4-CMTB - CAS 300851-67-6
Category: Inhibitor
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Molecular Formula:
C14H15ClN2OS
Molecular Weight:
294.80
COA:
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Targets:
GPR40
Description:
4-CMTB has been found to be a free fatty acid receptor FFA2 agonist and could modulate the activity of short-chain fatty acids.
Purity:
≥98% by HPLC
Appearance:
White Solid
Synonyms:
4-chloro-α-(1-methylethyl)-N-2-thiazolylbenzeneacetamide
MSDS:
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InChIKey:
AZYDQCGCBQYFSE-UHFFFAOYSA-N
InChI:
InChI=1S/C14H15ClN2OS/c1-9(2)12(10-3-5-11(15)6-4-10)13(18)17-14-16-7-8-19-14/h3-9,12H,1-2H3,(H,16,17,18)
Canonical SMILES:
CC(C)C(C1=CC=C(C=C1)Cl)C(=O)NC2=NC=CS2
1.Extracellular loop 2 of the free fatty acid receptor 2 mediates allosterism of a phenylacetamide ago-allosteric modulator.
Smith NJ;Ward RJ;Stoddart LA;Hudson BD;Kostenis E;Ulven T;Morris JC;Tränkle C;Tikhonova IG;Adams DR;Milligan G Mol Pharmacol. 2011 Jul;80(1):163-73. doi: 10.1124/mol.110.070789. Epub 2011 Apr 15.
Allosteric agonists are powerful tools for exploring the pharmacology of closely related G protein-coupled receptors that have nonselective endogenous ligands, such as the short chain fatty acids at free fatty acid receptors 2 and 3 (FFA2/GPR43 and FFA3/GPR41, respectively). We explored the molecular mechanisms mediating the activity of 4-chloro-α-(1-methylethyl)-N-2-thiazolylbenzeneacetamide (4-CMTB), a recently described phenylacetamide allosteric agonist and allosteric modulator of endogenous ligand function at human FFA2, by combining our previous knowledge of the orthosteric binding site with targeted examination of 4-CMTB structure-activity relationships and mutagenesis and chimeric receptor generation. Here we show that 4-CMTB is a selective agonist for FFA2 that binds to a site distinct from the orthosteric site of the receptor. Ligand structure-activity relationship studies indicated that the N-thiazolyl amide is likely to provide hydrogen bond donor/acceptor interactions with the receptor. Substitution at Leu(173) or the exchange of the entire extracellular loop 2 of FFA2 with that of FFA3 was sufficient to reduce or ablate, respectively, allosteric communication between the endogenous and allosteric agonists.
2.Short-Chain Fatty Acid Acetate Stimulates Adipogenesis and Mitochondrial Biogenesis via GPR43 in Brown Adipocytes.
Hu J;Kyrou I;Tan BK;Dimitriadis GK;Ramanjaneya M;Tripathi G;Patel V;James S;Kawan M;Chen J;Randeva HS Endocrinology. 2016 May;157(5):1881-94. doi: 10.1210/en.2015-1944. Epub 2016 Mar 18.
Short-chain fatty acids play crucial roles in a range of physiological functions. However, the effects of short-chain fatty acids on brown adipose tissue have not been fully investigated. We examined the role of acetate, a short-chain fatty acid formed by fermentation in the gut, in the regulation of brown adipocyte metabolism. Our results show that acetate up-regulates adipocyte protein 2, peroxisomal proliferator-activated receptor-γ coactivator-1α, and uncoupling protein-1 expression and affects the morphological changes of brown adipocytes during adipogenesis. Moreover, an increase in mitochondrial biogenesis was observed after acetate treatment. Acetate also elicited the activation of ERK and cAMP response element-binding protein, and these responses were sensitive to G(i/o)-type G protein inactivator, Gβγ-subunit inhibitor, phospholipase C inhibitor, and MAPK kinase inhibitor, indicating a role for the G(i/o)βγ/phospholipase C/protein kinase C/MAPK kinase signaling pathway in these responses. These effects of acetate were mimicked by treatment with 4-chloro-α-(1-methylethyl)-N-2-thiazolylbenzeneacetamide, a synthetic G protein-coupled receptor 43 (GPR43) agonist and were impaired in GPR43 knockdown cells.
3.Fabrication and Characterization of Surfaces Modified with Carboxymethylthio Ligands for Chelate-Assisted Trapping of Copper.
Adongo JO;Neubert TJ;Sun G;Janietz S;Lauermann I;Rademann K;Rappich J ACS Appl Mater Interfaces. 2017 Jul 19;9(28):24273-24281. doi: 10.1021/acsami.7b05131. Epub 2017 Jul 10.
The metal ion chelating property was conferred onto silicon (Si) and gold (Au) surfaces by direct electrografting of the 4-[(carboxymethyl)thio]benzenediazonium cation (4-CMTBD). Infrared spectroscopic ellipsometry showed the presence of characteristic phenyl and carbonyl vibrational bands on the functionalized surfaces as a proof of existence of surface-bound organic units of 4-[(carboxymethyl)thio]benzene, (4-CMTB). The loss of diazonium group (N≡N;+;) upon electrografting of 4-CMTBD was investigated using IR spectroscopy. A Faradaic efficiency of about 18.8-20.0% was realized in mass deposition experiments for grafting 4-CMTB on the Au surface using an electrochemical quartz crystal microbalance technique. Raman spectroscopy performed on the Si-(4-CMTB) surface after treatment with copper (Cu) ion solution provided evidence of metal ion chelation based on an observed v(Cu-O) peak at about 487 cm;-1; and a v(Cu-S) signal at about 267 cm;-1;. The binding of Cu ions by the chelating ligands also caused a red shift of about 10 cm;-1; in the Raman spectrum of the Si-(4-CMTB)-Cu surface within the spectral region, characteristic of the v(C-O) signal. X-ray photoelectron spectroscopy investigations showed indications of the Cu(II) ion species chelated by the surface-bound carboxymethylthio ligands.
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CAS 300851-67-6 4-CMTB

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CAS 300851-67-6 4-CMTB

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