Disease relevance of naphthalene

• Hemolysis from exposure to naphthalene mothballs [1].
• Here we report the directed evolution of the P450 from Pseudomonas putida to create mutants that hydroxylate naphthalene in the absence of cofactors through the 'peroxide shunt' pathway with more than 20-fold higher activity than the native enzyme [2].
• Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo [3].
• The 2,6-disubstituted naphthalene derivative FDDNP labeling reliably predicts Congo red birefringence of protein deposits in brain sections of selected human neurodegenerative diseases [4].
• We describe a 41-year-old man who developed systemic sclerosis after working for 15 years in a foundry, where he had extensive cutaneous contact with multiple organic solvents (trichloroethane, xylene, trimethylbenzene, and naphthalene) [5].

Psychiatry related information on naphthalene

• It was shown that the simple and mass-producible containment sensor exhibits good performance data: lower detection limit 0.1 mg/L naphthalene and 1 mg/L sensor-BOD; calibration range up to 30 mg/L; precision 3-6%; response time 2-3 min; service life up to 40 days; shelf life at 4 degrees C 6 months [6].
• 5. Pre-treatment with OOOMeP(S) prevented the lethargy and weight-loss associated with naphthalene poisoning but not the pulmonary injury [7].

High impact information on naphthalene

• The results suggest that indigo formation is due to the combined activities of tryptophanase and naphthalene dioxygenase [3].
• This phenomenon makes it possible to determine the molecular weights of polysulfated, -sulfonated, and -phosphorylated biomolecules such as cysteic acid-containing peptides, oligonucleotides, heparin-derived oligosaccharides, and suramin (a drug containing two trisulfonated naphthalene moieties) [8].
• We found that Evans blue, a biphenyl derivative of naphthalene disulfonic acid, blocks at low concentrations (IC50 = 355 nM for the subunit combination GluR1,2) KA-mediated responses of the subunits GluR1, GluR1,2, GluR1,3, and GluR2,3 expressed in Xenopus oocytes but not responses of GluR3 or GluR6 [9].
• Based on a previous observation that the naphthalene sulfonamide calmodulin antagonist W-7 can block Paramecium Ca channels at high concentration, we have synthesized analogs of W-7 that block these channels at concentrations of less than 1 microM [10].
• This discovery of the essential role of the intestinal microflora in the formation of naphthols from naphthalene indicates the existence of a novel pathway for hydroxylation of aromatic systems and challenges the current concept of the in vivo relevance of the in vitro production of naphthols from naphthalene 1,2-oxide [11].

Chemical compound and disease context of naphthalene

• To establish the capability of these cells to metabolize an agent that causes Clara cell-selective toxicity in vivo, we evaluated the metabolism of naphthalene in isolated cells under two distinct conditions, i.e., in homogenized cell preparations supplemented with glutathione and glutathione S-transferases and in intact cells [12].
• Role of p53 tumor suppressor gene in the toxicity of TCDD, endrin, naphthalene, and chromium (VI) in liver and brain tissues of mice [13].
• Vaginal gel formulations containing the naphthalene sulfonate polymer PRO 2000 are being developed as topical microbicides to protect against infection with sexually transmitted disease (STD) pathogens [14].
• This suggests that aldose reductase is linked to 1,2-dihydroxynaphthalene formation in rat lens and the subsequent formation of cataracts in naphthalene-fed rats [15].
• Furthermore, the naphthalene compounds 26, 28, 31, and 33 demonstrated antiproliferative activity in rat C6 glioma cells (EC(50) = 15.0 microM for 33), revealing a putative sigma(1) antagonist activity and opening a useful perspective in tumor research and therapy [16].

Biological context of naphthalene

• The kinetics of fluorescence decay of an oligomer containing the naphthalene chromophore only could be described precisely by a monoexponential function [17].
• The chromophores naphthalene and dansyl, which were used as donor and acceptor, respectively, fulfil the conditions necessary for energy transfer according to the Förster mechanism [17].
• Apparently, in vivo, naphthols and methylthio-containing metabolites of naphthalene are formed during enterohepatic circulation of 1,2-dihydro-1-hydroxy-2-S-cysteinylnaphthalene and 1,2-dihydro-1-hydroxy-2-S-(N-acetyl)cysteinylnaphthalene in a process dependent upon intestinal microflora [11].
• The nahR gene from the NAH7 naphthalene degradation plasmid encodes a LysR-type transcriptional activator of the nah and sal promoters (Pnah and Psal, respectively) that responds to the inducer salicylate [18].
• This work reports a genetic analysis of the interactions between NahR, the LysR-type regulator of the NAH operons for biodegradation of naphthalene in Pseudomonas, and its aromatic effectors [19].

Anatomical context of naphthalene

• Suramin, a polysulfonic naphthalene antihelminthic drug, inhibits proliferation of a variety of T-cell lines in vitro and induces immunosuppression in some human patients and thymic atrophy and splenic depletion in mice [20].
• Induction of myeloid differentiation of HL-60 cells with naphthalene sulfonamide calmodulin antagonists [21].
• Previous studies of naphthalene-induced bronchiolar injury and repair in the mouse have shown that epithelial cell proliferation is maximal 1 to 2 days after injury and complete 4 days after injury [22].
• Whole-mount airway preparations isolated from the lungs of mice treated by intraperitoneal injection of naphthalene and allowed to recover for 5 days were examined for the distribution and abundance of solitary pulmonary neuroendocrine cells (PNECs) and neuroepithelial bodies (NEBs) along the main axial pathway of the right middle lobe [23].
• These experiments indicate that the metabolites of naphthalene can cause alteration in the metabolism of the lens cells but may not cause apparent changes in the major proteins within the lens epithelium [24].

Associations of naphthalene with other chemical compounds

• A bifid peak observed in the 16-15 Se region was shown to be an artifact caused by the ribonuclease inhibitor, naphthalene disulfonate [25].
• Here we show that through mutagenesis of three active site residues, the catalytic activity of a multicomponent monooxygenase is altered so that it hydroxylates all three positions of toluene as well as both positions of naphthalene [26].
• The data reported argue against a selective functional coupling mechanism between cytochrome P-450c and epoxide hydrolase in the metabolism of naphthalene and anthracene to the 1,2-dihydrodiols [27].
• The products of these reactions were identified by 500 MHz nmr and electron impact mass spectrometry as adducts of the 1,2-quinone of naphthalene (m/e M+ = 234) and the 7,8-quinone of benzo[a]pyrene (m/e M+ = 358), which contained mercaptoethanol as a thioether at C-4 and C-10, respectively [28].
• Intramolecular energy transfer from pyrene or naphthalene residues to Bodipy is quantitative [29].

Gene context of naphthalene

• Distribution of epidermal growth factor receptor and ligands during bronchiolar epithelial repair from naphthalene-induced Clara cell injury in the mouse [22].
• Immediately after naphthalene injury (1 to 2 days), EGFR, EGF, and TGF-alpha are expressed in increased abundance in squamous epithelial cells of the injury target zone, distal bronchioles [22].
• Gene nahG of naphthalene/salicylate catabolic plasmid NAH7 encodes a protein of molecular weight 45,000, salicylate hydroxylase [30].
• Transfection with hGSTA1 or hGSTA2 protected these cells from H2O2- and naphthalene-induced LPO and attenuated H2O2- and naphthalene-induced apoptosis through inhibiting caspase 3 activation [31].
• The protective effects of the alpha-class GSTs against H2O2- and naphthalene-induced LPO and apoptosis were examined by transfecting HLE B-3 cells with cDNAs of hGSTA1 and hGSTA2 [31].

Analytical, diagnostic and therapeutic context of naphthalene

• We compared acute bronchiolar injury and repair in three strains of mice used in knockout mouse development (C57BL/6, 129/TerSv, and 129/SvEv) to the model strain (Swiss Webster) after treatment with the same dose of naphthalene and sacrificed at 1, 2, 4, 7, and 14 days after treatment [32].
• Ultraviolet, visible, infrared, and mass spectroscopy, along with gas chromatography, indicate that it is a molecular aggregate in which an aromatic double ring ("naphthalene") structural base serves as the electron "box" chromophore that gives rise to the envelope of the 2175 angstroms feature [33].
• Specific subcompartments of the respiratory system, obtained by microdissection, have been used to study the cytochrome P450-dependent metabolism of naphthalene and the epoxide hydrolase/glutathione transferase-dependent metabolism of naphthalene oxide [34].
• Although there was evidence of metabolic alterations in the cells with the metabolites of naphthalene, the protein profile by two-dimensional gel electrophoresis did not change and there was no indication of an increase in carbonyl formation in the soluble proteins of the cells [24].
• Structure-activity relationships indicated that in the rat CMC-LPS air-pouch model by oral administration the (Z)-2-substituted propenoic acids with 3-alkoxy, 5-alkyl, and 4-hydroxy substituents on the naphthalene ring exhibit optimal inhibition [35].

References