157604-55-2 Usage
Uses
(S)-SNAP 5114 is a GABA, GAT3 inhibitor.
Biological Activity
GABA transport inhibitor, showing selectivity for GAT-3 and GAT-2 (IC 50 values are 5, 21 and 388 μ M for hGAT-3, rGAT-2 and hGAT-1 respectively). Increases thalamic GABA levels and is an anticonvulsant following systemic administration in vivo .
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.
Check Digit Verification of cas no
The CAS Registry Mumber 157604-55-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,7,6,0 and 4 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 157604-55:
(8*1)+(7*5)+(6*7)+(5*6)+(4*0)+(3*4)+(2*5)+(1*5)=142
142 % 10 = 2
So 157604-55-2 is a valid CAS Registry Number.
InChI:InChI=1/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
157604-55-2Relevant articles and documents
Design, synthesis and evaluation of substituted triarylnipecotic acid derivatives as GABA uptake inhibitors: Identification of a ligand with moderate affinity and selectivity for the cloned human GABA transporter GAT- 3
Dhar,Borden,Tyagarajan,Smith,Branchek,Weinshank,Gluchowski
, p. 2334 - 2342 (2007/10/02)
γ-Aminobutyric acid (GABA) is the major inhibitory neurotransmitter in the mammalian central nervous system. Molecular biology has revealed the presence of four high-affinity GABA transporters in the brain, GAT-1, GAT-2, GAT-3, and BGT-1, the latter transporting both GABA and the osmolyte Betaine. We have shown that known GABA uptake inhibitors such as SK and F 89976-A, CI- 966, and Tiagabine exhibit high affinity and selectivity for GAT-1. In the present paper we describe the design and synthesis of a novel series of triarylnipecotic acid derivatives for evaluation as GABA uptake inhibitors. The design lead for this series of compounds was the nonselective GABA uptake inhibitor EGYT-3886, [(-)-2-phenyl-2-[(dimethylamino)ethoxy]-(1R)-1,7,7- trimethylbicyclo[2.2.1]heptane]. From this series of compounds (S)-1-[2- [tris(4-methoxyphenyl)methoxy]ethyl]-3-piperidinecarboxylic acid, 4(S) was identified as a novel ligand with selectivity for GAT-3. 4(S) displayed an IC50 of 5 μM at GAT-3, 21 μM at GAT-2, >200 μM at GAT-1, and 140 μM at BGT-1. This compound will be an important tool for evaluating the role of GAT-3 in neural function.
