The world's first wiki where authorship really matters (Nature Genetics, 2008). Due credit and reputation for authors. Imagine a global collaborative knowledge base for original thoughts. Search thousands of articles and collaborate with scientists around the globe.

wikigene or wiki gene protein drug chemical gene disease author authorship tracking collaborative publishing evolutionary knowledge reputation system wiki2.0 global collaboration genes proteins drugs chemicals diseases compound
Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

perylene     perylene

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of perylene

  • Photosensitization by anticancer agents 21: new perylene- and aminonaphthoquinones [1].
  • These data, coupled with the fact that the absence of the 4-5S binding protein in the -4S Sprague-Dawley rats did not affect AHH inducibility by MC, B[a]P or perylene, suggests that the 4-5S binding protein does not play a role in the transregulation of cytochrome P-4501A1 in the rat or rat hepatoma cells in culture [2].
  • In contrast, P. cepacia lipase was inactivated by perylene-containing two-chain phosphonate (XXII) to a larger extent as compared to the other inhibitors whereas Pseudomonas species lipase interacted efficiently and without any preferences with all inhibitors used in this study [3].
  • Hypocrellin, a photodynamic perylene quinonoid isolated from the Chinese medicinal fungus Hypocrella bambuase, was evaluated for antiviral activity against the human immunodeficiency virus (HIV-1) [4].
  • Two novel perylene oxide metabolites, altertoxins II and III, have been identified in extracts of A. alternata isolates that exhibit mutagenic responses in the Ames Salmonella typhimurium assay [5].

High impact information on perylene

  • In this report, measurements of the fluorescence polarization of perylene dissolved in isolated erythrocyte membranes are reported, which are indistinguishable for the two kinds of cells [6].
  • Intrachain processes dominate in solution where photoexcitation of the polyindenofluorene units induces a rather slow energy transfer to the perylene end moieties [7].
  • The nanoparticles consist of an organic photoisomerizable dye, spiropyran, as an optically responsive component and another fluorescent dye, perylene diimide, as a high-energy emitter [8].
  • A molecular square with dimensions of about 4 nm, incorporating sixteen pyrene chromophores attached to four ditopic bay-functionalized perylene bisimide chromophores, has been synthesized by coordination to four Pt(II) phosphine corner units and fully characterized via NMR spectroscopy and ESI-FTICR mass spectrometry [9].
  • After DPyPBI excitation, the strong fluorescence typical of this unit is completely quenched, and time-resolved spectroscopy reveals the occurrence of photoinduced electron transfer from the ruthenium porphyrin to the perylene bisimide dye (tau = 5.6 ps) followed by charge recombination (tau = 270 ps) [10].

Biological context of perylene

  • Water solubility was introduced first through the attachment of four hydrophilic substituents onto the bay region of the perylene dye [11].
  • The synthetic route used for the amino-functionalized perylene imide dyes involves the palladium-catalyzed amination of bromo-substituted precursors [12].
  • A simple member of the oxaarenecyclyne compounds undergoes the Ag(I)-induced cyclization leading to the quantitative formation of strongly luminescent perylene derivative [13].
  • Perylene diimide-oligonucleotide conjugates can form either duplex or hairpin dimer structures, depending upon the choice of oligonucleotide base sequence; we have used a combination of optical spectroscopy and molecular modeling to investigate the structures of the duplex and hairpin dimer [14].
  • Fourfold oligothiophene-functionalized perylene bisimides have been synthesized by esterification of hydroxyphenoxy-substituted perylene bisimides and their optical properties as well as electrochemical polymerization properties have been investigated [15].

Anatomical context of perylene


Associations of perylene with other chemical compounds


Gene context of perylene

  • Synthesis, optical properties, and aggregation behavior of a triad system based on perylene and oligo(p-phenylene vinylene) units [24].
  • These results show that there was a correlation between the Ah receptor binding affinities of MC, B[a]P and perylene and their potencies as AHH inducers in Sprague-Dawley rats, and this corresponds to previous correlations for the induction of AHH in rat hepatoma H-4-II E cells in culture [2].
  • For example, a complete set of emission and excitation spectra for perylene can be obtained in less than 2 s at concentrations of 10(-10) mol/liter [25].
  • Most of these compounds also bind double-stranded DNA and are cytotoxic at the concentrations required to inhibit telomerase; however, certain perylene diimides appear to be non-cytotoxic, G-quadruplex selective telomerase inhibitors [26].
  • The TEM images indicated that well-defined nanoscale rods with uniform diameter distribution could be fabricated by self-assembly of hydrogen-bonding interactions and pi-pi stacking interactions of perylene rings [27].

Analytical, diagnostic and therapeutic context of perylene


  1. Photosensitization by anticancer agents 21: new perylene- and aminonaphthoquinones. Diwu, Z.J., Haugland, R.P., Liu, J., Lown, J.W., Miller, G.G., Moore, R.B., Brown, K., Tulip, J., McPhee, M.S. Free Radic. Biol. Med. (1996) [Pubmed]
  2. Role of the 4-5S binding protein in the induction of aryl hydrocarbon hydroxylase in the rat. Harris, M., Kamps, C., Safe, S. Carcinogenesis (1988) [Pubmed]
  3. Fluorescent organophosphonates as inhibitors of microbial lipases. Oskolkova, O.V., Saf, R., Zenzmaier, E., Hermetter, A. Chem. Phys. Lipids (2003) [Pubmed]
  4. Hypocrellin, from Hypocrella bambuase, is phototoxic to human immunodeficiency virus. Hudson, J.B., Zhou, J., Chen, J., Harris, L., Yip, L., Towers, G.H. Photochem. Photobiol. (1994) [Pubmed]
  5. Mutagenic perylenequinone metabolites of Alternaria alternata: altertoxins I, II, and III. Stack, M.E., Mazzola, E.P., Page, S.W., Pohland, A.E., Highet, R.J., Tempesta, M.S., Corley, D.G. J. Nat. Prod. (1986) [Pubmed]
  6. Fluidity in the membranes of adult and neonatal human erythrocytes. Kehry, M., Yguerabide, J., Singer, S.J. Science (1977) [Pubmed]
  7. Interchain vs. intrachain energy transfer in acceptor-capped conjugated polymers. Beljonne, D., Pourtois, G., Silva, C., Hennebicq, E., Herz, L.M., Friend, R.H., Scholes, G.D., Setayesh, S., Mullen, K., Bredas, J.L. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  8. Reversibly photoswitchable dual-color fluorescent nanoparticles as new tools for live-cell imaging. Zhu, L., Wu, W., Zhu, M.Q., Han, J.J., Hurst, J.K., Li, A.D. J. Am. Chem. Soc. (2007) [Pubmed]
  9. Ultrafast energy-electron transfer cascade in a multichromophoric light-harvesting molecular square. Sautter, A., Kaletas, B.K., Schmid, D.G., Dobrawa, R., Zimine, M., Jung, G., van Stokkum, I.H., De Cola, L., Williams, R.M., Würthner, F. J. Am. Chem. Soc. (2005) [Pubmed]
  10. Wavelength-dependent electron and energy transfer pathways in a side-to-face ruthenium porphyrin/perylene bisimide assembly. Prodi, A., Chiorboli, C., Scandola, F., Iengo, E., Alessio, E., Dobrawa, R., Würthner, F. J. Am. Chem. Soc. (2005) [Pubmed]
  11. Towards highly fluorescent and water-soluble perylene dyes. Kohl, C., Weil, T., Qu, J., Müllen, K. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  12. New thermotropic dyes based on amino-substituted perylendicarboximides. Becker, S., Böhm, A., Müllen, K. Chemistry (Weinheim an der Bergstrasse, Germany) (2000) [Pubmed]
  13. Shape-persistency and molecular function in heteromacrocycles: creation of heteroarenecyclynes and arene-azaarenecyclynes. Yamaguchi, Y., Yoshida, Z. Chemistry (Weinheim an der Bergstrasse, Germany) (2003) [Pubmed]
  14. Duplex and hairpin dimer structures for perylene diimide-oligonucleotide conjugates. Zheng, Y., Long, H., Schatz, G.C., Lewis, F.D. Chem. Commun. (Camb.) (2005) [Pubmed]
  15. Synthesis and electropolymerization of novel oligothiophene-functionalized perylene bisimides. You, C.C., Saha-Moller, C.R., Wurthner, F. Chem. Commun. (Camb.) (2004) [Pubmed]
  16. Microviscosity of mucosal cellular membranes in toad urinary bladder: relation to antidiuretic hormone action on water permeability. Masters, B.R., Yguerabide, J., Fanestil, D.D. J. Membr. Biol. (1978) [Pubmed]
  17. DIfferential ability of Ambystoma tigrinum hepatic microsomes to produce mutagenic metabolites from polycyclic aromatic hydrocarbons and aromatic amines. Anderson, R.S., Döös, E.J., Rose, F.L. Cancer Lett. (1982) [Pubmed]
  18. Mechanisms of nitroso compound-induced inhibition of superoxide generation in neutrophils: fluorescence quenching of perylene by nitroso-compounds in the membrane fractions of neutrophils. Nasuda-Kouyama, A., Nakata, M., Iizuka, T., Isogai, Y. J. Biochem. (1997) [Pubmed]
  19. Polycyclic aromatic hydrocarbons in placenta. Gladen, B.C., Zadorozhnaja, T.D., Chislovska, N., Hryhorczuk, D.O., Kennicutt, M.C., Little, R.E. Human & experimental toxicology. (2000) [Pubmed]
  20. Selective interactions of perylene derivatives having different side chains with inter- and intramolecular G-quadruplex DNA structures. A correlation with telomerase inhibition. Rossetti, L., Franceschin, M., Schirripa, S., Bianco, A., Ortaggi, G., Savino, M. Bioorg. Med. Chem. Lett. (2005) [Pubmed]
  21. Bichromophoric perylene derivatives: energy transfer from non-fluorescent chromophores. Langhals, H., Saulich, S. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  22. Hindered depolarizing rotations of perylene in lipid bilayers. Detection by lifetime-resolved fluorescence anisotropy measurements. Lakowicz, J.R., Knutson, J.R. Biochemistry (1980) [Pubmed]
  23. In situ space- and time-resolved sorption kinetics of anionic dyes on individual LDH crystals. Roeffaers, M.B., Sels, B.F., Loos, D., Kohl, C., Müllen, K., Jacobs, P.A., Hofkens, J., De Vos, D.E. Chemphyschem : a European journal of chemical physics and physical chemistry. (2005) [Pubmed]
  24. Synthesis, optical properties, and aggregation behavior of a triad system based on perylene and oligo(p-phenylene vinylene) units. Syamakumari, A., Schenning, A.P., Meijer, E.W. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  25. Multicomponent analysis in clinical chemistry by use of rapid scanning fluorescence spectroscopy. Warner, I.M., Callis, J.B., Davidson, E.R., Christian, G.D. Clin. Chem. (1976) [Pubmed]
  26. G-Quadruplex DNA as a target for drug design. Kerwin, S.M. Curr. Pharm. Des. (2000) [Pubmed]
  27. Assembly and characterization of novel hydrogen-bond-induced nanoscale rods. Liu, Y., Li, Y., Jiang, L., Gan, H., Liu, H., Li, Y., Zhuang, J., Lu, F., Zhu, D. J. Org. Chem. (2004) [Pubmed]
  28. Short-term bioassays of nitro derivatives of benzo[a]pyrene and perylene. Löfroth, G., Toftgård, R., Nilsson, L., Agurell, E., Gustafsson, J.A. Carcinogenesis (1984) [Pubmed]
  29. Evaluation of binding of perylene diimide and benzannulated perylene diimide ligands to DNA by electrospray ionization mass spectrometry. Mazzitelli, C.L., Brodbelt, J.S., Kern, J.T., Rodriguez, M., Kerwin, S.M. J. Am. Soc. Mass Spectrom. (2006) [Pubmed]
  30. Evaluation of energy transfer in perylene-cored anthracene dendrimers. Takahashi, M., Morimoto, H., Miyake, K., Yamashita, M., Kawai, H., Sei, Y., Yamaguchi, K. Chem. Commun. (Camb.) (2006) [Pubmed]
  31. Efficacy of hypocrellin pharmacokinetics in phototherapy. Ali, S.M., Olivo, M. Int. J. Oncol. (2002) [Pubmed]
  32. Square, hexagonal, and row phases of PTCDA and PTCDI on Ag-Si(111)square root(3) x square root(3)R30 degrees. Swarbrick, J.C., Ma, J., Theobald, J.A., Oxtoby, N.S., O'Shea, J.N., Champness, N.R., Beton, P.H. The journal of physical chemistry. B, Condensed matter, materials, surfaces, interfaces & biophysical. (2005) [Pubmed]
WikiGenes - Universities