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M6316

Sigma-Aldrich

MRS 1754 hydrate

≥98% (HPLC), solid

Sinónimos:

8-[4-[((4-Cyanophenyl)carbamoylmethyl)oxy]phenyl]-1,3-di(n-propyl)xanthine hydrate

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About This Item

Fórmula empírica (notación de Hill):
C26H26N6O4 · xH2O
Número de CAS:
264622-58-4
Peso molecular:
486.52 (anhydrous basis)
Número MDL:
MFCD11046004
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24278793
NACRES:
NA.77

Nivel de calidad

100

Análisis

≥98% (HPLC)

formulario

solid

color

off-white

solubilidad

DMSO: soluble >10 mg/mL

temp. de almacenamiento

room temp

cadena SMILES

O.CCCN1C(=O)N(CCC)c2[nH]c(nc2C1=O)-c3ccc(OCC(=O)Nc4ccc(cc4)C#N)cc3

InChI

1S/C26H26N6O4.H2O/c1-3-13-31-24-22(25(34)32(14-4-2)26(31)35)29-23(30-24)18-7-11-20(12-8-18)36-16-21(33)28-19-9-5-17(15-27)6-10-19;/h5-12H,3-4,13-14,16H2,1-2H3,(H,28,33)(H,29,30);1H2

Clave InChI

ZACJDWOPQROWIK-UHFFFAOYSA-N

Información sobre el gen

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora2b(29316)

Aplicación

MRS 1754 hydrate has been used as an adenosine receptor A2B (RA2B) antagonist:
  • to study its effects on endothelial nitric oxide synthase (eNOS) phosphorylation induced by short-term acetate stimulation in human umbilical vein endothelial cells (HUVECs)
  • blastema formation in zebrafish
  • to serve as a positive control in the anti-sickling assay and to study the role of RA2B in the same

Acciones bioquímicas o fisiológicas

MRS 1754 hydrate is a p-cyanoanilide xanthine derivative. It might act as a potential anti-asthmatic drug.
MRS 1754 hydrate is a potent A2B adenosine receptor antagonist.

Características y beneficios

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Información legal

Manufactured and sold under license from Adenosine Therapeutics LLC.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Odailson Santos Paz et al.
European journal of medicinal chemistry, 136, 487-496 (2017-05-22)
Adenosine receptors are considered as potential targets for drug development against several diseases. The discovery of subtype 2B adenosine receptors role in erythrocyte sickling process proved its importance to neglected diseases such as sickle cell anemia, which affects approximately 29.000
[3H] MRS 1754, a selective antagonist radioligand for A2B adenosine receptors
Ji XD, et al.
Biochemical Pharmacology, 61(6), 657-663 (2001)
X Ji et al.
Biochemical pharmacology, 61(6), 657-663 (2001-03-27)
MRS 1754 [N-(4-cyanophenyl)-2-[4-(2,3,6,7-tetrahydro-2,6-dioxo-1,3-dipropyl-1H-purin-8-yl)-phenoxy]acetamide] is a selective antagonist ligand of A(2B) adenosine receptors. This is the least well-defined adenosine receptor subtype, and A(2B) antagonists have potential as antiasthmatic drugs. For use as a radioligand, MRS 1754, a p-cyanoanilide xanthine derivative, was
Vikas Saxena et al.
Cell reports, 39(3), 110727-110727 (2022-04-21)
Regulatory T cell (Treg) lymphatic migration is required for resolving inflammation and prolonging allograft survival. Focusing on Treg interactions with lymphatic endothelial cells (LECs), we dissect mechanisms and functional consequences of Treg transendothelial migration (TEM). Using three genetic mouse models of
Zhan-Guo Gao et al.
iScience, 26(7), 107178-107178 (2023-07-05)
Protein kinase C (PKC) isoforms regulate many important signaling pathways. Here, we report that PKC activation by phorbol 12-myristate 13-acetate (PMA) enhanced A2B adenosine receptor (AR)-mediated, but not β2-adrenergic receptor-mediated, cAMP accumulation, in H9C2 cardiomyocyte-like and HEK293 cells. In addition
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