Search Results (27)

The increasing emphasis on green chemistry and environmentally responsible organic synthesis highlights the need to evaluate not only the biological activity but also the ecological safety of bioactive molecules. Xanthone, cinnamic acid, and chalcone scaffolds are widely explored in pharmaceutical and cosmetic research, yet their environmental profiles remain insufficiently characterized. This study assessed the ecotoxicity of simple derivatives from these three structural classes using the Microtox assay with the bioluminescent bacteria Aliivibrio fischeri. Test compounds were synthesized or obtained commercially, dissolved in dimethyl sulfoxide (DMSO), and evaluated at two exposure times (5 and 15 min), with half maximal effective concentration (EC₅₀) values calculated based on luminescence inhibition. The results revealed substantial differences between the investigated groups: chalcone derivatives exhibited uniformly high ecotoxicity, whereas cinnamic acid derivatives showed the most favorable environmental profile with low variability in EC₅₀ values. Xanthone derivatives displayed the widest ecotoxicity range, with toxicity strongly dependent on substituent type and substitution position. Notably, chloro-substitution in cinnamic acid derivatives correlated with lower toxicity, while positional effects were critical in the xanthone series. A comparison with in silico predictions generated using the ADMETlab platform showed poor correlation with the experimental outcomes. The predictive model did not distinguish the differing ecotoxicological behavior of α,β-unsaturated systems in chalcones versus cinnamic acids and systematically flagged halogenation as a toxicity-driving feature, contrary to several of our in vitro observations. Together, these findings provide new insights into structure–ecotoxicity relationships and underscore the need to complement computational predictions with validated experimental assays when designing bioactive compounds with improved environmental safety. Full article

Soil contamination with petroleum hydrocarbons is a serious environmental issue, necessitating the development of effective and environmentally friendly remediation methods that align with the principles of sustainable development. This study investigated the impact of selected biosurfactants on the efficiency of the biodegradation of total petroleum hydrocarbons (TPH) and polycyclic aromatic hydrocarbons (PAHs) in contaminated soil. Six biosurfactants—poly-γ-glutamic acid (γ-PGA), rhamnolipid, surfactin, a mixture of γ-PGA, rhamnolipids, and surfactin (PSR), as well as two commercial formulations (JBR 425 and JBR 320)—were evaluated in combination with a bacterial consortium. Biodegradation experiments were conducted under laboratory conditions for a 90-day period. The effectiveness of the tested biosurfactants was assessed using respirometric analysis, the chromatographic determination of the residual hydrocarbon content, and toxicity assays. The results showed that the application of a bacterial consortium enriched with a mixture of biosurfactants PSR (a biosurfactant concentration in the inoculating mixture: 5 g/dm³) was the most effective approach, resulting in an oxygen uptake of 5164.8 mgO₂/dm³ after 90 days, with TPH and PAH degradation rates of 77.3% and 70.32%, respectively. Phytotoxicity values decreased significantly, with TU values ranging from 6.32 to 4.62 (growth inhibition) and 3.77 to 4.13 (germination). Toxicity also decreased in the ostracodtoxkit test (TU = 4.35) and the Microtox SPT test (TU = 4.91). Among the tested biosurfactants, surfactin showed the least improvement in its bioremediation efficiency. Under the same concentration as in the PSR mixture, the oxygen uptake was 3446.7 mgO₂/dm³, with TPH and PAH degradation rates of 60.64% and 52.64%, respectively. In the system inoculated with the bacterial consortium alone (without biosurfactants), the biodegradation efficiency reached 44.35% for TPH and 36.97% for PAHs. The results demonstrate that biosurfactants can significantly enhance the biodegradation of petroleum hydrocarbons in soil, supporting their potential application in sustainable bioremediation strategies. Full article

Fludioxonil is a widely used fungicide that is frequently used to combat fungal plant diseases. Consequently, excessive concentrations of fludioxonil may enter and accumulate over time in aquatic systems, harming (micro) organisms in several ways. Thus, it is of great importance to evaluate the potential toxic effects of fludioxonil using bioassays. In the present study, various in vitro assays were used to assess the possible effects of fludioxonil in human cells and aquatic microorganisms. For the investigation of the toxic effects of fludioxonil on freshwater microalgae, Scenedesmus rubescens and Dunaliella tertiolecta were exposed to various environmentally relevant concentrations of the fungicide for a period of 96 h. Fludioxonil at 50–200 μg L⁻¹ significantly limited the growth of both microalgae, especially in the first 24 h of the exposure, where inhibitions up to 82.34% were calculated. The toxicity of fludioxonil was further evaluated via the Microtox test, and the studied fungicide was found to be less toxic for the bacteria Aliivibrio fischeri. Regarding human cells, the fludioxonil’s toxic and cyto-genotoxic effects were assessed using the Trypan blue exclusion test and the Cytokinesis Block MicroNucleus (CBMN) assay. Cell viability in all fludioxonil-treated concentrations was similar to control values according to the results of the Trypan blue exclusion test. However, the CBMN assay was used and revealed that fludioxonil had genotoxic potential in higher concentrations and exerted cytotoxic activity against human lymphocytes. Specifically, only the highest dose of fludioxonil, i.e., 10 μg mL⁻¹, exerted genotoxic effects against human lymphocytes, whereas treatment with 0.5, 1, and 5 μg mL⁻¹ did not lead to statistically significant induction of micronuclei (MN) frequencies compared with the control culture. However, fludioxonil-mediated cytotoxicity was statistically significant, which was demonstrated by the decreased CBPI (cytokinesis block proliferation index) values in all cases except for the lowest dose, i.e., 0.5 μg mL⁻¹. Full article

Ofloxacin is one of the most commonly used antibacterial substances in the world. Like most medicines, it ends up in the environment through municipal sewage and undergoes various transformations, e.g., photodegradation. The aim of this study was an extensive analysis of ofloxacin photodegradation in both pure antibiotic and a commercial eye drop forms. In this study, a sunlight simulator, chromatographic methods of quantitative and qualitative determination, and biological methods for the evaluation of toxicity (Microbial Assay for Risk Assessment (MARA), Microtox^® and Spirotox) were used. The results showed that ofloxacin decomposed almost completely over 2 h of irradiation. Based on the high resolution mass spectrometry, 22 photoproducts were identified. The most sensitive strain of bacteria in the MARA test (Delftia acidovorans) responded at a concentration of 7.6 µg L⁻¹ of ofloxacin. The antibacterial activity of the irradiated samples was higher than that predicted based on the ofloxacin concentration. This suggests that the resulting photoproducts may have a bacteriostatic effect. The results of additional acute toxicity tests indicate the formation of toxic photoproducts, so it is reasonable to use other organisms that are not focused on a specific target. Such actions may allow for the capture of other, unexpected effects of formed photoproducts. Full article

Over the past few years, numerous bacterial strains have become resistant to selected drugs from various therapeutic groups. A potential tool in the fight against these strains is antimicrobial photodynamic therapy (APDT). APDT acts in a non-specific manner by generating reactive oxygen species and radicals, thereby inducing multidimensional intracellular effects. Importantly, the chance that bacteria will develop defense mechanisms against APDT is considered to be low. In our research, we performed the synthesis and physicochemical characterization of curcumin derivatives enriched with morpholine motifs. The obtained compounds were assessed regarding photostability, singlet oxygen generation, aggregation, and acute toxicity toward prokaryotic Aliivibrio fischeri cells in the Microtox^® test. The impact of the compounds on the survival of eukaryotic cells in the MTT assay was also tested (WM266-4, WM115—melanoma, MRC-5—lung fibroblasts, and PHDF—primary human dermal fibroblasts). Initial studies determining the photocytotoxicity, and thus the potential APDT usability, were conducted with the following microbial strains: Candida albicans, Escherichia coli, Staphylococcus aureus, Streptococcus pneumoniae, and Pseudomonas aeruginosa. It was noted that the exposure of bacteria to LED light at 470 nm (fluence: 30 J/cm²) in the presence of quaternized curcumin derivatives at the conc. of 10 µM led to a reduction in Staphylococcus aureus survival of over 5.4 log. Full article

Hawke’s Bay in New Zealand was impacted by Cyclone Gabrielle in 2023, experiencing intense weather conditions and rainfall. Rivers and streams surged beyond their banks, displacing large amounts of sediment. The sewage treatment plant and industries in the Waitangi catchment, south of the city of Napier, were heavily impacted, making them potential sources of contaminants. The aim of this study was to investigate the risk of displaced sediments deposited south of Napier City, using bioassays and chemical analysis methods. Sediment samples were collected across a gradient between the coastline and the Waitangi Stream. The toxicity of chemically extracted or elutriate samples was assessed by Microtox^®, mussel embryo–larval development, and aryl hydrocarbon and constitutive androstane receptor yeast two-hybrid assays. Targeted chemical analysis and automated identification and quantification system (AIQS-GC) methods were used to identify contaminants. The elutriates showed low toxicity and the yeast assays showed levels of activity like those previously reported. Chemical methods confirmed historical contamination by DDT and its metabolites DDE and DDD, as well as by plant sterols. Overall, the toxicity and chemicals detected are what would be expected from a typical agricultural soil. The risk posed by the displaced sediment in the Waitangi catchment can be considered low. Combining chemical and bioanalytical methods was an effective approach to investigate the potential risks of post-disaster contamination. Full article

The valorization of food industry byproducts has become a significant issue worldwide because of the drive towards a circular economy. The “zero waste target” in human activities seems to be a dominant objective in the design of future products by enterprises. In this work, food waste from the crayfish processing industry was converted into useful products (quantum dots), as nowadays, biowaste-derived materials tend to be more attractive than conventionally produced materials with a similar structure due to their lower production costs and environmentally friendly development processes. More specifically, shell waste from the crayfish industry was treated hydrothermally and, after a freeze-drying process, was transformed to useful quantum dots. Instrumental and chemical techniques, such as XRD, SEM-EDS, AFM, XPS, elemental analysis, fluorescence spectroscopy, TG, Microtox bioassay, and DPPH antioxidant activity, were employed to characterize the final product. The results indicated the existence of thermally stable spherical particles, with a diameter of 5–8 nm, which were mainly composed of carbon, oxygen, nitrogen, calcium, and sulfur. Their external surface was rough and rich with various functional groups that further contributed to their overall optical properties. The final product presented low ecotoxicity, as studied by the Microtox assay. The superior antioxidant activity of this product compared to other similar materials reported elsewhere renders it a potential material for, e.g., food packaging applications. In addition, for the first time, N/S-Carbon QDs were applied as an antioxidant/antibacterial agent for strawberry preservation, showing promising results as the coated strawberries maintained their color and weight for three consecutive days with no mold growth observed on their surface. Full article

Multi-contamination by organic pollutants and toxic metals is common in anthropogenic and industrial environments. In this study, the five fungal strains Chaetomium jodhpurense (MH667651.1), Chaetomium maderasense (MH665977.1), Paraconiothyrium variabile (MH667653.1), Emmia lacerata, and Phoma betae (MH667655.1), previously isolated in Tunisia, were investigated for the simultaneous removal and detoxification of phenanthrene (PHE) and benzo[a]anthracene (BAA), as well as heavy metals (HMs) (Cu, Zn, Pb and Ag) in Kirk’s media. The removal was analysed using HPLC, ultra-high performance liquid chromatography (UHPLC) coupled to a QToF mass spectrometer, transmission electron microscopy, and toxicology was assessed using phytotoxicity (Lepidium sativum seeds) and Microtox^® (Allivibrio fisherii) assays. The PHE and BAA degradation rates, in free HMs cultures, reached 78.8% and 70.7%, respectively. However, the addition of HMs considerably affected the BAA degradation rate. The highest degradation rates were associated with the significant production of manganese-peroxidase, lignin peroxidase, and unspecific peroxygenase. The Zn and Cu removal efficacy was considerably higher with live cells than dead cells. Transmission electron microscopy confirmed the involvement of both bioaccumulation and biosorption processes in fungal HM removal. The environmental toxicological assays proved that simultaneous PAH and HM removal was accompanied by detoxification. The metabolites produced during co-treatment were not toxic for plant tissues, and the acute toxicity was reduced. The obtained results indicate that the tested fungi can be applied in the remediation of sites simultaneously contaminated with PAHs and HMs. Full article

Olive leaves are rich in phenolic compounds, which give them antioxidant properties that are associated with a lower incidence of disease. Therefore, the aim of this work was to determine the phenolic content, antioxidant activity, and toxicity of the aqueous extracts of olive leaves of the main Spanish and Greek cultivated and wild genotypes. For these purposes, ‘Picual’ and ‘Arbequina’ leaves from Spain and ‘Koronoeiki’ and ‘Kalamon’ leaves from Greece were collected, as were wild olive leaves from both countries. The aqueous extracts of these genotypes were analyzed by HPLC-DAD, and the DPPH·, ABTS·⁺ Folin–Ciocalteu, and Microtox^® methods were also used. ‘Picual’ had the highest oleuropein values, followed by wild olive leaves from both countries and ‘Arbequina’. The latter was reflected in the antioxidant activity measured by DPPH· and ABTS·⁺, which positioned the leaves of ‘Arbequina’, ‘Picual’, and the wild genotypes as having the most antioxidant activity. As expected, these leaves also had the highest total phenol content, as measured by Folin–Ciocalteu. Regarding the inhibition of the bioluminescence of Aliivibrio fischeri of the aqueous leaf extracts measured by Microtox^®, the EC50₁₅ ranged between 11.82 and 82.50 mg/mL, demonstrating similar behavior to other herbal infusions. Full article

In this work, a composite material based on titanium(IV) oxide and iron(II,III) oxide was prepared using mechanothermal method. The obtained composite system was thoroughly characterized using techniques such as scanning electron microscopy, X-ray powder diffraction, thermogravimetric analysis, and nanoparticle tracking analysis. The acute toxicity of the composite material was evaluated with Microtox. In addition, the material’s photocatalytic potential was studied in photodegradation tests of ibuprofen. The composite system revealed magnetic properties of potential usage in its recovery after photocatalytic tests. However, the photocatalytic activity of TiO₂–Fe₃O₄ was lower than that of bare TiO₂. In the photocatalytic tests performed under UV (365 nm) light, a 44% reduction of initial ibuprofen concentration in the sample was noted for bare TiO₂, while for TiO₂–Fe₃O₄ composite, only a 19% reduction was observed. In visible light (525 nm), both materials achieved statistically insignificant photodegradation rates, which was contrary to the anticipated effect for TiO₂–Fe₃O₄. The observation was explained by a side oxidation reaction of Fe₃O₄ to Fe₂O₃ by the generated reactive oxygen species (ROS) in the photocatalytic process, which significantly diminished the amount of available ROS for ibuprofen degradation. The oxidation process appearing within TiO₂–Fe₃O₄ was evident and easily observed as the color of the material turned from gray to brown. Acute toxicity assay performed with the use of Microtox revealed reduced toxicity of TiO₂–Fe₃O₄ (32% inhibition of the Aliivibrio fischeri bacteria cell viability according to bioluminescence emitted) when compared to bare Fe₃O₄ (56% inhibition), whereas bare TiO₂ was non-toxic. In the study, the processes occurring during the photocatalytic reaction were analyzed and discussed in the context of the available literature data. Full article

The study’s aim was to synthesize new unsymmetrical sulfanyl zinc(II) porphyrazines and subject them to physicochemical and electrochemical characterization and also an initial acute toxicity assessment. The procedure was initiated from a commercially available dimercaptomaleonitrile disodium salt and o-phthalonitrile using Linstead’s macrocyclization reaction conditions, which led to magnesium(II) tribenzoporphyrazine with 4-(3,5-dibutoxycarbonylphenoxy)butylthio substituents. The obtained macrocycle was demetallated with trifluoroacetic acid and subsequently remetallated with zinc(II) acetate toward the zinc(II) porphyrazine derivative. The zinc(II) tribenzoporphyrazine with 4-(3,5-dibutoxycarbonylphenoxy)butylthio substituents was then subjected to the reduction reaction with LiAlH₄, yielding zinc(II) tribenzoporphyrazine with 4-[3,5-di(hydroxymethyl)phenoxy]butylthio substituents. The new zinc(II) tribenzoporphyrazines were characterized by UV-Vis spectroscopy, various NMR techniques (¹HNMR, ¹³CNMR, ¹H-¹H COSY, ¹H-¹³C HSQC, and ¹H-¹³C HMBC), and mass spectrometry. In the UV-Vis spectra, both macrocycles revealed characteristic Soret and Q-bands, whose positions were dependent on the solvent used for the measurements. Zinc(II) tribenzoporphyrazines were studied using electrochemical and photochemical methods, including the singlet oxygen generation assessment. Both zinc(II) porphyrazines revealed high singlet oxygen generation quantum yield values of up to 0.59 in DMSO, which indicates their potential photosensitizing potential for photodynamic therapy. In addition, new derivatives were subjected to a Microtox^® bioluminescence assay. Full article

Wound healing and skin tissue regeneration remain the most critical challenges faced by medical professionals. Titanium(IV) oxide-based materials were proposed as components of pharmaceutical formulations for the treatment of difficult-to-heal wounds and unsightly scarring. A gallic acid-functionalized TiO₂ nanomaterial (TiO₂-GA) was obtained using the self-assembly technique and characterized using the following methods: scanning electron microscopy (SEM), transmission electron microscopy (TEM), nanoparticle tracking analysis (NTA), X-ray powder diffraction (XRPD), infrared spectroscopy (IR), Raman spectroscopy and thermogravimetry (TG). Additionally, physicochemical and biological tests (DPPH assay, Microtox^® acute toxicity test, MTT assay) were performed to assess antioxidant properties as well as to determine the cytotoxicity of the novel material against eukaryotic (MRC-5 pd19 fibroblasts) and prokaryotic (Staphylococcus aureus, Escherichia coli, Candida albicans, Aliivibrio fischeri) cells. To determine the photocytotoxicity of the material, specific tests were carried out with and without exposure to visible light lamps (425 nm). Following the results, the TiO₂-GA material could be considered an additive to dressings and rinsing suspensions for the treatment of difficult-to-heal wounds that are at risk of bacterial infections. Full article

Contaminants of emerging concern (CEC) localize in the biome in variable combinations of complex mixtures that are often environmentally persistent, bioaccumulate and biomagnify, prompting a need for extensive monitoring. Many cosmetics include UV filters that are listed as CECs, such as benzophenone derivatives (oxybenzone, OXYB), cinnamates (2-ethylhexyl 4-methoxycinnamate, EMC) and camphor derivatives (4-methylbenzylidene-camphor, 4MBC). Furthermore, in numerous water sources, these UV filters have been detected together with Bisphenols (BPs), which are commonly used in plastics and can be physiologically detrimental. We utilized bioluminescent bacteria (Microtox assay) to monitor these CEC mixtures at environmentally relevant doses, and performed the first systematic study involving three sunscreen components (OXYB, 4MBC and EMC) and three BPs (BPA, BPS or BPF). Moreover, a breast cell line and cell viability assay were employed to determine the possible effect of these mixtures on human cells. Toxicity modeling, with concentration addition (CA) and independent action (IA) approaches, was performed, followed by data interpretation using Model Deviation Ratio (MDR) evaluation. The results show that UV filter sunscreen constituents and BPs interact at environmentally relevant concentrations. Of notable interest, mixtures containing any pair of three BPs (e.g., BPA + BPS, BPA + BPF and BPS + BPF), together with one sunscreen component (OXYB, 4MBC or EMC), showed strong synergy or overadditive effects. On the other hand, mixtures containing two UV filters (any pair of OXYB, 4MBC and EMC) and one BP (BPA, BPS or BPF) had a strong propensity towards concentration dependent underestimation. The three-component mixtures of UV filters (4MBC, EMC and OXYB) acted in an antagonistic manner toward each other, which was confirmed using a human cell line model. This study is one of the most comprehensive involving sunscreen constituents and BPs in complex mixtures, and provides new insights into potentially important interactions between these compounds. Full article

Quinoline is an N-heterocyclic compound commonly found in wastewater, especially that derived from coal processing, chemical, and pharmaceutical industries. In the present study, the microscopic fungus Curvularia lunata IM 4417, which is known to degrade various xenobiotics, was used. The aim of the research was to study the elimination of quinoline and its influence on fungal phospholipids, which are considered to be excellent indicators of environmental monitoring. Quinoline biodegradation products and phospholipid contents were analyzed using gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry. C. lunata IM 4417 degraded quinoline, which led to the formation of conjugates of glucose with hydroxylated derivatives of the compound. Toxicity tests (Artoxkit M and Microtox assay) indicated that the elimination of lower concentrations of quinoline was efficient and led to a reduction in sample toxicity. The presence of quinoline also significantly affected the profile of fatty acids and phospholipids. The addition of quinoline to a culture of C. lunata IM 4417 caused an increase in the content of phosphatidylcholine (PC) and a decrease in the amount of phosphatidylethanolamine (PE), two major structural lipids. Additionally, decreases in the contents of phosphatidylinositol (PI) and phosphatidylserine (PS), which are responsible for tolerance to toxic substances, cell viability, and signal transduction, were noted. Thus, it can be concluded that the presence of quinoline modifies the membrane composition, and this change may be an important indicator of the presence of N-heterocyclic compounds or other toxins in the environment. Full article

Zinc environmental levels are increasing due to human activities, posing a threat to ecosystems and human health. Therefore, new tools able to remediate Zn contamination in freshwater are highly recommended. Specimens of Dreissena polymorpha (zebra mussel) were exposed for 48 h and 7 days to a wide range of ZnCl₂ nominal concentrations (1–10–50–100 mg/L), including those environmentally relevant. Cellulose-based nanosponges (CNS) were also tested to assess their safety and suitability for Zn removal from freshwater. Zebra mussels were exposed to 50 mg/L ZnCl₂ alone or incubated with 1.25 g/L of CNS (2 h) and then removed by filtration. The effect of Zn decontamination induced by CNS has been verified by the acute toxicity bioassay Microtox^®. DNA primary damage was investigated by the Comet assay; micronuclei frequency and nuclear morphological alterations were assessed by Cytome assay in mussels’ haemocytes. The results confirmed the genotoxic effect of ZnCl₂ in zebra mussel haemocytes at 48 h and 7-day exposure time. Zinc concentrations were measured in CNS, suggesting that cellulose-based nanosponges were able to remove Zn(II) by reducing its levels in exposure waters and soft tissues of D. polymorpha in agreement with the observed restoration of genetic damage exerted by zinc exposure alone. Full article