JS-K | CAS#205432-12-8 | antiproliferative

MedKoo Cat#: 596297 | Name: JS-K

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

JS-K is a Nitric oxide donor; antiproliferative.

Chemical Structure

JS-K

CAS#205432-12-8

Theoretical Analysis

MedKoo Cat#: 596297

Name: JS-K

CAS#: 205432-12-8

Chemical Formula: C13H16N6O8

Exact Mass: 384.1030

Molecular Weight: 384.31

Elemental Analysis: C, 40.63; H, 4.20; N, 21.87; O, 33.30

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks

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Synonym

JS-K; JS K; JSK;

IUPAC/Chemical Name

(Z)-2-(2,4-dinitrophenoxy)-1-(4-(ethoxycarbonyl)piperazin-1-yl)diazene 1-oxide

InChi Key

DNJRNBYZLPKSHV-RGEXLXHISA-N

InChi Code

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-

SMILES Code

O=C(N1CCN(/[N+]([O-])=N/OC2=CC=C([N+]([O-])=O)C=C2[N+]([O-])=O)CC1)OCC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

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

Soluble in DMSO

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

JS-K is a NO donor that reacts with glutathione to generate NO at physiological pH. JS-K inhibits proliferation, induces apoptosis, and disrupts the cell cycle of Jurkat T acute lymphoblastic leukemia cells.

In vitro activity:

First, the inhibitory effects of proliferation by JS-K onC4-2 and LNCaP cells were investigated. JS-K inhibited growth of C4-2 and LNCaP cells in a time-dependent manner (Fig. 1a and b, respectively). Reference: BMC Cancer. 2017 May 26;17(1):376. https://pubmed.ncbi.nlm.nih.gov/28549433/

In vivo activity:

To investigate the effects of JS-K on tumor growth in vivo, this study used a mouse xenograft tumor model.These results indicated that JS-K (6 mg/kg) inhibited tumor growth and had a fewer side effects than treatment with Cisplatin (2 mg/kg) in vivo. Reference: BMC Cancer. 2019 Jul 1;19(1):645. https://pubmed.ncbi.nlm.nih.gov/31262254/

	Solvent	mg/mL	mM
Solubility
	DMF	0.5	1.30
	DMSO	0.3	0.78

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 384.31 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. Tan G, Qiu M, Chen L, Zhang S, Ke L, Liu J. JS-K, a nitric oxide pro-drug, regulates growth and apoptosis through the ubiquitin-proteasome pathway in prostate cancer cells. BMC Cancer. 2017 May 26;17(1):376. doi: 10.1186/s12885-017-3351-0. PMID: 28549433; PMCID: PMC5446692. 2. Qiu M, Chen L, Tan G, Ke L, Zhang S, Chen H, Liu J. JS-K promotes apoptosis by inducing ROS production in human prostate cancer cells. Oncol Lett. 2017 Mar;13(3):1137-1142. doi: 10.3892/ol.2016.5535. Epub 2016 Dec 27. PMID: 28454225; PMCID: PMC5403315. 3. Liu B, Huang X, Li Y, Liao W, Li M, Liu Y, He R, Feng D, Zhu R, Kurihara H. JS-K, a nitric oxide donor, induces autophagy as a complementary mechanism inhibiting ovarian cancer. BMC Cancer. 2019 Jul 1;19(1):645. doi: 10.1186/s12885-019-5619-z. PMID: 31262254; PMCID: PMC6604176. 4. Zhao X, Cai A, Peng Z, Liang W, Xi H, Li P, Chen G, Yu J, Chen L. JS-K induces reactive oxygen species-dependent anti-cancer effects by targeting mitochondria respiratory chain complexes in gastric cancer. J Cell Mol Med. 2019 Apr;23(4):2489-2504. doi: 10.1111/jcmm.14122. Epub 2019 Jan 22. PMID: 30672108; PMCID: PMC6433691.

In vitro protocol:

In vivo protocol:

1. Liu B, Huang X, Li Y, Liao W, Li M, Liu Y, He R, Feng D, Zhu R, Kurihara H. JS-K, a nitric oxide donor, induces autophagy as a complementary mechanism inhibiting ovarian cancer. BMC Cancer. 2019 Jul 1;19(1):645. doi: 10.1186/s12885-019-5619-z. PMID: 31262254; PMCID: PMC6604176. 2. Zhao X, Cai A, Peng Z, Liang W, Xi H, Li P, Chen G, Yu J, Chen L. JS-K induces reactive oxygen species-dependent anti-cancer effects by targeting mitochondria respiratory chain complexes in gastric cancer. J Cell Mol Med. 2019 Apr;23(4):2489-2504. doi: 10.1111/jcmm.14122. Epub 2019 Jan 22. PMID: 30672108; PMCID: PMC6433691.

1: Liu L, Huang Z, Chen J, Wang J, Wang S. Protein phosphatase 2A mediates JS-K-induced apoptosis by affecting Bcl-2 family proteins in human hepatocellular carcinoma HepG2 cells. J Cell Biochem. 2018 Apr 25. doi: 10.1002/jcb.26845. [Epub ahead of print] PubMed PMID: 29693750. 2: Kang F, Ai Y, Zhang Y, Huang Z. Design and synthesis of new hybrids from 2-cyano-3,12-dioxooleana- 9-dien-28-oic acid and O(2)-(2,4-dinitrophenyl) diazeniumdiolate for intervention of drug-resistant lung cancer. Eur J Med Chem. 2018 Apr 10;149:269-280. doi: 10.1016/j.ejmech.2018.02.062. Epub 2018 Feb 23. PubMed PMID: 29501947. 3: Huang Z, Wu J, Zou Y, Yuan H, Zhang Y, Fei Y, Bhardwaj A, Kaur J, Knaus EE, Zhang Y. Glutathione S-Transferase π-Activatable O(2)-(Sulfonylethyl Derived) Diazeniumdiolates Potently Suppress Melanoma in Vitro and in Vivo. J Med Chem. 2018 Mar 8;61(5):1833-1844. doi: 10.1021/acs.jmedchem.7b01178. Epub 2018 Feb 16. PubMed PMID: 29420887. 4: Li Q, Zou P, Sun J, Chen L. O(2)-(2,4-dinitrophenyl)diazeniumdiolates derivatives: Design, synthesis, cytotoxic evaluation and reversing MDR in MCF-7/ADR cells. Eur J Med Chem. 2018 Jan 1;143:732-744. doi: 10.1016/j.ejmech.2017.11.081. PubMed PMID: 29220794. 5: Sano N, Kim JS, Onda Y, Nomura T, Mochida K, Okamoto M, Seo M. RNA-Seq using bulked recombinant inbred line populations uncovers the importance of brassinosteroid for seed longevity after priming treatments. Sci Rep. 2017 Aug 14;7(1):8095. doi: 10.1038/s41598-017-08116-5. PubMed PMID: 28808238; PubMed Central PMCID: PMC5556009. 6: Heckler M, Osterberg N, Guenzle J, Thiede-Stan NK, Reichardt W, Weidensteiner C, Saavedra JE, Weyerbrock A. The nitric oxide donor JS-K sensitizes U87 glioma cells to repetitive irradiation. Tumour Biol. 2017 Jun;39(6):1010428317703922. doi: 10.1177/1010428317703922. PubMed PMID: 28653883. 7: Qiu M, Ke L, Zhang S, Zeng X, Fang Z, Liu J. JS-K, a GST-activated nitric oxide donor prodrug, enhances chemo-sensitivity in renal carcinoma cells and prevents cardiac myocytes toxicity induced by Doxorubicin. Cancer Chemother Pharmacol. 2017 Aug;80(2):275-286. doi: 10.1007/s00280-017-3359-9. Epub 2017 Jun 12. PubMed PMID: 28608259. 8: Liu Z, Li G, Gou Y, Xiao D, Luo G, Saavedra JE, Liu J, Wang H. JS-K, a nitric oxide prodrug, induces DNA damage and apoptosis in HBV-positive hepatocellular carcinoma HepG2.2.15 cell. Biomed Pharmacother. 2017 Aug;92:989-997. doi: 10.1016/j.biopha.2017.05.141. Epub 2017 Jun 8. PubMed PMID: 28605880. 9: Tan G, Qiu M, Chen L, Zhang S, Ke L, Liu J. JS-K, a nitric oxide pro-drug, regulates growth and apoptosis through the ubiquitin-proteasome pathway in prostate cancer cells. BMC Cancer. 2017 May 26;17(1):376. doi: 10.1186/s12885-017-3351-0. PubMed PMID: 28549433; PubMed Central PMCID: PMC5446692. 10: Qiu M, Chen L, Tan G, Ke L, Zhang S, Chen H, Liu J. JS-K promotes apoptosis by inducing ROS production in human prostate cancer cells. Oncol Lett. 2017 Mar;13(3):1137-1142. doi: 10.3892/ol.2016.5535. Epub 2016 Dec 27. PubMed PMID: 28454225; PubMed Central PMCID: PMC5403315. 11: Guenzle J, Wolf LJ, Garrelfs NW, Goeldner JM, Osterberg N, Schindler CR, Saavedra JE, Weyerbrock A. ATF3 reduces migration capacity by regulation of matrix metalloproteinases via NFκB and STAT3 inhibition in glioblastoma. Cell Death Discov. 2017 Feb 27;3:17006. doi: 10.1038/cddiscovery.2017.6. eCollection 2017. PubMed PMID: 28250971; PubMed Central PMCID: PMC5327503. 12: Dong R, Wang X, Wang H, Liu Z, Liu J, Saavedra JE. Effects of JS-K, a novel anti-cancer nitric oxide prodrug, on gene expression in human hepatoma Hep3B cells. Biomed Pharmacother. 2017 Apr;88:367-373. doi: 10.1016/j.biopha.2017.01.080. Epub 2017 Jan 22. PubMed PMID: 28122301. 13: Anand KV, Lal CA, Ac G, Js K, Saurabh A. Assessment of the relationship between microalbuminuria, diabetic nephropathy & diabetic retinopathy. J Assoc Physicians India. 2016 Jan;64(1):92. PubMed PMID: 27728114. 14: Xue R, Wu J, Luo X, Gong Y, Huang Y, Shen X, Zhang H, Zhang Y, Huang Z. Design, Synthesis, and Evaluation of Diazeniumdiolate-Based DNA Cross-Linking Agents Activatable by Glutathione S-Transferase. Org Lett. 2016 Oct 4. [Epub ahead of print] PubMed PMID: 27696880. 15: Günzle J, Osterberg N, Saavedra JE, Weyerbrock A. Nitric oxide released from JS-K induces cell death by mitotic catastrophe as part of necrosis in glioblastoma multiforme. Cell Death Dis. 2016 Sep 1;7(9):e2349. doi: 10.1038/cddis.2016.254. PubMed PMID: 27584787; PubMed Central PMCID: PMC5059858. 16: Liu L, Wang D, Wang J, Wang S. The Nitric Oxide Prodrug JS-K Induces Ca(2+)-Mediated Apoptosis in Human Hepatocellular Carcinoma HepG2 Cells. J Biochem Mol Toxicol. 2016 Apr;30(4):192-9. doi: 10.1002/jbt.21778. Epub 2015 Nov 30. PubMed PMID: 26616367. 17: Qiu M, Chen L, Tan G, Ke L, Zhang S, Chen H, Liu J. A reactive oxygen species activation mechanism contributes to JS-K-induced apoptosis in human bladder cancer cells. Sci Rep. 2015 Oct 13;5:15104. doi: 10.1038/srep15104. PubMed PMID: 26458509; PubMed Central PMCID: PMC4602210. 18: Zhang R, Yang J, Zhou Y, Shami PJ, Kopeček J. N-(2-Hydroxypropyl)methacrylamide Copolymer-Drug Conjugates for Combination Chemotherapy of Acute Myeloid Leukemia. Macromol Biosci. 2016 Jan;16(1):121-8. doi: 10.1002/mabi.201500193. Epub 2015 Jul 29. PubMed PMID: 26222892; PubMed Central PMCID: PMC4805371. 19: Fionda C, Abruzzese MP, Zingoni A, Soriani A, Ricci B, Molfetta R, Paolini R, Santoni A, Cippitelli M. Nitric oxide donors increase PVR/CD155 DNAM-1 ligand expression in multiple myeloma cells: role of DNA damage response activation. BMC Cancer. 2015 Jan 22;15:17. doi: 10.1186/s12885-015-1023-5. PubMed PMID: 25609078; PubMed Central PMCID: PMC4311457. 20: Kaur I, Kosak KM, Terrazas M, Herron JN, Kern SE, Boucher KM, Shami PJ. Effect of a Pluronic(®) P123 formulation on the nitric oxide-generating drug JS-K. Pharm Res. 2015 Apr;32(4):1395-406. doi: 10.1007/s11095-014-1542-9. Epub 2014 Oct 18. PubMed PMID: 25330743; PubMed Central PMCID: PMC4359075.