Disease relevance of beta-Naphthoquinone

• These results support the suggestion that the toxicity of 1-naphthol may be mediated by the formation of 1,2-naphthoquinone and/or 1,4-naphthoquinone, which may then be metabolised by one electron reduction to naphthosemiquinone radicals [1].
• The cytotoxicity of several PAH o-quinones derived from this reaction [naphthalene-1,2-dione (NPQ), benzo[a]pyrene-7,8-dione (BPQ), and 7,12-dimethylbenz[a]anthracene-3,4-dione (DMBAQ)] was examined in rat (H-4IIe) and human (Hep-G2) hepatoma cells which are known to express DD [2].
• The cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells [3].
• In order to test whether the cellular response is a common feature of quinone-induced cataracts, we injected in this work 1,2-naphthoquinone (NA) in the anterior chamber of mouse eye and followed cellular responses in the lens prior to opacity development [4].
• beta-Lapachone is an o-naphthoquinone found to have in vitro cytotoxicity in cancer cells, type I human immunodeficiency virus, and fungi [5].

High impact information on beta-Naphthoquinone

• Beta-Lapachone, a derivative of 1,2-naphthoquinone, inhibits the specific binding of [6,7-3H]triamcinolone acetonide (TA) to unbound hepatic and thymic glucocorticoid receptors in a dose-dependent manner with 50% of the maximal inhibition in thymus cytosol achieved at a final concentration of 5-10 microM [6].
• We also found that naphthoquinones, including 1,2-naphthoquinone, inhibit PTEN in the cell-free system, which suggested that the effect on PTEN (and thus the effect on phosphatidylinositol 3-kinase signaling) should be taken into account when examining the pharmacological actions of naphthoquinone derivatives [7].
• beta-Lapachone, an o-naphthoquinone, induces a novel caspase- and p53-independent apoptotic pathway dependent on NAD(P)H:quinone oxidoreductase 1 (NQO1) [8].
• The enzymatically generated o-quinones, e.g., naphthalene-1,2-dione and benzo[a]pyrene-7,8-dione are potent inhibitors of the dehydrogenase, yielding IC50 values of 5.0 and 10.0 microM, respectively [9].
• Addition of beta-lapachone, an o-naphthoquinone endowed with trypanocidal properties to respiring Trypanosoma cruzi epimastigotes induced the release of O2- and H2O2 from the whole cells to the suspending medium [10].

Chemical compound and disease context of beta-Naphthoquinone

• Aethiopinone (1), an o-naphthoquinone diterpene from Salvia aethiopis L. roots and two hemisynthetic derivatives 2 and 3 have been evaluated for toxicity, anti-inflammatory, analgesic, antipyretic, and haemostatic activities [11].

Biological context of beta-Naphthoquinone

• Superoxide dismutase (SOD) inhibited the rate of cytochrome c reduction and decreased the apparent rate of oxygen consumption by several DHLA/o-naphthoquinone systems [12].
• Polycyclic aromatic hydrocarbon (PAH) ortho-quinone conjugate chemistry: kinetics of thiol addition to PAH ortho-quinones and structures of thioether adducts of naphthalene-1,2-dione [13].
• Inhibition of endothelial nitric oxide synthase activity and suppression of endothelium-dependent vasorelaxation by 1,2-naphthoquinone, a component of diesel exhaust particles [14].
• The lipophilic o-naphthoquinone beta-lapachone produced structural alterations in kinetoplast membranes, that correlated with inhibition of oxidative phosphorylation [15].
• The response of the hexose monophosphate shunt (HMS) in organ-cultured guinea pig lens to 1,2-naphthoquinone and 5-hydroxy-1,4-naphthoquinone (juglone) has been investigated [16].

Anatomical context of beta-Naphthoquinone

• In addition, large amounts of Ca2+ were retained by T. cruzi mitochondria even after addition of thiols and NAD(P)H oxidants such as t-butyl hydroperoxide, diamide, and the 1,2-naphthoquinone beta-lapachone [17].
• An injection of 1,2-naphthoquinone (NQ) into the anterior chamber of mouse eye produces anterior cortical cataract [18].
• Effect of the lipophilic o-naphthoquinone CG 10-248 on rat liver mitochondria structure and function [19].
• Apoptogenic effect of the lipophilic o-naphthoquinone CG 10-248 on rat hepatocytes: light and electron microscopy studies [20].

Associations of beta-Naphthoquinone with other chemical compounds

• Aziridine was measured by HPLC after derivatization with 1,2-naphthoquinone 4-sulfate [21].
• Competitive ELISA showed that the antibodies specifically recognize the 1,2-naphthoquinone N-acetylcysteine adduct [22].
• Furthermore, 1,2-naphthoquinone, which is a metabolite of naphthalene and an actual inducer of naphthalene cataract, strongly inactivated porcine lens GST though it did not affect bovine enzyme [23].
• The quenching of the triplets of 1,2-naphthoquinone (NQ) and 1,2-naphthoquinone-4-sulfonic acid sodium salt (NQS) by various electron and H-atom donors was investigated by laser flash photolysis measurement in acetonitrile and benzene [24].
• The o-naphthoquinone derivative, CGS 8515 (I), is a potent inhibitor (IC50, 0.1 microM) of 5-lipoxygenase, but its therapeutic potential is compromised by a short plasma half-life (22 min) and extremely poor oral bioavailability (less than 2%) [25].

Gene context of beta-Naphthoquinone

• HPLC analysis of naphthalene-1, 2-dihydrodiol incubated with aldose reductase and NAD+indicated the formation of a metabolite peak corresponding to 1,2-naphthoquinone [26].
• 1. A 1,2-naphthoquinone adsorbent is described which allows simple purification of dihydropteridine reductase directly from crude extract [27].
• Comparative molecular similarity indices analysis (CoMSIA) studies of 1,2-naphthoquinone derivatives as PTP1B inhibitors [28].
• The reagent was 1,2-naphthoquinone 4-sulphonate, and a commercial C18 packing cartridge was used [29].
• Ketopantoyl lactone reductase (EC 1.1.1.168) of Saccharomyces cerevisiae was found to catalyze the reduction of a variety of natural and unnatural conjugated polyketone compounds and quinones, such as isatin, ninhydrin, camphorquinone and beta-naphthoquinone in the presence of NADPH [30].

Analytical, diagnostic and therapeutic context of beta-Naphthoquinone

• Solid-phase extraction techniques were evaluated for the treatment of urine samples in the analysis of amphetamine and methamphetamine by normal-phase high-performance liquid chromatography with 1,2-naphthoquinone 4-sulphonate [31].
• To determine whether zeta-crystallin is an inducible quinone reductase, cell cultures were exposed to the xenobiotics, 1,2-naphthoquinone and beta-naphthoflavone [32].

References