UBP302

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

MedKoo CAT#: 532855

CAS#: 745055-91-8

Description: UBP302 is a potent and selective GLUK5 (GluR5)-subunit containing kainate receptor antagonist (apparent KD = 402 nM). UBP302 displays ~ 260-fold selectivity over AMPA receptors, ~ 90-fold selectivity over recombinant human GLUK6- and GLUK2-containing kainate receptors and has little or no action at NMDA or group I mGlu receptors. UBP302 selectively blocks kainate receptor-mediated LTP induction in rat hippocampal mossy fibers.


Price and Availability

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UBP302 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 532855
Name: UBP302
CAS#: 745055-91-8
Chemical Formula: C15H15N3O6
Exact Mass: 333.0961
Molecular Weight: 333.3
Elemental Analysis: C, 54.05; H, 4.54; N, 12.61; O, 28.80


Synonym: UBP302, UBP-302, UBP 302

IUPAC/Chemical Name: 2-({3-[(2S)-2-amino-2-carboxyethyl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl}methyl)benzoic acid

InChi Key: UUIYULWYHDSXHL-NSHDSACASA-N

InChi Code: InChI=1S/C15H15N3O6/c16-11(14(22)23)8-17-6-5-12(19)18(15(17)24)7-9-3-1-2-4-10(9)13(20)21/h1-6,11H,7-8,16H2,(H,20,21)(H,22,23)/t11-/m0/s1

SMILES Code: O=C(O)C1=CC=CC=C1CN(C(N(C[C@H](N)C(O)=O)C=C2)=O)C2=O


Technical Data

Appearance:
White 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

Shelf Life:
>2 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).

Harmonized System Code:
293490


References

1: Miller SL, Aroniadou-Anderjaska V, Figueiredo TH, Prager EM, Almeida-Suhett CP, Apland JP, Braga MF. A rat model of nerve agent exposure applicable to the pediatric population: The anticonvulsant efficacies of atropine and GluK1 antagonists. Toxicol Appl Pharmacol. 2015 Apr 15;284(2):204-16. doi: 10.1016/j.taap.2015.02.008. Epub 2015 Feb 15. PubMed PMID: 25689173; PubMed Central PMCID: PMC4545593.

2: Andreou AP, Holland PR, Lasalandra MP, Goadsby PJ. Modulation of nociceptive dural input to the trigeminocervical complex through GluK1 kainate receptors. Pain. 2015 Mar;156(3):439-50. doi: 10.1097/01.j.pain.0000460325.25762.c0. PubMed PMID: 25679470.

3: Apland JP, Aroniadou-Anderjaska V, Figueiredo TH, Rossetti F, Miller SL, Braga MF. The limitations of diazepam as a treatment for nerve agent-induced seizures and neuropathology in rats: comparison with UBP302. J Pharmacol Exp Ther. 2014 Nov;351(2):359-72. doi: 10.1124/jpet.114.217299. Epub 2014 Aug 25. PubMed PMID: 25157087; PubMed Central PMCID: PMC4201270.

4: Ohkubo J, Ohbuchi T, Yoshimura M, Maruyama T, Ishikura T, Matsuura T, Suzuki H, Ueta Y. Electrophysiological effects of kainic acid on vasopressin-enhanced green fluorescent protein and oxytocin-monomeric red fluorescent protein 1 neurones isolated from the supraoptic nucleus in transgenic rats. J Neuroendocrinol. 2014 Jan;26(1):43-51. doi: 10.1111/jne.12128. PubMed PMID: 24341559.

5: Aroniadou-Anderjaska V, Pidoplichko VI, Figueiredo TH, Almeida-Suhett CP, Prager EM, Braga MF. Presynaptic facilitation of glutamate release in the basolateral amygdala: a mechanism for the anxiogenic and seizurogenic function of GluK1 receptors. Neuroscience. 2012 Sep 27;221:157-69. doi: 10.1016/j.neuroscience.2012.07.006. Epub 2012 Jul 13. PubMed PMID: 22796081; PubMed Central PMCID: PMC3443632.

6: Koga K, Sim SE, Chen T, Wu LJ, Kaang BK, Zhuo M. Kainate receptor-mediated synaptic transmissions in the adult rodent insular cortex. J Neurophysiol. 2012 Oct;108(7):1988-98. doi: 10.1152/jn.00453.2012. Epub 2012 Jul 11. PubMed PMID: 22786952.

7: Ho JW, Narduzzo KE, Outram A, Tinsley CJ, Henley JM, Warburton EC, Brown MW. Contributions of area Te2 to rat recognition memory. Learn Mem. 2011 Jun 23;18(7):493-501. doi: 10.1101/lm.2167511. Print 2011 Jul. PubMed PMID: 21700715; PubMed Central PMCID: PMC3125610.

8: Randall FE, Whittington MA, Cunningham MO. Fast oscillatory activity induced by kainate receptor activation in the rat basolateral amygdala in vitro. Eur J Neurosci. 2011 Mar;33(5):914-22. doi: 10.1111/j.1460-9568.2010.07582.x. Epub 2011 Jan 24. PubMed PMID: 21255131; PubMed Central PMCID: PMC3627304.

9: Gee CE, Benquet P, Demont-Guignard S, Wendling F, Gerber U. Energy deprivation transiently enhances rhythmic inhibitory events in the CA3 hippocampal network in vitro. Neuroscience. 2010 Jul 14;168(3):605-12. doi: 10.1016/j.neuroscience.2010.04.021. Epub 2010 Apr 18. PubMed PMID: 20403414.

10: Andreou AP, Holland PR, Goadsby PJ. Activation of iGluR5 kainate receptors inhibits neurogenic dural vasodilatation in an animal model of trigeminovascular activation. Br J Pharmacol. 2009 Jun;157(3):464-73. doi: 10.1111/j.1476-5381.2009.00142.x. Epub 2009 Mar 20. PubMed PMID: 19309356; PubMed Central PMCID: PMC2707992.

11: Wondolowski J, Frerking M. Subunit-dependent postsynaptic expression of kainate receptors on hippocampal interneurons in area CA1. J Neurosci. 2009 Jan 14;29(2):563-74. doi: 10.1523/JNEUROSCI.4788-08.2009. PubMed PMID: 19144856; PubMed Central PMCID: PMC2746435.

12: Apland JP, Aroniadou-Anderjaska V, Braga MF. Soman induces ictogenesis in the amygdala and interictal activity in the hippocampus that are blocked by a GluR5 kainate receptor antagonist in vitro. Neuroscience. 2009 Mar 3;159(1):380-9. doi: 10.1016/j.neuroscience.2008.11.053. Epub 2008 Dec 14. PubMed PMID: 19136046; PubMed Central PMCID: PMC2947795.

13: Perrais D, Pinheiro PS, Jane DE, Mulle C. Antagonism of recombinant and native GluK3-containing kainate receptors. Neuropharmacology. 2009 Jan;56(1):131-40. doi: 10.1016/j.neuropharm.2008.08.002. Epub 2008 Aug 12. PubMed PMID: 18761361.

14: Barker GR, Warburton EC. NMDA receptor plasticity in the perirhinal and prefrontal cortices is crucial for the acquisition of long-term object-in-place associative memory. J Neurosci. 2008 Mar 12;28(11):2837-44. doi: 10.1523/JNEUROSCI.4447-07.2008. PubMed PMID: 18337414.

15: Partovi D, Frerking M. Presynaptic inhibition by kainate receptors converges mechanistically with presynaptic inhibition by adenosine and GABAB receptors. Neuropharmacology. 2006 Nov;51(6):1030-7. Epub 2006 Aug 8. PubMed PMID: 16895731.

16: Mayer ML, Ghosal A, Dolman NP, Jane DE. Crystal structures of the kainate receptor GluR5 ligand binding core dimer with novel GluR5-selective antagonists. J Neurosci. 2006 Mar 15;26(11):2852-61. PubMed PMID: 16540562.

17: More JC, Nistico R, Dolman NP, Clarke VR, Alt AJ, Ogden AM, Buelens FP, Troop HM, Kelland EE, Pilato F, Bleakman D, Bortolotto ZA, Collingridge GL, Jane DE. Characterisation of UBP296: a novel, potent and selective kainate receptor antagonist. Neuropharmacology. 2004 Jul;47(1):46-64. PubMed PMID: 15165833.