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Details

Stereochemistry ACHIRAL
Molecular Formula C13H16N6O8
Molecular Weight 384.3015
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of JS-K

SMILES

CCOC(=O)N1CCN(CC1)[N+](\[O-])=N\OC2=CC=C(C=C2[N+]([O-])=O)[N+]([O-])=O

InChI

InChIKey=DNJRNBYZLPKSHV-RGEXLXHISA-N
InChI=1S/C13H16N6O8/c1-2-26-13(20)15-5-7-16(8-6-15)19(25)14-27-12-4-3-10(17(21)22)9-11(12)18(23)24/h3-4,9H,2,5-8H2,1H3/b19-14-

HIDE SMILES / InChI

Molecular Formula C13H16N6O8
Molecular Weight 384.3015
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28653883 | https://www.ncbi.nlm.nih.gov/pubmed/20797387 | https://www.ncbi.nlm.nih.gov/pubmed/20962031 | https://www.ncbi.nlm.nih.gov/pubmed/23927471

O2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate (JS-K) is an antiproliferative nitric oxide (NO) donor that reacts with glutathione to generate NO at physiological pH. It inhibits proliferation of HL-60 cells (IC50 = 0.5 µM), which is prevented by the glutathione precursor N-acetyl-L-cysteine, and inhibits growth of the solid tumor cell lines PPC-1, DLD-1, and Meth A. JS-K decreases tumor volume by over 50% in an HL-60 mouse xenograft model when used at a dose of 4 µmol/kg, i.v., three times per week. JS-K inhibits proliferation, induces apoptosis, and disrupts the cell cycle of Jurkat T acute lymphoblastic leukemia cells. It also induces S-nitrosylation of β-catenin followed by dose-dependent degradation of nuclear β-catenin and S-nitrosylated nuclear β-catenin levels.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

mice were treated three times a week for 3 weeks with intravenous tail vein injections of either vehicle (2.25% Pluronic P123 in PBS) or JS-K (6 μmol/kg in the vehicle).
Route of Administration: Intravenous
Human U87 cells (HTB-14), fibroblasts (CRL-1634), and astrocytes (CRL-8621; ATCC) were cultured in Dulbecco’s Minimal Essential Eagle Medium (DMEM; Gibco, USA) supplemented with 10% fetal calf serum (FCS) and penicillin (100U/mL)/streptomycin (100mg/mL) under normoxic conditions (95% air, 5% CO2, and 37°C). The nitric oxide donor JS-K (O2-(2.4-dinitrophenyl) 1-[(4-ethoxycarbonyl) piperazin-1-yl] diazen-1-ium1,2-diolate, CAS 7054 32-12-8) was dissolved in 100% dimethyl sulfoxide (DMSO) in a concentration of 5.2mM. U87 was incubated with JS-K doses of 0–15µM for 4 h. The JS-K solvent control (DMSO≤1%) was adjusted to the highest JS-K concentration used in these experiments. A cesium source emitting γ-radiation was used for radiotherapy (RT; 3×2Gy) with a 24-h interval between each RT dose (Isotopen Diagnostik CIS, Germany).
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:41:00 GMT 2023
Edited
by admin
on Sat Dec 16 06:41:00 GMT 2023
Record UNII
80P1Q21652
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
JS-K
Common Name English
1-PIPERAZINECARBOXYLIC ACID, 4-((2,4-DINITROPHENOXY)-NNO-AZOXY)-, ETHYL ESTER
Common Name English
O2-(2,4-DINITROPHENYL) 1-((4-ETHOXYCARBONYL)PIPERAZIN-1-YL)DIAZEN-1-IUM-1,2-DIOLATE
Common Name English
O2-(2,4-DINITROPHENYL) 1-((4-ETHOXYCARBONYL)PIPERAZIN-1YL)DIAZEN-1-IUM-1,2-DIOLATE
Systematic Name English
1-PIPERAZINECARBOXYLIC ACID, 4-(2-(2,4-DINITROPHENOXY)-1-OXIDODIAZENYL)-, ETHYL ESTER
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 414013
Created by admin on Sat Dec 16 06:41:00 GMT 2023 , Edited by admin on Sat Dec 16 06:41:00 GMT 2023
FDA ORPHAN DRUG 363412
Created by admin on Sat Dec 16 06:41:00 GMT 2023 , Edited by admin on Sat Dec 16 06:41:00 GMT 2023
Code System Code Type Description
CAS
205432-12-8
Created by admin on Sat Dec 16 06:41:00 GMT 2023 , Edited by admin on Sat Dec 16 06:41:00 GMT 2023
PRIMARY
PUBCHEM
9572720
Created by admin on Sat Dec 16 06:41:00 GMT 2023 , Edited by admin on Sat Dec 16 06:41:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID70174545
Created by admin on Sat Dec 16 06:41:00 GMT 2023 , Edited by admin on Sat Dec 16 06:41:00 GMT 2023
PRIMARY
FDA UNII
80P1Q21652
Created by admin on Sat Dec 16 06:41:00 GMT 2023 , Edited by admin on Sat Dec 16 06:41:00 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY