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PubMed1964

RESISTANCE AND CROSS-RESISTANCE OF ESCHERICHIA COLI S MUTANTS TO THE RADIOMIMETIC AGENT PROFLAVINE.

Woody-Karrer, Pearl (Palo Alto Medical Research Foundation, Palo Alto, Calif.), and Joseph Greenberg. Resistance and cross-resistance of Escherichia coli S mutants to the radiomimetic agent proflavine. J. Bacteriol. 87:536-542. 1964.-All 50 of the first-step mutants of Escherichia coli S selected for resistance to proflavine were resistant to ultraviolet light and each of five different radiomimetic chemicals. The mutants were classified into eight types on the basis of their relative resistance to six different radiomimetic drugs and on the basis of the shape of their ultraviolet survival curves. Three of these types are identical to types previously isolated with other radiomimetic drugs; five of the types are new. A high proportion of the clones surviving proflavine treatment were phenotypically but not genetically resistant, and no strains were isolated which were resistant to proflavine but were not resistant to radiation.

Acridines↗
PubMed2001

Proflavine-mediated inactivation of Salmonella dublin exposed to visible sunlight in natural fresh water.

The survival of Salmonella dublin exposed to visible sunlight, and heterotrophic bacteria in freshwater microcosms in the presence and absence of the photosensitizer proflavine, was studied. Enumeration of S. dublin and the heterotrophic bacteria showed that in both illuminated and nonilluminated systems (without proflavine) the bacteria remained viable and culturable for at least 6 days. The optimal proflavine concentration (no effect in the dark and a maximal photoinactivation of salmonellae after irradiation) was 2 mg l(-1). In contrast to S. dublin, the heterotrophic bacteria overcame the initial inhibitory effect of proflavine. The possible use of photosterilization against contamination with pathogenic bacteria in water model ecosystems, is discussed.

Bulgaria↗
PubMed1966

The effect of proflavine on HeLa cells.

1. The effect of proflavine on the metabolism of RNA, DNA and protein of HeLa cells was studied. 2. The synthesis of RNA, DNA and protein was progressively inhibited by concentrations of proflavine up to 43mum. 3. There was no simple relationship between the degrees of inhibition of synthesis of RNA, DNA and protein by increasing concentrations of proflavine: the synthesis of RNA was most readily inhibited, and the synthesis of protein was relatively insensitive. 4. A concentration of 22mum-proflavine inhibited synthesis of RNA and DNA and caused a progressive loss of RNA from both nucleus and cytoplasm without any accompanying loss of DNA or dry weight from the cells. 5. The rapidly labelled RNA in the nucleus was preferentially degraded and was not transferred in a stable form to the cytoplasm.

Acridines↗
PubMed1969

Stimulation of incorporation of nucleic acid precursors into HeLa cells caused by proflavine.

1. The effect of proflavine and other acridines on the incorporation of precursors into the nucleic acids of HeLa cells was examined. 2. Relatively low concentrations (50mum) of proflavine completely inhibited incorporation of precursors into DNA, but allowed a small extent of incorporation into RNA. 3. Acridine-resistant incorporation into RNA was unaffected by actinomycin D at 2mug./ml. and persisted even at high concentrations (500mum) of many acridines. 4. A few combinations of acridine and precursor, notably 250mum-proflavine and [(14)C]adenine, caused a stimulation of incorporation. 5. The proflavine-stimulated incorporation was into alkali-stable di- and tri-nucleotides. 6. It was concluded that the effect was due to the preferential inhibition of degradation of a fraction of RNA that normally turned over, thus allowing small radioactive oligonucleotides to accumulate in the cells.

Acridines↗
PubMed1990

Proflavin and microwave radiation: absence of a mutagenic interaction.

The potential ability of radiofrequency electromagnetic radiation (RFR) in the microwave range to induce mutagenesis, chromosomal aberrations, and sister chromatid exchanges in mammalian cells is being explored in our laboratories. In addition, we have also been examining the ability of simultaneous exposure to RFR and chemical mutagens to alter the genotoxic damage induced by chemical mutagens acting alone. We have performed experiments to determine whether there is an interaction between 2.45-GHz, pulsed-wave, RFR and proflavin, a DNA-intercalating drug. The endpoint studied was forward mutation at the thymidine kinase locus in L5178Y mouse leukemic cells. Any effect on the size distribution of the resulting colonies of mutated cells was also examined. The exposures were performed at net forward powers of 500 or 600 W, resulting in a specific absorption rate (SAR) of approximately 40 W/kg. The culture-medium temperature reached a 3 degrees C maximal increase during the 4-h exposure; appropriate 37 degrees C and convection-heating temperature controls (TC) were performed. In no case was there any indication of a statistically significant increase in the induced mutant frequency due to the simultaneous exposure to RFR and proflavin, as compared with the proflavin exposures alone. There was also no indication of any change in the colony-size distribution of the resulting mutant colonies, neither, and there was no evidence in these experiments of any mutagenic action by the RFR exposure alone.

Animals↗
PubMed1984

Proflavin binding within the fibrinopeptide groove adjacent to the catalytic site of human alpha-thrombin.

Human alpha-thrombin with high fibrinogen-clotting activity binds proflavin at a single specific site (n = 0.996 site/alpha-thrombin, Kd = 22.0 microM) with the same affinity as the bovine enzyme (Kd = 22 +/- 3 vs. 24 +/- 3 microM, respectively, at pH 7.4, approximately 23 degrees C). This human enzyme form further displayed no significant difference in its ability to bind the dye over a broad NaCl concentration range (0.15-3 microM), and its hydrolysis of Bz-Arg-OEt was inhibited by the dye in a simple competitive manner (Ki = 30 +/- 3 microM). Conversion of the human alpha- to gamma-thrombin by controlled tryptic digestion essentially destroyed clotting activity without appreciably altering synthetic substrate activities and caused only approximately 2-fold reduction in proflavin binding. Chemical modification of approximately four tryptophans or approximately four tyrosines per enzyme also caused analogous differential losses of clotting vs. synthetic substrate activities and reduced proflavin binding approximately 5- and approximately 10-fold, respectively. Inactivation of the enzyme by conjugation at the catalytic serine (Ser-195, chymotrypsin numbering) with MeSO2 -F, PhMeSO2 -F, or i- Pr2P -F decreased binding approximately 4-, 26-, and 55-fold, respectively, following the increasing size and steric hindrance properties of the conjugated group. Conjugation of the catalytic histidine (His-57) with Tos-Lys-CH2-Cl decreased binding only approximately 10-fold, suggesting partial displacement by the dye. Such partial displacement appeared to occur to a slightly greater extent with the conjugate of a large exo site affinity-labeling reagent, which covalently attaches to the enzyme within the fibrino-peptide groove distal to the catalytic site.(ABSTRACT TRUNCATED AT 250 WORDS)

Acridines↗
PubMed1980

X-ray-structure of a cytidylyl-3',5'-adenosine-proflavine complex: a self-paired parallel-chain double helical dimer with an intercalated acridine dye.

The non-self-complementary dinucleoside monophosphate cytidylyl-3',5'-adenosine (CpA) forms a base-paired parallel-chain dimer with an intercalated proflavine. The dimer complex possesses a right-handed helical twist. The dimer helix has an irregular girth with a neutral adenine-adenine (A-A) pair, hydrogen-bonded through the N6 and N7 sites (C1'...C1' separation of 10.97 A), and a triply hydrogen-bonded protonated cytosine-cytosine (C-C) pair with a proton shared between the base N3 sites (Cl'...Cl' separation of 9.59 A). The torsion angles of the sugar-phosphate backbone are within their most preferred ranges and the sugar puckering sequence (5' leads to 3') is C3'-endo, C2'-endo. There is also a second proflavine molecule sandwiched between CpA dimers on the 21-axis. Both proflavines are necessarily disordered, being on dyad axis, and this suggests possible insights into the dynamics of intercalation of planar drugs. This structure shows that intercalation of planar drugs in nucleic acids may not be restricted to antiparallel complementary Watson-Crick pairing regions and provides additional mechanisms for acridine mutagenesis.

Acridines↗
PubMed1983

Networks of water molecules in a proflavine deoxydinucleoside phosphate complex.

Using previously reported ab-initio atom-atom potentials for the interactions of a water molecule with phosphates, sugars and bases and newly computed ab-initio atom-atom potentials for the interaction between a proflavine ion and water, we have analyzed with the Monte-Carlo Metropolis method networks of water molecules hydrating a 2:2 complex of proflavine and deoxycytidylyl-3',5'-guanosine, recently studied with X-ray crystallography. From our simulations we have i) verified the quality of our atom-atom potentials by obtaining patterns of oxygen atoms in very good agreement with the X-ray patterns for the minor groove and in reasonable agreement in the major groove, ii) predicted the water's hydrogen atoms positions and iii) preliminarily predicted the number of water molecules not reported in the X-ray study but present in the major groove. The above data, even if preliminary, and the analyses on the energetics of the water-water, water-proflavine and water-dCpG interactions indicate that very detailed accounts on the water filaments in the above crystal can be obtained optimally by merging computer and X-ray experiments.

Acridines↗
PubMed1982

Visible-light-induced OH radicals in DNA-proflavine complexes: an e.p.r. and spin trapping study.

Using the spin-trapping technique, irradiation with visible light of complexes between DNA and proflavine was shown to generate OH radicals. The characteristic spectra were not obtained when proflavine or DNA were irradiated alone, nor when oxygen was absent. Using DMPO as a spin trap we found that the intensity of the DMPO-OH e.p.r. signal was enhanced when the molar ratio between bound proflavine and the DNA phosphorus increased up to a value of 0.15 demonstrating the efficiency of the intercalated dye molecules. A strong decrease of the e.p.r. signal was observed in the presence of various OH. scavengers like t-butanol, isopropanol or sodium benzoate. The OH. production was also decreased when the irradiation was made in the presence of SOD, ceruloplasmin or catalase and after addition of Chelex 100 resin.

Acridines↗
PubMed1981

Quantum chemical calculations on the two-step mechanism of proflavin binding to DNA.

Quantum chemical calculations on the binding of proflavin to DNA lead to a model in which the outside binding to a phosphate group leads to an induced fit in the intercalation receptor site. The calculations suggest hydrogen bonding of the amine groups of the outside bound proflavin to the anionic oxygen of the backbone phosphate. The resulting partial neutralization facilitates the conformational transitions required for intercalation. The results are consistent with the observed preference of proflavin for dCpdG over dGpdC sequences and with the observed kinetics of the binding reaction.

Acridines↗
PubMed1975

Comparison of the treatment of herpes genitalis in men with proflavine photoinactivation, idoxuridine ointment, and normal saline.

36 male patients with genital infection by HSV confirmed by culture were each allocated to one of three treatment groups: (1) Proflavine photoinactivation, (2) 0.5 per cent. idoxuridine ointment (IDU), (3) Normal saline. They were assessed objectively at each attendance by measurement of the lesions with an operating microscope fitted with a measuring grid in one eyepiece. Material for culture for HSV was taken at each visit; the presence of symptoms (pain, discomfort, and irritation) was noted. The areas of lesions in the proflavine photoinactivation group remained larger significantly longer than in the other groups, the healing time was slower, and HSV could be isolated for longer. It is concluded that proflavine photoinactivation is of no greater value than 0.5 per cent. IDU or normal saline in the treatment of genital infection by HSV in the male.

Acridines↗
PubMed1976

Inhibition of transfer ribonucleic acid nucleotidyl transferase (EC 2.7.7.25) from Ehrlich tumor cells by proflavine sulfate and ethidium bromide.

Transfer RNA nucleotidyl transferase from Ehrlich tumor cells was inhibited by proflavine sulfate and ethidium bromide but not by actinomycin D, chromomycin, rifamycin SV, rifampin, daunomycin, or alpha-amanitin. Complete inhibition of nucleotidyl transferase activity was attained at a final concentration of 1 mmol/1 proflavine sulfate, while 2 mmol/1 ethidium bromide was required to completely inhibit the enzyme. CMP incorporation into tRNA was more sensitive to both proflavine sulfate and ethidium bromide than was AMP incorporation.

Acridines↗
PubMed2006

Electrochemical and spectroscopic studies of the interaction of proflavine with DNA.

The interaction of proflavine with herring sperm DNA has been investigated by cyclic voltammetry and UV-Vis spectroscopy as well as viscosity measurements. Shifts in the peak potentials in cyclic voltammetry, spectral changes in UV absorption titration, an increase in viscosity of DNA and the results of the effect of ionic strength on the binding constant strongly support the intercalation of proflavine into the DNA double helix. The binding constant for the interaction between proflavine and DNA was K = 2.32 (+/- 0.41) x 10(4) M(-1) and the binding site size was 2.07 (+/- 0.1) base pairs, estimated in voltammetric measurements. The value of the binding site size was determined to be closer to that expected for a planar intercalating agent. The standard Gibbs free-energy change is ca. -24.90 kJ/mol at 25 degrees C, indicating the spontaneity of the binding interaction. The binding constant determined by UV absorption measurements was K = 2.20 (+/- 0.48) x 10(4) M(-1), which is very close to the value determined by cyclic voltammetry assuming that the binding equilibrium is static.

Animals↗
PubMedDate not supplied

[Study of the interaction of proflavin with deoxytetraribonucleoside triphosphate 5'-d(ApGpCpT) in aqueous solution by uni- and two-dimensional 1H-spectroscopy].

Complex formation between acridine dye proflavine and self-complementary deoxytetraribonucleoside triphosphate 5'-d(ApGpCpT) in water-salt solution was studied by the method of one- and two-dimensional 1H-NMR spectroscopy (500 MHz). Two-dimensional homonuclear 1H-NMR spectroscopy (2D-COSY and 2D-NOESY) was used for complete assignments of proton signals of molecules in solution and for qualitative analysis of the nature of interactions between proflavine and tetranucleotide. Concentration dependences of proton chemical shifts of the molecules were measured at 293 K. Equilibrium reaction constants and limiting chemical shifts of dye protons in the complexes were determined using suggested schemes of complex formation. Based on the obtained data possible types of complexes were considered. Analysis of relative content of different types of complexes was made and special features of dynamic equilibrium were revealed as a function of correlation of dye and tetranucleotide concentrations. The most favourable structure of 1:2 complex of dye with tetranucleotide was constructed using the calculated values of induced chemical shifts of proflavine protons and 2D-NOESY spectra.

Magnetic Resonance Spectroscopy↗
PubMed1978

[Elimination of multiple drug resistance of intestinal bacteria in white mice in vivo with proflavine and rimactan].

Albino mice, infected with 0.4 cu. cm of 10(10) microbial cells (S. Heidelberg), were treated with proflavin (0.4 cu. cm of a 0.3% solution) and rimactan rifamycin SV (0.4 cu. cm of a 0.4% solution). Proflavin was given singly and four times, daily, in the course of four days, and rimactan was applied four times. Given in a single dose proflavin was found to prolong twice as long the life span of albino mice infected with S. heidelberg. When injected four times it lowered considerably the mortality rate among the animals, the percent of survivals being 62. It was shown to hinder the transmission of multidrug resistance to the normally existing intestinal microflora. It also eliminated the multidrug resistance that intestinal bacteria had acquired in the course of the first several days of drug application. The action of rifamycin proved stronger: 83% of the albino mice treated survived. It eliminated the markers of resistance--both the acquired ones and those carried by the normal recipients (intestinal bacteria)--that substantiated multidrug resistance as well as some of the markers of the donor itself (S. heidelberg).

Acridines↗
PubMed1968

Sedimentation studies on the interaction of proflavine with deoxyribonucleic acid.

A method is described of using photography to measure the concentrations of a small ligand (proflavine) above and below the boundary of a macromolecule (DNA, both native and denatured) sedimenting in the ultracentrifuge. The measurements are used to determine the extent of the binding of proflavine to DNA, and the results compared with those obtained by a spectrophotometric method. The results obtained by the two methods agree within 10%, thus validating the spectrophotometric technique under these conditions. The variation of the sedimentation coefficient with the extent of binding of proflavine was also studied. The results are discussed in relation to previously observed changes in the viscosity of the solutions.

Acridines↗
PubMed1973

Cell-surface interactions: differential inhibition by proflavine of embryonic cell aggregation and production of specific cell-aggregating factor.

Cell recognition and morphogenetic aggregation of embryonic cells into tissues are mediated by specific macromolecules in the cell surface (cell-aggregating factors). A factor specific for embryonic neural retina cells was demonstrated; its synthesis is required for histotypic reaggregation of retina cell suspensions. We show that proflavine (3,6-diaminoacridine) preferentially and reversibly suppresses production of the cell-aggregating factor and thereby inhibits normal cell reaggregation. If such proflavine-treated retina cells are exogenously supplied with the retina-specific factor, they reaggregate. The selectivity of these effects supports the postulated significance of specific cell-surface components in cell association into tissues; the results indicate that proflavine may be a useful molecular probe for studying formation of specific cell-surface components and their role in various cell interactions.

Acridines↗
PubMed2000

Enantiospecific recognition of DNA sequences by a proflavine Tröger base.

The DNA interaction of a chiral Tröger base derived from proflavine was investigated by DNA melting temperature measurements and complementary biochemical assays. DNase I footprinting experiments demonstrate that the binding of the proflavine-based Tröger base is both enantio- and sequence-specific. The (+)-isomer poorly interacts with DNA in a non-sequence-selective fashion. In sharp contrast, the corresponding (-)-isomer recognizes preferentially certain DNA sequences containing both A. T and G. C base pairs, such as the motifs 5'-GTT. AAC and 5'-ATGA. TCAT. This is the first experimental demonstration that acridine-type Tröger bases can be used for enantiospecific recognition of DNA sequences.

Animals↗