(S)-SNAP 5114 - CAS 157604-55-2
Category: Inhibitor
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GABA Receptor
(S)-SNAP 5114 is a GABA transport inhibitor, displaying selectivity for GAT-3 and GAT-2 (IC50 = 5, 21 and 388 μM for hGAT-3, rGAT-2 and hGAT-1, respectively). (S)-SNAP 5114 was shown to increase thalamic GABA levels, and acts as an anticonvulsant following systemic administration in vivo.
Brife Description:
GABA transport inhibitor
≥98% by HPLC
1-[2-[tris(4-methoxyphenyl)methoxy]ethyl]-(S)-3-piperidinecarboxylic acid; (3S)-1-[2-[tris(4-methoxyphenyl)methoxy]ethyl]piperidine-3-carboxylic acid
Canonical SMILES:
1.Inhibition of GABA transporters fails to afford significant protection following focal cerebral ischemia.
Lie ME;Gowing EK;Clausen RP;Wellendorph P;Clarkson AN J Cereb Blood Flow Metab. 2018 Jan;38(1):166-173. doi: 10.1177/0271678X17743669. Epub 2017 Nov 17.
Brain ischemia triggers excitotoxicity and cell death, yet no neuroprotective drugs have made it to the clinic. While enhancing GABAergic signaling to counterbalance excitotoxicity has shown promise in animal models, clinical studies have failed. Blockade of GABA transporters (GATs) offers an indirect approach to increase GABA inhibition to lower the excitation threshold of neurons. Among the GATs, GAT1 is known to promote neuroprotection, while the protective role of the extrasynaptic transporters GAT3 and BGT1 is elusive. A focal lesion was induced in the motor cortex in two to four-month-old C57BL/6 J male mice by photothrombosis. The GAT1 inhibitor, tiagabine (1 and 10 mg/kg), the GAT2/3 inhibitor, ( S)-SNAP-5114 (5 and 30 mg/kg) and the GAT1/BGT1 inhibitor, EF-1502 (1 and 10 mg/kg) were given i.p. 1 and 6 h post-stroke to assess their impact on infarct volume and motor performance seven days post-stroke. One mg/kg tiagabine improved motor performance, while 10 mg/kg tiagabine, ( S)-SNAP-5114 and EF-1502 had no effect. None of the compounds affected infarct volume. Interestingly, treatment with tiagabine induced seizures and ( S)-SNAP-5114 led to increased mortality. Although we show that tiagabine can promote protection, our findings indicate that caution should be had when using GAT1 and GAT3 inhibitors for conditions of brain ischemia.
2.New highly potent GABA uptake inhibitors selective for GAT-1 and GAT-3 derived from (R)- and (S)-proline and homologous pyrrolidine-2-alkanoic acids.
Fülep GH;Hoesl CE;Höfner G;Wanner KT Eur J Med Chem. 2006 Jul;41(7):809-24.
We synthesized proline and pyrrolidine-2-alkanoic acid derivatives in their enantiomerically pure form and evaluated them for their affinity to the GABA transport proteins GAT-1 and GAT-3. Among the compounds presented herein, (R)-pyrrolidine-2-acetic acid (R)-4d substituted with a 2-[tris(4-methoxyphenyl)methoxy]ethyl residue at the nitrogen atom showed the highest affinity at GAT-3 (IC(50) = 3.1 microM) comparable with the well-known GAT-3 blocker (S)-SNAP-5114. Compound (R)-4d displayed excellent subtype selectivity for GAT-3 (GAT-3:GAT-1 = 20:1). (S)-2-pyrrolidineacetic acid derivatives (S)-4b provided with a 4,4-diphenylbut-3-en-1-yl moiety and (S)-4c substituted with a 4,4-[di(3-methylthiophen-2-yl)]phenylbut-3-en-1-yl residue at the nitrogen atom exhibited IC(50) values of 0.396 microM and 0.343 microM at the GAT-1 protein, respectively.
3.Comparison of the uptake of 5-aminolevulinic acid and its methyl ester in keratinocytes and skin.
Schulten R;Novak B;Schmitz B;Lübbert H Naunyn Schmiedebergs Arch Pharmacol. 2012 Oct;385(10):969-79. doi: 10.1007/s00210-012-0777-4. Epub 2012 Jul 17.
Photodynamic therapy is widely used in the treatment of superficial skin cancers. 5-Aminolevulinic acid (ALA) and its methylated form, methyl-ALA (MAL), are frequently used as precursors to photosensitizing substances. Nevertheless, the mechanism of the uptake of ALA and MAL in keratinocytes and of their skin penetration is still controversial. Since both compounds are not sufficiently lipophilic to penetrate through lipid membranes, they must employ specific uptake systems which may vary between different cell types. Here, we studied ALA and MAL uptake in keratinocyte cell lines originating from healthy cells (CCD 1106 KERTr cells) or keratinocyte tumors (A431 cells). ALA uptake resulted in faster protoporphyrin IX (PpIX) production than MAL uptake. A pharmacological characterization of the uptake systems revealed that PpIX formation was most efficiently reduced with GABA transporter (GAT) substrates. GABA, β-alanine, and (S)-SNAP-5114 reduced ALA uptake and, to a lesser extent, MAL uptake in the cell lines. The pharmacology of these compounds indicates that ALA and MAL are taken up by normal and pathological keratinocytes via GAT-3. Furthermore, the amino acids arginine, cysteine, and histidine also inhibited the uptake of ALA, and even more so MAL, suggestive of an additional involvement of amino acid transporters.
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CAS 157604-55-2 (S)-SNAP 5114

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