Toxicologic information on 2,4,5-trichlorophenol

McCollister, D.D.; Lockwood, Doreen T.; Rowe, V. K.

doi:10.1016/0041-008x(61)90009-6

Cited by 13 publications

(4 citation statements)

References 2 publications

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“…They have been used extensively as pesticides and preservatives, particularly for lumber and leather preservation, and as general herbicides and biocides. Unfortunately, human exposure likely causes various adverse health effects (2). The concern has prompted governments worldwide to classify several polychlorinated phenols as priority pollutants.…”

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confidence: 99%

Characterization of Chlorophenol 4-Monooxygenase (TftD) and NADH:FAD Oxidoreductase (TftC) of Burkholderia cepacia AC1100

Webb

Ballinger

Kim

et al. 2010

Journal of Biological Chemistry

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Burkholderia cepacia AC1100 completely degrades 2,4,5-trichlorophenol, in which an FADH 2 -dependent monooxygenase (TftD) and an NADH:FAD oxidoreductase (TftC) catalyze the initial steps. TftD oxidizes 2,4,5-trichlorophenol (2,4,5-TCP) to 2,5-dichloro-p-benzoquinone, which is chemically reduced to 2,5-dichloro-p-hydroquinone (2,5-DiCHQ). Then, TftD oxidizes the latter to 5-chloro-2-hydroxy-p-benzoquinone. In those processes, TftC provides all the required FADH 2 . We have determined the crystal structures of dimeric TftC and tetrameric TftD at 2.0 and 2.5 Å resolution, respectively. The structure of TftC was similar to those of related flavin reductases. The stacked nicotinamide:isoalloxazine rings in TftC and sequential reaction kinetics suggest that the reduced FAD leaves TftC after NADH oxidation. The structure of TftD was also similar to the known structures of FADH 2 -dependent monooxygenases. Its His-289 residue in the re-side of the isoalloxazine ring is within hydrogen bonding distance with a hydroxyl group of 2,5-Di-CHQ. An H289A mutation resulted in the complete loss of activity toward 2,5-DiCHQ and a significant decrease in catalytic efficiency toward 2,4,5-TCP. Thus, His-289 plays different roles in the catalysis of 2,4,5-TCP and 2,5-DiCHQ. The results support that free FADH 2 is generated by TftC, and TftD uses FADH 2 to separately transform 2,4,5-TCP and 2,5-DiCHQ. Additional experimental data also support the diffusion of FADH 2 between TftC and TftD without direct physical interaction between the two enzymes.

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confidence: 99%

Characterization of Chlorophenol 4-Monooxygenase (TftD) and NADH:FAD Oxidoreductase (TftC) of Burkholderia cepacia AC1100

Webb

Ballinger

Kim

et al. 2010

Journal of Biological Chemistry

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“…A great deal of information was available on animal exposure (Anderson, Arndt, Goldbey, and Jones, 1949;Farquharson, Gage, and Northover, 1958;McCollister, Lockwood, and Rowe, 1961) which indicated that trichlorophenol was not toxic unless given in massive dosage. Indeed, McCollister et al (1961) had shown that the rabbit, though not as resistant as the rat, did have a high tolerance to trichlorophenol.…”

Section: Discussionmentioning

confidence: 99%

Chloracne from the accidental production of tetrachlorodibenzodioxin

May

1973

Occupational and Environmental Medicine

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“…Mild centrilobular changes in the liver and changes in kidneys were to be observed, too (McCollister et al, 1961).…”

Section: Chronic Effectsmentioning

confidence: 95%

Aliphatic and aromatic halocarbons as potential mutagens in drinking water

Strobel

Grummt

1987

Toxicological & Environmental Chemistry

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Chlorinated phenols are either products of industrial chemical processes or the result of chlorination of drinking water. Often, the formation of chlorinated phenols is based upon naturally occurring phenol. The following chlorinated phenols have been selected for testing in the Ames-test for their mutagenic activity: 3-chlorophenol, 4-chlorophenol, 2,3,6-, 2,4,5-, 2,4,6-trichlorophenol, 4-chloro-2-methylphenol and 4-chloro-3-methylchlorophenol. The tester strains TA97, TA98, TA100 and TA104 were employed. All tested compounds produced mutagenic activity at least in one tester strain. The highest numbers of revertants were detected for 2,3,6-and 2,4,6-trichlorophenol. But in contrast to the other substances, these two induced only frameshift mutations in presence of a metabolizing system. The evidence of their presence in drinking water and of their mutagenic activity makes them to a potential health hazard.

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Toxicologic information on 2,4,5-trichlorophenol

Cited by 13 publications

References 2 publications

Characterization of Chlorophenol 4-Monooxygenase (TftD) and NADH:FAD Oxidoreductase (TftC) of Burkholderia cepacia AC1100

Characterization of Chlorophenol 4-Monooxygenase (TftD) and NADH:FAD Oxidoreductase (TftC) of Burkholderia cepacia AC1100

Chloracne from the accidental production of tetrachlorodibenzodioxin

Aliphatic and aromatic halocarbons as potential mutagens in drinking water

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