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M6316

Sigma-Aldrich

MRS 1754 hydrate

≥98% (HPLC), solid

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C26H26N6O4 · xH2O
CAS-Nummer:
264622-58-4
Molekulargewicht:
486.52 (anhydrous basis)
MDL-Nummer:
MFCD11046004
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278793
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

solid

Farbe

off-white

Löslichkeit

DMSO: soluble >10 mg/mL

Lagertemp.

room temp

SMILES String

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

InChIKey

ZACJDWOPQROWIK-UHFFFAOYSA-N

Angaben zum Gen

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

Anwendung

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

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Rechtliche Hinweise

Manufactured and sold under license from Adenosine Therapeutics LLC.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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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)
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
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
Vinegar intake enhances flow-mediated vasodilatation via upregulation of endothelial nitric oxide synthase activity
Sakakibara S, et al.
Bioscience, Biotechnology, and Biochemistry, 74(5), 1055-1061 (2010)
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