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M7571

Sigma-Aldrich

MK-571 sodium salt hydrate

≥95% (HPLC)

Synonym(s):
5-(3-(2-(7-Chloroquinolin-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoic acid sodium salt hydrate, L-660711
Empirical Formula (Hill Notation):
C26H26ClN2NaO3S2 · xH2O
CAS Number:
Molecular Weight:
537.07 (anhydrous basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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
[99]
  • to assess its effect on cell proliferation and 2D-migration in vitro in various cell lines of glioblastoma multiforme (GBM)
  • [19]
  • as multidrug resistance (MDR) transporter inhibitor to study its effects in ovarian cancer cells
  • [76]
  • as specific inhibitors of ABCC1/2 to investigate transport, toxicity, flow cytometry and arsenic efflux
  • [78]

    Packaging

    5, 25 mg in glass bottle

    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

    Signal Word

    Warning

    Hazard Statements

    Hazard Classifications

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

    Target Organs

    Respiratory system

    Storage Class Code

    11 - Combustible Solids

    WGK

    WGK 3

    Flash Point(F)

    Not applicable

    Flash Point(C)

    Not applicable

    Personal Protective Equipment

    dust mask type N95 (US), Eyeshields, Gloves

    Certificate of Analysis

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    Certificate of Origin

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