(S)-SNAP 5114

GABA uptake inhibitor CAS# 157604-55-2

(S)-SNAP 5114

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Chemical structure

(S)-SNAP 5114

3D structure

Chemical Properties of (S)-SNAP 5114

Cas No. 157604-55-2 SDF Download SDF
PubChem ID 10458835 Appearance Powder
Formula C30H35NO6 M.Wt 505.61
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 50 mM in ethanol and to 100 mM in DMSO
Chemical Name (3S)-1-[2-[tris(4-methoxyphenyl)methoxy]ethyl]piperidine-3-carboxylic acid
SMILES COC1=CC=C(C=C1)C(C2=CC=C(C=C2)OC)(C3=CC=C(C=C3)OC)OCCN4CCCC(C4)C(=O)O
Standard InChIKey VDLDUZLDZBVOAS-QFIPXVFZSA-N
Standard InChI InChI=1S/C30H35NO6/c1-34-26-12-6-23(7-13-26)30(24-8-14-27(35-2)15-9-24,25-10-16-28(36-3)17-11-25)37-20-19-31-18-4-5-22(21-31)29(32)33/h6-17,22H,4-5,18-21H2,1-3H3,(H,32,33)/t22-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of (S)-SNAP 5114

DescriptionGABA transport inhibitor, showing selectivity for GAT-3 and GAT-2 (IC50 values are 5, 21 and 388 μM for hGAT-3, rGAT-2 and hGAT-1 respectively). Increases thalamic GABA levels and is an anticonvulsant following systemic administration in vivo.

(S)-SNAP 5114 Dilution Calculator

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(S)-SNAP 5114 Molarity Calculator

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Preparing Stock Solutions of (S)-SNAP 5114

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9778 mL 9.889 mL 19.7781 mL 39.5562 mL 49.4452 mL
5 mM 0.3956 mL 1.9778 mL 3.9556 mL 7.9112 mL 9.889 mL
10 mM 0.1978 mL 0.9889 mL 1.9778 mL 3.9556 mL 4.9445 mL
50 mM 0.0396 mL 0.1978 mL 0.3956 mL 0.7911 mL 0.9889 mL
100 mM 0.0198 mL 0.0989 mL 0.1978 mL 0.3956 mL 0.4945 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on (S)-SNAP 5114

(S)-SNAP 5114 is a selective inhibitor of GABA transport with IC50 values of 5, 21 and 388 μM for hGAT-3, rGAT-2 and hGAT-1, respectively [1].

γ-Aminobutyric acid (GABA) is the major inhibitory neurotransmitter in the central nervous system (CNS) and plays a critical role in Huntington’s disease, Parkinson’s disease, epilepsy, schizophrenia and Alzheimer’s disease. GABA transporters transport GABA from extra- to intracellular side of glial and neuronal cells [2].

(S)-SNAP 5114 is a selective GABA transport inhibitor. In HEK-293 cell lines expressing mGAT1-4, (S)-SNAP 5114 exhibited inhibitory potencies with pIC50 values of 4.07, 5.29 and 5.71 for mGAT1, mGAT3 and mGAT4 respectively and inhibited mGAT2 by 56% [2]. SNAP-5114 (100 μM) increased GABA levels to 247% in the thalamus. In juvenile rats with maximal electroshock, SNAP-5114 inhibited tonic hindlimb extension. In DBA/2 mice, SNAP-5114 inhibited sound induced convulsions in a dose-dependent way with ED50 value of 110 μmol/kg [3]. In rats, SNAP5114 (10, 50, 100 or 200 μg) inhibited the late-phase response in the formalin test and prolonged withdrawal latencies in the tail flick test, which suggested that SNAP5114 inhibited chemical and thermal nociception. In the chronic constriction injury rats, SNAP5114 inhibited mechanical allodynia in a dose-dependent way [4].

References:
[1].  Borden LA, Dhar TG, Smith KE, et al. Cloning of the human homologue of the GABA transporter GAT-3 and identification of a novel inhibitor with selectivity for this site. Receptors Channels, 1994, 2(3): 207-213.
[2].  Pabel J, Faust M, Prehn C, et al. Development of an (S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid [(S)-SNAP-5114] carba analogue inhibitor for murine γ-aminobutyric acid transporter type 4. ChemMedChem, 2012, 7(7): 1245-1255.
[3].  Dalby NO. GABA-level increasing and anticonvulsant effects of three different GABA uptake inhibitors. Neuropharmacology, 2000, 39(12): 2399-2407.
[4].  Kataoka K, Hara K, Haranishi Y, et al. The antinociceptive effect of SNAP5114, a gamma-aminobutyric acid transporter-3 inhibitor, in rat experimental pain models. Anesth Analg, 2013, 116(5): 1162-1169.

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References on (S)-SNAP 5114

Development of an (S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid [(S)-SNAP-5114] carba analogue inhibitor for murine gamma-aminobutyric acid transporter type 4.[Pubmed:22544452]

ChemMedChem. 2012 Jul;7(7):1245-55.

A series of GABA uptake inhibitors related to (S)-1-{2-[tris(4-methoxyphenyl)methoxy]ethyl}piperidine-3-carboxylic acid [(S)-SNAP-5114], the most potent mGAT4 inhibitor known so far, were synthesized and biologically evaluated for their inhibitory potency at the four GABA uptake transporters mGAT1-4 stably expressed in HEK-293 cell lines. New analogues were developed with potencies that are similar to or slightly higher than those of current mGAT4 inhibitors, but with distinctly improved chemical stability. (S)-Nipecotic acid derivatives possessing a 2-[1-(4-methoxy-2-methylphenyl)-1,1-bis(4-methoxyphenyl)methoxy]ethyl (DDPM-859) or a 4,4,4-tris(4-methoxyphenyl)but-2-en-1-yl moiety (DDPM-1457) were found to exhibit pIC(50) values of 5.78 and 5.87, respectively. Thus, as mGAT4 inhibitors, these compounds compare well with (S)-SNAP-5114 (pIC(50) =5.71), but are far more stable than the latter. Moreover, DDPM-859 displays a more favorable subtype selectivity for mGAT4 versus mGAT3 than does (S)-SNAP-5114.

GABA-level increasing and anticonvulsant effects of three different GABA uptake inhibitors.[Pubmed:10974324]

Neuropharmacology. 2000 Sep;39(12):2399-407.

The present study examines the effect of tiagabine (a selective inhibitor of GABA transporter 1, GAT-1), SNAP-5114 (a semi-selective inhibitor of rat GAT-3/mouse GAT4) and NNC 05-2045 (a non-selective GABA uptake inhibitor) in modulating GABA levels in the hippocampus and thalamus. Anticonvulsant effects of the same compounds were assessed (after intranigral administration) after maximal electroshock (MES) in juvenile rats. Anticonvulsant effects were also tested after intraperitoneal (i.p.) administration against audiogenic seizures in DBA/2 mice and against pentylentetrazole (PTZ)-induced tonic convulsions or MES in NMRI mice. Tiagabine (30 microM, perfused through the microdialysis probe in halothane anaesthetized rats) increased GABA levels to (% basal+/-SEM) 645+/-69 in the hippocampus and 409+/-61 in the thalamus. SNAP-5114 (100 microM) increased GABA levels in the thalamus (% basal+/-SEM) to 247+/-27 but had no effect on hippocampal GABA-levels. NNC 05-2045 (100 microM) increased GABA levels both in the hippocampus (% basal+/-SEM, 251+/-51) and in the thalamus (298+/-27). All compounds protected against tonic hindlimb extension (THE) in juvenile male rats after intranigral administration. Sound induced convulsions in DBA/2 mice were dose-dependently inhibited by all compounds (administered intraperitoneal, i.p.) with ED(50) values of 1, 6 and 110 micromol/kg, for tiagabine, NNC 05-2045 and SNAP-5114, respectively. Tiagabine and NNC 05-2045 but not SNAP-5114 protected against PTZ-induced tonic convulsions whereas only NNC 05-2045 protected against MES-induced tonic convulsions in NMRI mice. However, tiagabine and NNC 05-2045 exerted a synergistic effect in the MES model. These findings substantiate and extend previous findings of different effects of selective versus non-selective GABA uptake inhibitors in animal models of epilepsy.

GABA transporter heterogeneity: pharmacology and cellular localization.[Pubmed:8939442]

Neurochem Int. 1996 Oct;29(4):335-56.

gamma-Aminobutyric acid (GABA) is the major inhibitory neurotransmitter in the mammalian brain. GABA is cleared from the synaptic cleft by specific, high-affinity, sodium- and chloride-dependent transporters, which are thought to be located on presynaptic terminals and surrounding glial cells. While early studies suggested a distinction between neuronal and glial GABA transport, molecular cloning has revealed the existence of genes for four distinct GABA transporters (termed GAT-1, GAT-2, GAT-3 and BGT-1), thus revealing a greater heterogeneity than previously suspected. Heterologous expression has allowed a detailed characterization of their pharmacological properties, and has revealed that GAT-1 is the site of action of the anticonvulsant drug, Tiagabine. In-situ hybridization and immunocytochemistry demonstrate that each transporter has a unique regional distribution in the brain; in conjunction with experiments utilizing cell cultures, the neuronal vs glial localization of the various transporters is being elucidated. Future studies will be directed at determining the role of each transporter in the regulation of GABAergic transmission, and in the design of additional subtype-specific inhibitors, which may serve as novel therapeutic agents for the treatment of neuropsychiatric disorders.

Cloning of the human homologue of the GABA transporter GAT-3 and identification of a novel inhibitor with selectivity for this site.[Pubmed:7874447]

Receptors Channels. 1994;2(3):207-13.

Molecular cloning has revealed the presence of four high-affinity GABA transporters in the brain. The existence of three of these sites, GAT-2, GAT-3, and BGT-1, was unknown prior to their cloning and almost nothing is known of the role they play in regulating GABAergic transmission. In large measure our paucity of knowledge is attributable to the lack of specific inhibitors for these sites. In the present communication we describe the cloning and expression of the human homologue of GAT-3, and the identification of an inhibitor, (S)-SNAP-5114, with selectivity for this site. (S)-SNAP-5114 displays an IC50 of 5 microM at GAT-3, 21 microM at GAT-2, and > or = 100 microM at GAT-1 and BGT-1. Due to its lipophilicity, (S)-SNAP-5114 is also expected to cross the blood-brain-barrier and therefore, should be an important tool for evaluating the role of GAT-3 in neural function.

Description

(S)-SNAP5114 is a selective GABA transport inhibitor, with IC50 values of 5 μM and 21 μM for hGAT-3 and rGAT-2, respectively. (S)-SNAP5114 is an anticonvulsant drug.

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