Olomoucine | CAS#101622-51-9 | CDK inhibitor

MedKoo Cat#: 406180 | Name: Olomoucine

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Description:

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

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. Cdk5 inhibition by Olomoucine significantly increases current density through Ca(V)1.3 (L-type) channels heterologously expressed in HEK293 cells.

Chemical Structure

Olomoucine

CAS#101622-51-9

Theoretical Analysis

MedKoo Cat#: 406180

Name: Olomoucine

CAS#: 101622-51-9

Chemical Formula: C15H18N6O

Exact Mass: 298.1542

Molecular Weight: 298.35

Elemental Analysis: C, 60.39; H, 6.08; N, 28.17; O, 5.36

Price and Availability

Size	Price	Availability
5mg	USD 385.00	2 Weeks
10mg	USD 620.00	2 Weeks
25mg	USD 950.00	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

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	66.7	223.46

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

1: Loncová B, Fabová Z, Sirotkin AV. Involvement of obestatin, cyclin-dependent kinase and protein kinase C in control of feline ovarian cell viability and hormones release. Reprod Biol. 2021 Dec;21(4):100560. doi: 10.1016/j.repbio.2021.100560. Epub 2021 Sep 16. PMID: 34536914. 2: Yew WP, Djukic ND, Jayaseelan JSP, Woodman RJ, Muyderman H, Sims NR. Differential effects of the cell cycle inhibitor, olomoucine, on functional recovery and on responses of peri-infarct microglia and astrocytes following photothrombotic stroke in rats. J Neuroinflammation. 2021 Jul 31;18(1):168. doi: 10.1186/s12974-021-02208-w. PMID: 34332596; PMCID: PMC8325288. 3: Gomez K, Vargas-Parada A, Duran P, Sandoval A, Delgado-Lezama R, Khanna R, Felix R. L5-6 Spinal Nerve Ligation-induced Neuropathy Changes the Location and Function of Ca2+ Channels and Cdk5 and Affects the Compound Action Potential in Adjacent Intact L4 Afferent Fibers. Neuroscience. 2021 Sep 1;471:20-31. doi: 10.1016/j.neuroscience.2021.07.013. Epub 2021 Jul 22. PMID: 34303780; PMCID: PMC8384716. 4: Olivos-Cisneros L, Ramírez-Santos J, Gutiérrez-Ospina G. Proliferation rate and differentiation potential are independent during the transition from neurogenesis to gliogenesis in the mouse embryonic spinal cord. IBRO Neurosci Rep. 2021 Jan 2;10:75-82. doi: 10.1016/j.ibneur.2020.11.004. PMID: 33842913; PMCID: PMC8019975. 5: Makki MST, Abdel-Rahman RM, Alshammari NAH. Synthesis of Novel Fluorine Compounds Substituted-4-thiazolidinones Derived from Rhodanine Drug as Highly Bioactive Probes. Curr Org Synth. 2019;16(3):413-422. doi: 10.2174/1570179416666190312150046. PMID: 31984903; PMCID: PMC7432185. 6: Loya-López S, Sandoval A, González-Ramírez R, Calderón-Rivera A, Ávalos- Fuentes A, Rodríguez-Sánchez M, Caballero R, Tovar-Soto D, Felix R, Florán B. Cdk5 phosphorylates CaV1.3 channels and regulates GABAA-mediated miniature inhibitory post-synaptic currents in striato-nigral terminals. Biochem Biophys Res Commun. 2020 Mar 26;524(1):255-261. doi: 10.1016/j.bbrc.2020.01.084. Epub 2020 Jan 23. PMID: 31983427. 7: Gomez K, Calderón-Rivera A, Sandoval A, González-Ramírez R, Vargas-Parada A, Ojeda-Alonso J, Granados-Soto V, Delgado-Lezama R, Felix R. Cdk5-Dependent Phosphorylation of CaV3.2 T-Type Channels: Possible Role in Nerve Ligation-Induced Neuropathic Allodynia and the Compound Action Potential in Primary Afferent C Fibers. J Neurosci. 2020 Jan 8;40(2):283-296. doi: 10.1523/JNEUROSCI.0181-19.2019. Epub 2019 Nov 19. PMID: 31744861; PMCID: PMC6948938. 8: Ding Y, Zhang T, Wu G, McBride DW, Xu N, Klebe DW, Zhang Y, Li Q, Tang J, Zhang JH. Astrogliosis inhibition attenuates hydrocephalus by increasing cerebrospinal fluid reabsorption through the glymphatic system after germinal matrix hemorrhage. Exp Neurol. 2019 Oct;320:113003. doi: 10.1016/j.expneurol.2019.113003. Epub 2019 Jun 28. PMID: 31260658; PMCID: PMC6709595. 9: Kwon DJ, Hwang IS, Kwak TU, Yang H, Park MR, Ock SA, Oh KB, Woo JS, Im GS, Hwang S. Effects of Cell Cycle Regulators on the Cell Cycle Synchronization of Porcine induced Pluripotent Stem Cells. Dev Reprod. 2017 Mar;21(1):47-54. doi: 10.12717/DR.2017.21.1.047. Epub 2017 Mar 31. PMID: 28484743; PMCID: PMC5409209. 10: Hyun HW, Min SJ, Kim JE. CDK5 inhibitors prevent astroglial apoptosis and reactive astrogliosis by regulating PKA and DRP1 phosphorylations in the rat hippocampus. Neurosci Res. 2017 Jun;119:24-37. doi: 10.1016/j.neures.2017.01.006. Epub 2017 Jan 30. PMID: 28153522. 11: Tsou YC, Wang HH, Hsieh CC, Sun KH, Sun GH, Jhou RS, Lin TI, Lu SY, Liu HY, Tang SJ. Down-regulation of BNIP3 by olomoucine, a CDK inhibitor, reduces LPS- and NO-induced cell death in BV2 microglial cells. Neurosci Lett. 2016 Aug 15;628:186-93. doi: 10.1016/j.neulet.2016.06.040. Epub 2016 Jun 21. PMID: 27345388. 12: Gray KA, Gresty KJ, Chen N, Zhang V, Gutteridge CE, Peatey CL, Chavchich M, Waters NC, Cheng Q. Correlation between Cyclin Dependent Kinases and Artemisinin-Induced Dormancy in Plasmodium falciparum In Vitro. PLoS One. 2016 Jun 21;11(6):e0157906. doi: 10.1371/journal.pone.0157906. PMID: 27326764; PMCID: PMC4915707. 13: Zhou Y, Zeng YP, Zhou Q, Guan JX, Lu ZN. The effect of cyclin-dependent kinases inhibitor treatment on experimental herpes simplex encephalitis mice. Neurosci Lett. 2016 Aug 3;627:71-6. doi: 10.1016/j.neulet.2016.05.059. Epub 2016 May 27. PMID: 27241721. 14: Akiba Y, Mizuta A, Kakihara Y, Nakata J, Nihara J, Saito I, Egusa H, Saeki M. The inhibitors of cyclin-dependent kinases and GSK-3β enhance osteoclastogenesis. Biochem Biophys Rep. 2015 Dec 30;5:253-258. doi: 10.1016/j.bbrep.2015.12.011. PMID: 28955831; PMCID: PMC5600418. 15: 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. 16: Bacot SM, Feldman GM, Yamada KM, Dhawan S. Pathogenic prion protein fragment (PrP106-126) promotes human immunodeficiency virus type-1 infection in peripheral blood monocyte-derived macrophages. Virology. 2015 Feb;476:372-376. doi: 10.1016/j.virol.2014.11.032. Epub 2015 Jan 9. PMID: 25589240; PMCID: PMC5282598. 17: Chen L, Li J, Wu L, Yang M, Gao F, Yuan L. Synergistic actions of olomoucine and bone morphogenetic protein-4 in axonal repair after acute spinal cord contusion. Neural Regen Res. 2014 Oct 15;9(20):1830-8. doi: 10.4103/1673-5374.143431. PMID: 25422646; PMCID: PMC4239774. 18: Ho HP, Rathod P, Louis M, Tada CK, Rahaman S, Mark KJ, Leng J, Dana D, Kumar S, Lichterfeld M, Chang EJ. Studies on quantitative phosphopeptide analysis by matrix-assisted laser desorption/ionization mass spectrometry without label, chromatography or calibration curves. Rapid Commun Mass Spectrom. 2014 Dec 30;28(24):2681-9. doi: 10.1002/rcm.7063. PMID: 25380489; PMCID: PMC4225566. 19: Norez C, Vandebrouck C, Bertrand J, Noel S, Durieu E, Oumata N, Galons H, Antigny F, Chatelier A, Bois P, Meijer L, Becq F. Roscovitine is a proteostasis regulator that corrects the trafficking defect of F508del-CFTR by a CDK- independent mechanism. Br J Pharmacol. 2014 Nov;171(21):4831-49. doi: 10.1111/bph.12859. PMID: 25065395; PMCID: PMC4294108. 20: 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.