Comparison of the effect of phenol and its derivatives on protein and free radical formation in human erythrocytes (in vitro).
The effect of phenolic compounds: phenol, 2,4-dichlorophenol (2,4-DCP), 2,4-dimethylphenol (2,4-DMP) and catechol on human erythrocytes was studied. The level of fluorescent label - 6-carboxy-2',7'-dichlorodihydrofluorescein diacetate (H(2)DCFDA) oxidation by phenolic compounds in erythrocytes as well as the carbonyl group content and hemoglobin denaturation were monitored. H(2)DCFDA has been utilized extensively as a marker for studies of oxidative stress at the cellular level. We noted that 2,4-DCP, 2,4-DMP and catechol induced an increase in the concentration- and time-dependent H(2)DCFDA oxidation. We also observed an increase in carbonyl group content and the changes in parameter T (denaturation of hemoglobin) in erythrocytes incubated with 2,4-DCP, catechol and 2,4-DMP. The highest level of H(2)DCFDA oxidation was provoked by 2,4-DCP. The biggest changes of proteins in erythrocytes measured as the carbonyl group content were induced by 2,4-DMP, but measured as parameter T they were induced by catechol. It was observed that phenol did not oxidize H(2)DCFDA up to the concentration of 2.5 mM after 3 h of incubation. Phenol did not affect the carbonyl group content but decreased parameter T (induced denaturation of hemoglobin). To sum up, the kind of the substituent in a phenolic ring determines the molecular mechanism of action of the individual compound and the capacity of reactive oxygen species generation and thus damages the specified structures in human erythrocytes.
Bukowska
B
B
Department of Biophysics of Environmental Pollution, University of Łódź, Banacha 12/16, 90-237 Łódź, Poland. bukow@biol.uni.lodz.pl
Michałowicz
J
J
Krokosz
A
A
Sicińska
P
P
D002396:Catechols / Q000633:toxicity; D002733:Chlorophenols / Q000633:toxicity; D004912:Erythrocytes / Q000187:drug effects* / Q000378:metabolism; D005452:Fluoresceins / Q000378:metabolism; D005609:Free Radicals / Q000378:metabolism*; D006454:Hemoglobins / Q000378:metabolism; D006801:Humans; D010084:Oxidation-Reduction; D018384:Oxidative Stress; D010636:Phenols / Q000633:toxicity*; D050050:Protein Carbonylation; D014992:Xylenes / Q000633:toxicity
C110400:2',7'-dichlorodihydrofluorescein diacetate; D002396:Catechols; D002733:Chlorophenols; D005452:Fluoresceins; D005609:Free Radicals; D006454:Hemoglobins; D010636:Phenols; D014992:Xylenes; C027804:2,4-dimethylphenol; C034221:catechol; C004762:2,4-dichlorophenol