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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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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