WAY 213613 - CAS 868359-05-1
Category: Inhibitor
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Molecular Formula:
C16H13BrF2N2O4
Molecular Weight:
415.19
COA:
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Targets:
EAAT2
Description:
WAY 213613 is a potent and non-substrate inhibitor of EAAT2 (GLT-1), displaying > 44-fold selectivity over EAAT1 and EAAT3 (IC50 = 85, 3787 and 5004 nM for EAAT2, EAAT3 and EAAT1, respectively). WAY 213613 exhibits no activity towards ionotropic and metabotropic glutamate receptors.
Brife Description:
EAAT2 (GLT-1) inhibitor
Purity:
≥99% by HPLC
Synonyms:
WAY 213613; WAY213613; WAY-213613; N-[4-(2-Bromo-4,5-difluorophenoxy)phenyl]-L-asparagine; (2S)-2-amino-4-[4-(2-bromo-4,5-difluorophenoxy)anilino]-4-oxobutanoic acid
MSDS:
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InChIKey:
BNYDDAAZMBUFRG-ZDUSSCGKSA-N
InChI:
InChI=1S/C16H13BrF2N2O4/c17-10-5-11(18)12(19)6-14(10)25-9-3-1-8(2-4-9)21-15(22)7-13(20)16(23)24/h1-6,13H,7,20H2,(H,21,22)(H,23,24)/t13-/m0/s1
Canonical SMILES:
C1=CC(=CC=C1NC(=O)CC(C(=O)O)N)OC2=CC(=C(C=C2Br)F)F
1.Protein kinase C-dependent trafficking of glutamate transporters excitatory amino acid carrier 1 and glutamate transporter 1b in cultured cerebellar granule cells.
Karatas-Wulf U;Koepsell H;Bergert M;Sönnekes S;Kugler P Neuroscience. 2009 Jul 7;161(3):794-805. doi: 10.1016/j.neuroscience.2009.04.017. Epub 2009 Apr 11.
Previous data showed that cell surface expression of the glutamate transporters GLT1a and excitatory amino acid carrier 1 (EAAC1), localized in glia and neurons of the CNS, can be regulated by protein kinase C (PKC). Regulation and physiological importance of GLT1b, a splice variant of GLT1a, is not understood. In the present study we used cultured cerebellar granule cells (CGCs) from mice to investigate PKC dependent trafficking of GLT1b in comparison to GLT1a and EAAC1 using immunohistochemistry and subcellular fractionation followed by Western blotting. In neurites of CGCs, GLT1b and EAAC1 were localized to different aggregates of vesicles that were different from vesicle aggregates containing vesicular glutamate transporters. In CGCs cultured with low-potassium medium, stimulation of PKC by phorbol ester enhanced the formation of large varicosities in neurites that exhibited immunoreactivity for GLT1a, GLT1b, and EAAC1. Stimulation of PKC leads to a significant increase of GLT1b and EAAC1 in the plasma membrane whereas GLT1a in the plasma membrane was decreased. Following PKC stimulation, also a significant increase of transporter-mediated glutamate uptake representing sodium dependent glutamate uptake, was observed.
2.Chemoenzymatic Synthesis and Pharmacological Characterization of Functionalized Aspartate Analogues As Novel Excitatory Amino Acid Transporter Inhibitors.
Fu H;Zhang J;Tepper PG;Bunch L;Jensen AA;Poelarends GJ J Med Chem. 2018 Aug 15. doi: 10.1021/acs.jmedchem.8b00700. [Epub ahead of print]
Aspartate (Asp) derivatives are privileged compounds for investigating the roles governed by excitatory amino acid transporters (EAATs) in glutamatergic neurotransmission. Here, we report the synthesis of various Asp derivatives with (cyclo)alkyloxy and (hetero)aryloxy substituents at C-3. Their pharmacological properties were characterized at the EAAT1-4 subtypes. The l- threo-3-substituted Asp derivatives 13a-e and 13g-k were nonsubstrate inhibitors, exhibiting pan activity at EAAT1-4 with IC;50; values ranging from 0.49 to 15 μM. Comparisons between (dl- threo)-19a-c and (dl- erythro)-19a-c Asp analogues confirmed that the threo configuration is crucial for the EAAT1-4 inhibitory activities. Analogues (3b-e) of l-TFB-TBOA (3a) were shown to be potent EAAT1-4 inhibitors, with IC;50; values ranging from 5 to 530 nM. Hybridization of the nonselective EAAT inhibitor l-TBOA with EAAT2-selective inhibitor WAY-213613 or EAAT3-preferring inhibitor NBI-59159 yielded compounds 8 and 9, respectively, which were nonselective EAAT inhibitors displaying considerably lower IC;50; values at EAAT1-4 (11-140 nM) than those displayed by the respective parent molecules.
3.Characterization of novel aryl-ether, biaryl, and fluorene aspartic acid and diaminopropionic acid analogs as potent inhibitors of the high-affinity glutamate transporter EAAT2.
Dunlop J;McIlvain HB;Carrick TA;Jow B;Lu Q;Kowal D;Lin S;Greenfield A;Grosanu C;Fan K;Petroski R;Williams J;Foster A;Butera J Mol Pharmacol. 2005 Oct;68(4):974-82. Epub 2005 Jul 13.
In this study, we describe the pharmacological characterization of novel aryl-ether, biaryl, and fluorene aspartic acid and diaminopropionic acid analogs as potent inhibitors of EAAT2, the predominant glutamate transporter in forebrain regions. The rank order of potency determined for the inhibition of human EAAT2 was N(4)-[4-(2-bromo-4,5-difluorophenoxy)phenyl]-L-asparagine (WAY-213613) (IC(50) = 85 +/- 5 nM) > N(4)-(2'-methyl-1,1'-biphenyl-4-yl)-L-asparagine (WAY-213394) (IC(50) = 145 +/- 22 nM) = N(4)-[7-(trifluoromethyl)-9H-fluoren-2-yl]-L-asparagine (WAY-212922) (IC(50) = 157 +/- 11 nM) = 3-{[(4'-chloro-2-methyl-1,1'-biphenyl-4-yl)carbonyl]amino}-L-alanine (WAY-211686) (IC(50) = 190 +/- 10 nM). WAY-213613 was the most selective of the compounds examined, with IC(50) values for inhibition of EAAT1 and EAAT3 of 5 and 3.8 microM, respectively, corresponding to a 59- and 45-fold selectivity toward EAAT2. An identical rank order of potency [WAY-213613 (35 +/- 7 nM) > WAY-213394 (92 +/- 13 nM) = WAY-212922 (95 +/- 8 nM) = WAY-211686 (101 +/- 20 nM)] was observed for the inhibition of glutamate uptake in rat cortical synaptosomes, consistent with the predominant contribution of EAAT2 to this activity.
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CAS 868359-05-1 WAY 213613

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