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SML0212

Sigma-Aldrich

PSB36

≥98% (HPLC)

Synonym(s):

1-Butyl-3-(3-hydroxypropyl)-8-(3-noradamantyl)xanthine, 1-Butyl-8-(hexahydro-2,5-methanopentalen-3a(1H)-yl)-3,9-dihydro-3-(3-hydroxypropyl)-1H-purine-2,6-dione, PSB-36

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About This Item

Empirical Formula (Hill Notation):
C21H30N4O3
CAS Number:
524944-72-7
Molecular Weight:
386.49
UNSPSC Code:
12352200
PubChem Substance ID:
329825233
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to tan

solubility

DMSO: ≥20 mg/mL

storage temp.

2-8°C

SMILES string

CCCCN1C(=O)N(CCCO)c2nc([nH]c2C1=O)C34C[C@@H]5C[C@@H](C[C@H]3C5)C4

InChI

1S/C21H30N4O3/c1-2-3-5-25-18(27)16-17(24(20(25)28)6-4-7-26)23-19(22-16)21-11-13-8-14(12-21)10-15(21)9-13/h13-15,26H,2-12H2,1H3,(H,22,23)/t13-,14+,15-,21-

InChI key

CIBIXJYFYPFMTN-FZUGUKJMSA-N

Application

PSB36 was used to examine the role of A1-adenosine receptor-mediated cell signaling in CD39 expression in pancreatic b-cells of streptozotocin-induced diabetic mice.

Biochem/physiol Actions

Inhibition of A1 adenosine receptor by PSB36 modulates the spinal antinociception in animal models.
PSB36 is a very potent, selective antagonist of the adenosine A1 receptor. The compound selectivity (Ki) for human A1, A2A, A2B and A3 receptors is 0.7, 980, 187 and 2300 respectively. PSB36 is considerably more potent that DPCPX (EC50 0.012 nM vs 2.9 nM)

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.

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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Yuta Tanaka et al.
Biological & pharmaceutical bulletin, 43(3), 516-525 (2019-12-24)
It is therapeutically important to elucidate the factors involved in the radiation resistance of tumors. We previously showed that ATP is released from mouse melanoma B16 cells in response to γ-irradiation, but the role of adenosine, a metabolite of ATP
Siqi Chen et al.
Cancer immunology research, 8(8), 1064-1074 (2020-05-10)
Accumulating evidence suggests that inhibiting adenosine-generating ecto-enzymes (CD39 and CD73) and/or adenosine A2A or A2B receptors (R) stimulates antitumor immunity and limits tumor progression. Although activating A2ARs or A2BRs causes similar immunosuppressive and protumoral functions, few studies have investigated the
Osama M Abo-Salem et al.
The Journal of pharmacology and experimental therapeutics, 308(1), 358-366 (2003-10-18)
Caffeine, an adenosine A1, A2A, and A2B receptor antagonist, is frequently used as an adjuvant analgesic in combination with nonsteroidal anti-inflammatory drugs or opioids. In this study, we have examined the effects of novel specific adenosine receptor antagonists in an
Luca Soattin et al.
Frontiers in physiology, 11, 493-493 (2020-07-01)
Adenosine leads to atrial action potential (AP) shortening through activation of adenosine 1 receptors (A1-R) and subsequent opening of G-protein-coupled inwardly rectifying K+ channels. Extracellular production of adenosine is drastically increased during stress and ischemia. The aim of this study
Kazuki Kitabatake et al.
Biological & pharmaceutical bulletin, 44(2), 197-210 (2020-12-04)
Glioblastoma is the most common malignant tumor of the central nervous system and is treated with a combination of surgery, radiation and chemotherapy. However, the tumor often acquires radiation resistance, which is characterized by an increased DNA damage response (DDR).
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