CYM 50308Potent and selective S1P4 agonist CAS# 1345858-76-5 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 1345858-76-5 | SDF | Download SDF |
PubChem ID | 49835928 | Appearance | Powder |
Formula | C20H21F2N3O2S | M.Wt | 405.46 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | Soluble to 10 mM in DMSO | ||
Chemical Name | (5Z)-5-[[1-(2,4-difluorophenyl)-2,5-dimethylpyrrol-3-yl]methylidene]-2-(2-methoxyethylimino)-3-methyl-1,3-thiazolidin-4-one | ||
SMILES | CC1=CC(=C(N1C2=C(C=C(C=C2)F)F)C)C=C3C(=O)N(C(=NCCOC)S3)C | ||
Standard InChIKey | BKQZKTRCUAWRHT-ONBPWHQPSA-N | ||
Standard InChI | InChI=1S/C20H21F2N3O2S/c1-12-9-14(13(2)25(12)17-6-5-15(21)11-16(17)22)10-18-19(26)24(3)20(28-18)23-7-8-27-4/h5-6,9-11H,7-8H2,1-4H3/b18-10-,23-20? | ||
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. |
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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. |
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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. |
Description | Potent and selective sphingosine-1-phosphate receptor 4 (S1P4) agonist (EC50 values are 56 nM and 2100 nM for S1P4 and S1P5 receptors, respectively). Displays no activity at S1P1, S1P2 and S1P3 receptors at concentrations up to 25 μM. |
CYM 50308 Dilution Calculator
CYM 50308 Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.4663 mL | 12.3317 mL | 24.6633 mL | 49.3267 mL | 61.6584 mL |
5 mM | 0.4933 mL | 2.4663 mL | 4.9327 mL | 9.8653 mL | 12.3317 mL |
10 mM | 0.2466 mL | 1.2332 mL | 2.4663 mL | 4.9327 mL | 6.1658 mL |
50 mM | 0.0493 mL | 0.2466 mL | 0.4933 mL | 0.9865 mL | 1.2332 mL |
100 mM | 0.0247 mL | 0.1233 mL | 0.2466 mL | 0.4933 mL | 0.6166 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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The S1P1 receptor-selective agonist CYM-5442 reduces the severity of acute GVHD by inhibiting macrophage recruitment.[Pubmed:25088224]
Cell Mol Immunol. 2015 Nov;12(6):681-91.
FTY720, an agonist for four of the five known sphingosine-1-phosphate (S1P) receptors, has been reported to inhibit acute graft-versus-host disease (aGVHD). Because FTY720 functions through multiple S1P receptors, the mechanism of action through one or more of these receptors may account for its side effects. Thus, more selective S1P receptor modulators are needed to evaluate the roles of different S1P receptors and their therapeutic efficacies. In this study, we investigated the effect of an S1P1-selective agonist, CYM-5442, on the progression of aGVHD. We showed that CYM-5442 significantly inhibited but did not prevent aGVHD. CYM-5442 did not affect the infiltration of the donor T cells into the target organs, while the number of macrophages in GVHD organs was significantly reduced by CYM-5442 treatment. In vivo proliferation assays showed that the proliferation of macrophages was not suppressed by CYM-5442. Further studies using human endothelial cells demonstrated that CYM-5442 treatment downregulated CCL2 and CCL7 expression in endothelial cells, therefore reducing the migration of monocytes, from which tissue macrophages originate. Our data demonstrate the therapeutic efficacy of an S1P1-selective agonist in aGVHD and its possible mechanism of action. The results suggest that further investigations are needed regarding CYM-5442 as a potential therapeutic regimen for aGVHD.
Dinuclear [{(p-cym)RuCl}2(mu-phpy)](PF6)2 and heterodinuclear [(ppy)2Ir(mu-phpy)Ru(p-cym)Cl](PF6)2 complexes: synthesis, structure and anticancer activity.[Pubmed:25160655]
Dalton Trans. 2014 Oct 21;43(39):14546-9.
Phpy bridged homodinuclear Ru-Ru () and heterodinuclear Ir-Ru complexes () have been developed. Complex induces autophagy towards the cisplatin resistant human breast cancer (MCF7) cell line, whereas is inactive.
A dinuclear [{(p-cym)Ru(II)Cl}2(mu-bpytz (-))](+) complex bridged by a radical anion: synthesis, spectroelectrochemical, EPR and theoretical investigation (bpytz = 3,6-bis(3,5-dimethylpyrazolyl)1,2,4,5-tetrazine; p-cym = p-cymene).[Pubmed:27435992]
Dalton Trans. 2016 Aug 2;45(31):12532-8.
The reaction of the chloro-bridged dimeric precursor [{(p-cym)Ru(II)Cl}(mu-Cl)]2 (p-cym = p-cymene) with the bridging ligand 3,6-bis(3,5-dimethylpyrazolyl)-1,2,4,5-tetrazine (bpytz) in ethanol results in the formation of the dinuclear complex [{(p-cym)Ru(II)Cl}2(mu-bpytz (-))](+), [1](+). The bridging tetrazine ligand is reduced to the anion radical (bpytz (-)) which connects the two Ru(II) centres. Compound [1](PF6) has been characterised by an array of spectroscopic and electrochemical techniques. The radical anion character has been confirmed by magnetic moment (corresponding to one electron paramagnetism) measurement, EPR spectroscopic investigation (tetrazine radical anion based EPR spectrum) as well as density functional theory based calculations. Complex [1](+) displays two successive one electron oxidation processes at 0.66 and 1.56 V versus Ag/AgCl which can be attributed to [{(p-cym)Ru(II)C}2(mu-bpytz (-))](+)/[{(p-cym)Ru(II)Cl}2(mu-bpytz)](2+) and [{(p-cym)Ru(II)Cl}2(mu-bpytz)](+)/[{(p-cym)Ru(III)Cl}2(mu-bpytz)](2+) processes (couples I and II), respectively. The reduction processes (couple III-couple V), which are irreversible, likely involve the successive reduction of the bridging ligand and the metal centres together with loss of the coordinated chloride ligands. UV-Vis-NIR spectroelectrochemical investigation reveals typical tetrazine radical anion containing bands for [1](+) and a strong absorption in the visible region for the oxidized form [1](2+), which can be assigned to a Ru(II) --> pi* (tetrazine) MLCT transition. The assignment of spectroscopic bands was confirmed by theoretical calculations.
Synthesis, characterisation and antibacterial activity of [(p-cym)RuX(L)](+/2+) (X = Cl, H2O; L = bpmo, bpms) complexes.[Pubmed:25675378]
Dalton Trans. 2015 Mar 21;44(11):5114-24.
Mononuclear half-sandwiched complexes [(p-cym)RuCl(bpmo)](ClO4) {[1](ClO4)} and [(p-cym)RuCl(bpms)](PF6) {[2](PF6)} have been prepared by reacting heteroscorpionate ligands bpmo = 2-methoxyphenyl-bis(3,5-dimethylpyrazol-1-yl)methane and bpms = 2-methylthiophenyl-bis(3,5-dimethylpyrazol-1-yl)methane, respectively, with a dimeric precursor complex [(p-cym)RuCl(mu-Cl)]2 (p-cym = 1-isopropyl-4-methylbenzene) in methanol. The corresponding aqua derivatives [(p-cym)Ru(H2O)(bpmo)](ClO4)2 {[3](ClO4)2} and [(p-cym)Ru(H2O)(bpms)](PF6)2 {[4](PF6)2} are obtained from {[1](ClO4)} and {[2](PF6)}, respectively, via Cl(-)/H2O exchange process in the presence of appropriate equivalents of AgClO4/AgNO3 + KPF6 in a methanol-water mixture. The molecular structures of the complexes {[1]Cl, [3](ClO4)2 and [4](PF6)(NO3)} are authenticated by their single crystal X-ray structures. The complexes show the expected piano-stool geometry with p-cym in the eta(6) binding mode. The aqua complexes [3](ClO4)2 and [4](PF6)2 show significantly good antibacterial activity towards E. coli (gram negative) and B. subtilis (gram positive) strains, while chloro derivatives ({[1](ClO4)} and {[2](PF6)} are found to be virtually inactive. The order of antibacterial activity of the complexes according to their MIC values is [1](ClO4) (both 1000 mug mL(-1)) < [2](PF6) (580 mug mL(-1) and 750 mug mL(-1)) < [3](ClO4)2 (both 100 mug mL(-1)) < [4](PF6)2 (30 mug mL(-1) and 60 mug mL(-1)) for E. coli and B. subtilis strains, respectively. Further, the aqua complexes [3](ClO4)2 and [4](PF6)2 show clear zones of inhibition against kanamycin, ampicillin and chloramphenicol resistant E. coli strains. The detailed mechanistic aspects of the aforesaid active aqua complexes [3](ClO4)2 and [4](PF6)2 have been explored, and it reveals that both the complexes inhibit the number of nucleoids per cell in vivo and bind to DNA in vitro. The results indeed demonstrate that both [3](ClO4)2 and [4](PF6)2 facilitate the inhibition of bacterial growth by binding to DNA.
Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype.[Pubmed:21982495]
Bioorg Med Chem Lett. 2011 Nov 15;21(22):6739-45.
High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P(4)-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2- (methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function.