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Results for “1-Naphthylamine”

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At least 19 recordsLinked to original sources
PubMed1978

Guanyl O6-arylamination and O6-arylation of DNA by the carcinogen N-hydroxy-1-naphthylamine.

The carcinogen N-hydroxy-1-naphthylamine reacted with nucleic acids and protein under slightly acidic conditions (pH 5) to form covalently bound derivatives with 3 to 20 naphthyl residues/1000 monomer units. The level of binding was in the following order: DNA greater than polyguanylic acid greater than denatured DNA and ribosomal RNA greater than serum albumin greater than transfer RNA greater than polyadenylic acid. Reactions with nucleosides and nucleotides were not detected, and the binding of N-hydroxy-1-naphthylamine to DNA was not inhibited by the addition of nucleosides, nucleotides, methionine, or glutathione. The reaction rates were first order with respect to both DNA and N-hydroxy-1-naphthylamine concentrations. Enzymatic hydrolysis of the DNA containing naphthyl residues yielded 3 nucleoside-arylamine adducts. The major adduct was identified by chemical, ultraviolet, nuclear magnetic resonance, and mass spectrometric analyses as N-(deoxyguanosin-O6-yl)-1-naphthylamine. The other two adducts were identified as 2-(deoxyguanosin-O6-yl)-1-naphthylamine and its decomposition product. Direct evidence for acid-dependent arylnitrenium ion formation was obtained by isotope exchange upon solvolysis of N-hydroxy-1-naphthylamine in acidic H2 18O, and carbocation formation was indicated by the formation of the solvolysis products, 1-amino-2-naphthol and 1-amino-4-naphthol. These studies demonstrated the conversion of a carcinogenic N-hydroxy arylamine to electrophilic arylnitrenium ion and carbocation species that display high selectivity toward macromolecules. The roles of these electrophiles and their macromolecular adducts in the initiation of urinary bladder carcinogenesis through formation of promutagenic lesions in DNA are suggested.

1-Naphthylamine↗
PubMed1979

Detection of early lymphocyte activation by the fluorescent cell membrane probe N-phenyl-1-naphthylamine.

N-phenyl-1-naphthylamine (NPN) becomes fluorescent after binding to hydrophobic regions of cell membranes. Rat and mouse lymphoid cell suspensions stained with NPN showed changes in fluorescence emission 30 min after stimulation with mitogen or antigen, detected by microfluorimetry. Incubation of NPN-labelled mouse and rat thymocytes with phytohaemagglutinin or concanavalin A (Con A) caused an increase in mean cell fluorescence intensity. The response to Con A was inhibited by sodium azide and alpha-methyl mannoside. Stimulation of spleen cells from mice by allogeneic cells, or from tumour-bearing rats by tumour antigen consistently resulted in decreased fluorescence. The 'mixed lymphocyte response' detected only certain genetic differences between mouse strains and was proportional to the ratio of stimulator to responder cell number. The NPN staining procedure offers a simple and rapid assay of immunoreactivity and a means of studying early subcellular changes following lymphocyte activation.

1-Naphthylamine↗
PubMed1975

The use of hexazonium-p-rosanilin in the histochemical demonstration of peptidases.

The suitability of hexazonium-p-rosanilin (HP) in the histochemical demonstration of peptidases was investigated. The detection was carried out in cold mictrotome sections adherent to slides or semipermeable membranes. Alanyl-1-naphthylamide, alanyl-2-naphthylamide, leucyl-2-naphthylamide, leucyl-4-methoxy-2-naphthylamide (all substrates in concentration of 0.4 mg/1 ml of citrate phosphate buffer pH 6.5), gamma-L-glutamyl-1-naphthylamide, gamma-L-glutamyl-2-naphthylamide (both substances in concentration of 0.24 mg/1 ml of acetate buffer pH 6.5) were used as the substrates. Results were compared with those obtained with Fast Blue B and Fast Garnet GBC. In comparison with Fast Blue B and Fast Garnet GBC HP is a faster coupler, furnishes azodyes which are stable, amorphous (even without lipid extractions from sections), more substantive and in the case of 1-naphthylamine almost insoluble in ordinary lipid solvents used for the dehydration and clearing of sections before mounting. The molecular extinction coefficient of azodyes furnished by HP is 1.5X higher for 1-naphthylamine than for 2-naphthylamine. It is higher than that of Fast Garnet GBC, however, lower than that of Fast Blue B. The inhibitory influence of individual diazonium salts on enzyme activity (activities) splitting leucyl-2-naphthylamide amounts to 36% (Fast Garnet GBC), 37% (Fast Blue B), 52% (HP, 0.03 ml/1 ml) and 63% (HP, 0.09 ml/1 ml) at pH 6.5. For gamma-glutamyl-transpeptidase the corresponding values are 50%, 59%, 62% and 67%. The higher inhibitory influence of HP is compensated by the possibility of its using in the technic of semipermeable membranes. HP improves greatly the localization of peptidases in cold microtome sections from which lipids were not extracted. The best results are furnished by 1-naphthylamine dervatives. In the case of 4-methoxy-2-naphthylamine derivatives the localization is very sharp, however, the azodye is less distinct than that of 2-naphthylamine. The localization as obtained with HP in combination with substrates derived of simple naphthylamines is similar or even better than with 4-methoxy-2-naphthylamine derivatives applied with Fast Blue B. Typical examples are shown.

1-Naphthylamine↗
PubMed1976

The study of rous sarcoma virus-transformed baby hamster kidney cells using fluorescent probes.

The fluorescent probes pyrene, pyrene butyric acid and N-phenyl 1-naphthylamine have been used to investigate the changes that accompany in vitro transformation of a baby hamster kidney cell line using Rous sarcoma virus. The fluorescent probes which reside in the membrane were used to compare the changes in microviscosity and polarity of the membranes of normal cells with two transformed cell lines. The spectrofluorimetric data indicate that following transformation the probe N-phenyl 1-naphthylamine resides in a more polar environment. However, using the probe pyrene, the yield of excimer indicates decreased mobility of this probe in the membrane of transformed cells. The data also indicate differences between the two transformed cell lines. Laser photolysis was used to study the lifetime of the pyrene probes and the quenching of the pyrene fluorescence in the membrane by several different quenching molecules. The data indicate differences between the three cell lines and suggest that transformation decreases movement within the membrane.

1-Naphthylamine↗
PubMed1979

Respiration-linked proton transport, changes in external pH, and membrane energization in cells of Escherichia coli.

The kinetics of respiration-dependent proton efflux and membrane energization have been studied in intact cells of logarithmic-phase Escherichia coli. Parallel measurements of the rate and extent of proton efflux into the external medium (half-time, about 10 s; ratio of H(+) to O, about 0.5) and the oxidation of E. coli cytochrome b (half-time, </=1 s; about 6% oxidized) after a pulse of 5.5 ng-atoms of O indicate that the rate of proton efflux is at least 10 times slower than expected from the time required for the cells to reduce the oxygen added in the pulse. The kinetics of formation and dissipation of the transmembrane electric potential (deltapsi) after an O(2) pulse were estimated from changes in the fluorescence properties of the cell envelope-bound probe N-phenyl-1-naphthylamine. Under anaerobic conditions, a small pulse of oxygen induced a rapid (half-time, </=1 s) partial decrease in the fluorescence intensity of the probe, followed by a slower relaxation of the fluorescence change to the original intensity. The extent of the initial rapid decrease was linearly dependent upon the amount of oxygen added in the pulse (0 to 11 ng-atoms of O per pulse), whereas the rate of the subsequent relaxation was accelerated by the uncoupler p-trifluoromethoxycarbonylcyanidephenylhydrazone and the K(+) ionophore colicin E1. This suggests that the initial fluorescence decrease after an O(2) pulse reflects the energization of the membrane, whereas the relaxation of the fluorescence decrease reflects the subsequent deenergization of the membrane arising from counterion redistributions. The fact that the efflux of H(+) into the external medium after an O(2) pulse was inefficient and much slower (half-time, about 10 s) than the reduction of the added O(2) (half-time, </=1 s) and the energization of the membrane (half-time </=1 s) suggests that some of the protons translocated across the cytoplasmic membrane during a brief pulse of respiratory activity are accumulated in a region of the cell which is not in rapid equilibrium with the external medium.

Carbonyl Cyanide p-Trifluoromethoxyphenylhydrazone↗
PubMed1977

Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis.

Uridine 5'-diphosphoglucuronic acid-fortified hepatic microsomes from dogs, rats, or humans rapidly metabolized [3H]-N-hydroxy-2-naphthylamine (N-HO-2-NA) to a water-soluble product that yielded 98% of the parent N-hydroxy amine upon treatment with beta-glucuronidase. The metabolite was identified as N-(beta-1-glucosiduronyl)-N-hydroxy-2-naphthylamine from ultraviolet, infrared, and mass spectral analyses of the glucuronide and its nitrone derivative. Incubation of N-hydroxy-1-naphthylamine (N-HO-1-NA), N-hydroxy-4-aminobiphenyl (N-HO-ABP), or the N-hydroxy derivatives of 2-aminofluorene, 4-aminoazobenzene, or N-acetyl-2-aminofluorene with uridine 5'-diphosphoglucuronic acid-fortified hepatic microsomes also yielded water-soluble products. beta-Glucuronidase treatment released 80 to 90% of the [3H]-NHO-1-NA and [3H]-N-HO-ABP conjugates as tritiated ether-extractable derivatives. N-HO-1-NA, N-HO-2-NA, and N-HO-ABP and the glucuronides of these N-hydroxy arylamines were relatively stable and nonreactive near neutral pH. At pH 5, the N-glucuronide of N-HO-2-NA and the presumed N-glucuronides of N-HO-1-NA and N-HO-ABP were rapidly hydrolyzed to the N-hydroxy arylamines that were then converted to reactive derivatives capable of binding covalently to nucleic acids. These data support the concept that arylamine bladder carcinogens are N-oxidized and N-glucuronidated in the liver and that the N-glucuronides are transported to the urinary bladder. The hydrolysis of the glucuronides to N-hydroxy arylamines and the conversion of the latter derivatives to highly reactive electrophilic arylnitrenium ions in the normally acidic urine of dogs and humans may be critical reactions for tumor induction in the urinary bladder.

Animals↗
PubMed1976

Enzymatic attack on side chains of synthetic polymers. Chymotrypsin-catalyzed hydrolysis of specific substrate groups attached to acrylamide or acrylic acid co-polymers.

Three vinyl monomers, M-1, M-3, and M-5, in which L-phenylalanine p-nitroanilide was acylated with CH2==CHCONH(CH2)nCO--(n = 1, 3, 5) were synthesized. They were co-polymerized with a large excess of acrylamide (co-polymers PAm-1, PAm-3, and PAm-5) and with a large excess of acrylic acid (co-polymers PAc=1, PAc-3, and PCc-5). In addition, M-5 was co-polymerized with acrylamide containing 2.8 mol % of the hydrophobic monomer N-acrylyl-1-naphthylamine (co-polymer PAm-5N). The rates of the chymotrypsin-catalyzed hydrolysis of the nitroanilide groups of M-5 and the various co-polymers were determined over a range of pH. For some of the systems data were also obtained over a range of substrate concentrations to derive values for Vmax and Km. Results obtained with PAm-5 were found to be independent of the chain length of the co-polymer. At pH 7, 25 degrees and with 2.7 X 10(-6) M enzyme, Vmax values for M-5, PAm-k, PAm-5N, and PAc-5 were 5.5, 5.5, 10, and 3.6 X 10(-8) M/S, while Km values were 8.5, 16.5, 10, and 2.2 X 10(-5),respectively, With PAc-5, the pH activity profile was shifted to higher acidities as compared to the profiles obtained with M-5 and PAm-5. The susceptibility of the co-polymers to chymotrypsin attack decreases sharply with a decreasing spacing of the L-phenylalanine p-nitroanilide residue from the backbone of the polymer chains.

Acrylamides↗
PubMed1979

Immunosurveillance in pre-malignant occupational bladder disease.

A population of workers exposed to bladder carcinogens has been studied by comparing their immunoreactivity against bladder cancer cells and against a control cancer cell with that found in normal individuals and in patients with bladder cancer. Data are presented which indicate equivalent increases in specific reactivity against bladder cancer cells in clinically normal carcinogen-exposed workers and in patients with bladder cancer. Increases in reactivity are related to degree of exposure and also to early malignant changes in the urothelium. This indicates that immune recognition of tumour antigens does occur before development of overt malignancy.

1-Naphthylamine↗
PubMed1975

Studies in lipid histochemistry. XIII. The OPA (osmiumtetroxide-periodic acid-alpha-naphthylamine) method for the detection of apolar lipids.

A new procedure for the detection of apolar lipids is described. It is a modification of the OTAN method (Adams, 1959) using periodic acid which oxidatively removes lower osmium derivatives from polar sites only, leaving those in apolar lipids intact and demonstrable with alpha-naphthylamine. Control steps for the exclusion of the possible interference of some less polar complex lipids and of lipopigments are described. The described technic is superior to the conventionally used sudan dyes due partly to the fact that only aqueous solutions are employed thus excluding any extraction of lipids, partly to the more distinct coloration.

1-Naphthylamine↗
PubMed1977

Aminotetralins as selective beta-adrenergic agonists.

Aminotetralin derivatives M-8 and JOD-176, were studied in relation to isoproterenol for beta-adrenergic activity. M-8 and JOD-176 were found to be very weak in activating cardiac beta-receptors. These compounds were also found to be considerably more active in uterine and bronchial smooth muscle. Because these compounds were also shown to be very inactive in vascular smooth muscle, the possibility that beta-receptors in different smooth muscle types may also differ was suggested.

1-Naphthylamine↗
PubMed1976

Studies on the chemical nature of urinary chemiluminescence.

Studies on the nature of the chemicals responsible for urinary chemiluminescence have been carried out. Urinary chemiluminescence can be increased slightly by sulphatase, more by glucuronidase but most of all by boiling for 1 hour at pH 1. It is suggested that most of the chemicals responsible for urinary chemiluminescence are bound as non-chemiluminescent precursors to sulphate, glucuronic acid and in other ways. Both the chemiluminescent material and the inactive precursors are freely ultrafiltrable with molecular weights below 500. A survey of various chemicals has revealed considerable chemiluminescence in certain metabolites of naphthylamines and known to cause bladder cancer but little or no chemoluminescence in the tryptophane metabolites that have been thought to cause bladder cancer.

1-Naphthylamine↗
PubMed1975

Fluorescent labeling of human platelets.

Noncovalently bound fluorescent probes have been used to study changes in the platelet which may occur during platelet aggregation. Platelets were exposed to either N-phenyl-naphthylamine (NPN) or 8-anilino-1-naphthalene-sulfonic acid (ANS). Both dyes were bound by the platelet, and platelet aggregation by collagen or thrombin was unaffected by the presence of the label. No change in fluorescence intensity or wavelength of maximum intensity was observed during platelet aggregation.

1-Naphthylamine↗
PubMed1975

[On the absorption of decongestive nose-drops-investigation with a radioactive labelled imidazoline-derivate (author's transl)].

In animal experiments, the absorption of a nasal decongestive substance after application to the nasal mucosa was studied. After an exposition-time of 60 minutes, about 1% of the substance applied could be measured in the total blood volume. An incorporation of the substance into proteins of the nasal mucosa could not be found. By means of frozen-section-autoradiography, the way of the applied decongestive substance through the mucosa could be investigated. The reasons for the relative small absorption rate are discussed. The chemical structure and the vasoconstrictory effect probably are reliable for that.

1-Naphthylamine↗