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Chemical Compound Review

pyrene     pyrene

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Disease relevance of pyrene


Psychiatry related information on pyrene


High impact information on pyrene

  • Here we test this idea by using a pyrene nucleoside triphosphate (dPTP) in which the fluorescent 'base' is nearly as large as an entire Watson-Crick base pair [7].
  • The outer (exofacial) and inner (endofacial) leaflets of the erythrocyte membrane differ in lipid composition, and recent studies using a group of membrane-impermeant pyrene fluorophores have demonstrated that the lipid fluidity of the outer leaflet exceeds that of the inner [8].
  • In pyrene actin assay, Cdc42 enhanced VirG-stimulating actin polymerization by N-WASP-actin-related protein (Arp)2/3 complex [9].
  • X-linked adrenoleukodystrophy fibroblasts accumulated pyrene-fatty acids and showed increased UV sensitivity only when exposed to longer-chain pyrene fatty acids [2].
  • Viscosity measurements and studies on the polymerization kinetics of pyrene-labeled actin showed that hsc70 increased the capping activity of cap32/34 up to 10-fold, whereas hsc70 alone had no effect on actin polymerization [10].

Chemical compound and disease context of pyrene

  • BeP clearly showed the least toxicity followed by pyrene and anthracene [11].
  • The uptake of a fluorescent derivative of a fatty acid (FDFA), 12-(1-pyrene) dodecanoic acid (P12) by murine erythroleukemia (MEL) cells was studied [12].
  • The well-characterized integral membrane protein lactose (lac) permease from Escherichia coli was reconstituted together with trace amounts (molar fraction X = 0.005 of the total phospholipid) of different pyrene-labeled phospholipid analogs into 1-palmitoyl-2-oleoyl-sn-glycero-3-sn-glycero-3-phospho-rac'-glycerol (POPG) liposomes [13].
  • Microcosms inoculated with the Mycobacterium sp. showed enhanced mineralization, singly and as components in a mixture, of 2-methylnaphthalene, phenanthrene, pyrene, and benzo[alpha]pyrene [14].
  • Mycobacterium sp. strain Pyr-1 cells, which were grown to the stationary phase in media with and without pyrene, were centrifuged and resuspended in a medium containing 1-nitropyrene [15].

Biological context of pyrene

  • Pyrene excimer fluorescence and resonance energy transfer studies on the labeled mutant troponin C reveal a Ca(2+)-induced increase in distance between the two cysteines [16].
  • On the other hand, the results of the quenching study with KI, excimer fluorescence, and polarization measurements of pyrene-labeled membranes suggested an increase of membrane fluidity on addition of KCl to medium [17].
  • To probe adriamycin-phospholipid interactions, the effects of this cytotoxin on the hydrolysis of a pyrene-labeled acidic alkyl-acyl phospholipid analog 1-octa-cosanyl-2-(6-pyren-1-yl)hexanoyl-sn-glycero-3-phos p hatidylmethanol (C28-O-PHPM) by porcine pancreatic phospholipase A2 (PLA2) were studied [18].
  • Although the pyrene tag weakens protein binding, unbiased protein-RNA association constants were obtained in competition experiments with untagged RNA [19].
  • These results provide important information regarding the role of lipids on membrane protein folding and conformation as well as demonstrate the usefulness of a pyrene-based system in studying the forces that govern interhelical packing [20].

Anatomical context of pyrene

  • Second, as measured with pyrene-labeled yeast actin, but not with intrinsic fluorescence, there is an overshoot in the fluorescence that has not been observed with skeletal muscle actin under the same conditions [21].
  • Toward this end, a monoclonal antibody against an antigen on the surface of T lymphocytes was covalently attached to liposomes containing a phototoxic drug, pyrene, bound to the lipid bilayer [22].
  • When a pyrene derivative of sphingomyelin was introduced into the lysosomes of cultured fibroblasts from a type A NPD patient by using apolipoprotein E-mediated endocytosis, only approximately 6% of the delivered substrate was degraded [23].
  • The interaction of actin filaments and monomers with human serum was studied by following the kinetics and extent of the depolymerization of pyrene-labeled F-actin and by analysis of serum proteins adhering to immobilized actin monomers [24].
  • These experiments suggest that thehydroxylase is important in determining the sensitivity of epithelial cells to the cytotoxic action of benzo (a) pyrene, but other factors may also modulate this sensitivity [25].

Associations of pyrene with other chemical compounds


Gene context of pyrene

  • To monitor binding of tropomyosin to yeast actin, we mutated S235 to C and labeled the actin with pyrene maleimide at both C235 and the normally reactive C374 [30].
  • 2. When PyrPC-rHDL was incubated with HDL3 in the presence of PLTP, a rapid decline of the pyrene excimer/monomer fluorescence ratio (E/M) occurred, demonstrating that PLTP induced mixing of the surface lipids of PyrPC-rHDL and HDL3 [31].
  • Adduction of the human N-ras codon 61 sequence with (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a] pyrene: structural refinement of the intercalated SRSR(61,2) (-)-(7S,8R,9S,10R)-N6-[10-(7,8,9,10- tetrahydrobenzo[a]pyrenyl)]-2'-deoxyadenosyl adduct from 1H NMR [32].
  • In occupationally exposed populations CYP2E1 and GSTM1 appear to play an important role in the metabolism of pyrene and naphthalene [33].
  • Pyrene excimer fluorescence of yeast alcohol dehydrogenase: a sensitive probe to investigate ligand binding and unfolding pathway of the enzyme [34].

Analytical, diagnostic and therapeutic context of pyrene


  1. Oxidation of the carcinogens benzo [a] pyrene and benzo [a] anthracene to dihydrodiols by a bacterium. Gibson, D.T., Mahadevan, V., Jerina, D.M., Yogi, H., Yeh, H.J. Science (1975) [Pubmed]
  2. Photosensitized killing of cultured fibroblasts from patients with peroxisomal disorders due to pyrene fatty acid-mediated ultraviolet damage. Hoefler, G., Paschke, E., Hoefler, S., Moser, A.B., Moser, H.W. J. Clin. Invest. (1991) [Pubmed]
  3. Targeted killing of cultured cells by receptor-dependent photosensitization. Mosley, S.T., Goldstein, J.L., Brown, M.S., Falck, J.R., Anderson, R.G. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  4. Adenomas induced by polycyclic aromatic hydrocarbons in strain A/J mouse lung correlate with time-integrated DNA adduct levels. Ross, J.A., Nelson, G.B., Wilson, K.H., Rabinowitz, J.R., Galati, A., Stoner, G.D., Nesnow, S., Mass, M.J. Cancer Res. (1995) [Pubmed]
  5. Isolation of dinitropyrene in emission gas from a municipal incinerator and its formation by a photochemical reaction. Kamiya, A., Ose, Y. Sci. Total Environ. (1988) [Pubmed]
  6. Ambient and biological monitoring of cokeoven workers: determinants of the internal dose of polycyclic aromatic hydrocarbons. Jongeneelen, F.J., van Leeuwen, F.E., Oosterink, S., Anzion, R.B., van der Loop, F., Bos, R.P., van Veen, H.G. British journal of industrial medicine. (1990) [Pubmed]
  7. A specific partner for abasic damage in DNA. Matray, T.J., Kool, E.T. Nature (1999) [Pubmed]
  8. Acanthocytosis and cholesterol enrichment decrease lipid fluidity of only the outer human erythrocyte membrane leaflet. Flamm, M., Schachter, D. Nature (1982) [Pubmed]
  9. Rho family GTPase Cdc42 is essential for the actin-based motility of Shigella in mammalian cells. Suzuki, T., Mimuro, H., Miki, H., Takenawa, T., Sasaki, T., Nakanishi, H., Takai, Y., Sasakawa, C. J. Exp. Med. (2000) [Pubmed]
  10. The heat shock cognate protein from Dictyostelium affects actin polymerization through interaction with the actin-binding protein cap32/34. Haus, U., Trommler, P., Fisher, P.R., Hartmann, H., Lottspeich, F., Noegel, A.A., Schleicher, M. EMBO J. (1993) [Pubmed]
  11. Pathologic changes induced in respiratory tract mucosa by polycyclic hydrocarbons of differing carcinogenic activity. Topping, D.C., Pal, B.C., Martin, D.H., Nelson, F.R., Nettesheim, P. Am. J. Pathol. (1978) [Pubmed]
  12. Uptake of fluorescent fatty acids by erythroleukemia cells. Effect of differentiation. Fibach, E., Nahas, N., Giloh, H., Gatt, S. Exp. Cell Res. (1986) [Pubmed]
  13. Evidence for phospholipid microdomain formation in liquid crystalline liposomes reconstituted with Escherichia coli lactose permease. Lehtonen, J.Y., Kinnunen, P.K. Biophys. J. (1997) [Pubmed]
  14. Polycyclic aromatic hydrocarbon degradation by a Mycobacterium sp. in microcosms containing sediment and water from a pristine ecosystem. Heitkamp, M.A., Cerniglia, C.E. Appl. Environ. Microbiol. (1989) [Pubmed]
  15. Reduction and mutagenic activation of nitroaromatic compounds by a Mycobacterium sp. Rafii, F., Selby, A.L., Newton, R.K., Cerniglia, C.E. Appl. Environ. Microbiol. (1994) [Pubmed]
  16. Characterization of the Ca(2+)-triggered conformational transition in troponin C. Wang, Z., Gergely, J., Tao, T. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  17. The effects of ionic strength on the protein conformation and the fluidity of porcine intestinal brush border membranes. Fluorometric studies using N-[7-dimethylamino-4-methylcoumarinyl]maleimide and pyrene. Ohyashiki, T., Taka, M., Mohri, T. J. Biol. Chem. (1985) [Pubmed]
  18. Activation of phospholipase A2 by adriamycin in vitro. Role of drug-lipid interactions. Mustonen, P., Kinnunen, P.K. J. Biol. Chem. (1991) [Pubmed]
  19. Interactions of the N-terminal domain of ribosomal protein L11 with thiostrepton and rRNA. Bausch, S.L., Poliakova, E., Draper, D.E. J. Biol. Chem. (2005) [Pubmed]
  20. Interhelical packing in detergent micelles. Folding of a cystic fibrosis transmembrane conductance regulator construct. Therien, A.G., Deber, C.M. J. Biol. Chem. (2002) [Pubmed]
  21. Yeast actin: polymerization kinetic studies of wild type and a poorly polymerizing mutant. Buzan, J.M., Frieden, C. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  22. Selective killing of T lymphocytes by phototoxic liposomes. Yemul, S., Berger, C., Estabrook, A., Suarez, S., Edelson, R., Bayley, H. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  23. Retroviral-mediated transfer of the human acid sphingomyelinase cDNA: correction of the metabolic defect in cultured Niemann-Pick disease cells. Suchi, M., Dinur, T., Desnick, R.J., Gatt, S., Pereira, L., Gilboa, E., Schuchman, E.H. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  24. Capacity of human serum to depolymerize actin filaments. Janmey, P.A., Lind, S.E. Blood (1987) [Pubmed]
  25. Benzo(alpha)pyrene effects on mouse epithelial cells in culture. Bartholomew, J.C., Salmon, A.G., Gamper, H.B., Calvin, M. Cancer Res. (1975) [Pubmed]
  26. Inhibition by 2,6-dithiopurine and thiopurinol of binding of a benzo(a)pyrene diol epoxide to DNA in mouse epidermis and of the initiation phase of two-stage tumorigenesis. MacLeod, M.C., Mann, K.L., Thai, G., Conti, C.J., Reiners, J.J. Cancer Res. (1991) [Pubmed]
  27. Structure and function in rhodopsin. Measurement of the rate of metarhodopsin II decay by fluorescence spectroscopy. Farrens, D.L., Khorana, H.G. J. Biol. Chem. (1995) [Pubmed]
  28. Labeling of a thiol residue in sarcoplasmic reticulum ATPase by pyrene maleimide. Solvent accessibility studied by fluorescence quenching. Kurtenbach, E., Verjovski-Almeida, S. J. Biol. Chem. (1985) [Pubmed]
  29. gamma-cyclodextrins greatly enhance translocation of hydrophobic fluorescent phospholipids from vesicles to cells in culture. Importance of molecular hydrophobicity in phospholipid trafficking studies. Tanhuanpää, K., Somerharju, P. J. Biol. Chem. (1999) [Pubmed]
  30. Differential interaction of cardiac, skeletal muscle, and yeast tropomyosins with fluorescent (pyrene235) yeast actin. Chen, W., Wen, K.K., Sens, A.E., Rubenstein, P.A. Biophys. J. (2006) [Pubmed]
  31. The mechanism of human plasma phospholipid transfer protein-induced enlargement of high-density lipoprotein particles: evidence for particle fusion. Lusa, S., Jauhiainen, M., Metso, J., Somerharju, P., Ehnholm, C. Biochem. J. (1996) [Pubmed]
  32. Adduction of the human N-ras codon 61 sequence with (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a] pyrene: structural refinement of the intercalated SRSR(61,2) (-)-(7S,8R,9S,10R)-N6-[10-(7,8,9,10- tetrahydrobenzo[a]pyrenyl)]-2'-deoxyadenosyl adduct from 1H NMR. Zegar, I.S., Kim, S.J., Johansen, T.N., Horton, P.J., Harris, C.M., Harris, T.M., Stone, M.P. Biochemistry (1996) [Pubmed]
  33. Effects of occupation, lifestyle and genetic polymorphisms of CYP1A1, CYP2E1, GSTM1 and GSTT1 on urinary 1-hydroxypyrene and 2-naphthol concentrations. Nan, H.M., Kim, H., Lim, H.S., Choi, J.K., Kawamoto, T., Kang, J.W., Lee, C.H., Kim, Y.D., Kwon, E.H. Carcinogenesis (2001) [Pubmed]
  34. Pyrene excimer fluorescence of yeast alcohol dehydrogenase: a sensitive probe to investigate ligand binding and unfolding pathway of the enzyme. Santra, M.K., Dasgupta, D., Panda, D. Photochem. Photobiol. (2006) [Pubmed]
  35. Two-site attachment of troponin to pyrene-labeled tropomyosin. Ishii, Y., Lehrer, S.S. J. Biol. Chem. (1991) [Pubmed]
  36. Mechanical properties of actin. Sato, M., Leimbach, G., Schwarz, W.H., Pollard, T.D. J. Biol. Chem. (1985) [Pubmed]
  37. 4-Aminobutyrate aminotransferase reaction of sulfhydryl residues connected with catalytic activity. Choi, S.Y., Churchich, J.E. J. Biol. Chem. (1985) [Pubmed]
  38. Side-chain dynamics of an alpha-helical polypeptide monitored by fluorescence. Duhamel, J., Kanagalingam, S., O'Brien, T.J., Ingratta, M.W. J. Am. Chem. Soc. (2003) [Pubmed]
  39. Design of an Emission Ratiometric Biosensor from MerR Family Proteins: A Sensitive and Selective Sensor for Hg(2+). Wegner, S.V., Okesli, A., Chen, P., He, C. J. Am. Chem. Soc. (2007) [Pubmed]
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