1,4-Naphthoquinone-d6

1,4-Naphthoquinone-d6 is the deuterium labeled 1,4-Naphthoquinone. 1,4-Naphthoquinone is an inhibitor with broad-spectrum inhibitory activity targeting DNA polymerase, NF-κB and monoamine oxidase (MAO-A/B), with antibacterial and anti-biofilm efficacy. 1,4-Naphthoquinone is a competitive inhibitor of MAO-B (Ki=1.4 μM) and a non-competitive inhibitor of MAO-A (Ki=7.7 μM) . 1,4-Naphthoquinone inhibits DNA polymerase pol α, β, γ, δ, ε, λ with IC50 ranging from 5.57-128 μM. 1,4-Naphthoquinone inhibits tumor cell proliferation, induces apoptosis and necrosis, and has anti-angiogenic and anti-inflammatory activities by inducing oxidative stress, depleting glutathione (GSH), inhibiting DNA polymerase-mediated DNA synthesis and blocking NF-κB nuclear translocation. 1,4-Naphthoquinone can be used in anti-bacterial , anti-tumor and anti-inflammatory studies, including inhibition of melanoma and colon cancer cell growth and endothelial cell function, as well as LPS-induced inflammation models[1][2][3][4][5][6].

Product Specifications

CAS Number

[26473-08-5]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Bacterial; DNA/RNA Synthesis; Isotope-Labeled Compounds; Monoamine Oxidase; NF-κB; TNF Receptor

Type

Isotope-Labeled Compounds

Related Pathways

Anti-infection; Apoptosis; Cell Cycle/DNA Damage; Neuronal Signaling; NF-κB; Others

Applications

Cancer-programmed cell death

Field of Research

Cancer; Infection; Inflammation/Immunology

Purity

99.20

Solubility

10 mM in DMSO

Smiles

O=C1C2=C([2H])C([2H])=C([2H])C([2H])=C2C(C([2H])=C1[2H])=O

Molecular Formula

C10D6O2

Molecular Weight

164.19

Precautions

H302, H315, H319, H335

References & Citations

[1]Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53 (2) :211-216.|[2]Kumar MR, et al. Cytotoxic, genotoxic and oxidative stress induced by 1,4-naphthoquinone in B16F1 melanoma tumor cells. Toxicol In Vitro. 2009 Mar;23 (2) :242-50.|[3]Kayashima T, et al. 1,4-Naphthoquinone is a potent inhibitor of human cancer cell growth and angiogenesis. Cancer Lett. 2009 Jun 8;278 (1) :34-40.|[4]Kobayashi K, et al. Effects of quinone derivatives, such as 1,4-naphthoquinone, on DNA polymerase inhibition and anti-inflammatory action. Med Chem. 2011 Jan;7 (1) :37-44.|[5]Samreen, et al. Antibacterial and anti-biofilm efficacy of 1,4-naphthoquinone against Chromobacterium violaceum: an in vitro and in silico investigation. Arch Microbiol. 2024 Dec 7;207 (1) :11.|[6]Coelho Cerqueira E, et al. Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO. Bioorg Med Chem. 2011 Dec 15;19 (24) :7416-24.