UCPH-101
featured

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

MedKoo CAT#: 532868

CAS#: 1118460-77-7

Description: UCPH-101 is a selective excitatory amino acid transporter subtype 1 (EAAT1) inhibitor.


Price and Availability

Size
Price

10mg
USD 325
Size
Price

50mg
USD 1250
Size
Price

UCPH-101, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 532868
Name: UCPH-101
CAS#: 1118460-77-7
Chemical Formula: C27H22N2O3
Exact Mass: 422.163
Molecular Weight: 422.48
Elemental Analysis: C, 76.76; H, 5.25; N, 6.63; O, 11.36


Synonym: UCPH-101, UCPH 101, UCPH101

IUPAC/Chemical Name: 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

InChi Key: YBMGNDPBARCLFT-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H22N2O3/c1-31-19-11-9-17(10-12-19)25-22(15-28)27(29)32-24-14-18(13-23(30)26(24)25)21-8-4-6-16-5-2-3-7-20(16)21/h2-12,18,25H,13-14,29H2,1H3

SMILES Code: N#CC1=C(N)OC2=C(C(CC(C3=C4C=CC=CC4=CC=C3)C2)=O)C1C5=CC=C(OC)C=C5


Technical Data

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

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: Haym I, Huynh TH, Hansen SW, Pedersen MH, Ruiz JA, Erichsen MN, Gynther M, Bjørn-Yoshimoto WE, Abrahamsen B, Bastlund JF, Bundgaard C, Eriksen AL, Jensen AA, Bunch L. Bioavailability Studies and in vitro Profiling of the Selective Excitatory Amino Acid Transporter Subtype 1 (EAAT1) Inhibitor UCPH-102. ChemMedChem. 2016 Feb 17;11(4):403-19. doi: 10.1002/cmdc.201500527. Epub 2016 Jan 21. PubMed PMID: 26797816.

2: Hansen SW, Erichsen MN, Huynh TH, Ruiz JA, Haym I, Bjørn-Yoshimoto WE, Abrahamsen B, Hansen J, Storgaard M, Eriksen AL, Jensen AA, Bunch L. New Insight into the Structure-Activity Relationships of the Selective Excitatory Amino Acid Transporter Subtype 1 (EAAT1) Inhibitors UCPH-101 and UCPH-102. ChemMedChem. 2016 Feb 17;11(4):382-402. doi: 10.1002/cmdc.201500525. Epub 2016 Jan 12. PubMed PMID: 26757239.

3: Erichsen MN, Hansen J, Ruiz JA, Demmer CS, Abrahamsen B, Bastlund JF, Bundgaard C, Jensen AA, Bunch L. Probing for improved potency and in vivo bioavailability of excitatory amino acid transporter subtype 1 inhibitors UCPH-101 and UCPH-102: design, synthesis and pharmacological evaluation of substituted 7-biphenyl analogs. Neurochem Res. 2014 Oct;39(10):1964-79. doi: 10.1007/s11064-014-1264-8. Epub 2014 Feb 28. PubMed PMID: 24682739.

4: Abrahamsen B, Schneider N, Erichsen MN, Huynh TH, Fahlke C, Bunch L, Jensen AA. Allosteric modulation of an excitatory amino acid transporter: the subtype-selective inhibitor UCPH-101 exerts sustained inhibition of EAAT1 through an intramonomeric site in the trimerization domain. J Neurosci. 2013 Jan 16;33(3):1068-87. doi: 10.1523/JNEUROSCI.3396-12.2013. PubMed PMID: 23325245.

5: Takaki J, Fujimori K, Miura M, Suzuki T, Sekino Y, Sato K. L-glutamate released from activated microglia downregulates astrocytic L-glutamate transporter expression in neuroinflammation: the 'collusion' hypothesis for increased extracellular L-glutamate concentration in neuroinflammation. J Neuroinflammation. 2012 Dec 23;9:275. doi: 10.1186/1742-2094-9-275. PubMed PMID: 23259598; PubMed Central PMCID: PMC3575281.

6: Huynh TH, Abrahamsen B, Madsen KK, Gonzalez-Franquesa A, Jensen AA, Bunch L. Design, synthesis and pharmacological characterization of coumarin-based fluorescent analogs of excitatory amino acid transporter subtype 1 selective inhibitors, UCPH-101 and UCPH-102. Bioorg Med Chem. 2012 Dec 1;20(23):6831-9. doi: 10.1016/j.bmc.2012.09.049. Epub 2012 Oct 2. PubMed PMID: 23072958.

7: Lane DJ, Lawen A. The glutamate aspartate transporter (GLAST) mediates L-glutamate-stimulated ascorbate-release via swelling-activated anion channels in cultured neonatal rodent astrocytes. Cell Biochem Biophys. 2013 Mar;65(2):107-19. doi: 10.1007/s12013-012-9404-8. PubMed PMID: 22886112.

8: Huynh TH, Shim I, Bohr H, Abrahamsen B, Nielsen B, Jensen AA, Bunch L. Structure-activity relationship study of selective excitatory amino acid transporter subtype 1 (EAAT1) inhibitor 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chrom ene-3-carbonitrile (UCPH-101) and absolute configurational assignment using infrared and vibrational circular dichroism spectroscopy in combination with ab initio Hartree-Fock calculations. J Med Chem. 2012 Jun 14;55(11):5403-12. doi: 10.1021/jm300345z. Epub 2012 May 17. PubMed PMID: 22594609.

9: Erichsen MN, Huynh TH, Abrahamsen B, Bastlund JF, Bundgaard C, Monrad O, Bekker-Jensen A, Nielsen CW, Frydenvang K, Jensen AA, Bunch L. Structure-activity relationship study of first selective inhibitor of excitatory amino acid transporter subtype 1: 2-Amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chrom ene-3-carbonitrile (UCPH-101). J Med Chem. 2010 Oct 14;53(19):7180-91. doi: 10.1021/jm1009154. PubMed PMID: 20857912.