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J4137

Sigma-Aldrich

JS-K

≥97%

Synonym(s):

O2-(2,4-Dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate

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About This Item

Empirical Formula (Hill Notation):
C13H16N6O8
CAS Number:
205432-12-8
Molecular Weight:
384.30
MDL number:
MFCD06407868
UNSPSC Code:
12352200
PubChem Substance ID:
24724519
NACRES:
NA.77

Quality Level

100

assay

≥97%

storage condition

desiccated

solubility

DMSO: soluble 9.3 mg/mL
H2O: insoluble

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCOC(=O)N1CCN(CC1)\[N+]([O-])=N\Oc2ccc(cc2[N+]([O-])=O)[N+]([O-])=O

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-

InChI key

DNJRNBYZLPKSHV-RGEXLXHISA-N

Biochem/physiol Actions

JS-K belongs to the class of diazeniumdiolate prodrug. It generates nitric oxide when metabolized by glutathione S-transferases (GST), which ensures optimal activity of JS-K. It has tumor growth inhibition action in human prostate cancer and leukemia.
Nitric oxide donor; antiproliferative.

Legal Information

Covered by US Patent No 6,610,660

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Ray Dong et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 88, 367-373 (2017-01-26)
JS-K is a novel anticancer nitric oxide (NO) prodrug effective against a variety of cancer cells, including the inhibition of AM-1 hepatoma cell growth in rats. To further evaluate anticancer effects of JS-K, human hepatoma Hep3B cells were treated with
Martin Laschak et al.
BMC cancer, 12, 130-130 (2012-04-03)
Nitric oxide (NO) and its oxidative reaction products have been repeatedly shown to block steroid receptor function via nitrosation of zinc finger structures in the DNA-binding domain (DBD). In consequence NO-donors could be of special interest for the treatment of
Zeqing Song et al.
Oncology reports, 41(6), 3475-3487 (2019-04-20)
Lung cancer is one of the most common malignancies worldwide, with high mortality and morbidity rates. O2‑​(2,4‑​dinitrophenyl)‑1‑​[(4‑ethoxycarbonyl)piperazin‑1‑yl]diazen‑1‑ium‑1,2‑diolate (JS‑K) is a potent anticancer agent that acts against a subset of human non‑small cell lung cancer (NSCLC) cell lines; however, the underlying
Zhengyun Liu et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 92, 989-997 (2017-06-14)
Hepatocellular carcinoma (HCC) is the most important cause of cancer-related death, and 85% of HCC is caused by chronic HBV infection, the prognosis of patients and the reduction of HBV DNA levels remain unsatisfactory. JS-K, a nitric oxide-releasing diazeniumdiolates, is
Bin Liu et al.
BMC cancer, 19(1), 645-645 (2019-07-03)
Ovarian cancer (OC) is the second most frequent gynecological cancer and is associated with a poor prognosis because OC progression is often asymptoma-tic and is detected at a late stage. There remains an urgent need for novel targeted therapies to
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