Related CAS #
1802226-78-3 (free acid)
Synonym
PSB-12379; PSB 12379; PSB12379; PSB-12379 disodium; N6-Benzyl-α,β-methyleneadenosine 5'-diphosphate disodium salt.
IUPAC/Chemical Name
sodium hydrogen (((((2R,3S,4R,5R)-5-(6-(benzylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)oxidophosphoryl)methyl)phosphonate
InChi Key
CGXINRNHTNDEBI-BUPZQQHBSA-L
InChi Code
InChI=1S/C18H23N5O9P2.2Na/c24-14-12(7-31-34(29,30)10-33(26,27)28)32-18(15(14)25)23-9-22-13-16(20-8-21-17(13)23)19-6-11-4-2-1-3-5-11;;/h1-5,8-9,12,14-15,18,24-25H,6-7,10H2,(H,29,30)(H,19,20,21)(H2,26,27,28);;/q;2*+1/p-2/t12-,14-,15-,18-;;/m1../s1
SMILES Code
O[C@@H]1[C@H](O[C@H]([C@@H]1O)N2C3=NC=NC(NCC4=CC=CC=C4)=C3N=C2)COP(CP(O)(O[Na])=O)(O[Na])=O
Appearance
Colorless liquid
Purity
>98% ((pre-dissolved in water at a concentration of 10 mM).
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
PSB-12379 is a selective high affinity ecto-5'-nucleotidase/CD73 inhibitor (Ki values are 2.21 and 9.03 nM at human and rat CD73, respectively). PSB-12379 blocks ecto-5'-nucleotidase-mediated adenosine production by preventing the conversion of AMP to adenosine.
In vitro activity:
PSB-12379 demonstrated significant in vitro activity as an eN, CD73 inhibitor. It exhibited a Ki value of 9.03 nM. PSB-12379 showed high selectivity against other ecto-nucleotidases and ADP-activated P2Y receptors and demonstrated high metabolic stability.
Reference: J Med Chem. 2015 Aug 13;58(15):6248-63. https://pubmed.ncbi.nlm.nih.gov/26147331/
In vivo activity:
To be determined
Preparing Stock Solutions
The following data is based on the
product
molecular weight
559.32
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Schmies CC, Rolshoven G, Idris RM, Losenkova K, Renn C, Schäkel L, Al-Hroub H, Wang Y, Garofano F, Schmidt-Wolf IGH, Zimmermann H, Yegutkin GG, Müller CE. Fluorescent Probes for Ecto-5'-nucleotidase (CD73). ACS Med Chem Lett. 2020 Sep 3;11(11):2253-2260. doi: 10.1021/acsmedchemlett.0c00391. PMID: 33214837; PMCID: PMC7667873.
2. Bhattarai S, Freundlieb M, Pippel J, Meyer A, Abdelrahman A, Fiene A, Lee SY, Zimmermann H, Yegutkin GG, Sträter N, El-Tayeb A, Müller CE. α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5'-Nucleotidase (CD73) Inhibitors. J Med Chem. 2015 Aug 13;58(15):6248-63. doi: 10.1021/acs.jmedchem.5b00802. Epub 2015 Jul 30. PMID: 26147331.
In vitro protocol:
1. Schmies CC, Rolshoven G, Idris RM, Losenkova K, Renn C, Schäkel L, Al-Hroub H, Wang Y, Garofano F, Schmidt-Wolf IGH, Zimmermann H, Yegutkin GG, Müller CE. Fluorescent Probes for Ecto-5'-nucleotidase (CD73). ACS Med Chem Lett. 2020 Sep 3;11(11):2253-2260. doi: 10.1021/acsmedchemlett.0c00391. PMID: 33214837; PMCID: PMC7667873.
2. Bhattarai S, Freundlieb M, Pippel J, Meyer A, Abdelrahman A, Fiene A, Lee SY, Zimmermann H, Yegutkin GG, Sträter N, El-Tayeb A, Müller CE. α,β-Methylene-ADP (AOPCP) Derivatives and Analogues: Development of Potent and Selective ecto-5'-Nucleotidase (CD73) Inhibitors. J Med Chem. 2015 Aug 13;58(15):6248-63. doi: 10.1021/acs.jmedchem.5b00802. Epub 2015 Jul 30. PMID: 26147331.
In vivo protocol:
To be determined
1: Bhattarai S, Freundlieb M, Pippel J, Meyer A, Abdelrahman A, Fiene A, Lee SY,
Zimmermann H, Yegutkin GG, Sträter N, El-Tayeb A, Müller CE. α,β-Methylene-ADP
(AOPCP) Derivatives and Analogues: Development of Potent and Selective
ecto-5'-Nucleotidase (CD73) Inhibitors. J Med Chem. 2015 Aug 13;58(15):6248-63.
doi: 10.1021/acs.jmedchem.5b00802. PubMed PMID: 26147331.
2: Viczjan G, Erdei T, Ovari I, Lampe N, Szekeres R, Bombicz M, Takacs B, Szilagyi A, Zsuga J, Szilvassy Z, Juhasz B, Gesztelyi R. A Body of Circumstantial Evidence for the Irreversible Ectonucleotidase Inhibitory Action of FSCPX, an Agent Known as a Selective Irreversible A1 Adenosine Receptor Antagonist So Far. Int J Mol Sci. 2021 Sep 11;22(18):9831. doi: 10.3390/ijms22189831. PMID: 34575993; PMCID: PMC8464902.
