BMS 470539 dihydrochlorideMC1 receptor,potent and selective CAS# 457893-92-4 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 457893-92-4 | SDF | Download SDF |
| PubChem ID | 60210130 | Appearance | Powder |
| Formula | C32H43Cl2N5O4 | M.Wt | 632.62 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in water and to 100 mM in DMSO | ||
| Chemical Name | (2S)-2-amino-N-[(2R)-1-(4-butanoyl-4-phenylpiperidin-1-yl)-3-(4-methoxyphenyl)-1-oxopropan-2-yl]-3-(3-methylimidazol-4-yl)propanamide;dihydrochloride | ||
| SMILES | CCCC(=O)C1(CCN(CC1)C(=O)C(CC2=CC=C(C=C2)OC)NC(=O)C(CC3=CN=CN3C)N)C4=CC=CC=C4.Cl.Cl | ||
| Standard InChIKey | DUAOBJHRUKFKIH-YDVFRNEYSA-N | ||
| Standard InChI | InChI=1S/C32H41N5O4.2ClH/c1-4-8-29(38)32(24-9-6-5-7-10-24)15-17-37(18-16-32)31(40)28(19-23-11-13-26(41-3)14-12-23)35-30(39)27(33)20-25-21-34-22-36(25)2;;/h5-7,9-14,21-22,27-28H,4,8,15-20,33H2,1-3H3,(H,35,39);2*1H/t27-,28+;;/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. |
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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, selective melanocortin MC1 receptor agonist (IC50 = 120 nM). Exhibits anti-inflammatory properties following ischemia-reperfusion in the vasculature. Inhibits leukocyte trafficking. |
BMS 470539 dihydrochloride Dilution Calculator
BMS 470539 dihydrochloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.5807 mL | 7.9036 mL | 15.8073 mL | 31.6146 mL | 39.5182 mL |
| 5 mM | 0.3161 mL | 1.5807 mL | 3.1615 mL | 6.3229 mL | 7.9036 mL |
| 10 mM | 0.1581 mL | 0.7904 mL | 1.5807 mL | 3.1615 mL | 3.9518 mL |
| 50 mM | 0.0316 mL | 0.1581 mL | 0.3161 mL | 0.6323 mL | 0.7904 mL |
| 100 mM | 0.0158 mL | 0.079 mL | 0.1581 mL | 0.3161 mL | 0.3952 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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BMS 470539 dihydrochloride is a potent and selective melanocortin-1 (MC1) receptor agonist with IC50 of 120 nM [1].
The melanocortin-1 receptor (MC-1R) is a G protein-coupled receptor involved in blocking inflammation and augmenting skin pigmentation [1].
In human melanoma cells, which endogenously express MC-1R, BMS-470539 inhibited TNF- -induced activation of a NF-κB transcriptional reporter in a dose-dependent way.
In a murine LPS (lipopolysaccharide) induced cytokine accumulation model, BMS 470539 dihydrochloride reduced TNF-α levels by 65% and 82% at 11umol/kg and 33umol/kg respectively in a dose-dependent way [1]. In a murine lung inflammation model, BMS 470539 (15umol/kg) reduced LPS-induced leukocyte infiltration (comprised primarily of neutrophils) by 45%. In a delayed-type hypersensitivity model, BMS 470539 reduced paw swelling by 59% [2]. In mice with IR, BMS 470539 (doses of 6.16 and 18.47 mg/kg) significantly inhibited leucocyte adhesion and emigration in a dose-dependent way. In the cremasteric microcirculation inflamed by platelet-activating factor, BMS-470539 inhibited cell emigration, but did not affect cell adhesion [3].
References:
[1]. Herpin TF, Yu G, Carlson KE, et al. Discovery of tyrosine-based potent and selective melanocortin-1 receptor small-molecule agonists with anti-inflammatory properties. J Med Chem, 2003, 46(7): 1123-1126.
[2]. Kang L, McIntyre KW, Gillooly KM, et al. A selective small molecule agonist of the melanocortin-1 receptor inhibits lipopolysaccharide-induced cytokine accumulation and leukocyte infiltration in mice. J Leukoc Biol, 2006, 80(4): 897-904.
[3]. Leoni G, Voisin MB, Carlson K, et al. The melanocortin MC(1) receptor agonist BMS-470539 inhibits leucocyte trafficking in the inflamed vasculature. Br J Pharmacol, 2010, 160(1): 171-180.
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The melanocortin MC(1) receptor agonist BMS-470539 inhibits leucocyte trafficking in the inflamed vasculature.[Pubmed:20331604]
Br J Pharmacol. 2010 May;160(1):171-80.
BACKGROUND AND PURPOSE: Over three decades of research evaluating the biology of melanocortin (MC) hormones and synthetic peptides, activation of the MC type 1 (MC(1)) receptor has been identified as a viable target for the development of novel anti-inflammatory therapeutic agents. Here, we have tested a recently described selective agonist of MC(1) receptors, BMS-470539, on leucocyte/post-capillary venule interactions in murine microvascular beds. EXPERIMENTAL APPROACH: Intravital microscopy of two murine microcirculations were utilized, applying two distinct modes of promoting inflammation. The specificity of the effects of BMS-470539 was assessed using mice bearing mutant inactive MC(1) receptors (the recessive yellow e/e colony). KEY RESULTS: BMS-470539, given before an ischaemia-reperfusion protocol, inhibited cell adhesion and emigration with no effect on cell rolling, as assessed 90 min into the reperfusion phase. These properties were paralleled by inhibition of tissue expression of both CXCL1 and CCL2. Confocal investigations of inflamed post-capillary venules revealed immunostaining for MC(1) receptors on adherent and emigrated leucocytes. Congruently, the anti-inflammatory properties of BMS-470539 were lost in mesenteries of mice bearing the inactive mutant MC(1) receptors. Therapeutic administration of BMS-470539 stopped cell emigration, but did not affect cell adhesion in the cremasteric microcirculation inflamed by superfusion with platelet-activating factor. CONCLUSIONS AND IMPLICATIONS: Activation of MC(1) receptors inhibited leucocyte adhesion and emigration. Development of new chemical entities directed at MC(1) receptors could be a viable approach in the development of novel anti-inflammatory therapeutic agents with potential application to post-ischaemic conditions.
A selective small molecule agonist of the melanocortin-1 receptor inhibits lipopolysaccharide-induced cytokine accumulation and leukocyte infiltration in mice.[Pubmed:16888084]
J Leukoc Biol. 2006 Oct;80(4):897-904.
It is well established that melanocortins are peptides that have potent anti-inflammatory activity. Recent research has focused on understanding which of the known melanocortin receptors mediates the anti-inflammatory actions of the melanocortins. The aim of this study was to assess the anti-inflammatory activity of a synthetic MC-1R agonist. BMS-470539 is a potent, selective, full agonist of human and murine MC-1R with EC(50) values in a cAMP accumulation assay of 16.8 and 11.6 nM, respectively. BMS-470539 dose-dependently inhibited TNF-alpha-induced activation of a NF-kappaB transcriptional reporter in human melanoma cells, which endogenously express MC-1R. In vivo studies with BMS-470539 demonstrated that subcutaneous administration of BMS-470539 resulted in a dose-dependent inhibition of LPS-induced TNF-alpha production in BALB/c mice. In this model, the compound had an ED(50) of approximately 10 micromol/kg and a pharmacodynamic half-life of approximately 8 h. Pharmacokinetic analysis of the compound indicated that the compound had a t(1/2) of 1.7 h. In a model of lung inflammation, administration of 15 micromol/kg BMS-470539 resulted in a 45% reduction in LPS-induced leukocyte infiltration (an infiltrate comprised primarily of neutrophils). The compound was also effective in a model of delayed-type hypersensitivity, reducing paw swelling by 59%, comparable with that seen with 5 mg/kg dexamethasone. These studies demonstrate that a selective small molecule agonist of the melanocortin-1 receptor is a potent anti-inflammatory agent in vivo and provides compelling evidence for the involvement of this receptor in the modulation of inflammation.
Discovery of tyrosine-based potent and selective melanocortin-1 receptor small-molecule agonists with anti-inflammatory properties.[Pubmed:12646021]
J Med Chem. 2003 Mar 27;46(7):1123-6.
The melanocortin-1 receptor (MC-1R) is a G-protein-coupled receptor involved in inflammation and skin pigmentation. Compound 2 is the first highly potent and selective MC-1R small-molecule agonist reported. Compound 2 showed efficacy in an acute model of inflammation, which has demonstrated the role of MC-1R in modulation of inflammation.
