6956-96-3

Usage

Uses

Used in Pharmaceutical and Biomedical Research:
DMNQ is used as a non-alkylating redox cycling quinone for studying the effects of oxidative stress on cells and investigating the mechanisms of cell death and survival under different conditions.
Used in Nephrology Research:
In the field of nephrology, DMNQ is employed to investigate the impact of ethanol on podocyte apoptosis under hypoxic and hyperoxic conditions, providing insights into the pathophysiology of kidney diseases and potential therapeutic targets.
Overall, DMNQ serves as a valuable tool in various research areas, particularly in understanding the role of oxidative stress in cellular processes and disease mechanisms.

Biochem/physiol Actions

2,3-dimethoxy-1,4-naphthoquinone (DMNQ) has the ability to produce H2O2?through redox cycling but fails to conjugate with glutathione (GSH).

References

References/Citations 1) Gant?et al. (1988)?Redox Cycling and Sulphydryl Arylation; Their Relative Importance in the Mechanism of Quinone Cytotoxicity to Isolated Hepatocytes; Chem. Biol. Interactions;?65?157 2) Stubberfield and Cohen (1989)?Interconversion of NAD(H) to NADP(H). A cellular response to quinone-induced oxidative stress in isolated hepatocytes; Biochem. Pharmacol.,?38?2631 3) Dypbukt?et al?(1994)?Different prooxidant levels stimulate growth, trigger apoptosis or produce necreosis of insulin-secreting RINm5F cells. The role of intracellular polyamines; J. Biol. Chem.,?269?30553 4) Henry and Wallace (1996)?Differential mechanisms of cell killing by redox cycling and arylating quinones; Arch. Toxicol.,?70?482

InChI:InChI=1/C12H10O4/c1-15-11-9(13)7-5-3-4-6-8(7)10(14)12(11)16-2/h3-6H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 605-37-8 isonaphthazarine 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 124-41-4 sodium methylate 
• 19774-34-6 (E)-1-ethoxybuta-1,3-diene 
• 3117-02-0 2,3-dimethoxy-1,4-benzoquinone 
• 1515-76-0 1-acetoxybuta-1,3-diene 
• 10103-06-7 2,3-dimethoxynaphthalene 
• 67-56-1 methanol 
• 98122-97-5 2,3-dimethoxy-4-hydroxy-4-phenyl-2-cyclobuten-1-one 
• 15707-32-1 2-chloro-3-methoxy-1,4-naphthoquinone 
• 130-15-4 [1,4]naphthoquinone 
• 5150-42-5 2,3-dimethoxyphenol 

Downstream Products

• 1421252-40-5 2-dibenzoylamino-3-methoxy-1,4-naphthoquinone 
• 1421252-46-1 2-bis(2-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-44-9 2-bis(3-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-42-7 2-bis(4-chlorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-48-3 2-bis(4-fluorobenzoyl)amino-3-methoxy-1,4-naphthoquinone 
• 1421252-50-7 2-bis(4-tert-butylbenzoyl)amino-3-methoxy-1,4-naphthoquinone 

Relevant academic research and scientific papers

Studies on quinones. Part 43: Synthesis and cytotoxic evaluation of polyoxyethylene-containing 1,4-naphthoquinones

A series of naphthoquinones 2,3-disubstituted with chlorine and oxyethylene groups have been prepared from 2,3-dichloro- and 2,3-dimethoxy-1,4-naphthoquinone. The members of these series were tested on normal human fibroblasts and on a panel of four human cancer cell lines. Antitumor activities, which were in the range of IC50 1.3-89.5 μM, discussed in terms of LUMO energy, lipophilicity and size of the polyoxyethylene moiety.

Plumbagin-Serum Albumin Interaction: Spectral, Electrochemical, Structure-Binding Analysis, Antiproliferative and Cell Signaling Aspects with Implications for Anticancer Therapy

Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) is a small molecule with potent anticancer activity. Like other 1,4-naphthoquinones, it exhibits electrophilic reactivity towards biological nucleophiles. We demonstrate that plumbagin and structurally related 1,4-naphthoquinones with at least one unsubstituted quinoid carbon (C2 or C3) bind to albumin, an ubiquitously present nucleophile, with minimum recovery of free drug. Extraction recovery of plumbagin from albumin in solution showed one-phase exponential decline with a half-live of 9.3 min at 10 μmol/L. In the presence of albumin, plumbagin exhibited instant changes in UV/Vis absorption bands. Electrochemical analysis using cyclic voltammetry showed a decrease in redox peak currents over time until electro-inactivity, thus suggesting the formation of a supramolecular adduct inaccessible for electron transfer. The adduct inhibited cell growth and caused cell-cycle arrest of prostate cancer cells, in part by decreasing levels of the cell-cycle regulator RBBP. The conjugate displayed similar cellular effects to those described for plumbagin, such as decreased levels of androgen receptor and protein kinase C epsilon. The effect of plumbagin-albumin on cancer cells was species-specific, suggesting a receptor-mediated mechanism. Furthermore, it was blocked by cathepsin inhibitor pepstatin A, indicating that lysosomal degradation is involved in the processing of plumbagin-albumin adduct. The spontaneously formed adduct of plumbagin with serum albumin is likely to mediate the biological activities of plumbagin in vivo and to fundamentally influence its pharmacodynamics.

A new 2,3-dimethoxy-1,4-naphthoquinone redox anolyte for non-aqueous organic static redox battery

Redox flow batteries (RFB) are the choice for grid-level large-scale energy storage applications. Especially, the non-aqueous variant of RFB is considered for its unique advantages such as low cost, diverse engineering possibility of redox molecules, and

Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents

Ruthenium-catalysis enabled the C-5 selective C-H oxygenation of naphthoquinones, and also sets the stage for the site-selective introduction of a hydroxyl group into anthraquinones. A-ring modified naphthoquinoidal compounds represent an important class of bioactive quinones for which the present study encompasses the first C-H oxygenation strategy by weak O-coordination.

Method for inhibiting Trypanosoma cruzi

Methods are provided to inhibit proliferation of Trypanosoma cruzi with imido-substituted 1,4-naphthoquinones, including novel compounds. Administering an imido-substituted 1,4-naphthoquinone can be used to provide prophylaxis or treatment to a patient in

COMPOSITIONS AND METHODS FOR TREATMENT OF PROSTATE CARCINOMA

Disclosed herein are 1,4-naphthoquinone analogs, pharmaceutical compositions that include one or more of such 1,4-naphthoquinone analogs, and methods of treating and/or ameliorating diseases and/or conditions associated with a cancer, such as prostate can

Synthesis and characterization of novel unsymmetrical and symmetrical 3-halo- or 3-methoxy-substituted 2-dibenzoylamino-1,4-naphthoquinone derivatives

Symmetrical and unsymmetrical 3-halo- or 3-methoxy- substituted 2-dibenzoylamino- 1,4-naphthoquinone analogs were synthesized with an average yield of 45% via sodium hydride promoted bis-acylation of 2-amino-3-chloro-1,4- naphthoquinone, 2-amino-3-bromo- 1,4-naphthoquinone and 2-amino-3-methoxy-1,4- naphthoquinone.

METHOD FOR INHIBITING TRYPANSOMA CRUZI

In its broadest aspect, a method for treating a mammalian patient at risk or suffering from a disease caused by a kinetoplastid parasite comprises administering to such subject an effective kinetoplasticidal amount of an imido-substituted 1,4- naphthoquin

New insights into cyclobutenone rearrangements: A total synthesis of the natural ROS-generating anti-cancer agent cribrostatin 6

Aryl- and heteroarylcyclobutenone rearrangements proceed in excellent yield under continuous-flow conditions. The former shows a Hammett correlation with σI providing strong evidence that electrocyclisation is the rate-determining step and has a late transition state. The reaction has been modelled by using DFT and CCSD(T) methods, with the latter giving excellent correlation with the experimental rate constant. A short and efficient total synthesis of cribrostatin 6, an anti-neoplastic and anti-microbial agent, provides a topical demonstration of the value of this method.

Chemoselective reactions of 2,3-dichloro-1,4-naphthoquinone

The reaction of 2,3-dichloro-1,4-naphthoquinone with alkoxides, primary amines, and phenols was shown to proceed chemoselectively rather to the corresponding 2-substituted 3-chloro-naphthoquinones or 2,3-disubstituted quinones than to brazanquinone deriva