Genetic toxicology of folpet and captan

Arce, Gail Theall; Gordon, Elliot B.; Cohen, Samuel M.; Singh, Phirtu

doi:10.3109/10408444.2010.481663

Cited by 41 publications

(29 citation statements)

References 85 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…These colonies were unable to grow on glycerol as only carbon source and confirmed as petite (respiratory deficient) mutants. The highest frequency of petite mutants can be attributed to the direct mutagenic action of the tiophosgene moiety of the captan molecule [4], to high ROS accumulation, and the adaptive advantage of mitochondrial defective petite yeast under the stress condition imposed by the fungicide [22].…”

Section: Resultsmentioning

confidence: 99%

“…In the presence of exposed thiol groups, captan oxidize thiols and is hydrolyze to its reactive thiophosgene (SCCl 3 ) moiety, and the 1,2,3,6-tetrahydrophthalimide ring [4]. In vitro genotoxicity studies indicated that phtalimide fungicides were associated to point mutations, and gene conversion [5,6], been classified as potential human carcinogen.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The effect of the fungicide captan onSaccharomyces cerevisiaeand wine fermentation

et al. 2016

View full text Add to dashboard Cite

Abstract. Fungicides, particularly those used during grape maturation, as captan, can affect the natural yeast population of grapes, and can reach grape must affecting wine fermentation. The objective of the present work was to study the effect of captan on the viability and fermentative behavior of S. cerevisiae. S. cerevisiae (BY4741) on exponential phase was treated with captan (0 to 40 µM) for different periods, and their cell viability analyzed. Cell membrane integrity, thiols concentration, and reactive oxygen species (ROS) accumulation was determined. The fermentation experiments were conducted in synthetic must using wine yeast strain Y904. The results showed that under aerobic conditions, 20 µM of captan reduce 90% of yeast viability in 6 hours. Captan treated cells exhibited alteration of membrane integrity, reduction of thiol compounds and increase in intracellular ROS concentration, suggesting a necrotic and pro-oxidant activity of the fungicide. Fermentative experiments showed that concentrations above 2.5 µM captan completely inhibited fermentation, while a dose dependent fermentation delay associated with the reduction of yeast viability was detected in sub-inhibitory concentrations. Petit mutants increase was also observed. In conclusion, the captan induces yeast necrotic cell death on both aerobic and anaerobic conditions causing fermentation delay and/or sucking fermentations.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The effect of the fungicide captan onSaccharomyces cerevisiaeand wine fermentation

et al. 2016

View full text Add to dashboard Cite

show abstract

“…Structurally, the only difference between the 2 was in the cyclic group: an aromatic ring (phthalimide) in the case of folpet and tetrahydrophthalimide in the case of captan. A previous study for in vitro mutagenesis showed that tetrahydrophthalimide was not mutagenic when compared to folpet and captan, which were mutagenic in vitro [11], although in vivo study did not confirm it [1]. Therefore, the trichloromethylthio moiety seems to be the reactive moiety.…”

Section: Discussionmentioning

confidence: 98%

“…These chemicals have been used for over 60 years. Originally, folpet, captan, and captafol were considered to be mutagenic compounds [1]. However, they were not found to possess mutagenic effects in vivo [1].…”

mentioning

confidence: 99%

Effects of Folpet, Captan, and Captafol on Human Aromatase in JEG-3 Cells

Chen

et al. 2018

Pharmacology

View full text Add to dashboard Cite

Background: Estradiol, produced by aromatase (CYP19A1), is very important for reproduction. Folpet, captan, and captafol belong to the phthalimide class of fungicides. They are used to protect the leaves of plants or fruits. They could be endocrine disruptors and may disrupt CYP19A1 activity. Methods: In the present study, we investigated the effects of folpet, captan, and captafol on estradiol production and human CYP19A1 activity in JEG-3 cells. Results: Folpet, captan, and captafol decreased estradiol production in JEG-3 cells in a concentration-dependent manner. Folpet, captan, and captafol inhibited human CYP19A1 with inhibitory concentration (IC₅₀) values of 3.55, 10.68, and 1.14 μmol/L respectively. These chemicals competitively inhibited human CYP19A1. Molecular docking simulation analysis showed that they tended to bind to the steroid-binding pocket of the CYP19A1. However, the required concentrations may not be relevant to the negligible systemic exposures in humans to these chemicals. Conclusion: Folpet, captan, and captafol are potential inhibitors of human CYP19A1.

show abstract

“…Chemical properties of the agent, its metabolites and/or its degradation products 3.1.1. Captan (information is from [28,29] unless otherwise indicated).…”

Section: Examples Of Mutagenic Mode Of Action Determinationsmentioning

confidence: 99%

Factors influencing mutagenic mode of action determinations of regulatory and advisory agencies

Eastmond

2012

Mutation Research/Reviews in Mutation Research

View full text Add to dashboard Cite

The determination of whether a chemical induces cancer through a mutagenic or genotoxic mechanism frequently plays an important role in evaluating the risks associated with low dose exposure. Although various approaches are employed for making mode of action decisions, a systematic investigation to identify the major factors that influence these determinations has not been performed. To accomplish this, over 40 chemical risk assessments conducted by U.S. or international regulatory agencies and organizations were reviewed to identify components that had played a significant role, either directly or indirectly, in the decision-making process. The major factors identified included the chemical properties of the agent, its metabolites and degradation products; its metabolism and toxicokinetics; genotoxic effects seen in vivo, particularly in the target organ; structural or metabolic similarities to known mutagenic or nonmutagenic chemicals; characteristics of the tumors induced in the animal bioassays; and the origin of the observed effects. The quality of the data, the specific genotoxic endpoint and its sensitivity to assay conditions and toxicity were also important considerations. In all cases, the authoritative groups used a weight-of-evidence approach and, in most cases where evaluations were conducted by more than one authoritative body, similar conclusions were reached. In summary, a critical evaluation of the data as well as expert judgment is necessary in reaching mechanism of action conclusions. These determinations should be made within the broader context of evaluating the chemical's overall toxicity and carcinogenicity.

show abstract

Genetic toxicology of folpet and captan

Cited by 41 publications

References 85 publications

The effect of the fungicide captan onSaccharomyces cerevisiaeand wine fermentation

The effect of the fungicide captan onSaccharomyces cerevisiaeand wine fermentation

Effects of Folpet, Captan, and Captafol on Human Aromatase in JEG-3 Cells

Factors influencing mutagenic mode of action determinations of regulatory and advisory agencies

Contact Info

Product

Resources

About