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Chemical Compound Review

Naftalen     naphthalene

Synonyms: antimitr, Mothballs, Naphthene, mothballr, naftaleno, ...
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Disease relevance of naphthalene


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


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


Analytical, diagnostic and therapeutic context of naphthalene


  1. Hemolysis from exposure to naphthalene mothballs. Todisco, V., Lamour, J., Finberg, L. N. Engl. J. Med. (1991) [Pubmed]
  2. Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Joo, H., Lin, Z., Arnold, F.H. Nature (1999) [Pubmed]
  3. Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo. Ensley, B.D., Ratzkin, B.J., Osslund, T.D., Simon, M.J., Wackett, L.P., Gibson, D.T. Science (1983) [Pubmed]
  4. The 2,6-disubstituted naphthalene derivative FDDNP labeling reliably predicts Congo red birefringence of protein deposits in brain sections of selected human neurodegenerative diseases. Smid, L.M., Vovko, T.D., Popovic, M., Petric, A., Kepe, V., Barrio, J.R., Vidmar, G., Bresjanac, M. Brain Pathol. (2006) [Pubmed]
  5. Systemic sclerosis associated with cutaneous exposure to solvent: case report and review of the literature. Brasington, R.D., Thorpe-Swenson, A.J. Arthritis Rheum. (1991) [Pubmed]
  6. Multimicrobial sensor using microstructured three-dimensional electrodes based on silicon technology. König, A., Reul, T., Harmeling, C., Spener, F., Knoll, M., Zaborosch, C. Anal. Chem. (2000) [Pubmed]
  7. Selective inhibition and induction of CYP activity discriminates between the isoforms responsible for the activation of butylated hydroxytoluene and naphthalene in mouse lung. Verschoyle, R.D., Martin, J., Dinsdale, D. Xenobiotica (1997) [Pubmed]
  8. Mass spectrometric molecular-weight determination of highly acidic compounds of biological significance via their complexes with basic polypeptides. Juhasz, P., Biemann, K. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  9. Identification of a subunit-specific antagonist of alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionate/kainate receptor channels. Keller, B.U., Blaschke, M., Rivosecchi, R., Hollmann, M., Heinemann, S.F., Konnerth, A. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  10. Paramecium calcium channels are blocked by a family of calmodulin antagonists. Ehrlich, B.E., Jacobson, A.R., Hinrichsen, R., Sayre, L.M., Forte, M.A. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  11. Catabolism of premercapturic acid pathway metabolites of naphthalene to naphthols and methylthio-containing metabolites in rats. Bakke, J., Struble, C., Gustafsson, J.A., Gustafsson, B. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  12. Metabolism and cytotoxicity of naphthalene and its metabolites in isolated murine Clara cells. Chichester, C.H., Buckpitt, A.R., Chang, A., Plopper, C.G. Mol. Pharmacol. (1994) [Pubmed]
  13. Role of p53 tumor suppressor gene in the toxicity of TCDD, endrin, naphthalene, and chromium (VI) in liver and brain tissues of mice. Bagchi, D., Balmoori, J., Bagchi, M., Ye, X., Williams, C.B., Stohs, S.J. Free Radic. Biol. Med. (2000) [Pubmed]
  14. The topical microbicide PRO 2000 protects against genital herpes infection in a mouse model. Bourne, N., Bernstein, D.I., Ireland, J., Sonderfan, A.J., Profy, A.T., Stanberry, L.R. J. Infect. Dis. (1999) [Pubmed]
  15. Aldose reductase the major protein associated with naphthalene dihydrodiol dehydrogenase activity in rat lens. Sato, S. Invest. Ophthalmol. Vis. Sci. (1993) [Pubmed]
  16. Methyl substitution on the piperidine ring of N-[omega-(6-methoxynaphthalen-1-yl)alkyl] derivatives as a probe for selective binding and activity at the sigma(1) receptor. Berardi, F., Ferorelli, S., Abate, C., Pedone, M.P., Colabufo, N.A., Contino, M., Perrone, R. J. Med. Chem. (2005) [Pubmed]
  17. Distribution of end-to-end distances of oligopeptides in solution as estimated by energy transfer. Haas, E., Wilchek, M., Katchalski-Katzir, E., Steinberg, I.Z. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  18. In vivo interactions of the NahR transcriptional activator with its target sequences. Inducer-mediated changes resulting in transcription activation. Huang, J.Z., Schell, M.A. J. Biol. Chem. (1991) [Pubmed]
  19. Effector specificity mutants of the transcriptional activator NahR of naphthalene degrading Pseudomonas define protein sites involved in binding of aromatic inducers. Cebolla, A., Sousa, C., de Lorenzo, V. J. Biol. Chem. (1997) [Pubmed]
  20. Suramin prevents binding of interleukin 2 to its cell surface receptor: a possible mechanism for immunosuppression. Mills, G.B., Zhang, N., May, C., Hill, M., Chung, A. Cancer Res. (1990) [Pubmed]
  21. Induction of myeloid differentiation of HL-60 cells with naphthalene sulfonamide calmodulin antagonists. Veigl, M.L., Sedwick, W.D., Niedel, J., Branch, M.E. Cancer Res. (1986) [Pubmed]
  22. Distribution of epidermal growth factor receptor and ligands during bronchiolar epithelial repair from naphthalene-induced Clara cell injury in the mouse. Van Winkle, L.S., Isaac, J.M., Plopper, C.G. Am. J. Pathol. (1997) [Pubmed]
  23. Alteration of pulmonary neuroendocrine cells during epithelial repair of naphthalene-induced airway injury. Peake, J.L., Reynolds, S.D., Stripp, B.R., Stephens, K.E., Pinkerton, K.E. Am. J. Pathol. (2000) [Pubmed]
  24. Effects of naphthalene metabolites on cultured cells from eye lens. Russell, P., Yamada, T., Xu, G.T., Garland, D., Zigler, J.S. Free Radic. Biol. Med. (1991) [Pubmed]
  25. Identification of the products of mitochondrial transcription in the walker corcinosarcoma by the use of actinomycin D and ethidium bromide. González-Cadavid, N.F., Pérez, J.L. Cancer Res. (1976) [Pubmed]
  26. Controlling the regiospecific oxidation of aromatics via active site engineering of toluene para-monooxygenase of Ralstonia pickettii PKO1. Fishman, A., Tao, Y., Rui, L., Wood, T.K. J. Biol. Chem. (2005) [Pubmed]
  27. Differential stereoselectivity of cytochromes P-450b and P-450c in the formation of naphthalene and anthracene 1,2-oxides. The role of epoxide hydrolase in determining the enantiomer composition of the 1,2-dihydrodiols formed. van Bladeren, P.J., Sayer, J.M., Ryan, D.E., Thomas, P.E., Levin, W., Jerina, D.M. J. Biol. Chem. (1985) [Pubmed]
  28. Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. A potential route of proximate carcinogen metabolism. Smithgall, T.E., Harvey, R.G., Penning, T.M. J. Biol. Chem. (1988) [Pubmed]
  29. Synthesis and photophysical properties of borondipyrromethene dyes bearing aryl substituents at the boron center. Goze, C., Ulrich, G., Mallon, L.J., Allen, B.D., Harriman, A., Ziessel, R. J. Am. Chem. Soc. (2006) [Pubmed]
  30. Nucleotide sequence analysis of the Pseudomonas putida PpG7 salicylate hydroxylase gene (nahG) and its 3'-flanking region. You, I.S., Ghosal, D., Gunsalus, I.C. Biochemistry (1991) [Pubmed]
  31. Protection of HLE B-3 cells against hydrogen peroxide- and naphthalene-induced lipid peroxidation and apoptosis by transfection with hGSTA1 and hGSTA2. Yang, Y., Sharma, R., Cheng, J.Z., Saini, M.K., Ansari, N.H., Andley, U.P., Awasthi, S., Awasthi, Y.C. Invest. Ophthalmol. Vis. Sci. (2002) [Pubmed]
  32. Mouse strain modulates the role of the ciliated cell in acute tracheobronchial airway injury-distal airways. Lawson, G.W., Van Winkle, L.S., Toskala, E., Senior, R.M., Parks, W.C., Plopper, C.G. Am. J. Pathol. (2002) [Pubmed]
  33. Experimental indication of a naphthalene-base molecular aggregate for the carrier of the 2175 angstroms interstellar extinction feature. Beegle, L.W., Wdowiak, T.J., Robinson, M.S., Cronin, J.R., McGehee, M.D., Clemett, S.J., Gillette, S. Astrophys. J. (1997) [Pubmed]
  34. Relationship of cytochrome P450 activity to Clara cell cytotoxicity. IV. Metabolism of naphthalene and naphthalene oxide in microdissected airways from mice, rats, and hamsters. Buckpitt, A., Chang, A.M., Weir, A., Van Winkle, L., Duan, X., Philpot, R., Plopper, C. Mol. Pharmacol. (1995) [Pubmed]
  35. A novel orally active inhibitor of IL-1 generation: synthesis and structure-activity relationships of 3-(4-hydroxy-1-naphthalenyl)-2-propenoic acid derivatives. Tanaka, M., Chiba, K., Okita, M., Kaneko, T., Tagami, K., Hibi, S., Okamoto, Y., Shirota, H., Goto, M., Obaishi, H. J. Med. Chem. (1992) [Pubmed]
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