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Compound Information

Compound Name: O2-(2,4-Dinitrophenyl) 1-[(4-Ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate

Compound

Figure: JS-K Structure

  1. Category Information
  2. Nickname: JS-K
  3. CAS Registry Number: 205432-12-8
  4. Molecular Formula: C13H16N6O8
  5. Molecular Weight: 384
  6. Half-life at pH 7.4 and 37oC:
  7. Moles of NO/Mole of Compound: 2 in presence of suitable nucleophiles.
  8. Solubility: Soluble in organic solvents, sparingly soluble in water (10 µM maximum)
  9. UV Spectrum

          λmax(nm):

          ε(mM-1cm-1):      

    300 (Ethanol)

    12
  10. X-Ray Crystallographic Data:
  11. Special Comments: This is a stable solid (mp 140-141oC). It reacts with nucleophiles to generate nitric oxide. Slows growth of multiple myeloma, leukemia, and prostate cancer xenografts in mice, also orthotopic liver tumors in rats. This compound is known to be commercially available.

Reference and Patent Information

Reference TypeKeywordsReferenceText
BiologicalAnti-Angiogenic In Vivo Kiziltepe, T.; Anderson, K. C.; Kutok, J. L.; Jia, L.; Boucher, K. M.; Saavedra, J. E.; Keefer, L. K.; Shami, P. J. JS-K has potent anti-angiogenic activity in vitro and inhibits tumour angiogenesis in a multiple myeloma model in vivo. J. Pharm. Pharmacol. 2010, 61 (1), 145-151. Pubmed Abstract
BiologicalAntiproliferative against Glioma in vitro and in vivo Weyerbrock, A.; Osterberg, N.; Psarras, N.; Baumer, B.; Kogias, E.; Werres, A.; Bette, S.; Saavedra, J. E.; Keefer, L. K.; Papazoglou, A. JS-K, a glutathione S-transferase-activated nitric oxide donor with antineoplastic activity in malignant gliomas. Neurosurgery 2012, 70 (2), 497-510. Pubmed Abstract
BiologicalBreast Cancer McMurtry, V.; Saavedra, J. E.; Nieves-Alicea, R.; Simeone, A.; Keefer, L. K.; Tari, A. M. JS-K, a nitric oxide-releasing prodrug, induces breast cancer cell death while sparing normal mammary epithelial cells. Int. J. Onc. 2011, 38 (4), 963-971. Pubmed Abstract
BiologicalLeukemia Cell, Apoptosis Udupi, V.; Yu, M.; Malaviya, S.; Saavedra, J. E.; Shami, P. J. JS-K, a nitric oxide prodrug, induces cytochrome c release and caspase activation in HL-60 myeloid leukemia cells.Leuk. Res. 2006, 30 (10), 1279-1283. Pubmed Abstract
BiologicalLeukemia, Prostate Cancer Shami, P. J.; Saavedra, J. E.; Wang, L. Y.; Bonifant, C. L.; Diwan, B. A.; Singh, S. V.; Gu, Y.; Fox, S. D.; Buzard, G. S.; Citro, M. L.; Waterhouse, D. J.; Davies, K. M.; Ji, X.; Keefer, L. K. JS-K, a glutathione/glutathione S-transferase-activated nitric oxide donor of the diazeniumdiolate class with potent antineoplastic activity. Mol. Cancer Ther. 2003, 2, 409-417. Pubmed Abstract
BiologicalLiver Cancer, Structure-Activity Shami, P. J.; Saavedra, J. E.; Bonifant, C. L.; Chu, J.; Udupi, V.; Malaviya, S.; Carr, B. I.; Kar, S.; Wang, M.; Jia, L.; Ji, X.; Keefer, L. K. Antitumor activity of JS-K [O2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and related O2-aryl diazeniumdiolates in vitro and in vivo. J. Med. Chem. 2006, 49 (14), 4356-4366. Pubmed Abstract
BiologicalLung, Colon, Ovarian, Prostate, and Renal Cancer Chakrapani, H.; Kalathur, R. C.; Maciag, A. E.; Citro, M. L.; Ji, X.; Keefer, L. K.; Saavedra, J. E. Synthesis, mechanistic studies, and anti-proliferative activity of glutathione/glutathione S-transferase activated nitric oxide prodrugs. Biorg. Med. Chem. 2008, 16 (22), 9764-9771. Pubmed Abstract
BiologicalMechanism of Action Blood Tumor Barrier in Glioma Weidensteiner, C.; Reichardt, W.: Shami, P. J.; Saavedra, J. E.; Keefer, L. K.; Baumer, B.; Werres, A.; Jasinski, R.; Osterberg, N.; Weyerbrock, A. Effects of the nitric oxide donor JS-K on the blood-tumor barrier and on orthotopic U87 rat gliomas assessed by MRI. Nitric Oxide. 2013, 30, 17-25. Pubmed Abstract
BiologicalMechanisms of Action Maciag, Anna E.; Nandurdikar, Rahul S.; Hong, Sam Y.; Chakrapani, Harinath; Diwan, Bhalchandra; Morris, Nicole L.; Shami, Paul J.; Shiao, Yih-Horng; Anderson, Lucy M.; Saavedra, Joseph E. Activation of the c-Jun N-terminal Kinase/Activating Transcription Factor 3 (ATF3) Pathway Characterizes Effective Arylated Diazeniumdiolate-Based Nitric Oxide-Releasing Anticancer Prodrugs. J. Med. Chem. 2011, 54 (22), 7751-7758. Pubmed Abstract
BiologicalMechanisms of Action Kitagaki, J.; Yang, Y.; Saavedra, J. E.; Colburn, N. H.; Keefer, L. K.; Perantoni, A. O. Nitric oxide prodrug JS-K inhibits ubiquitin E1 and kills tumor cells retaining wild-type p53. Oncogene 2009, 28 (4), 619-624. Pubmed Abstract
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