Disease relevance of NSC7389

• Localization of arginine-rich protein in cytomegalovirus dense bodies using phenanthrenequinone fluorescence [1].
• Complete 1H- and 13C-NMR Spectral Data of Piloquinone, a 9,10-Phenanthrenequinone Derivative from Streptomyces pilosus [2].
• Together, these observations suggest an unexpected oxygen-independent mechanism in the toxicity of 9,10-phenanthrenequinone [3].
• The Tat-binding site of the bovine immunodeficiency virus TAR RNA hairpin has been targeted by Rh(phen)2phi3+ (phen = phenanthroline, phi = 9,10-phenanthrenequinone diimine), a photochemical probe of RNA tertiary structure [4].
• Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line, T47D [5].

High impact information on NSC7389

• 9,10-Phenanthraquinone in diesel exhaust particles downregulates Cu,Zn-SOD and HO-1 in human pulmonary epithelial cells: intracellular iron scavenger 1,10-phenanthroline affords protection against apoptosis [6].
• The enantiomers of the symmetric metallointercalator complex 1-Rh(MGP)2phi5+ [MGP = 4-(guanidylmethyl)-1,10-phenanthroline; phi = phenanthrenequinone diimine] bound to DNA decamer duplexes containing their respective 6 bp recognition sequences have been investigated using 1H NMR [7].
• The three-dimensional folding of Xenopus oocyte 5S rRNA has been examined using the coordination complex Rh(phen)2phi3+ (phen = phenanthroline; phi = phenanthrenequinone diimine) as a structural probe [8].
• Guanidino compounds in CSF of 57 human subjects were determined fluorometrically after reaction with phenanthrenequinone in alkali solution, using HPLC [9].
• PHCR has the ability to catalyze efficiently the reduction of 9,10-phenanthrenequinone (PQ) contained in diesel exhaust particles (DEPs) [10].

Chemical compound and disease context of NSC7389

• The toxicities of phenanthrene (PHE) and 9,10-phenanthrenequinone (PHQ) with or without Cu were determined using Daphnia magna [11].

Biological context of NSC7389

• Among the quinones tested, 9,10-phenanthraquinone (PQ), corresponding to an E17 value of -124 mV, exhibited the most potent inhibiton of citrulline formation (IC50 value = 10 microM) [12].
• Analysis of inhibition kinetics revealed that aspirin was uncompetitive inhibitor (K(i) 0.64 mM) with respect to NADPH and non-competitive inhibitor (K(i) 1.6 mM) with respect to the substrate, 9,10-phenanthrenequinone (PQ) [13].
• Furthermore, an intraperitoneal injection of phenanthraquinone (0.36 mmol/kg) to rats resulted in an elevation of blood pressure (1.4-fold, P < 0.01); under this condition, plasma levels of stable NO metabolites, nitrite/nitrate, in phenanthraquinone-treated rats was reduced to 68% of control levels [14].
• Phenanthraquinone inhibits eNOS activity and suppresses vasorelaxation [14].
• The observation that superoxide dismutase and a dismutase "mimic," 3-carboxy-2,2,5,5-tetramethylpyrrolidine-1-oxyl, inhibit the redox cycling of 9,10-phenanthrenequinone suggests a mechanism whereby cells could be protected against oxidative stress caused by certain quinones [15].

Anatomical context of NSC7389

• Phenanthraquinone was also capable of modifying thiol groups in pulmonary microsomes from rats and total membrane preparation isolated from bovine aortic endothelial cells (BAEC), but not bovine serum albumin (BSA), which has a Cys34 as a reactive monothiol group [16].
• We found that both acenaphthenequinone (AcQ) and 9,10-phenanthrenequinone (PQ) enhanced ROS generation and that AcQ translocated NF-kappaB from the cytosol to the nucleus [17].
• Phenanthraquinone challenge revealed an increase in the numbers of neutrophils and eosinophils in BALF as compared to vehicle challenge (P < 0.05 at 48 h post-instillation) [18].
• Previously, we have shown that the mouse enzyme is present in a range of tissues including liver, kidney, testis and brain, and is able to reduce several carbonyl compounds, including succinic semialdehyde, 2-carboxybenzaldehyde, 4-nitrobenzaldehyde and 9,10-phenanthrenequinone [FEBS Lett. 523 (2002) 213] [19].
• Phenanthrenequinone induces moderate to intense fluorescence in gastric chief cells, parenchymal cells of the pancreas, and certain peptide hormone-producing cell types such as the GH cells of the adenohypophysis and the glucagon cells of the pancreatic islets [20].

Associations of NSC7389 with other chemical compounds

• NADP+ showed a mixed type of inhibition with respect to NADPH, while it was a competitive inhibitor with respect to PQ [21].
• Of quinones tested, 9,10-phenanthrenequinone, a component of diesel exhaust particles, was the most potent inhibitor for the all-trans retinal reduction, and a significant inhibition was also observed for plumbagin and menadione [22].
• Bulbophyllanthrone: A Cytotoxic Phenanthraquinone from the New Zealand Orchid, Earino autumnalis [23].
• 5. The isoenzyme CM-2 had an isoelectric point of 9.3 and was a very active quinone reductase with phenanthrene-9,10-quinone as substrate [24].
• The enzymes had an activity towards 9,10-phenanthrenequinone (PQ) and/or 4,5-pyrenequinone (PyQ), and the relative amounts varied with the pH of the culture media [25].

Gene context of NSC7389

• Phenanthraquinone induced the lung expression of interleukin (IL)-5 and eotaxin 48 h and 24 h after the challenge, respectively [18].
• Consistent with this, NADPH was able to substantially protect zeta-crystallin against aspirin, whereas PQ did not provide any protection [13].
• The Km (10 microm) and k(cat)/K(m) (1.7 s(-1) x microm(-1)) values for isatin at pH 7.0 were comparable to those for phenanthrenequinone, the best xenobiotic substrate of carbonyl reductase [26].
• It is likely that 9,10-phenanthrenequinone strongly inhibits the reduction of all-trans retinal to all-trans retinol by acting as the substrate inhibitor of pig heart carbonyl reductase present in pig heart cytosol [22].
• ASA (1 mM) was incubated with NOR-2, NOC-7 or 3-morpholinosydomine hydrochloride (SIN-1) at 37 degrees C. GSA was determined by HPLC using a cationic resin for separation and phenanthrenequinone as an indicator [27].

Analytical, diagnostic and therapeutic context of NSC7389

• Tanshinone II-A (TSII-A) isolated from the root of Salvia miltorrhiza Bunge, a traditional medicine in China, is a derivative of phenanthrenequinone, which is known to have antioxidant properties [28].
• MG and creatol were determined by high-performance liquid chromatography using 9,10-phenanthrenequinone for the post-labeling [29].

References