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PubMed1986

Relationship between mutagenic potency in Salmonella typhimurium strains and the chemical structure of nitro biphenyls.

Most of the positional isomers of mono-, di-, tri- and tetranitrobiphenyls were synthesized and assayed for their mutagenicity in Salmonella typhimurium strains TA98, TA98NR and TA98/1,8DNP6 in the absence of S9 mix. In mono- and dinitrobiphenyls, the structure requirements favoring mutagenic activity are the presence of a nitro group at the 4-position and its absence at the 2-position. TA98 and TA98/1,8DNP6 were reverted by 2-position-free 4-nitro analogues, but TA98NR was not reverted. The results suggest that direct-acting mutagenicity involves the reduction of the nitro group by bacterial nitroreductase but does not involve specific esterification enzymes. Some of the tri- and tetranitrobiphenyls e.g. 3,4,3'-, 3,4,4'-, 3,4,3',4'- and 3,4,2',4'-derivatives reverted not only TA98 and TA98/1,8DNP6 but also TA98NR. Those derivatives commonly have 2 nitro groups at an adjoining position (3,4-dinitro group), whereas 2,4,2',4'-tetranitrobiphenyl, which has strong potency not only in TA98 and TA98/1,8DNP6 but also in TA98NR, possesses 2 nitro groups at the 2-position of each benzene ring.

Biphenyl Compounds↗
PubMed1998

New NO-donors with antithrombotic and vasodilating activities, Part 19. Pseudonitroles and their dimeric azodioxides.

Thirteen geminally substituted nitro-nitroso compounds (pseudonitroles) have been synthesized, four of them for the first time. In the solid state the pseudonitroles are dimerized to azodioxides. This is proved by IR spectroscopy, with the dimeric N-O valence vibration being observed between 1293 and 1306 cm-1. Only 1,3-diphenyl-2-nitro-2-nitrosopropane is monomeric even when solid. This is backed by its blue color and an IR band at 1574 cm-1. When dissolved in chloroform these azodioxides dissociate completely to the blue monomers (lambda max approximately 650 nm). Eight pseudonitroles inhibited the aggregation of blood platelets half-maximally at concentrations below 10 microM (Born test, collagen). When administered orally to rats (60 mg/kg) the thrombus formation in mesenteric arterioles and venules was inhibited up to 25 percent (k; 1-nitro-1-nitrosocyclohexane). When kept in aqueous media at 37 degrees C nitric oxide and its reduced from, i.e. nitrosohydrogen, are released. This suggests that the above biological effects arise from an NO dependent mechanism. The lack of influence on the blood pressure of spontaneously hypertensive rats, however, strongly suggests that an enzyme supported rather than a thermal formation of NO occurs in vivo.

Animals↗
PubMed1993

Antibacterial organophosphorus compounds: phosphoranilidohydrazones of 5-nitro-2-furaldehyde.

A series of phosphoranilidohydrazones of 5-nitro-2-furaldehyde was synthesized and evaluated for antibacterial activity. The series was prepared to examine the applicability of phosphoramidic hydrazones as carriers for the antibacterial nitrofuran moiety. Designed as analogues of nitrofurantoin, members of the series were chosen according to the Topliss approach to analogue design. The title compounds were devoid of gram-negative activity but possessed moderate antistaphylococcal activity. The most potent members of the series were equipotent with nitrofurantoin against Staphylococcus aureus. The relationship between structure and antistaphylococcal activity is discussed.

Anti-Bacterial Agents↗
PubMed1999

Depletion and restoration of the putative photosensitive materials store yielding nitric oxide in the isolated mouse gastric fundus.

We investigated the possibility of there being any photosensitive materials stores yielding nitric oxide (NO), and combined for the first time electrical field stimulation (EFS)- and UV light-induced relaxations in mouse gastric fundus. The tissue responded with relaxation to long wave UV light (366 nm). Repeated exposure to light decreased the fundic photorelaxation in that the initial photorelaxation was 31.5 +/- 6.9% whereas the last (10th) photorelaxation was 2.3 +/- 0.8%. There were no significant differences between EFS (30 V, 0.5 ms, 1 Hz, 15 s)-induced relaxations obtained before (39.7 +/- 7.7%) and after (33.4 +/- 9.1%) UV irradiation, which were completely blocked by 10(-4) M L-N(G)-nitro-arginine methyl ester. Treatment of the tissue with NaNO(2), L-N(G)-nitro-arginine, S-nitrosoglutathione, or sodium nitroprusside for 30 min followed by prolonged washout restored the photorelaxation, whereas glyceryl trinitrate or L-arginine did not produce any improvement. EFS (30 V, 0.5 ms, 3 Hz) applied for 60 min significantly recovered the reduction of the photorelaxation. L-N-(delta)iminoethyl-L-ornithine, which does not contain NO(2) moiety, abolished electrically induced relaxation; however, it did not change photorelaxations. UV irradiation caused relaxation only when the adventitial surface of the preparation was oriented to the source of UV light. These results indicate that there could be a photosensitive relaxant materials store yielding NO in the smooth muscle layer of the gastric fundus from mouse. This putative store can be refilled by NaNO(2), L-N(G)-nitro-arginine, sodium nitroprusside, S-nitrosoglutathione, or long-term EFS but not glyceryl trinitrate or L-arginine. Possible candidates for NO-yielding substances might not be an organic nitrate but an intracellular nitrite, nitrosylated substances, and unknown nitro-containing compounds, which could be all sensitive to UV light.

Animals↗
PubMed1986

Mode of action of the antimicrobial compound 5-bromo-5-nitro-1,3-dioxane (bronidox).

The mode of action of the antimicrobial agent, 5-bromo-5-nitro-1,3-dioxane (bronidox), was studied in detail for gram-positive and gram-negative bacteria, yeast and fungi. The studies included MIC testing, thiol inhibition of activity, intracellular leakage, oxygen consumption, incorporation of 3H-uridine, scanning electron microscopy, inhibition of enzyme activity (papain) and in vitro oxidation of thiols to disulfides. It appears that the primary mode of action of bronidox is the same as, or similar to, that of bronopol, i.e. the oxidation of essential protein thiol causing inhibition of enzyme activity and subsequent inhibition of microbial growth.

Anti-Bacterial Agents↗
PubMed2001

Structure-activity relationships of phenylcyclohexene and biphenyl antitubulin compounds against plant and mammalian cells.

Phenylcyclohexenes (PCHs) [e.g., trans-4-nitro-5-(2,3,4-trimethoxyphenyl)cyclohexene, 2d] were found to bind weakly to the colchicine site of bovine tubulin, but are the first mimics of colchicine found to have high activity towards plant cells. Structure-activity relationships for PCHs and biphenyl AC-ring analogues of colchicine (e.g., 2,3,4,4'-tetramethoxy-2'-methyl-1,1'-biphenyl, 3e) are discussed.

Animals↗
PubMed1986

Inhibition of acetyl-coenzyme A dependent activation of N-hydroxyarylamines by phenolic compounds, pentachlorophenol and 1-nitro-2-naphthol.

Pentachlorophenol (PCP) and 1-nitro-2-naphthol were found to be potent inhibitors of enzymatic acetyl-CoA dependent activation, which is suggested as proceeding through direct O-acetylation, of N-hydroxyarylamines to tRNA binding by liver cytosolic enzymes from hamsters and rats. IC50 values of PCP for the activation of 2-hydroxyamino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (N-OH-Glu-P-1), 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole (N-OH-Trp-P-2) and N-hydroxy-2-aminofluorene (N-OH-AF) were 20, 25 and 17 microM, respectively, in hamster cytosol system. Similar inhibition was observed with rat liver cytosol (IC50 values of PCP and 1-nitro-2-naphthol were 13 and 12 microM, respectively, for the binding of N-OH-Glu-P-1). PCP is known as an inhibitor of sulfotransferase; however, another potent inhibitor of sulfotransferase, 2,6-dichloro-4-nitrophenol, did not inhibit the acetyl-CoA dependent binding. Antibiotic thiolactomycin, which inhibits bacterial O-acetyltransferase, did not affect the activation by hamster and rat cytosol, indicating the difference in property between bacterial and mammalian enzymes. The kinetic data obtained with hamster cytosol suggested the competitive inhibition of PCP with substrate, N-OH-Glu-P-1, and non-competitive inhibition with acetyl-CoA. In addition to the O-acetylation, PCP and 1-nitro-2-naphthol also inhibited N-acetylation of arylamines and N,O-acetyltransfer reaction of N-hydroxy-2-acetylaminofluorene (N-OH-AAF) by hamster cytosol. IC50 values for these two types of acetyltransfer reactions, however, were slightly higher than those observed for acetyl-CoA dependent activations of N-hydroxyarylamines.

Acetyl Coenzyme A↗
PubMed2001

Nitroanilines are the reduction products of benzofuroxan system by oxyhemoglobin (HbO2 2+).

Benzofuroxans are interesting compounds which display several biochemical and pharmacological properties. Recent studies from our laboratory demonstrate that they are reduced by ferrous salts at room temperature and that the principal reaction products are o-nitroanilines. This paper shows that simple benzofuroxan derivatives are also able to oxidise HbO2 2+ to methemoglobin (MetHb3+) (UV detection) and to form o-nitroanilines (HPLC detection). From a toxicological point of view this reaction is interesting, since it indicates that the blood is a site for metabolism of these compounds with consequent methemoglobinemia and formation of toxic compounds.

Aniline Compounds↗