DMNQ | CAS 6956-96-3 - Order from Adipogen

Specifications / Handling

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

Product-specific References

Description

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

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)
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)
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)
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)
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)
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)
Naphthoquinone-induced DNA damage in the absence of oxidative stress: W.A. Morgan; Biochem. Soc. Trans. 23, 225S (1995)
Differential mechanisms of cell killing by redox cycling and arylating quinones: T.R. Henry & K.B. Wallace; Arch. Toxicol. 70, 482 (1996)
Naphthazarin derivatives: synthesis, cytotoxic mechanism and evaluation of antitumor activity: Y.J. You, et al.; Arch. Pharm. Res. 21, 595 (1998)
Temperature-dependent quinone cytotoxicity in platelets involves arylation: Y.A. Kang, et al.; J. Toxicol. Environ. Health A 65, 1367 (2002)
Superoxide targets calcineurin signaling in vascular endothelium: D. Namgaladze, et al.; BBRC 334, 1061 (2005)
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)
Caspase-2 activation in neural stem cells undergoing oxidative stress-induced apoptosis: C. Tamm, et al.; Apoptosis 13, 354 (2008)
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)
Airway epithelial Paraoxonase-2 in obese asthma: D.E. Winnica, et al.; PLoS One 17, e0261504 (2022)

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