2-hydroxy-4-methoxybenzophenone
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Ultraviolet (UV) radiation is a non-ionizing radiation, which has a cytotoxic potential, and it is therefore necessary to protect against it. Human skin is exposed to the longer-wavelength components of UV radiation (UVA and UVB) from the sun. In the present paper, we focused on the study of eight organic UV-absorbing compounds: astragalin, beta-carotene, 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, hyperoside, 3-(4-methylbenzylidene)camphor, pachypodol, and trans-urocanic acid, as possible protectives of skin cells against UVA and UVB radiation. Their protective effects on skin cell viability, ROS production, mitochondrial membrane potential, liposomal permeability, and DNA integrity were investigated. Only some of the compounds studied, such as trans-urocanic acid and hyperoside, had a significant effect on the examined hallmarks of UV-induced cell damage. This was also confirmed by an atomic force microscopy study of morphological changes in HaCaT cells or a study conducted on a 3D skin model. In conclusion, hyperoside was found to be a very effective UV-protective compound, especially against UVA radiation. Commonly used sunscreen compounds such as 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, and 3-(4-methylbenzylidene)camphor turned out to be only physical UV filters, and pachypodol with a relatively high absorption in the UVA region was shown to be more phototoxic than photoprotective.
- Klíčová slova
- 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 3-(4-methylbenzylidene)camphor, UV-absorbing compounds, astragalin, beta-carotene, hyperoside, pachypodol, phototoxicity, trans-urocanic acid,
- MeSH
- kůže metabolismus MeSH
- kyselina urokanová * farmakologie MeSH
- lidé MeSH
- přípravky chránící proti slunci farmakologie MeSH
- ultrafialové záření * škodlivé účinky MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- 2,4-dihydroxybenzophenone MeSH Prohlížeč
- enzacamene MeSH Prohlížeč
- hyperoside MeSH Prohlížeč
- kyselina urokanová * MeSH
- oxybenzone MeSH Prohlížeč
- přípravky chránící proti slunci MeSH
Effective removal of organic UV filters from aquatic environmental compartments and swimming waters is very important because these substances are hazardous to humans and wildlife at low concentrations and act as endocrine disruptors. Therefore, the aim of the present article is to determine the extraction efficiencies of hydrophobic deep eutectic solvents (HDES) for the selected UV filters based on benzophenone structure (benzophenone, 2,4-dihydroxybenzophenone, 2,2´,4,4´-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,2´-dihydroxy-4-methoxybenzophenone, 4-methacryloxy-2-hydroxybenzophenone) from aqueous matrices. For this purpose, six HDESs based on dl-menthol in combination with caprylic, decanoic and lauric acid are prepared and compared with referent terpene solvents such as terpineol and linalool. The effect of various parameters such as HDES composition, volume ratio, frequency and shaking time are studied. The highest extraction efficiency is shown by HDES of menthol:caprylic acid (1:1) composition at the aqueous:organic phase volume ratio of 1:1, shaking frequency of 1500 rpm and shaking time of 15 min. The achieved extraction efficiencies are higher than 99.6 % for all benzophenones studied in the purification of stagnant pond water, swimming pool water and river water samples. After a simple and fast sample treatment, the residual levels of benzophenones in the waters are controlled by a newly developed sensitive HPLC-MS/MS method with LOQs in the range of 0.7 - 5.0 ng/mL.
- Klíčová slova
- Benzophenone, Hydrophobic deep eutectic solvent, Liquid chromatography, Mass spectrometry, Solvent reuse, Water purification,
- MeSH
- benzofenony * chemie MeSH
- chemické látky znečišťující vodu * analýza chemie MeSH
- čištění vody * metody MeSH
- hluboce eutektická rozpouštědla * chemie MeSH
- hydrofobní a hydrofilní interakce * MeSH
- kapryláty chemie MeSH
- menthol chemie MeSH
- přípravky chránící proti slunci * chemie toxicita MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- benzofenony * MeSH
- benzophenone MeSH Prohlížeč
- chemické látky znečišťující vodu * MeSH
- hluboce eutektická rozpouštědla * MeSH
- kapryláty MeSH
- menthol MeSH
- oxybenzone MeSH Prohlížeč
- přípravky chránící proti slunci * MeSH
UV filters belong to a group of compounds that are used by humans and are present in municipal waste-waters, effluents from sewage treatment plants and surface waters. Current information regarding UV filters and their effects on fish is limited. In this study, the occurrence of three commonly used UV filters - 2-phenylbenzimidazole-5-sulfonic acid (PBSA), 2-hydroxy-4-methoxybenzophenone (benzophenone-3, BP-3) and 5-benzoyl-4-hydroxy-2-methoxy-benzenesulfonic acid (benzophenone-4, BP-4) - in South Bohemia (Czech Republic) surface waters is presented. PBSA concentrations (up to 13μgL(-1)) were significantly greater than BP-3 or BP-4 concentrations (up to 620 and 390ngL(-1), respectively). On the basis of these results, PBSA was selected for use in a toxicity test utilizing the common model organism rainbow trout (Oncorhynchus mykiss). Fish were exposed to three concentrations of PBSA (1, 10 and 1000µgL(-1)) for 21 and 42 days. The PBSA concentrations in the fish plasma, liver and kidneys were elevated after 21 and 42 days of exposure. PBSA increased activity of certain P450 cytochromes. Exposure to PBSA also changed various biochemical parameters and enzyme activities in the fish plasma. However, no pathological changes were obvious in the liver or gonads.
- Klíčová slova
- 2-Phenylbenzimidazole-5-sulfonic acid, 2-ethyl-hexyl-4-trimethoxycinnamate, 2-phenylbenzimidazole-5-sulfonic acid, 4-methyl-benzylidene camphor, 4MBC, BP-3, BP-4, Chronic toxicity test, EHMC, OC, PBSA, PPCPs, Rainbow trout, Surface water, UV filters, benzophenone-3, benzophenone-4, octocrylene, pharmaceuticals and personal care products,
- MeSH
- benzimidazoly analýza toxicita MeSH
- chemické látky znečišťující vodu toxicita MeSH
- cytochromy metabolismus MeSH
- játra účinky léků MeSH
- kyseliny sulfonové analýza toxicita MeSH
- Oncorhynchus mykiss fyziologie MeSH
- oxidační stres účinky léků MeSH
- přípravky chránící proti slunci analýza toxicita MeSH
- testy chronické toxicity MeSH
- voda chemie MeSH
- zvířata MeSH
- Check Tag
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Geografické názvy
- Česká republika MeSH
- Názvy látek
- benzimidazoly MeSH
- chemické látky znečišťující vodu MeSH
- cytochromy MeSH
- ensulizole MeSH Prohlížeč
- kyseliny sulfonové MeSH
- přípravky chránící proti slunci MeSH
- voda MeSH