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PubMed1996

Chloro(2,3,7,8,12,13,17,18-octaethylporphinato)gallium(III).

The crystal structure of [Ga(C36H44N4)Cl].1.45CH2C(l)2 has been determined. Examination of the crystal established a two-molecule triclinic unit cell with space group P1. The asymmetric unit contains one porphyrin molecule and two solvate molecules, one as an approximate half molecule with required inversion symmetry. All measurements were made at 127(2) K. The average Ga-N distance is 2.035(4) A and the axial Ga-Cl distance 2.240(1) A. The displacement of the Ga atom from the N4 porphyrin plane is 0.40 A.

Crystallography, X-Ray↗
PubMed1998

Manganese water-soluble porphyrin senses DNA conformation.

We have determined the sites that are preferentially cleaved by Mn(T4MPyP) (where T4MPyP is the dianion of 5, 10, 15, 20, tetrakis (4-N-methylpyridine)porphyrin) on synthetic DNAs and on both intrinsically curved and average-shaped natural DNA sequences. On the basis of cleavage selectivity and of DNase I footprinting we show that the recognition specificity by this compound is based on steric properties: the preferred conformation is a DNA minor groove narrower than average and dimensionally defined. This conclusion is reached on the basis of: (i) the localization of the preferential cleavage sites at the 3' extremity of short A-tracts, known to undergo minor groove directional narrowing; (ii) the effects of temperature on cleavage specificity on curved sequences; (iii) the localization of cleavage sites in synthetic constructs whose crystal and solution structure was previously defined, and in programmed sequence variants thereoff; (iv) the effects of base substitutions on cleavage efficiency; (v) DNase I footprinting analysis. Several of these evidences argue against the possibility that Mn(T4MPyP)/DNA site selection occurs on the basis of electrostatic potential effects.Mn(T4MPyP) provides a tool for the analysis of DNA conformation whose selectivity is complementary to that of DNase I and hydroxyl radicals.

Animals↗
PubMed1989

Mechanism of iron potentiation of hepatic uroporphyria: studies in cultured chick embryo liver cells.

Effects of iron were studied in cultured chick embryo liver cells to help elucidate the effect of hepatic iron in the human disease porphyria cutanea tarda and in toxic porphyria caused by chemicals. These cultures have proven useful because (a) phenobarbital and phenobarbital-like drugs induce a common form(s) of cytochrome P-450 (P-450-phenobarbital) in these cultures; (b) 20-methylcholanthrene and certain other polycyclic hydrocarbons induce a different form(s) (P-450-methylchol-anthrene), and (c) uroporphyria can be produced rapidly by exposure to suitable chemicals. In these cultures, treatment with iron alone did not produce porphyrin accumulation, and treatment with iron + 5-aminolevulinate caused accumulation of protoporphyrin, as did treatment with 5-aminolevulinate alone. However, treatment with phenobarbital-like drugs and iron, the latter at a concentration as low as 0.2 microM, led to accumulation of uro- and heptacarboxylporphyrins. Potentiation of uroporphyrin accumulation by iron began before there was a detectable synergistic increase in activity of 5-aminolevulinate synthase, the rate-controlling enzyme of heme synthesis. In contrast, treatment of cultures with 20-methylcholanthrene, in the presence or absence of iron, did not result in uroporphyrin accumulation or an increase in the activity of 5-aminolevulinate synthase. Uroporphyrinogen decarboxylase activity was unchanged by drug and iron treatments. Inhibitors of P-450-phenobarbital, SKF525A and piperonyl butoxide, as well as cadmium and cycloheximide prevented the porphyrin accumulation produced by glutethimide + iron, even though, except with cycloheximide, these substances further increased 5-aminolevulinate synthase activity. In vitro, uroporphyrin was oxidized autocatalytically by iron. In intact hepatocytes, even low concentrations of iron (0.2 to 20 microM), in the presence of a form of cytochrome P-450 induced by phenobarbital-like chemicals, produces uroporphyria primarily by enhancing uroporphyrinogen oxidation, not by inhibition of the decarboxylase. Induction of 5-aminolevulinate synthase amplifies the porphyrin overproduction.

5-Aminolevulinate Synthetase↗
PubMed1977

A fluorescence detector for high-pressure liquid chromatography.

We describe a fluorescence spectrophotometer adapted with a micro quartz flow cell to record the output of modern liquid chromatographs. The optical system is double beam in that the light source variations are cancelled out by a second photomultiplier, thus enhancing the sensitivity of the technique. The emission spectra may be scanned by stopping the flow in the chromatographic column and scanning the fluorescence detector. Many specific applications have been studied: polycyclic aromatic hydrocarbons, several vitamins, porphyrins, methyl anthranilate, etc. These are studied in natural samples and it is shown that the specificity of the fluorescence detector frequently obviates the need for sample preparation. The sensivitity available with the fluorescence detector for fluorescing compounds is often much greater than is available with variable-wavelength ultraviolet spectrophotometers. We report picogram-level detectability in real samples for many of the compounds that we have studied.

Animals↗
PubMed2006

Characterization of various analytes using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and 2-[(2E)-3-(4-tert-butylphenyl)-2-methylprop-2-enylidene]malononitrile matrix.

2-[(2E)-3-(4-tert-Butylphenyl)-2-methylprop-2-enylidene]malononitrile (DCTB) is a nonpolar, aprotic matrix and was used in the analysis of a variety of compounds by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOFMS). The classes of compounds include coordination compounds, organometallics, conjugated organic compounds (including porphyrins and phthalocyanines), carbohydrates, calixarenes, and macrocycles. For some samples, comparisons are made with spectra acquired with the use of 1,8,9-trihydroxyanthracene (dithranol), 2,5-dihydroxybenzoic acid, and 2,4,6-trihydroxyacetophenone matrixes. Traditionally, the majority of these compounds would have been analyzed by fast-atom bombardment (FAB), liquid secondary ion mass spectrometry (LSIMS), or electrospray techniques, but this work shows that MALDI-TOFMS using DCTB has advantages over these techniques, particularly FAB and LSIMS. Certain limitations of DCTB are noted, for example, in the analysis of water-soluble compounds such as peptides, proteins, and oligonucleotides, and good working practices for the use of the matrix are also outlined.

Journal Article↗
PubMed1998

Photodynamic tumor therapy: mitochondrial benzodiazepine receptors as a therapeutic target.

BACKGROUND: Photodynamic therapy employs photosensitive agents such as porphyrins to treat a variety of tumors accessible to light-emitting probes. This approach capitalizes on the selective retention of porphyrins by cancer cells. Cancer cells also have elevated levels of mitochondrial benzodiazepine receptors which bind porphyrins with high affinity. METHODS: Cultured cancer cell lines were exposed to porphyrin and porphyrin-like compounds and then irradiated with light. Cytotoxicity of this treatment was measured via clonogenic assays. Mitochondrial benzodiazepine receptor pharmacology was studied using [3H] PK11195 binding to cancer cell homogenates and isolated kidney mitochondrial membranes. RESULTS: We show that therapeutic potencies of porphyrins correlate closely with affinities for mitochondrial benzodiazepine receptors. Sensitivities of tumor cell lines to photodynamic therapy parallel their densities of these receptors. CONCLUSION: We propose that porphyrin photodynamic therapy is mediated by mitochondrial benzodiazepine receptors.

Mitochondria↗
PubMed2002

Switchable electronic coupling in model oligoporphyrin molecular wires examined through the measurement and assignment of electronic absorption spectra.

The use of a quinone functionality in the linkage unit of laterally bridged oligoporphyrins as a switch for controlling electronic coupling between the termini is examined. The quinone-bridged bisporphyrin P(2)TA-O(2) was synthesized by condensation of 2 equiv of the dione 2,3-dioxo-5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)chlorin with 2,3,5,6-tetraamino-1,4-benzoquinone. The electronic absorption spectra of P(2)TA-O(2) and its conjugated benzenoid analogue P(2)TA are measured and assigned, in conjunction with the spectra of the fragment monomers and porphyrin-bridge compounds. Band homologies and CASPT2 calculations are used to make the assignments. Chemically, the dimer in one case is bridged by a through-conjugated, pi-delocalized 1,4,5,8-tetraazaanthracene molecule. This is shown to display significant inter-porphyrin coupling, with an observed difference in the exciton couplings of the B(x) and B(y) bands being ca. 0.18 eV. However, the other dimer is bridged using a derivative in which the central ring is converted to a cross-conjugated, pi-localized quinonoid form; this molecule displays no observable inter-porphyrin coupling. This scenario provides a paradigm for the use of molecular electronic devices in sensing, control, and high-capacity relatively low-speed data storage applications.

Journal Article↗
PubMed2005

5'-Porphyrin-oligonucleotide conjugates: neutral porphyrin-DNA interactions.

[chemical reaction: see text]. Incorporation of hydrophilic tetraarylporphyrin phosphoramidites into the 5'-termimus of the DNA as well as noncharged porphyrin-DNA interactions have been studied. Porphyrin-modified oligonucleotides show lower melting temperatures than their unmodified analogues. Single-stranded DNA interacts more strongly with porphyrin and causes more intense chiral disturbance in the porphyrin environment than the corresponding double strand.

Base Composition↗
PubMed2003

Synthesis, characterization and molecular structures of six-coordinate manganese nitrosyl porphyrins.

Manganese(II) porphyrins are isoelectronic with iron(III) porphyrins, and previously reported work suggests that manganese nitrosyl porphyrins are good structural models for their kinetically unstable and biologically relevant ferric-NO analogues. We have prepared a new set of six-coordinate manganese nitrosyl porphyrins of the general form (por)Mn(NO)(L)(por = TTP, T(p-OCH3)PP; L = piperidine, methanol, 1-methylimidazole) in moderate to high yields. The (por)Mn(NO)(pip) complexes were prepared from the reductive nitrosylation of the (por)MnCl compounds with NO in the presence of piperidine. The IR spectra of the (por)Mn(NO)(pip) compounds as KBr pellets show new strong bands at 1746 cm(-1)(for TTP) and 1748 cm(-1)(for (T(p-OCH3)PP) due to the NO ligands. Attempted crystallization of one of these compounds (por = TTP) from dichloromethane-methanol resulted in the generation of the methanol complex (TTP)Mn(NO)(CH3OH). Reaction of the (por)Mn(NO)(pip) compounds with excess 1-methylimidazole gave the (por)Mn(NO)(1-MeIm) derivatives in good yields. The IR spectra of these compounds show nu(NO) bands that are approximately 12 cm(-1) lower than those of the (por)Mn(NO)(pip) precursors, indicative of greater Mn-->NO pi-backdonation in the 1-MeIm derivatives. X-Ray crystal structures of three of these compounds, namely (TTP)Mn(NO)(CH3OH), (TTP)Mn(NO)(1-MeIm) and (T(p-OCH3)PP)Mn(NO)(1-MeIm) were obtained, and reveal that the NO ligands in these complexes are linear.

Manganese↗
PubMed2005

Photodynamic inactivation of Escherichia coli by novel meso-substituted porphyrins by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl and 4-(trifluoromethyl)phenyl groups.

The photodynamic effect of novel cationic porphyrins, with different pattern of meso-substitution by 4-(3-N,N,N-trimethylammoniumpropoxy)phenyl (A) and 4-(trifluoromethyl)phenyl (B) groups, have been studied in both solution bearing photooxidizable substrates and in vitro on a typical Gram-negative bacterium Escherichia coli. In these sensitizers, the cationic groups are separated from the macrocycle ring by a propoxy spacer. Thus, the charges have a high mobility and a minimal influence on photophysical properties of the porphyrin. These compounds produce singlet molecular oxygen, O2(1Delta(g)), with quantum yields of approximately 0.41-0.53 in N,N-dimethylformamide. In methanol, the l-tryptophan photodecomposition increases with the number of cationic charges in the sensitizer. In vitro investigations show that cationic porphyrins are rapidly bound to E. coli cells in approximately 5 min. A higher binding was found for A3B3+ porphyrin, which is tightly bound to cells still after three washing steps. Photosensitized inactivation of E. coli cellular suspensions follows the order: A3B3+ > A44+>> ABAB2+ > AB3+. Under these conditions, a negligible effect was found for 5,10,15,20-tetra(4-sulfonatophenyl)porphyrin (TPPS4(4-)) that characterizes an anionic sensitizer. Also, the results obtained for these new cationic porphyrins were compared with those of 5,10,15,20-tetra(4-N,N,N-trimethylammonium phenyl)porphyrin (TTAP4+), which is a standard active sensitizer established to eradicate E. coli. The photodynamic activity of TTAP4+ is quite similar to that produced by A4(4+). Studies in an anoxic condition indicate that oxygen is necessary for the mechanism of action of photodynamic inactivation of bacteria. The higher photodynamic activity of A3B3+ was confirmed by growth delay experiments. Photodynamic inactivation capacities of these sensitizers were also evaluated in E. coli cells immobilized on agar surfaces. Under these conditions, A3B3+ porphyrin retains a high activity to inactivate localized bacterial cells. Therefore, tricationic porphyrin A3B3+ is an interesting sensitizer with potential applications in photodynamic inactivation of bacteria in liquid suspensions or on surfaces.

Benzene Derivatives↗