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PubMed2000

Photochemical oxygen consumption sensitized by a porphyrin phosphorescent probe in two model systems.

Phosphorescence quenching of certain metalloporphyrins is used to measure tissue and microvascular pO(2). Oxygen quenching of metalloporphyrin triplet states creates singlet oxygen, which is highly reactive in biological systems, and these oxygen-consuming reactions are capable of perturbing tissue oxygenation. Kinetics of photochemical oxygen consumption were measured for a Pd-porphyrin in two model systems in vitro over a range of irradiances (1.34-134 mW cm(-2)). For a given irradiance, and, after correction for differing porphyrin concentrations, rates of oxygen consumption were similar when the Pd-porphyrin was bound to bovine serum albumin and when it was taken up by tumor cells in spheroids. At irradiances comparable to those used in imaging superficial anatomy, rates of oxygen consumption were sufficiently low (2.5 microM s(-1)) that tissue oxygenation would be reduced by a maximum of 6%. An irradiance of 20 mW cm(-2), however, initiated a rate of oxygen consumption capable of reducing tissue pO(2) by at least 20-40%. These measured rates of consumption impose limitations on the use of phosphorescence quenching in thick tissues. The irreversible photobleaching of the Pd-porphyrin was also measured indirectly. The bleaching branching ratio, 23 M(-1), is significantly lower than that of porphyrin photodynamic agents.

Animals↗
PubMed1995

Determination of the orientation distribution of adsorbed fluorophores using TIRF. II. Measurements on porphyrin and cytochrome c.

The theory for determination of the orientation of adsorbed fluorescent molecules using total internal reflection fluorescence, as explained in part I of this series, is illustrated by measurements on adsorbed tetramethylpyridinium porphyrin (H2TMPyP) and porphyrin cytochrome c molecules. The results are encouraging, although for porphyrin cytochrome c the scatter in the obtained order parameters is substantial. For H2TMPyP molecules adsorbed on glass the orientation distribution depends on the solution concentration. At low concentration, the H2TMPyP molecules are more or less randomly oriented, whereas at high concentrations a broad distribution around an angle of 46 degrees between the porphyrin plane and surface was found. For cytochrome c adsorbed on glass and indium tin oxide it was impossible to interpret the data in terms of orientation distributions because of the scatter in the results. The total fluorescence as a function of the polarization angle psi of the incident light beam corresponds to an average angle between the porphyrin group and the surface of 30 degrees-40 degrees. Despite the strong electric dipole moment of the protein, the orientation distribution seems to be independent on the (imposed) electrical potential of the interface.

Adsorption↗
PubMed1997

Lipid peroxidation induced by meso-tetrakis[3,4-bis(carboxymethyleneoxy)phenyl] porphyrin on photosensitization in hepatic and tumor microsomes.

The ability of a novel porphyrin, meso-tetrakis[3,4-bis(carboxymethyleneoxy)phenyl]porphyrin (T3,4-CPP), to induce photodamage in subcellular membranes, in the form of rat hepatic and tumor microsomes, was evaluated with a view to locating suitable porphyrin derivative for possible use in photodynamic therapy. This water-soluble porphyrin, on exposure to visible light, induced a significant extent of membrane lipid peroxidation as assessed by the formation of thiobarbituric acid reactive substances, lipid hydroperoxides and conjugated dienes. The peroxidation induced in hepatic microsomes is both time- and concentration-dependent. Using inhibitors of reactive oxygen species and comparing products of peroxidation, it is shown that the damage induced is mainly due to singlet oxygen and partly due to other species like free radicals. T3,4-CPP also caused the generation of singlet oxygen as a function of illumination time. Since membrane damage induced by a sensitizer on photoexcitation has been considered to be an important mechanism by which photodynamic cell killing of tumor occurs, the studies on this novel porphyrin indicate the possible potential of this compound in photodynamic therapy.

Animals↗
PubMed2000

Determination of porphyrin carbon isotopic composition using gas chromatography-isotope ratio monitoring mass spectrometry.

Carbon isotopic compositions of aetio I occurring in the form of free-base, nickel, demetallation, dihydroxysilicon(IV) and bis(tert.-butyldimethylsiloxy)silicon(IV) [(tBDMSO)2Si(IV)] have shown that it has experienced no obvious isotope fractionation during the synthesis of [(tBDMSO)2Si(IV)] porphyrin from aetio I. Here, aetio I porphyrin species such as free-base, nickel, demetallated and dihydroxysilicon were analyzed by the conventional method, namely it is combusted in sealed system, and followed by isotope ratio monitoring mass spectrometric analysis. [(tBDMSO)2Si(IV)] aetio I was assayed by gas chromatography-isotope ratio monitoring mass spectrometry (GC-IRMS). A porphyrin mixture of [(tBDMSO)2Si(IV)] aetio I and octaethylporphyrin was also prepared. Their carbon isotopic compositions measured by GC-IRMS indicate that no isotope exchange took place between the porphyrins during the synthesis of [(tBDMSO)2Si(IV)] porphyrins. This method is employed for delta13C determination of geoporphyrins from the Maoming and Jianghan oil shales.

Carbon Isotopes↗
PubMed1990

Capillary electrophoresis of urinary porphyrins with absorbance and fluorescence detection.

Urinary porphyrins are separated in a 72 cm x 50 microns I.D. fused-silica capillary by micellar electrokinetic capillary chromatography with 100 mM sodium dodecyl sulfate and 20 mM 3-(cyclohexylamino)-1-propanesulfonic acid at pH 11. Detection is accomplished by absorbance at 400 nm or fluorescence with excitation at 400 nm and emission at wavelengths above 550 nm. Substantial trace enrichment is found for porphyrins in urine samples or for porphyrin standards prepared without surfactant in the injection buffer. Limits of detection are in the 100 pmol/ml concentration range with an optimized fluorescence system. The method is shown suitable for the determination of porphyrins in clinical urine specimens. Comparisons are made between electrophoretic and chromatographic methods for the separation and detection of urinary porphyrins.

Chromatography, Liquid↗
PubMed1999

Shape-selective separation of polycyclic aromatic hydrocarbons on protoporphyrin-silica phases. Effect of surface porphyrin distribution on column efficiency.

The chromatographic performance of various metalloprotoporphyrin-silica (MProP-silica) packing materials prepared using different porphyrin immobilization schemes is examined. Column efficiency and solute resolution for the shape-selective separation of polycyclic aromatic hydrocarbons (PAHs) can be improved significantly by preparing phases with lower porphyrin coverages and with a more homogeneous distribution of the porphyrin species on the surface. The latter is accomplished by spreading/diluting the number of aminopropyl reactive sites on the silica surface via mixing an inert methyltrimethoxysilane with 3-aminopropyltriethoxysilane during this preliminary reaction step. Subsequent covalent attachment of the ProP via amide bonds to the pendant amine sites results in a more even distribution of the porphyrins on the surface. Band shapes and retention times as a function of injected solute concentration as well as HPLC separation of various test mixtures of PAHs (including standard reference material SRM 869) are used to confirm the enhanced performance of these so-called "spread" phases. Changes in the nature of the immobilized porphyrin distribution on the silica surface are further probed by a coupled redox/UV-Vis absorbance method, and results suggest a decrease in the number of ProP species immobilized as aggregates on the surface.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

The use of porphyrins as a non-destructive biomarker of exposure to contaminants in two sea lion populations.

This study was carried out in two populations of Otariaflavescens, living in a polluted and in a reference site, in order to validate the use of porphyrins as a non-destructive biomarker of exposure to environmental contaminants. Analysis of porphyrins was carried out in the feces, blood and fur of free ranging sea lions and in the liver and kidney of stranded specimens. The results show that: (a) all biological materials used were useful for porphyrin determinations; (b) no clear seasonal variations in porphyrin accumulation and excretion were found; (c) differences in fecal porphyrin levels existed between the two colonies.

Animals↗
PubMed2000

A new thioether-ligated iron porphyrin as a model of a protonated form of P450 active site.

Thioether-ligated iron porphyrin (complex 1) was synthesized as a model of the protonated form of P450 to explore the possible involvement of the protonated form in the catalytic cycle, and ether-ligated iron porphyrin (complex 2) was also synthesized for comparison. The thioether and ether ligands enhanced heterolytic O-O bond cleavage of peroxy acid-iron porphyrin complex even in highly hydrophobic media without the assistance of acid or base, using mCPPAA as an oxidant. Competitive oxidation of cyclooctane/cyclooctene catalyzed by iron porphyrins showed that complexes 1 and 2 are less effective than heme thiolate (P450 and a synthetic heme thiolate (SR complex)) in oxidizing alkane. The possibility that thiol-ligated heme, which is a protonated form of heme thiolate, is not involved in the active intermediate structure of P450 is indicated by this result. This is the first report concerning the oxidizing ability of a thioether-ligated iron porphyrin.

Binding Sites↗
PubMed2002

Synthesis and selective tumor targeting properties of water soluble porphyrin-Pt(II) conjugates.

We have designed and synthesized a series of novel water soluble porphyrins and their platinum(II) conjugates, cis-[(Por)Pt(dmso)X], where Por=5-(4-pyridyl)-10,15,20-tris(4-sulfonatophenyl)porphyrin) (PyTPPS) or 5-[4-(3-aminopropyl)pyridiniumyl]-10,15,20-tris(4-sulphonatophenyl)porphyrin (PyTPPS-NPn), X=2Cl, 1,1-cyclobutanedicarboxylic acid, oxalate, or malonate. Their biodistribution in tumor bearing mouse was examined along with their antitumor activity against murine leukemia L1210 cell line. The representative complex 1 exhibited a significant accumulation in tumor tissue with a tumor/muscle ratio of 7 after 24 h post injection. The antitumor activity of the title compounds was marginal (T/C: 95-117%), but it was found that platinum(II) coordination to the porphyrin periphery did not affect the tumor accumulating properties of the porphyrin permitting further derivatization for efficient delivery of the Pt(II) antitumor agent.

Animals↗
PubMed1998

Early-stage HIV infection and hepatitis C virus infection are associated with elevated serum porphyrin levels.

BACKGROUND: Porphyria cutanea tarda is known to be associated with HIV infection and hepatitis C virus (HCV). OBJECTIVE: Our purpose was to evaluate whether early infection with HIV, with or without HCV infection, is associated with elevated serum porphyrin levels. METHODS: Serum porphyrin levels were measured in samples obtained from 103 patients with early HIV infection. The results were compared with those of 89 late-stage HIV-positive patients and 78 HIV-negative patients. RESULTS: The highest median porphyrin level was in early-stage HIV-positive/HCV-positive samples, followed in decreasing order by those in early-stage HIV-positive/HCV-negative, late-stage HIV-positive/HCV-positive, late-stage HIV-positive/HCV-negative, HIV-negative/HCV-positive, and HIV-negative/HCV-negative groups. Elevated porphyrin levels were independently associated with early-stage HIV infection (P < .0001) and HCV infection (P = .03). CONCLUSION: This finding suggests abnormal porphyrin metabolism is most noticeable in early-stage HIV infection; it becomes less severe with the progression of HIV disease.

Adult↗
PubMed2005

[Porphyrins in renal calculi (review)].

We performed a review of the porphyrines content in a type of black, charcoal-like, renal calculi exhibiting infrared spectra (IRS) similar to those characteristic of "organic material" which has not yet been fully elucidate. Several other types of renal calculi, mainly those of small size, spontaneous passage renal stone, may also have diffuse or isolated dark charcoal components showing "organic material" IRS. After observing that haemoglobin has an "organic material" IRS, we studied, by a sensitive thin layer chromatography method, the presence of porphyrines in several types of dark or charcoal renal stones, since porphyrines are the physiological precursors of haemo group biosynthesis. We found two types of porphyrine content: coproporphyrin, in patients suffering from hepatopathy, and uroporphyrin and heptacarboxil-porphyrin in patients with some types of porphyria or with chronic renal failure.

Humans↗
PubMed1999

Cationic porphyrins bearing diazolium rings: synthesis and their interaction with calf thymus DNA.

Two novel cationic porphyrins bearing five-membered rings at the meso-positions, meso-tetrakis(1,3-dimethylimidazolium-2-yl)porphyrin (H2TDMImP) and meso-tetrakis(1,2-dimethylpyrazolium-4-yl)porphyrin (H2TDMPzP), have been synthesized. These two compounds interact with calf thymus DNA (CTDNA) in different binding modes from that of mesotetrakis(N-methylpyridinium-4-yl)porphyrin (H2TMPyP). H2TDMImP outside binds to the minor groove of CTDNA while H2TDMPzP intercalates into CTDNA. These two novel cationic porphyrins strongly bind to CTDNA even at high ionic strength and the binding constant of H2TDMPzP to CTDNA is comparable to that of H2TMPyP. The binding of H2TDMImP to CTDNA is enthalpically driven. The favorable free energy changes in binding of H2TDMPzP to CTDNA come from the large negative enthalpy changes accompanied by small positive entropy changes.

Animals↗
PubMed1999

Effects of hexachlorobenzene on phospholipid and porphyrin metabolism in Harderian glands: a time-course study in two strains of rats.

Hexachlorobenzene, one of the most persistent environmental pollutants, induces uroporphyria and phospholipid alterations in rat liver. Harderian glands produce a secretion that is rich in lipids and accumulate large amounts of protoporphyrin. The aim of the present study was to determine if hexachlorobenzene administration to rats affects phospholipid and porphyrin metabolisms in Harderian glands and if these effects are strain dependent. For this purpose, a time-course study (2, 3 and 4 weeks of hexachlorobenzene treatment) of phospholipid pattern and porphyrin content was performed comparatively in two strains of rats (Wistar and Chbb THOM) which differ in their susceptibility to develop HCB-induced porphyria. Hexachlorobenzene produced decreases in several phospholipid contents, but no changes in phosphatidylcholine levels. While the sphingomyelin/phosphatidylcholine molar ratio remained essentially constant until the third week in Chbb THOM rats, it showed a constant drop in Wistar rats, suggesting a more pronounced alteration of membrane fluidity in the later strain. In regard to porphyrin metabolism, Wistar rats showed an increase in the porphyrin content of the gland, while Chbb THOM animals showed a decrease. The study revealed that not only are the normal parameters of phospholipid and porphyrin metabolism in rat Harderian glands strain dependent, but the response to hexachlorobenzene is also.

Animals↗
PubMed2002

Potent DNA photocleavage by zinc(II) complexes of cationic bis-porphyrins linked with aliphatic diamine.

We have prepared zinc(II) complexes of cationic bis-porphyrins, as one of the attempts to improve less DNA photocleavage activities of the metal-free bis-porphyrins composed of two H(2)TMPyP-like chromophores, linked with a series of aliphatic diamines. The less activities seemed to be derived from their intermolecular self-aggregation properties in aqueous solution. The zinc(II) insertion into the metal-free cationic bis-porphyrins completely removed their self-aggregation properties, most probably due to steric hindrance between axial ligands of zinc(II) chromophores of the cationic bis-porphyrins. The DNA photocleavage activities of the zinc(II) complexes were fully enhanced, which were three times larger than that of the lead compound H(2)TMPyP. Quantitative analysis of singlet oxygen production by photosensitization of cationic bis-porphyrins was performed using 1,3-diphenylisobenzofuran, and the singlet oxygen productivities of them were found to be related to their solution properties. There is a good relationship between the activities and the productivities, which will provide insights into the further development of more effective DNA photocleavage agents.

Cations↗
PubMed2002

Kinetic study of delta-Ala induced porphyrins in mice using photoacoustic and fluorescence spectroscopies.

The production of delta-aminolevulinic acid (ALA)-induced porphyrins in mice skin and blood was studied by photoacoustic and fluorescence spectroscopies. Mice were intraperitoneally administered with 30 mg/kg of ALA. The abdominal skin was subsequently excised at specific times within an 8-h interval and its absorption spectrum obtained by photoacoustics. The highest porphyrins concentration in skin, determined from the optical absorption of the Soret band at 410 nm, was found to occur nearly 2 h after ALA administration, but a first peak was also observed at approximately 15 min. Our hypothesis that the first peak represents the porphyrins content in blood vessels within the skin, whereas the second peak corresponds to porphyrins production in skin tissue, was confirmed by analysing the evolution of protoporphyrin IX content in plasma extracted intracardiacally. By finally applying phase resolved photoacoustic spectroscopy, we were able to evaluate the mean depth at which porphyrins are generated.

Aminolevulinic Acid↗
PubMed1997

Phototoxicity of some novel porphyrin hybrids against the human leukemic cell line TF-1.

Photodynamic induced cytotoxicity by porphyrin-DNA cross linker/intercalator hybrid diads and triads has been studied on the human leukemic cell line TF-1. Cells were incubated for 1 to 4 h with these new photosensitizers and irradiated with white light. Cell survival was assessed by the propidium iodide staining, using flow cytometry analysis. A comparison of the dark and light cell survival factor values suggests that irradiation has a significant effect on the toxicity at low concentrations for the porphyrin-chlorambucil diad and to a lesser extent at high concentrations for the porphyrin-acridone diad, the porphyrin-acridine diad and the porphyrin-cholic acid-chlorambucil triad. While the intrinsic antileukemic (via DNA cross-linking) activity of the chlorambucil moiety and the structural details may be responsible for the photoenhancement of the toxicity, the presence of acridine or acridone which are avid intercalators of DNA, is responsible for a similar effect seen for diads.

Acridines↗
PubMedDate not supplied

Porphyrin-induced protein structural alterations of heme enzymes.

Some alterations in the protein structure of delta-aminolevulinic acid dehydratase (ALA-D) and porphobilinogen deaminase (PBG-D) induced by uroporphyrin (URO) and prototoporphyrin (PROTO) have been observed previously. To obtain further evidence of these phenomena, the absorption and fluorescence spectra of ALA-D and PBG-D and the total protein content of sulfhydryl and free amino groups were analyzed after exposure of the enzymes to URO I and PROTO IX, ALA-D and PBG-D were partially purified from bovine liver and exposed to URO I or PROTO IX, both in the dark and under UV light. All experiments were performed in the enzyme solutions after removing the porphyrins. Absorbance spectra changes in the region of 220-300 nm were registered, indicating the interaction of the porphyrins with the molecular structure of the enzymes. The main changes in the fluorescence spectra were observed in the spectral region of 555 nm, and only slight modifications in the spectral region of 340-360 nm; moreover, alterations were stronger upon UV irradiation and in the presence of URO I when compared with darkness and PROTO IX. Variations in total SH groups would suggest the formation of disulfur bridges induced by URO I and the rupture of some S-S groups induced by PROTO IX. The effect of porphyrins on free amino groups would reflect a combination of cross-linking and fragmentation of proteins. Structural changes were observed when the enzymes were exposed to the porphyrin both in the dark or under UV light; however, they were stronger in the latter condition. These results suggest that porphyrins per se could act directly on the protein structure and that this action would be enhanced upon UV irradiation.

Amino Acids↗
PubMed2000

Investigation of the SERS behaviour of porphyrins with different surface concentrations on electrochemically prepared Ag-surface.

Surface-enhanced Raman scattering (SERS) spectra, taken with 632.8 nm excitation are reported for the water-soluble tetrakis(3-N-methylpyridyl)porphyrin chloride (TMPyP(3)), tetrakis(4-N-methylpyridyl)porphyrin chloride (TMPyP(4)) and Sn(IV)tetrakis(4-N-methylpyridyl)porphyrin chloride (Sn(IV)TMPyP(4)) using an electrochemically prepared Ag surface with an area ca. 12.56 mm2. It was found that the spectra vary as increasing amounts of the compounds are placed on the surface, with surface concentrations in the approximate range 1000-5 pmol/12.56 mm2. We suggest that the reasons for the changes be that the reaction means between porphyrin molecules and Ag surface is different and the porphyrin macrocyclic molecules adopt different orientation as the surface concentrations decrease.

Electrochemistry↗