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Hindered depolarizing rotations of perylene in lipid bilayers. Detection by lifetime-resolved fluorescence anisotropy measurements.

Oxygen quenching of perylene fluorescence was used to vary its fluorescence lifetime. 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. These lifetime-resolved anisotropy measurements indicate that the anisotropy of perylene in propylene glycol decays to zero at times long compared to its fluorescence lifetime. In contrast, the asymptotic or "limiting" anistropy values at these long times (r infinity) are nonzero in vesicles of dimyristoyl-phosphatidylcholine (DMPC). r infinity values are largest at temperatures below the DMPC phase transition temperature of 23 degrees C. Representative values of r infinity for perylene in DMPC vesicles are 0.16 and 0.02 at 5 and 47 degrees C, respectively. Thus, in contrast to the free rotations observed for perylene in propylene glycol, perylene rotations are hindered in lipid bilayers. Less marked, yet significant, rotational hindrance was observed in dioleoylphosphatidylcholine (DOPC) vesicles. Representative values for r infinity in this unsaturated lipid are 0.05 and 0.01 at 2 and 45 degrees C, respectively. Steady-state anisotropy measurements with short-wavelength excitations were used to investigate whether the in-plane or out-of-plane rotations of perylene were responsible for the observed r infinity values. In DMPC vesicles we conclude that both rotations are partially hindered. In DOPC vesicles we can only conclude that one or both of these rotations are partially hindered, but both are not free. Most importantly, the existence of fundamentally different diffusive behavior for perylene in solvents and in lipids calls into question the meaning of membrane microviscosities which are derived via such comparisons.

Benz(a)Anthracenes

The local anaesthetic tetracaine as a quencher of perylene fluorescence in micelles.

At neutral pH the local anaesthetic tetracaine hydrochloride quenches the fluorescence of the lipophilic dye perylene incorporated into non-ionic micelles. The process follows the Stern-Volmer equation, suggesting that quenching occurs through encounter of fluorophore and quencher. As the pH is lowered from 5 to 1, the apparent quenching constant decreases sigmoidally, the midpoint of the curve being at pH 2.3, close to the pK value characterizing the ionization of the anaesthetic aromatic butylamino group. Quenching is completely reversed below pH 1. These results show that the ability of tetracaine to quench the fluorescence of perylene incorporated into micelles depends on the absence of charge on its aromatic amine. Quenching was also studied in homogeneous dioxane-water solution. In this system the quenching constant also decreases sigmoidally as the pH is lowered. The infection point of the curve is nearly coincident with the pK of tetracaine butylamino group in the same partially non-aqueous medium. Protonation of this group induces 60% reversal of the quenching, suggesting that the main mechanism of fluorescence extinction could be the electron transfer from unprotonated tetracaine aromatic amine to perylene in the excited state. However, an additional process which remains operative even when such an amino group is positively charged must also be involved. It can be concluded that the complete reversal of tetracaine quenching of perylene fluorescence in micelles induced by low pH is due to the inability of the anaesthetic to become partitioned into micelles upon protonation of its aromatic amine. In contrast, at neutral pH the local anaesthetic is able to reach the micelle non-polar core where perylene is located. This is consistent with the models, suggesting that the membrane-bound tetracaine assumes a rod-like configuration parallel to the surface normal with the aromatic butylamino group located into a highly hydrophobic region.

Electron Transport

The effects of pressure and cholesterol on rotational motions of perylene in lipid bilayers.

Using steady-state fluorescence polarization measurements, an isothermal pressure-induced phase transition was observed in dimyristoyl-L-alpha-phosphatidylcholine multilamellar vesicles containing perylene. The temperature-to-pressure equivalence, dT/dP, estimated from the phase transition pressure, P1/2, is about 22 K X kbar-1, which is comparable to values determined from diphenylhexatriene polarization (Chong, P.L.-G. and Weber, G. (1983) Biochemistry 22, 5544-5550). In addition, we have employed a new method, introduced in this paper, to calculate the rate of in-plane rotation (Rip) and the rate of out-of-plane rotation (Rop) of perylene in lipid bilayers. The effects of pressure and cholesterol on the rotational rates of perylene in two lipid bilayer systems have been examined. They are 1-palmitoyl-2-oleoyl-L-alpha-phosphatidylcholine (POPC) multilamellar vesicles (MLV) and 50 mol% cholesterol in POPC (MLV). Rop is smaller than Rip due to the fact that the out-of-plane rotation requires a larger volume change than the in-plane rotation. Cholesterol seems not to affect Rop significantly, but pressure causes a decrease in Rop by about a factor of three. In contrast, the effects of pressure and cholesterol on Rip are less straightforward. At 1 atm cholesterol increases Rip by a factor of about two. Similarly, in the absence of cholesterol 1.5 kbar pressure essentially triples Rip. However, if both cholesterol is added and pressure is applied, Rip decreases sharply. The possible interactions between cholesterol and perylene are discussed.

Benz(a)Anthracenes

Labelling of liposomes with intercalating perylene fluorescent dyes.

The high fluorescent potential and the exceptional photostability of lipophilic derivatives of perylene-3,4:9,10-bis(dicarboximides) are utilized for the fluorescence-labelling of liposomes. The preparation of the liposomes is effected by supersonic starting from a lipid mixture consisting of the matrix lipids soy lecithin, cholesterol, alpha-tocopherol and the perylene dyes. From a multitude of perylene derivatives investigated only those are optimally incorporated into the bilayer membrane of unilamellar liposomes which are substituted at both nitrogen atoms by one or two linear hydrocarbon groups. In order to attain an optimal fluorescent quantum yield, about 200 to 300 dye molecules can be incorporated per liposome. The liposomes thus obtained have a diameter of about 70 to 80 nm, are homogeneous and may be stored for more than seven months. Neither the fluorescent properties nor the stability of these liposomes are influenced by the additional incorporation of various ara C-derivatives and lipophilic anchor groups which subsequently enable the coupling of antibodies to the liposomes. As the water-insoluble perylene dyes are incorporated into the bilayer membrane, the aqueous inner volume of the liposomes remains available for a further utilization.

Cholesterol

Dinitro and mononitrobenzo(ghi)perylenes and mononitrocoronene are highly mutagenic in the Ames Salmonella assay.

Benzo(ghi)perylene (B(ghi))Per, (191-24-2)) and coronene (Cor, (191-07-1)) are major constituents of the polycyclic aromatic hydrocarbons (PAH) found in automobile exhaust and polluted air [eg, Grimmer et al, 1981]. Nitration of these PAH by NO2 and traces of HNO3, which are also formed in automobile exhaust, seems highly probable. To identify the presence of these nitroarenes in environmental samples and to examine their mutagenic potencies we synthesized and characterized nitro derivatives of both PAH. 5-NO2B(ghi)Per (81316-87-2) and 1-NO2Cor (81316-84-9) produced 405 and 340 revertants/nmole respectively in TA98 in the presence of 0.6 mg of microsomal enzymes (S-9) per plate in the Ames test. 5,8-diNO2B(ghi)Per (83292-25-5) and 5,10-diNO2B(ghi)Per (83292-26-6) produced 21,500 and 4,000 revertants/nmole in TA98 without microsomal activation. Mutagenicity for the dinitrobenzo(ghi)perylenes was also high in TA98NR and TA97 but was reduced by 97% in TA98-1,8DNP. There is close similarity in the orientation and distances between reactive sites (nitrenium ion and carbocation) on the dinitrobenzo(ghi)perylenes and 1,6-dinitropyrene (42397-64-8) and 1,8-dinitropyrene (42397-65-9).

Animals

[Structural changes in the myelin sheath membranes detectable by using the nonpolar probe perylene. A fluorescence polarization study].

Perylene as a fluorescent probe has been used to investigate membranes of the myelin sheath of surviving nerve fibres. Fluorescence polarization (P) of perylene was measured in stained nerve fibres, and their dependence on the angle (AD) between the geometrical axis of the fibre and electrical vector of exciting light was studied. The dependence of AD on the temperature showed that P (90 degrees) decreased gradually when the temperature increased at heating within the range of 0-32 degrees. A model of the prove movement in the lipid matrix is described. This model considers the rotation around the axis perpendicular to the plane of the perylene molecule only. Comparison of the results of model calculations and the experimental data allows to estimate the value of energy of viscosity activation. It proved to be 20-25 kcal/mol. Possible causes of such a high value of the kinetic barrier are discussed.

Animals

[Intensity and anisotropy decays measurement of perylene in pigeon erythrocyte membrane. Comparison with an isotropic viscous medium (author's transl)].

Using synchrotron radiation as the excitation light, we studied the fluorescence parameters of perylene incubated with pigeon erythrocyte membranes and with an isotropic viscous medium, the Primol 342 oil. From 4 to 37 degrees C, we observed a single lifetime of 4.5 ns in the oil and two with the membrane (tau 1 = 1-1.4 ns and tau 2 = 5.4-6.1 ns). The dependence upon temperature of the rotation correlation time of perylene (theta) in the oil was characteristic of an isotropic medium, whereas the limiting value of anitropy (r infinity) was zero. With the membrane, r infinity decreased from 0.14 to 0.06 and theta from 2.9 to 0.5 ns, indicating a greater amplitude and frequency of molecular motions. The addition of chlorpromazine, indomethacine, tetracaine, n-octylamine, octanol or octanoic acid to the membrane decreased the tau 1 and tau 2 values. This would stem from the disorganization of the membrane induced by the drugs.

Animals

Antitumor agents. 134. New shiraiachrome-A- and calphostin-C-related perylene derivatives as cytotoxic and antiviral agents and inhibitors of protein kinase C.

Shiraiachrome-A and -B have been isolated from the mycelium of the Chinese bamboo fungus Shiraia bambusicola as the cytotoxic principles. A series of new perylene derivatives (7-27) related to Shiraiachrome-A and -B as well as Calphostin-C have been synthesized and evaluated for their cytotoxicity, antiviral activity, and inhibitory activity against protein kinase C. The results indicated that 11 and 12 are potent cytotoxic agents against HCT-8, RPMI-7951, and TE-671 solid tumor cells, whereas 24 and 26 demonstrated strong antiviral activity against HSV-1 and HSV-2. Compound 10 is an inhibitor of protein kinase C.

Animals

Short-term bioassays of nitro derivatives of benzo[a]pyrene and perylene.

Several nitroarenes derived from benzo[a]pyrene and perylene and the parent hydrocarbons have been assayed for mutagenicity in the Salmonella microsome test and for affinity for the 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-receptor protein in rat liver cytosol. 1- and 3-nitrobenzo[a]pyrene are mutagenic in the absence of S9 and have a response pattern in several Salmonella strains resembling that shown by 1-nitropyrene. 6-Nitrobenzo[a]pyrene, 3-nitroperylene as well as the parent unsubstituted hydrocarbons require S9 for activation. The 3,6- and 3,7-dinitroperylenes and a mixture of 3,9-/3,10-dinitroperylene are all mutagenic in the absence of S9. The response pattern of 3,9-/3,10-dinitroperylene resembles that shown by 1,6- and 1,8-dinitropyrenes. The nitro derivatives which are active in the absence of S9 are all inactivated by the addition of an incomplete S9 lacking NADP but activity is regained in the presence of the complete S9 for 1-and 3-nitrobenzo[a]pyrene and 3,6-dinitroperylene, showing that these compounds are also activated by S9 enzymes. Benzo[a]pyrene, 1- and 3-nitrobenzo[a]pyrene, 3-nitroperylene and the mixture of 3,9-/3,10-dinitroperylene have a high affinity for the TCDD-receptor protein whereas the affinity is low or below the detection level for the other compounds. These results are in good agreement with known structural requirements for receptor binding.

Animals

A charge-transfer complex of benzene with a highly twisted perylene derivative.

2C6H6.C26H6Cl8N2O4, benzene-1,2,5,6,7,8-11,12-octachloro-N,N'-dimethylperylene-3 ,4:9,10-bis- (dicarboximide) (Cl8DMP) (2/1), Mr = 850.20, orthorhombic, Pna2(1), a = 23.076 (2), b = 7.2492 (6), c = 20.277 (2) A, V = 3392.0 (8) A3, Z = 4, Dm = 1.69 (1), Dx = 1.665 g cm-3, mu (Mo K alpha, lambda = 0.71073 A) = 7.1 cm-1, F(000) = 1712, T = 297 (1) K, RF = 0.061 for 2134 observed reflections. The structure contains alternating benzene and Cl8DMP molecules stacked along b to form a 2:1 donor-acceptor complex. The Cl8DMP molecule is highly twisted as a result of short intramolecular bay Cl...Cl contacts [3.109 (3), 3.136 (3) A]. The central ring of the perylene fragment is substantially distorted from planarity; internal torsion angles range from 16 (1) to 32 (1) degrees.

Benz(a)Anthracenes

Effect of CoQ homologues on the fluidity of phospholipid bilayers a studied by fluorescence polarization of perylene.

The effect of Coenzyme Q analogues on the fluidity of egg lecithin bilayers was studied by fluorescence polarization of perylene. The parameter was clearly affected by the side-chain length of the quinones, by their concentration, and by their redox state. With increasing concentration, short-chain quinones decreased the bilayer fluidity, and did so to an even greater extent in their reduced state. On the contrary, long-chain analogues fluidized the bilayer, the effect being independent of their redox state. Such observations might explain the lower efficiency of short-chain quinones, as compared to the long-chain analogues, in restoring, in vitro, the respiratory activity of CoQ2-depleted mitochondria.

Benz(a)Anthracenes

Effect of anesthetics on membrane fluidity tested by two different techniques: EPR spin labels and polarization of perylene fluorescence.

We have investigated the effect of n-butanol on the spectroscopic properties of two types of probes, that are usually employed to detect membrane fluidity, in mitochondrial phospholipid vesicles and mitochondrial membranes. Although both a spin label (16-doxylstearate) and the fluorescent probe perylene detect a higher immobilization of the membrane in comparison with phospholipid vesicles, the effect of butanol in the case of the membrane is strikingly different with the two techniques employed, showing increased fluidity in the case of the spin label and decreased fluidity with the fluorescent probe.

Anesthetics

Effect of some lipophilic substances on fluorescence polarization of perylene in lipid vesicles and mitochondrial membranes.

Short-chain ubiquinones were observed to increase the fluorescence polarization associated with perylene, indicating a decrease in the fluidity of the mitochondrial membrane. The results indicated that the perturbation induced by low homologs results indicated that the perturbation induced by low homologs of ubiquinone on the physical state of membrane lipids is quite different from that of other lipophilic substances which have been considered.

Animals

A specific decrease of the fluorescence depolarization of perylene in muscle membranes from mice with muscular dystrophy.

The microviscosity of erythrocyte membranes and muscle microsomes from age matched 6-week old control mice REJ 129 Dy/Dy, and mice with muscular dystrophy REJ 129 DY/DY has been estimated by measuring the fluorescence depolarization of perylene. There was no difference between the erythrocyte membranes. The muscle microsomes from dystrophic animals had about 20% lower values than the controls. The temperature dependence indicated that a transition occurs in both sets of muscle microsomes, but the transition temperature was lower in the dystrophic microsomes. Cholesterol, phospholipid and triglyceride analyses of the membranes showed no difference between the erythrocyte membranes. The largest difference in the muscle microsomes was a two-fold increase in cholesterol level found in the dystrophic microsomes. No simple correlation could be made between the lipid analysis and the microviscosity measurements. Since the change in microviscosity is found in membranes isolated from the tissue primarily affected by the dy gene, we suggest that the change in microviscosity may be important in the development of the disease.

Animals

High-pressure liquid chromatography of benzo(a) pyrene and benzo (ghi) perylene in oil-contaminated shellfish.

A high-pressure liquid chromatographic procedure is described for the determination of benzo(a) pyrene and benzo(ghi) perylene. These polynuclear aromatics are extracted with acetonitrile and partitioned into petroleum ether, the petroleum ether is removed, and the residue is saponified. The compounds are purified and isolated by passing the residue through a silica gel column and a high-pressure liquid chromatographic column, and detected by their ultraviolet absorption. Recoveries of standards through the procedure averaged 104%.

Benzopyrenes

Time-resolved fluorescence anisotropies of diphenylhexatriene and perylene in solvents and lipid bilayers obtained from multifrequency phase-modulation fluorometry.

Time-resolved decays of fluorescence anisotropy were obtained from frequency-domain measurements of the phase angle difference between the parallel and perpendicular components of the polarized emission and the ratio of the modulated amplitudes. These data were measured at modulation frequencies ranging from 1 to 200 MHz. To demonstrate the general applicability of this method, we describe the resolution of both simple and complex decays of anisotropy. In particular, we resolved single, double, and triple exponential decays of anisotropy and the hindered rotational motions of fluorophores within lipid bilayers. The ease and rapidity with which these results were obtained indicate that frequency-domain measurements are both practical and reliable for the determination of complex decays of anisotropy.

Benz(a)Anthracenes