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]}.

1. This compound can be used as a tracer.
2. This compound can be used as an internal standard for quantitative analysis by NMR, GC-MS, or LC-MS.

Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

164.19

C₁₀D₆O₂

26473-08-5

130-15-4

Solid

Light yellow to yellow

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

Room temperature in continental US; may vary elsewhere.

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

• [1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019 Feb;53(2):211-216.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]

  [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.  [Content Brief]