Synthesis, application, and antibacterial activity of new direct dyes based on chromene derivatives

Aim: The goal of this study is to synthesise, analyse, and employ two new direct dyes based on chromenes derivatives as the chromophoric moiety in dyeing wool, silk, and cotton, with good colour strength, light fastness, and other desirable features. Background: The quest for new direct dyes with antimicrobial qualities for Gram-positive, Gram-negative bacteria, and fungus is underway. These dyes are commonly used on cotton, silk, and wool materials, which have great light fastness, washing, rubbing, and sweating fastness. Methods: Antibacterial activity has been measured for all dyeing fabrics. The parent structure 1 has been synthesized previously as part of the experiment. Then, these dyes are prepared by diazotization followed by coupling reaction, Results and Discussion: The p-Aminobenzenesulfonic acid (C1) and 4-Aminoazobenzene-3,4'-disulfonic acid (C2) are diazotized in hydrochloric acid with sodium nitrite, then coupled with compound 1 in a molar ratio (1: 1) at 250C until the pH is fixed at 5. Finally, the monoazo and diazo direct dyes (D1 and D2) are created. Conclusion: Wool, silk, and cotton materials benefit from the synthetic dyes' increased antibacterial action and dyeing qualities (exhaustion and fixing). They also offer better fastness qualities (light, rubbing, and perspiration).

A Simple and Sensitive Inhibitory Kinetic Method for the Carbocisteine Determination

A fast, reproducible, and sensitive method is proposed for the kinetic determination of carbocisteine (CCys). The method depends on the inhibitory property of carbocisteine, which reduces the Hg2+ catalyzed substitution rate of cyanide from [Ru(CN)6]4- with N-R-salt (1-Nitroso-2-naphthol-3,6-disulfonic acid disodium salt) via forming a stable complex with Hg2+. Spectrophotometric measurements were carried out by recording the absorbance at 525 nm (λmax of [Ru(CN)5 Nitroso-R-Salt]3- complex) at a fixed time of 10 and 15 min under the optimized reaction conditions with [N-R-salt] = 4.5 × 10-4 M, I = 0.05 M (KNO3), Temp = 45.0 ± 0.2 o C, pH = 7.0 ± 0.03, [Hg2+] = 8.0 × 10-5 M and [Ru(CN)64-] = 4.25 × 10-5 M. With the proposed method, CCys can be determined quantitatively down to 3.0 × 10-6 M. This methodology can be effectively used for the rapid quantitative estimation of CCys in the pharmaceutical samples with good accuracy and reproducibility. The addition of common excipients in pharmaceuticals even up to 1000 times with [CCys] does not interfere significantly in the estimation of CCys. Resumen. Se propone un método rápido, reproducibley sensible para la determinación cinética de la carbocisteina (CCys). El método depende de la propiedad inhibitoria de la carbocisteina que reduce la tasa de sustitución catalizada por Hg2+ del cianuro de [Ru(CN)6]4- con la sal N-R (sal disódica del ácido 1-Nitroso-2-naftol-3,6-disulfónico) mediante la formación de un complejo estable con Hg2+. Las mediciones espectrofotométricas se llevaron a cabo registrando la absorbancia a 525 nm (λmax del complejo [Ru(CN)5 Sal-Nitroso-R]3-) en un tiempo fijo de 10 y 15 min en las condiciones de reacción optimizadas con [sal-NR] = 4.5 × 10-4 M, I = 0.05 M (KNO3), Temp = 45.0 ± 0.2 o C, pH = 7.0 ± 0.03, [Hg2+] = 8.0 × 10-5 M y [Ru(CN)64-] = 4.25 × 10-5 M. Con el método propuesto, CCys se puede determinar cuantitativamente hasta 3,0 × 10-6 M. Esta metodología se puede utilizar eficazmente para la estimación cuantitativa rápida de CCys en las muestras farmacéuticas con buena precisión y reproducibilidad. La adición de excipientes comunes en productos farmacéuticos incluso hasta 1000 veces con [CCys] no interfiere significativamente en la estimación de CCys.

Determination of N-Acetyl-l-cysteine Ethyl Ester (NACET) by Flow Injection Analysis and Spectrophotometric Detection Using Different Thiol-Sensitive Ligands

A new flow injection spectrophotometric method for the determination of N-acetyl-l-cysteine ethyl ester (NACET) was developed and validated. The method is based on the reduction of Cu(II)-ligand complexes to chromophoric Cu(I)-ligand complexes with the analyte. The studied ligands were neocuproine (NCN), bicinchoninic acid (BCA) and bathocuproine disulfonic acid (BCS). The absorbance of the Cu(I)-ligand complex was measured at 458, 562 and 483 nm for the reactions of NACET with NCN, BCA and BCS, respectively. The method was validated in terms of linear dynamic range, limit of detection and quantitation, accuracy, selectivity, and precision. Experimental conditions were optimized by a univariate method, yielding linear calibration curves in a concentration range from 2.0 × 10−6 mol L−1 to 2.0 × 10−4 mol L−1 using NCN; 2.0 × 10−6 mol L−1 to 1.0 × 10−4 mol L−1 using BCA and 6.0 × 10−7 mol L−1 to 1.2 × 10−4 mol L−1 using BCS. The achieved analytical frequency was 90 h−1 for all three ligands. The method was successfully employed for NACET determination in pharmaceutical preparations, indicating that this FIA method fulfilled all the essential demands for the determination of NACET in quality control laboratories, as it combined low instrument and reagent costs with a high sampling rate.

Study the fluorescent and conductivity properties of a 4-hydroxy-3-nitro-1,8-naphthalic anhydride

The compound of (4-hydroxy-3-nitro-1,8-naphthalic anhydride) and the dopant material (4-hydroxy-m-benzene-disulfonic acid) were synthesized. The UV-Vis absorption and fluorescence spectra of the compound were recorded. The bathochromic shifts in absorption due to the changes in the solvent polarity was observed, in DMSO solvent, the compound shows different peaks, three bands in the UV region and one band in the visible region, one absorption peak at 402 nm, which might be attributed to the (ICT) band. The emission spectra of this compound were sensitive to the solvent polarity. They moved to lower energies with increasing the polarity of the solvent. The influence of the solvent polarity on the fluorescence maximum was more pronounced compared with the absorption maximum, showing ca. 3 nm red shift on moving from butanol to DMSO. The effect of the dopant material on the conductivities (ionic and specific) of the compound was studied, the ionic conductivity was increased as the weight of the dopant material increases, and the ionic conductivity (G) was measured in water as a solvent. the (G) of the compound was 2.4X10-6 Siemens at 0.01 gm of the dopant material, and was 2.62X10-4 Siemens after the dopant material was added (0.1 gm).

Molecular Determinant of DIDS Analogs Targeting RAD51 Activity

RAD51 is the central protein in DNA repair by homologous recombination (HR), involved in several steps of this process. It is shown that overexpression of the RAD51 protein is correlated with increased survival of cancer cells to cancer treatments. For the past decade, RAD51 overexpression-mediated resistance has justified the development of targeted inhibitors. One of the first molecules described to inhibit RAD51 was the 4,4′-diisothiocyanato-stilbene-2,2′-disulfonic acid (DIDS) molecule. This small molecule is effective in inhibiting different functions of RAD51, however its mode of action and the chemical functions involved in this inhibition have not been identified. In this work, we used several commercial molecules derived from DIDS to characterize the structural determinants involved in modulating the activity of RAD51. By combining biochemical and biophysical approaches, we have shown that DIDS and two analogs were able to inhibit the binding of RAD51 to ssDNA and prevent the formation of D-loop by RAD51. Both isothiocyanate substituents of DIDS appear to be essential in the inhibition of RAD51. These results open the way to the synthesis of new molecules derived from DIDS that should be greater modulators of RAD51 and more efficient for HR inhibition.

The signaling role of extracellular ATP in co-culture of Shiraia sp. S9 and Pseudomonas fulva SB1 for enhancing hypocrellin A production

Background Adenosine 5′-triphosphate (ATP) plays both a central role as an intracellular energy source, and a crucial extracellular signaling role in diverse physiological processes of animals and plants. However, there are less reports concerning the signaling role of microbial extracellular ATP (eATP). Hypocrellins are effective anticancer photodynamic therapy (PDT) agents from bambusicolous Shiraia fungi. The co-culture of Shiraia sp. S9 and a bacterium Pseudomonas fulva SB1 isolated from Shiraia fruiting bodies was established for enhanced hypocrellin A (HA) production. The signaling roles of eATP to mediate hypocrellin biosynthesis were investigated in the co-culture. Results The co-culture induced release of eATP at 378 nM to the medium around 4 h. The eATP release was interdependent on cytosolic Ca2+ concentration and reactive oxygen species (ROS) production, respectively. The eATP production could be suppressed by the Ca2+ chelator EGTA or abolished by the channel blocker La3+, ROS scavenger vitamin C and NADPH oxidase inhibitor diphenyleneiodonium chloride (DPI). The bacterium-induced H2O2 production was strongly inhibited by reactive blue (RB), a specific inhibitor of membrane purinoceptors, but dependent on the induced Ca2+ influx in the co-culture. On the other hand, the application of exogenous ATP (exATP) at 10–300 µM to Shiraia cultures also promoted fungal conidiation and HA production, both of which were blocked effectively by the purinoceptor inhibitors pyridoxalphosphate-6-azophenyl-2′, 4′-disulfonic acid (PPADS) and RB, and ATP hydrolase apyrase. Both the induced expression of HA biosynthetic genes and HA accumulation were inhibited significantly under the blocking of the eATP or Ca2+ signaling, and the scavenge of ROS in the co-culture. Conclusions Our results indicate that eATP release is an early event during the intimate bacterial–fungal interaction and eATP plays a signaling role in the bacterial elicitation on fungal metabolites. Ca2+ and ROS are closely linked for activation of the induced ATP release and its signal transduction. This is the first report on eATP production in the fungal–bacterial co-culture and its involvement in the induced biosynthesis of fungal metabolites. Graphic abstract

Effect of Net Charge on DNA-Binding, Protein-Binding and Anticancer Properties of Copper(I) Phosphine-Diimine Complexes

The syntheses of [Cu(PPh3)2(L)]NO3 and [Cu(PPh3)2(L-SO3Na)]NO3 were achieved through the reaction of Cu(PPh3)2NO3 and equimolar amount of the ligands (L = 5,6-diphenyl-3-[2-pyridyl]-1,2,4-triazine; LSO3Na = 5,6-diphenyl-3-[2-pyridyl]-1,2,4-triazine-4,4′-disulfonic acid disodium salt). The complexes were characterized by NMR and IR spectroscopy and mass spectrometry. The compounds exhibit similar absorption and emission spectra, suggesting a similar electronic structure. Ct-DNA binding studies show the strong influence of the net charge as Cu-L (positively charged) is able to bind to ct-DNA while Cu-LSO3Na (negatively charged) is not. The net charge of the complexes affects the thermodynamic and kinetic binding parameters toward human serum albumin. HSA-binding of the complexes was further investigated by molecular docking, revealing different binding sites on the HSA protein as a function of the net charge. The different anticancer activities of the complexes towards ovcar-3 and hope-62 cancer cell lines are suggestive of a role for the overall charge of the complexes. Interaction with the DNA is not the major mechanism for this class of complexes. The overall net charge of the pharmacophore (anticancer agent) should be a key consideration in the design of anticancer metal complexes.