DMNQ

CHF 95.00
In stock
AG-CR1-3598-M0055 mgCHF 95.00
AG-CR1-3598-M01010 mgCHF 135.00
AG-CR1-3598-M02525 mgCHF 270.00
More Information
Product Details
Synonyms 2,3-Dimethoxy-1,4-naphthoquinone; 2,3-diOMe-1,4-NQ
Product Type Chemical
Properties
Formula

C12H10O4

MW 218.2
CAS 6956-96-3
Purity Chemicals ≥99% (NMR)
Appearance Yellow crystalline solid.
Solubility Soluble in DMSO or methanol.
Identity Determined by 1H-NMR.
InChi Key ZEGDFCCYTFPECB-UHFFFAOYSA-N
Smiles COC1=C(OC)C(=O)C2=C(C=CC=C2)C1=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Cell permeable, non-alkylating, non-thiol, adduct-forming, redox cycling quinone.
  • Intracellular superoxide anion formation/ROS generation inducer.
  • Anticancer agent. Shown to induce cell proliferation, apoptosis, necrosis and necroptosis in vitro, dependent on concentration, time, temperature and cell type.
  • Valuable tool for the generation of reactive oxygen species (ROS) in order to study the role of ROS in cell toxicity, apoptosis and necrosis.
  • Useful as reference compound in characterizing the effects of oxidative stress. Can be used to eliminate any mechanistic ambiguity involving redox cycling quinoids as the source of reactive oxidant species/oxidative stress in biological studies.
Product References
  1. The role of oxidative processes in the cytotoxicity of substituted 1,4-naphthoquinones in isolated hepatocytes: D. Ross, et al.; Arch. Biochem. Biophys. 248, 460 (1986)
  2. Redox cycling and sulphydryl arylation; their relative importance in the mechanism of quinone cytotoxicity to isolated hepatocytes: T.W. Gant, et al.; Chem. Biol. Interact. 65, 157 (1988)
  3. Quinone-induced DNA single strand breaks in rat hepatocytes and human chronic myelogenous leukaemic K562 cells: W.A. Morgan, et al.; Biochem. Pharmacol. 44, 215 (1992)
  4. Quinone-induced oxidative stress elevates glutathione and induces gamma-glutamylcysteine synthetase activity in rat lung epithelial L2 cells: M.M. Shi, et al.; J. Biol. Chem. 269, 26512 (1994)
  5. Different prooxidant levels stimulate growth, trigger apoptosis, or produce necrosis of insulin-secreting RINm5F cells: J.M. Dypbukt, et al.; J. Biol. Chem. 269, 30553 (1994)
  6. DNA single-strand breakage in mammalian cells induced by redox cycling quinones in the absence of oxidative stress: W.A. Morgan; J. Biochem. Toxicol. 10, 227 (1995)
  7. Naphthoquinone-induced DNA damage in the absence of oxidative stress: W.A. Morgan; Biochem. Soc. Trans. 23, 225S (1995)
  8. Differential mechanisms of cell killing by redox cycling and arylating quinones: T.R. Henry & K.B. Wallace; Arch. Toxicol. 70, 482 (1996)
  9. Naphthazarin derivatives: synthesis, cytotoxic mechanism and evaluation of antitumor activity: Y.J. You, et al.; Arch. Pharm. Res. 21, 595 (1998)
  10. Temperature-dependent quinone cytotoxicity in platelets involves arylation: Y.A. Kang, et al.; J. Toxicol. Environ. Health A 65, 1367 (2002)
  11. Superoxide targets calcineurin signaling in vascular endothelium: D. Namgaladze, et al.; BBRC 334, 1061 (2005)
  12. Oxidative stress promotes polarization of human T cell differentiation toward a T helper 2 phenotype: M.R. King, et al.; J. Immunol. 176, 2765 (2006)
  13. Caspase-2 activation in neural stem cells undergoing oxidative stress-induced apoptosis: C. Tamm, et al.; Apoptosis 13, 354 (2008)
  14. A Receptor-interacting Protein 1 (Rip1) Independent Necrotic Death Under The Control Of Protein Phosphatase Pp2a That Involves The Reorganization Of Actin Cytoskeleton And The Action Of Cofilin-1: A. Tomasella, et al.; J. Biol. Chem. 289, 25699 (2014)
  15. Airway epithelial Paraoxonase-2 in obese asthma: D.E. Winnica, et al.; PLoS One 17, e0261504 (2022)
© 2017 Adipogen Life Sciences. Pictures: © 2012 Martin Oeggerli. All Rights Reserved.