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

• The microviscosity of cellular membranes (or membrane fluidity) was measured in suspensions of single mucosal cells isolated from the urinary bladder of the toad, Bufo marinus, by the technique of polarized fluorescence emission spectroscopy utilizing the hydrophobic fluorescent probe, perylene [16].
• However, 2 polycyclic aromatic hydrocarbons (PAH) (benzo[alpha]pyrene (BaP) and perylene) that are rendered mutagenic by mammalian microsomes are not activated by Ambystoma mixed-function oxidases [17].
• Mechanisms of nitroso compound-induced inhibition of superoxide generation in neutrophils: fluorescence quenching of perylene by nitroso-compounds in the membrane fractions of neutrophils [18].
• Concentrations of chrysene, benz [a] anthracene, benzo [a]-pyrene, benzo [b] fluoranthene, indeno [1,2,3-c,d] pyrene, dibenz [a,h] anthracene, and benzo [g,h,i] perylene were measured in placentas from 200 women from two cities in Ukraine, Kyiv and Dniprodzerzhinsk [19].
• The different efficiencies of the six perylene derivatives in interacting both with inter- and intramolecular G-quadruplex structures satisfactorily correlate with telomerase inhibition in cell-free systems [20].

Associations of perylene with other chemical compounds

• To this end, anthraquinone, fluorenone and anthracene derivatives have been linked to the perylene bisimides by non-conjugating spacers and fluorescence quantum yield of such assemblies have been determined as a function of the wavelengths of excitation [21].
• The energy of excitation at non-fluorescent chromophores such as fluorenone and anthraquinone has been trapped by a fast energy transfer to the highly fluorescent perylene bisimides [21].
• Steady-state fluorescence anisotropy measurements under these quenching conditions were used to investigate the diffusive motions of perylene in the isotropic solvent propylene glycol and in lipid bilayers [22].
• Fluorescence spectroscopy is employed to follow the ion exchange of an emissive dye--a carboxylated perylene imide--on a layered double hydroxide [23].
• CPK models with a dimeric structure, in which two perylene molecules are held together by intermolecular hydrogen bonding with the perylene core shifted slightly with respect to one another, could account for the optical properties and the observation of the four different peaks in the (1)H NMR spectra in polar solvent [24].

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

• Short-term bioassays of nitro derivatives of benzo[a]pyrene and perylene [28].
• Electrospray ionization mass spectrometry (ESI-MS) and spectroscopic studies in solution were used to evaluate the self-association, G-quadruplex DNA binding, and selectivity of a series of perylene diimides (PDIs) (PIPER, Tel01, Tel11, Tel12, and Tel18) or benzannulated perylene diimide ligands (Tel34 and Tel32) [29].
• Quantitative evaluation of Förster-type fluorescence resonance energy transfer (FRET) was undertaken by statistical investigations on perylene-cored anthracene dendrimers [30].
• Heen found in the People's Republic of China and other parts of Asia including Sri Lanka. These agents, which belong to the general class of perylene quinonoid pigments, have a long history of traditional medicinal agents especially in Asia. Hypocrellins are under extensive investigation as photosensitizing agents for photodynamic therapy (PDT) [31].
• We have investigated the ordered phases of the perylene derivatives perylene-3,4,9,10-tetracarboxylic-3,4,9,10-dianhydride (PTCDA) and the imide analogue PTCDI on the Ag-Si(111)square root(3) x square root(3)R30 degrees surface using scanning tunneling microscopy [32].

References