M6316

MRS 1754 hydrate

Name: MRS 1754 hydrate
Brand: SIGMA
Price: 292 USD

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₆H₂₆N₆O₄ · xH₂O

CAS Number:

264622-58-4

Molecular Weight:

486.52 (anhydrous basis)

MDL number:

MFCD11046004

UNSPSC Code:

12352200

PubChem Substance ID:

24278793

NACRES:

NA.77

Key Documents

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Quality Level

100

assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: soluble >10 mg/mL

storage temp.

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

InChI key

ZACJDWOPQROWIK-UHFFFAOYSA-N

Gene Information

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

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1 of 4

This Item	O1385	P0039	PZ0136
Sigma-Aldrich M6316 MRS 1754 hydrate	Sigma-Aldrich O1385 Ozagrel hydrochloride hydrate	Sigma-Aldrich P0039 PHPS1 sodium salt hydrate	Sigma-Aldrich PZ0136 CP-100263 dihydrochloride hydrate
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥97% (HPLC)
form solid	form solid	form solid	form solid
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. room temp	storage temp. room temp	storage temp. 2-8°C	storage temp. room temp
solubility DMSO: soluble >10 mg/mL	solubility H₂O: soluble	solubility DMSO: 10 mg/mL, clear (warmed)	solubility H₂O: ≥5 mg/mL
color off-white	color white to off-white	color red	color white to off-white

Application

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)[1]
blastema formation in zebrafish[2]
to serve as a positive control in the anti-sickling assay and to study the role of RA2B in the same[3]

Biochem/physiol Actions

MRS 1754 hydrate is a p-cyanoanilide xanthine derivative. It might act as a potential anti-asthmatic drug.[4]

MRS 1754 hydrate is a potent A_2B adenosine receptor antagonist.

Features and Benefits

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.

Legal Information

Manufactured and sold under license from Adenosine Therapeutics LLC.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000292270

0000096941

119K4608V

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Nanomolar anti-sickling compounds identified by ligand-based pharmacophore approach.

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 A(2B) adenosine receptors.

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

Treg tissue stability depends on lymphotoxin beta-receptor- and adenosine-receptor-driven lymphatic endothelial cell responses.

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

[3H] MRS 1754, a selective antagonist radioligand for A2B adenosine receptors

Ji XD, et al.

Biochemical Pharmacology, 61(6), 657-663 (2001)

Adenosine enhances progenitor cell recruitment and nerve growth via its A2B receptor during adult fin regeneration.

Christine Rampon et al.

Purinergic signalling, 10(4), 595-602 (2014-08-03)

A major issue in regenerative medicine is the control of progenitor cell mobilisation. Apoptosis has been reported as playing a role in cell plasticity, and it has been recently shown that apoptosis is necessary for organ and appendage regeneration. In

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MRS 1754 hydrate