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Merck
CN

SML1983

PSB-603

≥98% (HPLC)

Synonym(s):

8-(4-(4-(4-Chlorophenyl)piperazide-1-sulfonyl)phenyl)-1-propylxanthine, 8-[4-[[4-(4-Chlorophenyl)-1-piperazinyl]sulfonyl]phenyl]-3,9-dihydro-1-propyl-1H-purine-2,6-dione, PSB 603, PSB603

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About This Item

Empirical Formula (Hill Notation):
C24H25ClN6O4S
CAS Number:
1092351-10-4
Molecular Weight:
529.01
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Assay

≥98% (HPLC)

form

powder

color

white to brownish

solubility

DMSO: 2 mg/mL to clear

shipped in

ambient

storage temp.

2-8°C

SMILES string

O=C(N1CCC)NC2=C(N=C(C3=CC=C(S(=O)(N4CCN(C5=CC=C(Cl)C=C5)CC4)=O)C=C3)N2)C1=O

InChI

1S/C24H25ClN6O4S/c1-2-11-31-23(32)20-22(28-24(31)33)27-21(26-20)16-3-9-19(10-4-16)36(34,35)30-14-12-29(13-15-30)18-7-5-17(25)6-8-18/h3-10H,2,11-15H2,1H3,(H,26,27)(H,28,33)

InChI key

OVHCTHHFOHMNFV-UHFFFAOYSA-N

Biochem/physiol Actions

A high-affinity, selective antagonist against A2b adenosine receptor (A2b-AR, A2bR).
PSB-603 is an adenosine receptor A2b antagonist (IC50 = 1.13 nM against 10 μM A2bR agonist NECA-induced calcium response in Jurkat T cells in the presence of 200 nM A2aR antagonist MSX-2) that targets A2bR with high affinity (KD = 0.403 nM/human, 0.457 nM/rat, 4.09 nM/mouse A2bR; Ki against 0.3 nM [3H]PSB-603 = 0.553 nM/human, 0.355 nM/rat, 0.265 nM/mouse A2bR) and selectivity, exhibiting little affinity toward A1, A2a, or A3 adenosine receptors by competition binding assay (Ki >10 μM against 0.4 nM [3H]DPCPX for human/rat A1R, 1 nM [3H]MSX-2 for human/mouse/rat A2aR, 10 nM [3H]NECA for human/mouse/rat A3R) with the exception of mouse A1R (Ki = 42.2 nM against 0.4 nM [3H]DPCPX).
PSB-603 is known to modify cellular metabolism and enhance cellular sensitivity for chemotherapy. Thus, PSB-603 is recognized to possess anticancer action, which has been studied in colorectal cancer.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000406407
0000406407
0000140493
0000113309
0000083756

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Christina Mølck et al.
Cancer letters, 383(1), 135-143 (2016-10-30)
Adenosine is a multifaceted regulator of tumor progression. It modulates immune cell activity as well as acting directly on tumor cells. The A The A PSB-603 alters cellular metabolism in colorectal cancer cells and increases their sensitivity to chemotherapy. Although
Mohamad Wessam Alnouri et al.
Purinergic signalling, 11(3), 389-407 (2015-07-02)
Adenosine receptors (ARs) have emerged as new drug targets. The majority of data on affinity/potency and selectivity of AR ligands described in the literature has been obtained for the human species. However, preclinical studies are mostly performed in mouse or
The A2b adenosine receptor antagonist PSB-603 promotes oxidative phosphorylation and ROS production in colorectal cancer cells via adenosine receptor-independent mechanism.
M?lck C, et al.
Cancer Letters, 383(1), 135-143 (2016)
Denis Chang et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(44), 27502-27508 (2020-10-23)
Cyclic dinucleotides (CDNs) are secondary messengers used by prokaryotic and eukaryotic cells. In mammalian cells, cytosolic CDNs bind STING (stimulator of IFN gene), resulting in the production of type I IFN. Extracellular CDNs can enter the cytosol through several pathways
Thomas Borrmann et al.
Journal of medicinal chemistry, 52(13), 3994-4006 (2009-07-03)
A new series of 1-alkyl-8-(piperazine-1-sulfonyl)phenylxanthines was designed, synthesized, and characterized in radioligand binding and functional assays at A(2B) adenosine receptors. A(2B) antagonists with subnanomolar affinity and high selectivity were discovered. The most potent compounds were 1-ethyl-8-(4-(4-(4-trifluoromethylbenzyl)piperazine-1-sulfonyl)phenyl)xanthine (24, PSB-09120, K(i) (human

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