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SML3089

Sigma-Aldrich

MRS-1706

≥98% (HPLC)

Synonym(s):

8-[4-[((4-Acetylphenyl)carbamoylmethyl)oxy]phenyl]-1,3-di(n-propyl)xanthine, MRS 1706, MRS1706, N-(4-Acetylphenyl)-2-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)phenoxy)acetamide, N-(4-Acetylphenyl)-2-[4-(2,3,6,9-tetrahydro-2,6-dioxo-1,3-dipropyl-1H-purin-8-yl)phenoxy]acetamide

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About This Item

Empirical Formula (Hill Notation):
C27H29N5O5
CAS Number:
264622-53-9
Molecular Weight:
503.55
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O=C(COC1=CC=C(C=C1)C2=NC3=C(N2)N(C(N(C3=O)CCC)=O)CCC)NC4=CC=C(C=C4)C(C)=O

InChI

1S/C27H29N5O5/c1-4-14-31-25-23(26(35)32(15-5-2)27(31)36)29-24(30-25)19-8-12-21(13-9-19)37-16-22(34)28-20-10-6-18(7-11-20)17(3)33/h6-13H,4-5,14-16H2,1-3H3,(H,28,34)(H,29,30)

InChI key

ZKUCFFYOQOJLGT-UHFFFAOYSA-N

Biochem/physiol Actions

MRS-1706 is a high-affinity, potent and selective adenosine 2B receptor (A2B) antagonist/inverse agonist (human A1/A2A/A2B/A3 Ki = 157/112/1.39/230 nM; rat A1/A2A Ki = 37.6/548 nM). MRS-1706 (20 nM), but not the A2A antagonist SCH 58261 (20 nM), completely blocks the enhancement of electrically evoked tritium overflow from isolated rat tail artery by 10 μM adenosine receptor agonist NECA in the presence of 30 nM A1 antagonist DPCPX.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Y C Kim et al.
Journal of medicinal chemistry, 43(6), 1165-1172 (2000-03-29)
No highly selective antagonists of the A(2B) adenosine receptor (AR) have been reported; however such antagonists have therapeutic potential as antiasthmatic agents. Here we report the synthesis of potent and selective A(2B) receptor antagonists. The structure-activity relationships (SAR) of 8-phenyl-1
The Effect of Adenosine A2A and A2B Antagonists on Tracheal Responsiveness, Serum Levels of Cytokines and Lung Inflammation in Guinea Pig Model of Asthma.
Pejman, et al.
Advanced Pharmaceutical Bulletin, 4, 131-138 (2020)
Carmen Diniz et al.
European journal of pharmacology, 504(1-2), 17-25 (2004-10-28)
Adenosine receptors involved in the modulation of noradrenaline release from postganglionic sympathetic nerves in rat tail artery were characterized by studying the effects of adenosine-receptor agonists and antagonists on electrically evoked tritium overflow (100 pulses, 5 Hz) and by immunohistochemistry.
Ecto-5'-nucleotidase (CD73) attenuates inflammation after spinal cord injury by promoting macrophages/microglia M2 polarization in mice.
Xu, et al.
Journal of Neuroinflammation, 15, 155-155 (2019)
Jingman Xu et al.
Free radical biology & medicine, 106, 208-218 (2017-02-22)
While it is well known that adenosine receptor activation protects the heart from ischemia/reperfusion injury, the precise mitochondrial mechanism responsible for the action remains unknown. This study probed the mitochondrial events associated with the cardioprotective effect of 5'-(N-ethylcarboxamido) adenosine (NECA)
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