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
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-
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19538173Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19538173
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0007263 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23927471 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20962031
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28653883
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
Edited
Sat Dec 16 06:41:00 GMT 2023
by
admin
on
Sat Dec 16 06:41:00 GMT 2023
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Record UNII |
80P1Q21652
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
414013
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FDA ORPHAN DRUG |
363412
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205432-12-8
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9572720
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DTXSID70174545
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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
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