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Isolation of a bacterial strain with the ability to utilize the sulfonated azo compound 4-carboxy-4'-sulfoazobenzene as the sole source of carbon and energy.

A bacterial strain (strain S5) which grows aerobically with the sulfonated azo compound 4-carboxy-4'-sulfoazobenzene as the sole source of carbon and energy was isolated. This strain was obtained by continuous adaptation of "Hydrogenophaga palleronii" S1, which has the ability to grow aerobically with 4-aminobenzenesulfonate. Strain S5 probably cleaves 4-carboxy-4'-sulfoazobenzene reductively under aerobic conditions to 4-aminobenzoate and 4-aminobenzene-sulfonate, which are mineralized by previously established degradation pathways.

Azo Compounds↗

The bis-azo compound FP-21399 inhibits HIV-1 replication by preventing viral entry.

The bis-azo compound FP-21399 inhibits HIV-1 infection. We now show that FP-21399 acts on the HIV-1 envelope glycoprotein to prevent viral replication. This compound targets the entry step of the HIV-1 replication cycle as demonstrated by time-of-addition and single cycle viral entry assays. The entry of SIVmac239, which uses the same coreceptors (CD4/CCR5) as HIV-1, was not inhibited by FP-21399, indicating that the antiviral effect of FP-21399 is specific for the HIV-1 envelope glycoprotein and is not dependent upon the cellular receptors CD4 and CCR5. FP-21399 inhibits neither the activity of HIV-1 reverse transcriptase nor the expression of HIV-1 early mRNA. Finally, this compound inhibits gp120 shedding of the T-tropic virus. Our results suggest that the anti-HIV activity of FP-21399 is due to its interaction with HIV-1 gp120/41 complex during viral entry.

Animals↗

Constituents of Agaricus xanthodermus Genevier: the first naturally endogenous azo compound and toxic phenolic metabolites.

Extraction of fresh sporophores of the fungus Agaricus xanthodermus yields 4,4'-dihydroxy-azobenzene, phenol, p-quinol, and 4,4'-dihydroxybiphenyl. This is the first report of an azo compound arising endogenously in nature, while phenol, p-quinol and 4,4'-dihydroxybiphenyl have not previously been isolated from higher fungi. Phenol is present in fruitbodies in sufficiently high concentration to account for the toxicity of A. xanthodermus.

Agaricales↗

Chromosomal effects of newly identified water pollutants PBTA-1 and PBTA-2 and their possible mother compounds (azo dyes) and intermediates (non-ClPBTAs) in two Chinese hamster cell lines.

We performed the in vitro micronucleus (MN) test on 2-[2-(acetylamino)-4-[bis(2-methoxyethyl)amino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-1) and 2-[2-(acetylamino)-4-[N-(2-cyanoethyl)-ethylamino]-5-methoxyphenyl]-5-amino-7-bromo-4-chloro-2H-benzotriazole (PBTA-2), which are newly identified water pollutants from the Nishitakase river in Kyoto, Japan, and on their possible mother compounds (AZO DYE) and intermediates (non-ClPBTAs). We tested these compounds in the absence and presence of S9 mix in two Chinese hamster cell lines CHL and V79-MZ and scored MN, polynuclear and karyorrhectic (PN), and mitotic (M) cells. PBTA-2 in the absence of S9 mix induced the strongest responses in both cell lines. It was also a strong inducer of binucleate cells in PN cells in both cell lines, which suggested that it induced polyploidy. PBTA-1 showed clear positive results only in the absence of S9 mix and only in V79-MZ cells, inducing aneuploidy. In CHL cells AZO DYE-1 significantly induced MN cells in the presence of S9 mix, and AZO DYE-2 induced MN and PN cells, including binucleate cells and cells with a multilobed nucleus, in the absence of S9 mix. In V79-MZ cells, AZO DYE-1 and -2 induced primarily M cells in the presence of S9 mix. 9% of the M cells treated with 50 microg/ml AZO DYE-1 showed endoreduplication. AZO DYE-2 at 200 microg/ml condensed the chromatin in 100% of the cells. The non-ClPBTAs were a bit more cytotoxic than the other compounds and induced a slight increase in MN cells in both cell lines. Some of the chemicals tested induced a characteristic karyomorphology that might reflect abnormal cell division. Abnormalities of cell division could be detected in PN and M cells as well as in MN cells. Structure-activity relationships have also been discussed.

Animals↗

Synthesis of a vanadium(III) tris(arylthiolato) complex and its reactions with azide and azo compounds: formation of a sulfenamide complex via cleavage of an azo N=N bond.

The tris(arylthiolate) vanadium(III) complex (1) has been synthesized in good yield. This complex is found to undergo CH activation across a V-S bond in the presence of TMEDA to give a cyclometalated species along with free arylthiol. Complex 1 behaves as a two-electron reductant toward Ad-N(3), yielding an imide complex. Treatment of 1 with azobenzene produces an imide-sulfenamide compound, in which an azo N=N bond cleavage takes place concomitant with formation of a V=N and an S-N bond.

Journal Article↗

Catalytic enantioselective hetero-Diels-Alder reactions of an azo compound.

This communication describes studies in which an azo hetero-Diels-Alder adduct was furnished in high regio- and enantioselectivity using azopyridine as a reagent and silver as a catalyst. The obtained hetero-Diels-Alder adduct was easily converted to the corresponding chiral 1,4-diamino alcohol.

Azo Compounds↗

In vitro effects of an azo compound on the haemolysis and unsaturated fatty acids of red blood cells.

Human red blood cells were treated with 4,4'-azo-bis-(4-cyanovaleric acid) (0-27 x 10(-3) M) in order to determine the effect of the compound on red blood cell haemolysis and unsaturated fatty acids. Maximum haemolysis amounting to approximately 100%, occurred after 60 min incubation with 15 x 10(-3) M azo compound and did not change to any significant extent by increasing incubation time to 4 h. The azo compound caused a decrease in unsaturated fatty acids unrelated to the number of double bonds. The percentage loss of unsaturated fatty acids was 60-100. Therefore the present study reveals that incubation of red blood cells with 15 x 10(-3) M 4,4'-azo-bis-(4-cyanovaleric acid) for 1 h causes maximum haemolysis. Also the damaging effect of the compound on red blood cell unsaturated fatty acids is parallel to haemolysis. These results show that this compound might have relevance for pathophysiology of red blood cells.

Azo Compounds↗