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M0319

Sigma-Aldrich

MRS 2578

≥95% (HPLC)

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Synonym(s):
1,4-Di[3-(3-isothiocyanatophenyl)thioureido]butane
Empirical Formula (Hill Notation):
C20H20N6S4
CAS Number:
711019-86-2
Molecular Weight:
472.67
MDL number:
MFCD07370141
UNSPSC Code:
12352200
PubChem Substance ID:
24724530
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

DMSO: >5 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

S=C=Nc1cccc(NC(=S)NCCCCNC(=S)Nc2cccc(c2)N=C=S)c1

InChI

1S/C20H20N6S4/c27-13-23-15-5-3-7-17(11-15)25-19(29)21-9-1-2-10-22-20(30)26-18-8-4-6-16(12-18)24-14-28/h3-8,11-12H,1-2,9-10H2,(H2,21,25,29)(H2,22,26,30)

InChI key

QOHNRGHTJPFMSL-UHFFFAOYSA-N

Application

MRS 2578 has been used an antagonist of purinoceptor P2Y6:
  • to study the role of purinergic receptor in Up4A-induced relaxation in coronary small arteries from swine
  • in P. aeruginosa infected mice to test its effect on the inflammatory responses
  • to test its inhibition on neutrophil extracellular traps and monosodium urate (MSU) crystals formation in polymorphonuclear leukocytes

Biochem/physiol Actions

MRS 2578 elicits cytoprotective functionality in neuroblastoma cells and prevents dopaminergic neuron death under in vitro and in vivo conditions. It also protects microglia by delaying lipopolysaccharide-induced death.
Potent and irreversible antagonist of P2Y6 nucleotide receptor.

Features and Benefits

This compound is featured on the P2 Receptors: P2Y G-Protein Family page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Liaman K Mamedova et al.
Biochemical pharmacology, 67(9), 1763-1770 (2004-04-15)
The physiological role of the P2Y(6) nucleotide receptor may involve cardiovascular, immune and digestive functions based on the receptor tissue distribution, and selective antagonists for this receptor are lacking. We have synthesized a series of symmetric aryl diisothiocyanate derivatives and
Junbo Zheng et al.
Respiratory research, 19(1), 190-190 (2018-10-01)
Pneumonia is a major cause of high morbidity and mortality in critically illness, and frequently requires support with mechanical ventilation. The latter can lead to ventilator-induced lung injury characterized by neutrophil infiltration. The cationic human neutrophil peptides (HNP) stored in
Ágatha Oliveira-Giacomelli et al.
Frontiers in cellular neuroscience, 13, 476-476 (2019-12-04)
Parkinson's disease (PD) is a neurodegenerative disorder characterized by decreased dopamine bioavailability in the substantia nigra and the striatum. Taking into account that adenosine-5'-triphosphate (ATP) and its metabolites are intensely released in the 6-hydroxydopamine (6-OHDA) animal model of PD, screening
Zhichao Zhou et al.
Purinergic signalling, 13(3), 319-329 (2017-05-26)
We previously demonstrated that uridine adenosine tetraphosphate (Up4A) induces potent and partially endothelium-dependent relaxation in the healthy porcine coronary microvasculature. We subsequently showed that Up4A-induced porcine coronary relaxation was impaired via downregulation of P1 receptors after myocardial infarction. In view
Tamara C Hornik et al.
Journal of cell science, 129(1), 65-79 (2015-11-15)
Some apoptotic processes, such as phosphatidylserine exposure, are potentially reversible and do not necessarily lead to cell death. However, phosphatidylserine exposure can induce phagocytosis of a cell, resulting in cell death by phagocytosis: phagoptosis. Phagoptosis of neurons by microglia might
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