To further support implementation of monitoring by passive sampling, robust sampler-water partition coefficients (Kpw) are required to convert data from passive sampler into aqueous phase concentrations. In this work silicone-water partition coefficients were determined for ∼80 hydrophobic organic contaminants using the cosolvent method. Partition coefficients (Kpm) were measured in pure water and water-methanol mixtures up to a methanol mole fraction of 0.3 (50% v/v). Subsequently, logKpw in pure water was determined as the intercept of linear regression of the logKpm with the corresponding methanol mole fractions. LogKpw were determined for phthalates, musks, organo phosphorus flame-retardants, chlorobenzenes, pesticides, some PCBs and a number of miscellaneous compounds. The median standard error and 95% confidence interval of the measured logKpw was 0.06 and 0.13, respectively. The overall relationship between Kpw and Kow seems insufficient to predict Kpw for unknown compounds. Prediction may work within a group of compounds with similar nature, e.g. homologues but HCH isomers having the same Kow exhibit Kpw ranging over an order of magnitude. Long alkyl-chain phthalates and tris(2-ethylhexyl) phosphate; all having a molecular volume >400 Å3, deviated the most from the Kpw-Kow relationship.
- Klíčová slova
- Cosolvent, Hydrophobic organic compounds, Passive sampling, Silicone–water partition coefficient,
- MeSH
- chemické látky znečišťující vodu chemie MeSH
- chlorbenzeny chemie MeSH
- fosfáty chemie MeSH
- kyseliny ftalové chemie MeSH
- kyseliny mastné mononenasycené MeSH
- pesticidy chemie MeSH
- polychlorované bifenyly chemie MeSH
- retardanty hoření MeSH
- silikony chemie MeSH
- voda chemie MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- chemické látky znečišťující vodu MeSH
- chlorbenzeny MeSH
- fosfáty MeSH
- kyseliny ftalové MeSH
- kyseliny mastné mononenasycené MeSH
- musk MeSH Prohlížeč
- pesticidy MeSH
- phthalic acid MeSH Prohlížeč
- polychlorované bifenyly MeSH
- retardanty hoření MeSH
- silikony MeSH
- voda MeSH
A series of racemic 3-phenyl-5-methyl-2H,5H-furan-2-ones related to a natural product, (-)incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural feature, furanone ring, was closed via H2SO4-mediated cyclization of 2-phenylpent-4-enoic acids. The compounds displayed antifungal activity, especially against filamentous fungi. Expressed as the minimum inhibition concentration (MIC) in micromol/L, the activity of the most promising derivative against Absidia corymbifera matched that of ketoconazole (31.25 micromol/L). In terms of microg/mL, the substance was more active (7.6 microg/mL) than this standard antifungal drug (16.6 microg/mL).
- MeSH
- antifungální látky chemická syntéza chemie farmakologie MeSH
- chlorbenzeny chemická syntéza chemie farmakologie MeSH
- cyklizace MeSH
- gama-butyrolakton analogy a deriváty chemická syntéza chemie farmakologie MeSH
- houby účinky léků MeSH
- ketokonazol farmakologie MeSH
- lidé MeSH
- molekulární struktura MeSH
- racionální návrh léčiv MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- 3-(3,4-dichlorophenyl)-5-methyl-2H,5H-furan-2-one MeSH Prohlížeč
- antifungální látky MeSH
- chlorbenzeny MeSH
- gama-butyrolakton MeSH
- incrustoporin MeSH Prohlížeč
- ketokonazol MeSH
We studied metabolism of monochlorobenzene (MCB), 1,2-dichlorobenzene (1,2-DCB) and 1,4-DCB in liver microsomes from untreated male and female Wistar rats and B6C3F1 mice or in those after the induction of CYP3A or 2E1 as well as in human male liver microsomes. MCB and 1,2-DCB were oxidised mainly by rat and human CYP2E1. It was found that 1,4-DCB was oxidised by rat and human CYP2E1 at a several-fold lower rate than 1,2-DCB, but a greater part to covalently binding products. In contrast to previous studies showing rat CYP3A1 as the main CYP form oxidising both DCBs, our experiments indicate only a certain role of rat and human CYP3A in MCB, 1,2-DCB and 1,4-DCB oxidation to covalently bound products. The relative roles of human liver CYP2E1 and 3A4 in the metabolism of 1,4-DCB seem to be individually different. Metabolic rates of MCB, 1,2-DCB and 1,4-DCB correlated with CYP2E1 immunochemical level in microsomes from 11 different human livers and with metabolic rates of CYP2E1 substrates. These rates in different human livers were up to 10-fold different and were generally several-fold higher than those in untreated rats or mice. Metabolic activation of MCB and 1,2-DCB to products binding covalently to microsomal proteins and to calf-thymus DNA, respectively, mostly corresponded to production of water-soluble metabolites. Significant species and sex differences in the oxidation of MCB, 1,2-DCB and 1,4-DCB were reflected in a markedly higher oxidation in male mice than male rats and higher oxidation in male than female mice. The formation of covalently bound products generally corresponded to production of soluble metabolites, but female rats formed significantly less covalently bound products of 1,4-DCB (and also of 1,2-DCB and MCB) than male rats and mice of both sexes, in possible reflection of the fact that 1,4-DCB is not carcinogenic in female rats despite its carcinogenicity for male rats and both sexes of mice.
- MeSH
- aromatické hydroxylasy * MeSH
- chlorbenzeny chemie metabolismus MeSH
- cytochrom P-450 CYP3A MeSH
- druhová specificita MeSH
- inhibitory cytochromu P450 MeSH
- jaterní mikrozomy enzymologie MeSH
- krysa rodu Rattus MeSH
- lidé MeSH
- myši MeSH
- oxidace-redukce MeSH
- potkani Wistar MeSH
- sexuální faktory MeSH
- systém (enzymů) cytochromů P-450 metabolismus MeSH
- zvířata MeSH
- Check Tag
- krysa rodu Rattus MeSH
- lidé MeSH
- mužské pohlaví MeSH
- myši MeSH
- ženské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- srovnávací studie MeSH
- Názvy látek
- 2-dichlorobenzene MeSH Prohlížeč
- 4-dichlorobenzene MeSH Prohlížeč
- aromatické hydroxylasy * MeSH
- chlorbenzeny MeSH
- chlorobenzene MeSH Prohlížeč
- Cyp3a23-3a1 protein, rat MeSH Prohlížeč
- cytochrom P-450 CYP3A MeSH
- inhibitory cytochromu P450 MeSH
- systém (enzymů) cytochromů P-450 MeSH
