Design, synthesis, antimicrobial, antibiofilm evaluation and Z/E-isomerization of novel 6-((arylamino)methylene)benzo[a] phenazin-5(6H)-ones induced by organic solvent.

New 6-((arylamino)methylene)benzo[a]phenazin-5(6H)-one derivatives were synthesized, and good-to-high yields were achieved through one-pot, four-component condensation of 2-hydroxy-1,4-naphthoquinone, 1,2-phenylenediamine, aromatic amines and triethyl orthoformate using formic acid as catalyst under solvent-free conditions at 90 °C. The structure of these new compounds was confirmed using FT-IR and 1H-NMR as well as MS spectroscopy. Investigation of spectroscopy data indicated that the synthesized compounds exist in the keto-enamine tautomeric form and undergo Z/E-isomerization around the C[double bond, length as m-dash]C bond in DMSO-d6 at room temperature. Furthermore, intramolecular hydrogen bond has been observed in the synthesized E- and Z-ketoenamines. The noticeable features of the present procedure availability of starting materials, very simple operation, easy work-up, short reaction times, good to high yields and no need for column chromatography separation of benzophenazine enamines. The newly synthesized compounds were evaluated in vitro for their antibacterial, antifungal and antibiofilm activities against some of the tested microorganisms. The results demonstrated that compound 6b showed the maximum antibacterial activity, 6d exhibited the maximum antifungal activity and 6b had the most efficiency to inhibit biofilm formation of Bacillus subtilis (80%) at 200 µg mL-1 concentration.

Effect of iron and silver nanoparticles on coenzyme Q10 production by Gluconobacter japonicus FM10.

BACKGROUND AND OBJECTIVES: Coenzyme Q10 is an anti-aging agent whose demand is increasing progressively. There are various strategies used for increasing coenzyme Q10 production by microorganisms. In this study, for the first time, we investigated the effect of iron oxide and silver nanoparticles on coenzyme Q10 production by Gluconobacter japonicus FM10. MATERIALS AND METHODS: In the first step, a preliminary experiment was set and carried out to obtain the minimum inhibitory concentrations of the nanoparticles on the strain FM10. Then the sub-MIC concentrations were used to investigate their effect on coenzyme Q10 production in the stationary and exponential phases of the growth, separately. RESULTS: The results showed that coenzyme Q10 production increased in the presence of the iron oxide and silver nanoparticles. The silver nanoparticles induced 1.9 times higher coenzyme Q10 production. The highest level of coenzyme Q10 was induced when the silver nanoparticles were added to the culture medium at the stationary phase. CONCLUSION: This should be noticed that so far nanoparticles have been considered as antibacterial agents, rather than being considered to cause probable beneficial effects on the induction of useful products in the microbial world. In this regard, their potential for increasing coenzyme Q10 production has received no attention. However, our present results showed that the nanoparticles can be used to increase the production efficiency of coenzyme Q10 in Gluconobacter.

Introducing a thermotolerant Gluconobacter japonicus strain, potentially useful for coenzyme Q10 production.

In this report, Gluconobacter strains were screened for coenzyme Q10 (CoQ10) production. A thermotolerant strain, Gluconobacter japonicus FM10, was eventually employed for CoQ10 production optimization. To do so, a two-step optimization strategy was used. The first step focused on biomass increase and the second step focused on increase in CoQ10 production. Factors including temperature, pH, carbon, and nitrogen sources were optimized at the first step, and temperature, pH, and aeration were optimized at the second step. The batch culture fermentation was used with the optimized factors of the first phase (30 °C, pH 6.5, D-sorbitol, and yeast extract-peptone as the carbon and nitrogen sources). After 18 h, the temperature, pH, and aeration were shifted to the optimized values of the second step (36 °C, pH 7, and no aeration). By this strategy, the dry cell mass (17.1 g/L) and CoQ10 (23.2 mg/L) were obtained after 20 h, which the latter was 2.3 times higher than that of the first step of optimization. Among the conditions tested, carbon source was the most important factor on the cell growth at the first step while no aeration was the key factor for CoQ10 production in the second step of optimization.