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diff --git a/bibliography.bib b/bibliography.bib index ca5c3da..0fea5e0 100644 --- a/bibliography.bib +++ b/bibliography.bib @@ -1,6 +1,104 @@ +@incollection{Piegorsch1991, + author = {Piegorsch, W.W. and Zeiger, E.}, + booktitle = {Statistical Methods in Toxicology, Lecture Notes in Medical Informatics}, + editor = {Hotorn, L.}, + publisher = {Springer-Verlag}, + year = 1991, + title = {Measuring intra-assay agreement for the Ames salmonella assay}, + pages = {35–41}, +} + +@article{Dunkel1984, +author = {Dunkel, Virginia C. and Zeiger, Errol and Brusick, David and McCoy, Elena and McGregor, Douglas and Mortelmans, Kristien and Rosenkranz, Herbert S. and Simmon, Vincent F.}, +title = {Reproducibility of microbial mutagenicity assays: I. Tests with Salmonella typhimurium and Escherichia coli using a standardized protocol}, +journal = {Environmental Mutagenesis}, +volume = {6}, +number = {S2}, +pages = {1-50}, +keywords = {mutagenicity, Salmonella, E. coli, interlaboratory reproducibility, collaborative study, standardized protocol}, +doi = {https://doi.org/10.1002/em.2860060702}, +url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/em.2860060702}, +eprint = {https://onlinelibrary.wiley.com/doi/pdf/10.1002/em.2860060702}, +year = {1984} +} + + + +@article{Kamber2009, + author = {Kamber, Markus and Flückiger-Isler, Sini and Engelhardt, Günter and Jaeckh, Rudolf and Zeiger, Errol}, + title = "{Comparison of the Ames II and traditional Ames test responses with respect to mutagenicity, strain specificities, need for metabolism and correlation with rodent carcinogenicity}", + journal = {Mutagenesis}, + volume = {24}, + number = {4}, + pages = {359-366}, + year = {2009}, + month = {05}, + abstract = "{The Ames II Salmonella mutagenicity assay procedure was used to test 71 chemicals, and the results were compared with those from the traditional Ames Salmonella test using the NTP database as the reference. All Ames II tests were performed using a fluctuation procedure in microplate format, using TAMix for the detection of base pair substitutions and TA98 to detect frameshift mutations. There was 84\\% agreement between the two procedures in identifying mutagens and non-mutagens, which is equivalent to the intra- and interlaboratory reproducibility of 87\\% for the traditional test. The two tests also performed similarly in their predictions of rodent carcinogenicity.}", + issn = {0267-8357}, + doi = {10.1093/mutage/gep017}, + url = {https://doi.org/10.1093/mutage/gep017}, + eprint = {https://academic.oup.com/mutage/article-pdf/24/4/359/3787533/gep017.pdf}, +} + +@article{Rutz2020, + author = {Rutz, L. and Gao, L. and Küpper, J.H. and others}, + title = {Structure-dependent genotoxic potencies of selected pyrrolizidine alkaloids in metabolically competent HepG2 cells}, + journal = {Arch. Toxicol.}, + number = 94, + pages = {4159–4172}, + year = 2020, + doi = {https://doi.org/10.1007/s00204-020-02895-z}, +} + +@article{Merz2016, +title = {Interim relative potency factors for the toxicological risk assessment of pyrrolizidine alkaloids in food and herbal medicines}, +journal = {Toxicology Letters}, +volume = {263}, +pages = {44-57}, +year = {2016}, +issn = {0378-4274}, +doi = {https://doi.org/10.1016/j.toxlet.2016.05.002}, +url = {https://www.sciencedirect.com/science/article/pii/S0378427416300911}, +author = {Karl-Heinz Merz and Dieter Schrenk}, +keywords = {Pyrrolizidine alkaloids, Relative potency factors, Risk assessment, Toxicity}, +abstract = {Pyrrolizidine alkaloids (PAs) are among the most potent natural toxins occurring in a broad spectrum of plant species from various families. Recently, findings of considerable contamination of teas/herbal infusions prepared from non-PA plants have been reported. These are obviously due to cross-contamination with minor amounts of PA plants and can affect both food and herbal medicines. Another source of human exposure is honey collected from PA plants. These findings illustrate the requirement for a comprehensive risk assessment of PAs, hampered by the enormous number of different PA congeners occurring in nature. Up to now, risk assessment is based on the carcinogenicity of certain PAs after chronic application to rats using the sum of detected PAs as dose metric. Because of the well-documented large structure-dependent differences between sub-groups of PA congeners with respect to their genotoxicity and (cyto)toxicity, however, this procedure is inadequate. Here we provide an overview of recent attempts to assess the risk of PA exposure and the available literature on the toxic effects and potencies of different congeners. Based on these considerations, we have derived interim Relative Potency (REP) factors for a number of abundant PAs suggesting a factor of 1.0 for cyclic di-esters and open-chain di-esters with 7S configuration, of 0.3 for mono-esters with 7S configuration, of 0.1 for open-chain di-esters with 7R configuration and of 0.01 for mono-esters with 7R configuration. For N-oxides we suggest to apply the REP factor of the corresponding PA. We are confident that the use of these values can provide a more scientific basis for PA risk assessment until a more detailed experimental analysis of the potencies of all relevant congeners can be carried out.} +} + +@article{Yan2008, + author = {J. Yan and Q. Xia and M.W. Chou and P.P. Fu}, + year = 2008, + title = {Metabolic activation of retronecine and retronecine {N-oxide} - formation of {DHP}-derived {DNA} adducts}, + journal = {Toxicol. Ind. Health}, + number = {24(3)}, + pages = {181-8}, + doi = {https://doi.org/https://doi.org/10.1177/0748233708093727}, +} + +@misc{HMPC2014, + author = {HMPC}, + year = 2014, + title = {Public statement on the use of herbal medicinal products 5 containing toxic, unsaturated pyrrolizidine alkaloids (PAs), European Medicines Agency, Committee on Herbal Medicinal Products (HMPC) EMA/HMPC/8931082011}, +} + +@misc{EMA2020, + author = {EMA}, + year = 2020, + title = {Public statement on the use of herbal medicinal products containing toxic, unsaturated pyrrolizidine alkaloids (PAs) including recommendations regarding contamination of herbal medicinal products with pyrrolizidine alkaloids. European Medicines Agency, Committee on Herbal Medicinal Products (HMPC), EMA/HMPC/893108/2011 Rev.1}, +} + +@article{Forsch2018, + author = {Forsch, K. and V. Schöning and L. Disch and B. Siewert and M. Unger and J. Drewe}, + year = 2018, + title = {Development of an in vitro screening method of acute cytotoxicity of the pyrrolizidine alkaloid lasiocarpine in human and rodent hepatic cell lines by increasing susceptibility}, + journal = {Journal of Ethnopharmacology}, + number = 217, + pages = {134-139}, + doi = {https://doi.org/10.1016/j.jep.2018.02.018}, +} + @misc{ICH2017, - author = {International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use (ICH)}, - title = {Assessment and control of DNA reactive (mutagenic) impurities in pharmaceuticals to limit potential carcinogenic risk M7(R1)}, + author = {{International Council for Harmonisation of Technical Requirements for Pharmaceuticals for Human Use (ICH)}}, + title = {Assessment and control of {DNA} reactive (mutagenic) impurities in pharmaceuticals to limit potential carcinogenic risk M7(R1)}, year = 2017, note = {\url{https://database.ich.org/sites/default/files/M7_R1_Guideline.pdf}}, note = {Accessed: 29-03-2021}, @@ -21,7 +119,8 @@ title = {Mutagenicity of pyrrolizidine alkaloids in the Salmonella typhimurium/mammalian microsome system}, journal = {Mutation research}, number = 281, - pages = {143–147} + pages = {143–147}, + doi = {https://doi.org/https://doi.org/10.1016/0165-7992(92)90050-r} } @article{Chen2010, @@ -30,38 +129,54 @@ title = {Genotoxicity of pyrrolizidine alkaloids}, journal = {J. Appl. Toxicol.}, numbr = 30, - pages = {183-96} + pages = {183-96}, + doi = {https://doi.org/10.1002/jat.1504} } @article{Li2013, - authors = {Li YH, Kan WL, Li N, Lin G}, - year = 2013, - title = {Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model}, - journal = {J. Ethnopharmacol.}, - number = 150, - pages = {560-7} +title = {Assessment of pyrrolizidine alkaloid-induced toxicity in an in vitro screening model}, +journal = {Journal of Ethnopharmacology}, +volume = {150}, +number = {2}, +pages = {560-567}, +year = {2013}, +issn = {0378-8741}, +doi = {https://doi.org/10.1016/j.jep.2013.09.010}, +url = {https://www.sciencedirect.com/science/article/pii/S0378874113006430}, +author = {Yan Hong Li and Winnie Lai Ting Kan and Na Li and Ge Lin}, +keywords = {Pyrrolizidine alkaloids, model, Cytotoxicity, HepG2 cell}, +abstract = {Ethnopharmacological relevance +Pyrrolizidine alkaloids (PAs) are a group of heterocyclic phytotoxins present in a wide range of plants. The consumption of PA-containing medicinal herbs or PA-contaminated foodstuffs has long been reported to cause human hepatotoxicity. However, the degrees of hepatotoxicity of different PAs are unknown, which makes it difficult to determine a universal threshold of toxic dose of individual PAs for safe regulation of PA-containing natural products. The aim of the present study is to develop a simple and convenient in vitro model to assess the hepatotoxicity of different PAs. +Material and methods +Six common cytotoxicity assays were used to evaluate the hepatotoxicity of different PAs in human hepatocellular carcinoma HepG2 cells. +Results +The combination of MTT and bromodeoxyuridine incorporation (BrdU) assays demonstrated to be a suitable method to evaluate the toxic potencies of various PAs in HepG2 cells, and the results indicated that otonecine-type PA (clivorine: IC20=0.013±0.004mM (MTT), 0.066±0.031mM (BrdU)) exhibited significantly higher cytotoxic and anti-proliferative effects than retronecine-type PA (retrorsine: IC20=0.27±0.07mM (MTT), 0.19±0.03mM (BrdU)). While as expected, the known less toxic platyphylline-type PA (platyphylline: IC20=0.85±0.11mM (MTT), 1.01±0.40mM (BrdU)) exhibited significantly less toxicity. The different cytotoxic and anti-proliferative potencies of various PAs in the same retronecine-type could also be discriminated by using the combined MTT and BrdU assays. In addition, the developed assays were further utilized to test alkaloid extract of Gynura segetum, a senecionine and seneciphylline-containing herb, the overall cytotoxicity of two PAs in the extract was comparable to that of these two PAs tested individually. +Conclusion +Using the developed in vitro model, the cytotoxicity of different PAs and the extract of a PA-containing herb were investigated in parallel in one system, and their different hepatotoxic potencies were determined and directly compared for the first time. The results suggested that the developed model has a great potential to be applied for the quick screening of the toxicity of PAs and PA-containing natural products.} } @article{Xia2013, - authors = {Xia, Q. and Zhao, Y. and Von Tungeln, L.S. and Doerge, D.R. and Lin, G. and et al.}, + author = {Q. Xia and Y. Zhao and L.S. Von Tungeln and D.R. Doerge and G. Lin and G. Cai and P.P. Fu}, year = 2013, - title = {Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity}, + title = {Pyrrolizidine alkaloid-derived {DNA} adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity}, journal = {Chem Res. Toxicol.}, number = 26, - pages = {1384-96} + pages = {1384-96}, + doi = {https://doi.org/https://doi.org/10.1021/tx400241c} } @article{Fu2004, - authors = {Fu, P.P. and Xia, Q. and, Lin, G. and Chou, M.W.}, + author = {P. P. Fu and Xia, Q. and Lin, G. and Chou, M. W.}, year = 2004, title = {Pyrrolizidine alkaloids--genotoxicity, metabolism enzymes, metabolic activation, and mechanisms}, journal = {Drug Metab. Rev.}, number = 36, - pages = {1-55} + pages = {1-55}, + doi = {https://doi.org/https://doi.org/10.1081/dmr-120028426} } @article{Louisse2019, - title = {Determination of genotoxic potencies of pyrrolizidine alkaloids in HepaRG cells using the γH2AX assay}, + title = {Determination of genotoxic potencies of pyrrolizidine alkaloids in {HepaRG} cells using the {γH2AX} assay}, journal = {Food and Chemical Toxicology}, volume = {131}, pages = {110532}, @@ -75,7 +190,7 @@ } @article{Allemang2018, - title = {Relative potency of fifteen pyrrolizidine alkaloids to induce DNA damage as measured by micronucleus induction in HepaRG human liver cells}, + title = {Relative potency of fifteen pyrrolizidine alkaloids to induce {DNA} damage as measured by micronucleus induction in {HepaRG} human liver cells}, journal = {Food and Chemical Toxicology}, volume = {121}, pages = {72-81}, @@ -88,7 +203,7 @@ abstract = {Plant-based 1,2-unsaturated Pyrrolizidine Alkaloids (PAs) can be found as contaminants in foods like teas, herbs and honey. PAs are responsible for liver genotoxicity/carcinogenicity following metabolic activation, making them a relevant concern for safety assessment. Current regulatory risk assessments take a precautionary approach and assume all PAs are as potent as the known most potent representatives: lasiocarpine and riddelliine. Our study investigated whether genotoxicity potency differed as a consequence of structural differences, assessing micronuclei in vitro in HepaRG cells which express metabolising enzymes at levels similar to primary human hepatocytes. Benchmark Dose (BMD) analysis was used to calculate the critical effect dose for 15 PAs representing 6 structural classes. When BMD confidence intervals were used to rank PAs, lasiocarpine was the most potent PA and plotted distinctly from all other PAs examined. PA-N-oxides were least potent, notably less potent than their corresponding parent PA's. The observed genotoxic potency compared favorably with existing in vitro data when metabolic competency was considered. Although further consideration of biokinetics will be needed to develop a robust understanding of relative potencies for a realistic risk assessment of PA mixtures, these data facilitate understanding of their genotoxic potencies and affirm that not all PAs are created equal.} } @article{Hadi2021, - title = {Genotoxicity of selected pyrrolizidine alkaloids in human hepatoma cell lines HepG2 and Huh6}, + title = {Genotoxicity of selected pyrrolizidine alkaloids in human hepatoma cell lines {HepG2} and {Huh6}}, journal = {Mutation Research/Genetic Toxicology and Environmental Mutagenesis}, volume = {861-862}, pages = {503305}, @@ -120,10 +235,10 @@ The widely available human hepatoma cell lines HepG2 and Huh6 were suitable for } @article{Langel2011, - author = {Langel, D. and Ober, D. and Pelser P.B.}, + author = {Langel, D. and Ober, D. and Pelser, P.B.}, year = 2011, title = {The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the Senecioneae}, - jounrnal = {Phytochemistry Reviews}, + journal = {Phytochemistry Reviews}, number = 10, pages = {3-74} } @@ -154,15 +269,7 @@ The widely available human hepatoma cell lines HepG2 and Huh6 were suitable for year = 2017, number = 160, pages = {361-370}, -} - -@article{EFSA2011, - author = {EFSA}, - title = {Scientific Opinion on Pyrrolizidine alkaloids in food and feed}, - journal = {EFSA Journal}, - year = 2011, - number = 9, - pages = {1-134}, + doi = {https://doi.org/https://doi.org/10.1093/toxsci/kfx187}, } @book{Mattocks1986, @@ -174,7 +281,7 @@ The widely available human hepatoma cell lines HepG2 and Huh6 were suitable for @article{Maaten2008, author = {van der Maaten, L.J.P. and Hinton, G.E.}, - title = {Visualizing Data Using t-SNE}, + title = {Visualizing Data Using {t-SNE}}, journal = {Journal of Machine Learning Research}, year = 2008, number = 9, @@ -238,12 +345,13 @@ eprint = { } @article{Yap2011, - author = "Yap, CW.", + author = "Yap, C.W.", year = 2011, - title = "PaDEL-descriptor: an open source software to calculate molecular descriptors and fingerprints", + title = {{PaDEL-descriptor}: an open source software to calculate molecular descriptors and fingerprints}, journal = "Journal of computational chemistry", number = 32, - pages = "1466-74" + pages = "1466-74", + doi = {https://doi.org/10.1002/jcc.21707} } @Article{Bender2004, @@ -504,15 +612,24 @@ eprint = { pages = "215--220", } -@Article{EFSA2016, - author = {EFSA}, - year = "2016", - title = "Guidance on the establishment of the residue - definition for dietary assessment: {EFSA} panel on Plant - Protect Products and their Residues ({PPR})", - journal = "EFSA Journal", - number = "14", - pages = "1--12", +@article{EFSA2011, + author = {EFSA}, + title = {Scientific Opinion on Pyrrolizidine alkaloids in food and feed}, + journal = {EFSA Journal}, + year = 2011, + number = 9, + pages = {1-134}, + doi = {https://doi.org/10.2903/j.efsa.2011.2406}, +} + +@article{EFSA2016, + author = {{EFSA}}, + title = {Guidance on the establishment of the residue definition for dietary assessment: {EFSA} panel on Plant Protect Products and their Residues ({PPR})}, + journal = {EFSA Journal}, + year = 2016, + number = 14, + pages = {1-12}, + doi = {https://doi.org/10.2903/j.efsa.2016.4549}, } @TechReport{ECHA2008, |