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Merck

M7571

Sigma-Aldrich

MK-571 sodium salt hydrate

≥95% (HPLC), powder, leukotriene D4 antagonist

Sinónimos:

5-(3-(2-(7-Chloroquinolin-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoic acid sodium salt hydrate, L-660711

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About This Item

Fórmula empírica (notación de Hill):
C26H26ClN2NaO3S2 · xH2O
Número de CAS:
Peso molecular:
537.07 (anhydrous basis)
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

product name

MK-571 sodium salt hydrate, ≥95% (HPLC)

Quality Level

assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 15 mg/mL, clear

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

shipped in

wet ice

storage temp.

−20°C

SMILES string

O.[Na+].CN(C)C(=O)CCSC(SCCC([O-])=O)c1cccc(\C=C\c2ccc3ccc(Cl)cc3n2)c1

InChI

1S/C26H27ClN2O3S2.Na.H2O/c1-29(2)24(30)12-14-33-26(34-15-13-25(31)32)20-5-3-4-18(16-20)6-10-22-11-8-19-7-9-21(27)17-23(19)28-22;;/h3-11,16-17,26H,12-15H2,1-2H3,(H,31,32);;1H2/q;+1;/p-1/b10-6+;;

InChI key

MSHRPLRGSQECLY-DOLBFOAYSA-M

Application

MK-571 sodium salt hydrate has been used:
  • as an efflux inhibitor for monitoring multidrug resistance protein (MRP)-function and to avoid redundancy of other transporters
  • to assess its effect on cell proliferation and 2D-migration in vitro in various cell lines of glioblastoma multiforme (GBM)
  • as multidrug resistance (MDR) transporter inhibitor to study its effects in ovarian cancer cells
  • as specific inhibitors of ABCC1/2 to investigate transport, toxicity, flow cytometry and arsenic efflux

Biochem/physiol Actions

MK 571 is a potent and selective leukotriene D4 (LTD4) antagonist and ABCC multidrug resistance protein 1(MRP1) inhibitor. The cysteinyl leukotrienes (CysLTs), LTC4, LTD4, and LTE4, mediate their actions through two distinct G-protein coupled receptors. LTD4 is the preferred ligand for the CysLT1 receptor, whereas LTC4 and LTD4 bind with approximately equal affinity to the CysLT2 receptor. MK 571 is a selective, orally active CysLT1 receptor antagonist. It blocks the binding of LTD4, but not LTC4, to human and guinea pig lung membranes with Ki values of 0.22 nM and 2.1 nM, respectively. MK 571 effectively blocks LTD4 activation of recombinant human and mouse CysLT1 receptors but is ineffective at blocking LTC4 or LTD4 activation of the recombinant human or murine CysLT2 receptors. It potentially inhibits MRP1 and has been shown to overcome acquired arsenic tolerance.

Features and Benefits

This compound is featured on the Leukotriene Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Winfried Neuhaus et al.
Frontiers in cellular neuroscience, 8, 352-352 (2014-11-13)
Stabilization of the blood-brain barrier during and after stroke can lead to less adverse outcome. For elucidation of underlying mechanisms and development of novel therapeutic strategies validated in vitro disease models of the blood-brain barrier could be very helpful. To
Ravi S Kasinathan et al.
PLoS neglected tropical diseases, 5(12), e1425-e1425 (2011-12-14)
P-glycoprotein (Pgp) and multidrug resistance-associated proteins (MRPs) are ATP-dependent transporters involved in efflux of toxins and xenobiotics from cells. When overexpressed, these transporters can mediate multidrug resistance (MDR) in mammalian cells, and changes in Pgp expression and sequence are associated
The mechanisms of detoxification of As (III), dimethylarsinic acid (DMA) and As (V) in the microalga Chlorella vulgaris
Munoz L P, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 175, 56-72 (2016)
Joseph P Campanale et al.
Development (Cambridge, England), 139(4), 783-792 (2012-01-26)
ATP-binding cassette (ABC) transporters protect embryos and stem cells from mutagens and pump morphogens that control cell fate and migration. In this study, we measured dynamics of ABC transporter activity during formation of sea urchin embryonic cells necessary for the
Hui-fang Su et al.
Acta pharmacologica Sinica, 37(4), 545-554 (2016-03-15)
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