. PubMed PMID: 19723061.

6: Fei XF, Qin ZH, Xiang B, Li LY, Han F, Fukunaga K, Liang ZQ. Olomoucine inhibits cathepsin L nuclear translocation, activates autophagy and attenuates toxicity of 6-hydroxydopamine. Brain Res. 2009 Apr 6;1264:85-97. doi: 10.1016/j.brainres.2009.01.057. Epub 2009 Feb 6. PubMed PMID: 19368812.

7: 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. PubMed PMID: 19251823.

8: Jhou RS, Sun KH, Sun GH, Wang HH, Chang CI, Huang HC, Lu SY, Tang SJ. Inhibition of cyclin-dependent kinases by olomoucine and roscovitine reduces lipopolysaccharide-induced inflammatory responses via down-regulation of nuclear factor kappaB. Cell Prolif. 2009 Apr;42(2):141-9. doi: 10.1111/j.1365-2184.2009.00584.x. Epub 2009 Feb 24. PubMed PMID: 19250292.

9: Tripathi BK, Stepp MA, Gao CY, Zelenka PS. The Cdk5 inhibitor olomoucine promotes corneal debridement wound closure in vivo. Mol Vis. 2008 Mar 17;14:542-9. PubMed PMID: 18385789; PubMed Central PMCID: PMC2274924.

10: Wesierska-Gadek J, Gueorguieva M, Kramer MP, Ranftler C, Sarg B, Lindner H. A new, unexpected action of olomoucine, a CDK inhibitor, on normal human cells: up-regulation of CLIMP-63, a cytoskeleton-linking membrane protein. J Cell Biochem. 2007 Dec 15;102(6):1405-19. PubMed PMID: 17975794.