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At least 19 recordsLinked to original sources
PubMed1976

Acceleration of hepatocarcinogenesis of 2,7-bis(acetamido)fluorene by carbon tetrachloride and time relation of treatment.

The role of period between administration of CCl4 and feeding of 2,7-bis-(acetamido)fluorene in the hepatocarcinogenesis of mice was analyzed by using 14 groups of different feeding schedules. Simultaneous treatment with CCl4 and either continuous or intermittent feeding of 2,7-bis(acetamido)fluorene increased the average number of hepatic nodules and the incidence of hepatomas, while separation of 8-week feeding of 2,7-bis(acetamido)fluorene from 8 week treatment with CCl4 did not accelerate the hepatocarcinogenesis. Alternate treatment with CCl4 and 2,7-bis(acetamido)fluorene increased the average number of hepatic nodules but failed to induce hepatomas. Allyl alcohol, which is a hepatotoxic substance as is CCl4, also failed to accelerate hepatocarcinogenesis of 2,7-bis(acetamido)fluorene. Concerning the feeding schedule of 2,7-bis(acetamido)fluorene alone, the intermittent one-week feeding of the carcinogen with 3-week intervals decreased the average number of hepatic nodules as compared with the continuous feeding of the carcinogen.

2-Acetylaminofluorene↗
PubMed1992

Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products.

An Arthrobacter sp. strain, F101, able to use fluorene as the sole source of carbon and energy, was isolated from sludge from an oil refinery wastewater treatment plant. During growth in the presence of fluorene, four major metabolites were detected and isolated by thin-layer chromatography and high-performance liquid chromatography. 9-Fluorenol, 9H-fluoren-9-one, and 3,4-dihydrocoumarin were identified by UV spectra, mass spectrometry, and 300-MHz proton nuclear magnetic resonance. The fourth metabolite has been characterized, but precise identification was not possible. Since strain F101 is not able to grow with fluorenone, two different pathways of fluorene biodegradation are suggested: one supports cell growth and produces 3,4-dihydrocoumarin as an intermediate and probably the unidentified metabolite, and the other produces 9-fluorenol and 9H-fluoren-9-one and appears to be a dead-end route.

Arthrobacter↗
PubMed1976

Comparative orientation of the fluorene residue in native DNA modified by N-acetoxy-N-2-acetylaminofluorene and two 7-halogeno derivatives.

Native calf thymus DNA was reacted with N-acetoxy-N-2-acetylaminofluorene (N-AcO-AAF) and its 7-fluoro and 7-iodo derivatives. Different ways of purification of the fluorene modified DNA samples were checked in order ot obtain a nucleic acid free from all noncovalently bound fluorene residues. The decrease in melting temperature in DNA samples modified by N-AcO-AAF(DNA-AAF) was carefully reinvestigated. From these experiments, we conclude that the melting temperature decrease is equal to 1.15 degree C per percent of modified bases, in DNA-AAF samples. Electric dichroism measurements on sonicated DNA samples modified by the different fluorene derivatives show the fluorene ring perpendicular to the helix axis in the case of the N-AcO-AAF and its fluoro derivative, and lying alone the phosphate-sugar backbone in the case of the iodo derivative. The results presented in this paper, along with those obtained earlier, led us to propose an "insertion-denaturation model" for the mode of binding of N-Aco-AAF and its fluoro derivative, and an "outside binding model" for the iodo derivative. Discrepancies with the data obtained by Chang et al.((1974) Biochemistry 13,2142-2148) concerning the melting temperature decrease and the electric dichroism results are observed and discussed.

Acetoxyacetylaminofluorene↗
PubMedDate not supplied

[Experimental study of the new medicinal form of the antiviral preparation fluorenal].

Repository forms of a 0.1% fluorenal solution prepared with buffered polyglucin and a 1% polyacryamide were found to be curatively effective in experimental herpetic keratitis in rabbits. When stored in small tube-droppers for not less than 12 months (observation time) the repository fluorenal eye drops retain their therapeutic activity. In its new presentation the drug is highly effective, stable and convenient in use. This medicinal preparation of fluorenal permits reduce its concentration and the number of instillations.

Acrylamides↗
PubMed1990

Degradation of phenanthrene, fluorene and fluoranthene by pure bacterial cultures.

Bacterial mixed cultures able to degrade the polycyclic aromatic hydrocarbons (PAH) phenanthrene, fluorene and fluoranthene, were obtained from soil using conventional enrichment techniques. From these mixed cultures three pure strains were isolated: Pseudomonas paucimobilis degrading phenanthrene; P. vesicularis degrading fluorene and Alcaligenes denitrificans degrading fluoranthene. The maximum rates of PAH degradation ranged from 1.0 mg phenanthrene/ml per day to 0.3 mg fluoranthene/ml per day at doubling times of 12 h to 35 h for growth on PAH as sole carbon source. The protein yield during PAH degradation was about 0.25 mg/mg C for all strains. Maximum PAH oxidation rates and optimum specific bacterial growth were obtained near pH 7.0 and 30 degrees C. After growth entered the stationary phase, no dead end-products of PAH degradation could be detected in the culture fluid.

Alcaligenes↗
PubMed1979

Mutagenicity of fluorene derivatives: a proposed mechanism.

Several derivatives of fluorene, a tricyclic, organic molecule, have been found to induce both frameshift mutations and base-pair substitutions in Salmonella typhimurium strains developed by Ames. Comparisons of the mutagenic potency of these derivatives for several strains of Salmonella suggest the importance of a carbonyl group substituted at the carbon-9 position of mutagenic derivatives, with respect to mutagenic potency. In this study, we present a feasible mechanism for the interaction of mutagenic fluorene derivatives with deoxyribonucleic acid. This mechanism requires the interaction of the mutagenic molecule with carbon-8 of guanine and a second concurrent interaction with the C-4 amino group of an adjacent cytosine residue.

DNA, Bacterial↗
PubMed1975

Drug-induced foam cell reactions in rats, II. Chemical analysis of lipids stored in lungs and foam cells after treatment with chlorphentermine, 5-[p-(fluoren-9-ylidenemethyl)phenyl]-2-piperidineethanol (RMI 10.393) and 1-chloramitriptyline.

Lipidosis and foam cell reaction was induced in rat lungs by repeated administration of chlorphentermine, RMI 10.393 (=5-[p-(fluoren-9-ylidenemethyl)phenyl]-2-piperidineethanol), and 1-chloramitriptyline. Foam cell and lung lipids were extracted and separated in classes by thin-layer chromatography. Phospholipids were determined by phosphorus analysis, while neutral lipids were measured densitometrically. In lungs of drug-treated rats lecithin, phosphatidyl glycerol, phosphatidic acid, phosphatidyl inositol and free fatty acids accumulated in varying amounts. All other lipids were present in normal or reduced concentrations. Foam cells of chlorphentermine- and RMI 10.393-treated rats contained mainly phospholipids, i.e. lecithin and only small amounts of neutral lipids, i.e. cholesterol. Foam cells induced by 1-chloramitriptyline contained besides phospholipids also large amounts of neutral lipids, i.e. cholesterol, free fatty acids and cholesterol esters. This study and recent reports of others show that certain drugs produce a generalized metabolic disturbance characterized by accumulation of various lipids in several tissues. The distribution patterns of lipids induced by various drugs may differ considerably. This indicates that several biochemical mechanisms may be involved in the pathogenesis of drug-induced lipidosis.

Amitriptyline↗
PubMed1979

Establishment of photoaffinity label derivatives of fluorene as probes in studies of chemical carcinogenesis in mammalian cell culture.

Several azido fluorenes, photosensitive analogs of the established carcinogen 2-acetylaminofluorene, have been synthesized to serve as probes in chemical carcinogenesis and mutagenesis studies. Unlike 2-acetylaminofluorene, these compounds do not require metabolic activation. However, alkylation to critical targets is achieved through the generation of nitrenes by photolysis at 360 nm in situ. We have found that the bifunctional azidofluorenes 2,5-diazidofluorene and 2,7-diazidofluorene were more toxic to and more transforming of the mouse embryo C3H 10T1/2 clone 8 cells when photolyzed in situ than were the monofunctional azides 2-azidofluorene and 7-bromo-2-azidofluorene. When the drugs were photolyzed in phosphate-buffered saline (pH 7.4) and then added to the cells these preirradiated derivatives were not transforming but were slightly toxic. However, there is not relationship between the number of photosensitive azido groups and the cytotoxicities of the preirradiated derivatives as measured by the plating efficiency method. The transformation experiments were performed under conditions in which photolysis was carried out for as little as 15 sec. This is significant because the major events that lead to oncogenesis apparently can occur within this narrow time channel, thereby making the drugs excellent probes in studies in chemical carcinogenesis. Although near ultraviolet light alone may transform the cells (8 to 16 min of irradiation), under the conditions studied ultraviolet light was neither toxic nor transforming.

Affinity Labels↗
PubMed1978

Effects of selenium and retinoic acid on the metabolism of N-acetylaminofluorene and N-hydroxyacetylamino-fluorene.

Male albino rats were given 4 ppm selenium (Se(as Na2SeO3) in the water, or 0.25% retinoic acid was added to the basal diet for 3 days. Control and treated animals were given 17 mg acetylaminofluorene (AAF)-9-14C or N-hydroxyacetylaminofluorene (NOHAAF)-9-14C/kg body wt. The administration of Se enhanced glucuronyl transferase activity by 100% and inhibited p-nitrophenol-sulfotransferase by 50%. Retinoic acid enhanced the glucuronyl transferase 37% and inhibited the p-nitrophenol-sulfotransferase by 50%. Pretreatment with Se lowered levels of both AAF and NOHAAF in liver tissue by 30%. Se administration lowered the binding of the labeled carcinogens, or metabolites thereof, to the liver DNA and tRNA.

2-Acetylaminofluorene↗
PubMedDate not supplied

Depression of the hepatic cytochrome P-450 mono-oxygenase system by administered tilorone (2,7-bis(2-(diethylamino)ethoxy)fluoren-9-one dihydrochloride).

The oral administration of the antiviral agent, tilorone-HCl (50 mg/day for 4 days) to rats caused losses of hepatic microsomal ethylmorphine N-demethylase, benzo(a)pyrene hydroxylase and aniline hydroxylase activities of 50, 44 and 22%, respectively. Microsomal levels of cytochrome P-450 and NADPH-cytochrome c reductase were lowered by 40 and 20% respectively, but levels of cytochrome b5 and NADH-cytochrome c reductase remained unchanged. After a single oral dose of tilorone-HCl (50 mg/kg) a loss of 38% of the microsomal cytochrome P-450 and 25% of the ethylmorphine N-demethylase activity was observed within 24 hr; recovery was complete within 8 to 10 days. Hexobarbital sleeping times and blood levels were elevated after tilorone administration (20 or 50 mg/kg/day for 4 days). In vitro, tilorone-HCl showed no inhibitory effect on microsomal drug metabolism nod did it affect the cytochrome P-450 content of the microsomes. The rate of incorporation of delta-amino(3H)levulinic acid into cytochrome P-450 was not affected by tilorone-HCl.

Aniline Hydroxylase↗
PubMedDate not supplied

Arylamination and arylation of 4,4,4-trifluoro-1-phenyl-1,3-butanedione with N-acetoxy derivatives of 2-aminofluorene.

The present study investigated the reaction of carcinogenic electrophiles with beta-diketones which possess an active methylene group. N-Acetoxy-2-(acetylamino)fluorene bound to tRNA at 37 degrees C, pH 7.0, and this reaction was inhibited by 4,4,4-trifluoro-1-phenyl-1,3-butanedione or 2-thenoyltrifluoroacetone. N-Acetoxy-2-(acetylamino)fluorene reacted with these active methylene compounds to form transitory 3-substituted 2-(acetylamino)fluorene intermediates, which, following cleavage of the trifluoroacetyl group, yielded 3-phenacyl-2-(acetylamino)fluorene or 3-(2-thenoylmethyl)-2-(acetylamino)fluorene. N-Acetoxy-2-[(trifluoroacetyl)amino]fluorene reacted with 4,4,4-trifluoro-1-phenyl-1,3-butanedione to yield two products, N-phenacyl-1-(trifluoroacetyl)-2-aminofluorene and N-phenacyl-3-(trifluoroacetyl)-2-aminofluorene. The ratio of these two products was approximately 1:2. The same N-phenacyl products were produced by incubation of the beta-diketone, N-hydroxy-2-(acetylamino)fluorene, and rat liver cytosol which catalyzed the formation of N-acetoxy-2-aminofluorene. Thus, the inhibitions by beta-diketones of nucleic acid-binding and bacterial mutagenesis of carcinogens are likely due to their trapping of the carcinogens.

Acetoxyacetylaminofluorene↗
PubMed1978

Synthesis of spirofluorenes of biological interest.

1'-Substituted spiro[fluorene-9,3'-pyrrolidine-2',5'-diones], 1',1''' - (1,4-piperazinediyldimethylene) bis[spiro[fluorene-9,3'-pyrrolidine-2',5'-dione]], and 1'-arylspiro[fluorene-9,3'-pyrrolidines] were synthesized from spiro[fluorene-9,3'-tetrahydrofuran-2',5'-dione]. The rat passive cutaneous anaphylaxis assay showed that one compound possessed slight antiallergic activity. Synthesis of 3-substituted 1-aryl-4-oxospiro[azetidine-2,9'-fluorenes] and 1,1''-p-phenylenebis[4-oxospiro[azetidine-2,9'-fluorenes]] was achieved via the reaction of appropriate N-fluorenylideneanilines with tert-butylcyanoketene and cyclopentamethyleneketene, respectively.

Animals↗
PubMed1976

[Synthetic low-molecular weight interferon inducers: derivatives of diaminofluoren-9-one, diaminobenzophenones and diamino biphenyls].

Among the aminoacyl derivatives of 2,7-diaminofluoren-9-one a few compounds were found capable of inducing interferon in the mouse when administered perorally. One of them, 2,7-bis[(diethylamino)acetylamino]fluoren-9-one exhibited an inducing activity comparable to that of 2,7-bis-(2-diethylaminoethoxy)-fluoren-9-one (tilorone). The synthesis of derivatives of fluorene, fluorenol, fluorenone, diaminobenzophenone, diaminiodiphenylmethane and benzidine, all of them with corresponding side chains, allowed to establish structural requirements for interferon inducing capability.

Amides↗