Relevant bibliographies by topics / Heterocyclic aromatic amines

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Academic literature on the topic 'Heterocyclic aromatic amines'

Author: Grafiati
Published: 4 June 2021
Last updated: 18 February 2022

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Journal articles on the topic "Heterocyclic aromatic amines"

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D.A., Utyanov, Kulikovskii A.V., Knyazeva A.S., and Kurzova A.A. "Studies of the accumulation of HAA in chilled second dinner dishes with garnish." Vsyo o myase, no. 5 (October 30, 2020): 30–32. http://dx.doi.org/10.21323/2071-2499-2020-5-30-32.

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The studies carried out made it possible to establish that during the industrial preparation of second lunch dishes with a garnish, heterocyclic aromatic amines are formed in the meat components. Heterocyclic aromatic amines were found in all samples tested. However, the lack of information on the preparation technology of the selected samples does not allow a full analysis of the results obtained. The largest amount of heterocyclic aromatic amines was formed in samples with chicken meat, which was prepared at the highest temperatures relative to other samples. The presence of heterocyclic aromatic amines in all studied samples indicates the potential harm of consumption of such products for human health
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OZ, FATIH, and MUKERREM KAYA. "HETEROCYCLIC AROMATIC AMINES IN MEAT." Journal of Food Processing and Preservation 35, no. 6 (April 26, 2011): 739–53. http://dx.doi.org/10.1111/j.1745-4549.2011.00524.x.

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Murkovic, M. "Analysis of heterocyclic aromatic amines." Analytical and Bioanalytical Chemistry 389, no. 1 (June 2, 2007): 139–46. http://dx.doi.org/10.1007/s00216-007-1306-z.

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Chen, Yuanguang, Fangyu Du, Fengyang Chen, Qifan Zhou, and Guoliang Chen. "Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation." Synthesis 51, no. 24 (October 14, 2019): 4590–600. http://dx.doi.org/10.1055/s-0039-1690702.

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In the selective N-arylation of amines or azoles with aryl halides­, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.
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Richling, E., M. Herderich, D. Häring, and P. Schreier. "Analysis of heterocyclic aromatic amines (HAA)." Fresenius' Journal of Analytical Chemistry 360, no. 7-8 (April 2, 1998): 804. http://dx.doi.org/10.1007/s002160050812.

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Fujita, Ken-ichi, Genki Toyooka, and Akiko Tuji. "Efficient and Versatile Catalytic Systems for the N-Methylation of Primary Amines with Methanol Catalyzed by N-Heterocyclic Carbene Complexes of Iridium." Synthesis 50, no. 23 (August 30, 2018): 4617–26. http://dx.doi.org/10.1055/s-0037-1610252.

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Efficient and versatile catalytic systems were developed for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. Iridium complexes bearing an N-heterocyclic carbene (NHC) ligand exhibited high catalytic performance for this type of transformation. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures (50–90 °C). For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished by simply changing the reaction conditions (presence or absence of a base with an appropriate catalyst). These findings can be used to develop methods for synthesizing useful amine compounds having N-methyl or N,N-dimethyl moieties.
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Ebrahimi, Behzad, and Maryam Farshidi. "Innovative Approaches for the Degradation of Biogenic Amines in Foods." Current Nutrition & Food Science 15, no. 6 (September 18, 2019): 627–28. http://dx.doi.org/10.2174/1573401314666180620161417.

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Biogenic Amines (BA) are low molecular weight organic bases that have biological activity, they can be formed and degraded as a result of normal metabolic activity in animals, plants and microorganisms, and are usually produced by the decarboxylation of amino acids. The most common biogenic amines which can be found in foods are aliphatic (putrescine, cadaverine, spermine, spermidine), aromatic (tyramine, phenylethyl amine) or heterocyclic (histamine, tryptamine) structures.
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Lušnic Polak, Mateja, Lea Demšar, Iva Zahija, and Tomaž Polak. "Influence of temperature on the formation of heterocyclic aromatic amines in pork steaks." Czech Journal of Food Sciences 38, No. 4 (August 31, 2020): 248–54. http://dx.doi.org/10.17221/144/2019-cjfs.

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The aim of the present study was to evaluate the effects of grilling temperatures on the formation of heterocyclic aromatic amines (HAAs) in steaks from the pork loin (longissimus lumborum muscle). Grilling was carried out on a double hot plate grill set to the usual grilling temperatures of 120 °C to 280 °C and stopped when the internal temperature of 72 °C was reached. Among individual HAAs, the most abundant was 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine (PhIP), as a maximum of 28.62 ng g<sup>–1</sup> pork steak. in general, the total HAA levels increased with increasing grilling temperature. Higher HAA levels were observed at 260 °C compared to 240 °C, at 13.97 ng g<sup>–1</sup>, as a 68.7% increase. The highest total HAA levels were found at 280 °C (29.64 ng g<sup>–1</sup> grilled pork steak), as a 258.0% increase compared to 240 °C. These data indicate that the formation of potentially carcinogenic HAAs during the grilling of pork steaks can be minimised by the using of lower grilling temperatures (≤ 240 °C).
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Janoszka, Beata, Agnieszka Nowak, Magdalena Szumska, Ewa Śnieżek, and Krystyna Tyrpień-Golder. "HUMAN EXPOSURE TO BIOLOGICALLY ACTIVE HETEROCYCLIC AROMATIC AMINES ARISING FROM THERMAL PROCESSING OF PROTEIN RICH FOOD." Wiadomości Lekarskie 72, no. 8 (2019): 1542–50. http://dx.doi.org/10.36740/wlek201908123.

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Frequent consumption of thermally processed meat was classified by the International Agency for Research on Cancer to directly carcinogenic agents for humans. During the heat treatment of high protein food, mutagenic and carcinogenic, as well as neurotoxic heterocyclic aromatic amines are formed. Epidemiological studies confirm that exposure to some of these compounds may increase the risk of cancer in humans, especially the colon cancer. Most heterocyclic amines contain fried and grilled meat products, and the lowest content of these compounds can be found in boiled and slightly baked dishes. The use of spices and vegetable additives with antioxidant properties allows to obtain dishes with reduced content of these xenobiotics. An effective way to reduce human exposure to cancerogenic amines may be simultaneous consumption, together with meat dishes, products containing fiber which can adsorb molecules of heterocyclic amines in the gastrointestinal tract, as well as enrichment of the diet in the crucifers plants, as isothiocyanates released from them can inhibit the metabolic activation processes of heterocyclic amines. Raising the public awareness of the formation of mutagenic and carcinogenic compounds, including heterocyclic aromatic amines, during the intensive heat treatment of high protein food, as well as the dissemination of knowledge on the conditions regarding the preparation of dishes with reduced content of such compounds could become one of the components of cancer prevention programs in Poland.
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Murkovic, M., Manfred Friedrich, and Werner Pfannhauser. "Heterocyclic aromatic amines in fried poultry meat." Zeitschrift f�r Lebensmitteluntersuchung und -Forschung A 205, no. 5 (October 28, 1997): 347–50. http://dx.doi.org/10.1007/s002170050178.

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Dissertations / Theses on the topic "Heterocyclic aromatic amines"

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Ayrton, Andrew David. "Food mutagens : factors that modulate their metabolic activation." Thesis, University of Surrey, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.328576.

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Hubbard, Sara E. "The solid-matrix luminescence of heterocyclic aromatic amines in sugar glasses." Laramie, Wyo. : University of Wyoming, 2008. http://proquest.umi.com/pqdweb?did=1597616951&sid=1&Fmt=2&clientId=18949&RQT=309&VName=PQD.

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Lu, Fei. "Formation and control of heterocyclic amines and polycyclic aromatic hydrocarbons during meat processing." Thesis, University of Reading, 2018. http://centaur.reading.ac.uk/77712/.

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Heterocyclic amines (HCAs) and polycyclic aromatic hydrocarbons (PAHs) formed during meat processing may pose health risk to the public. This project aimed to investigate the occurrence of HCAs and PAHs in highly consumed cooked meat products including ready-to-eat (RTE) meat, patties and meatballs, and their health risk was also assessed according to the dietary pattern. Different strategies including replacing fat with vegetable oils and adding spices were applied in order to reduce the formation of HCAs and PAHs in final meat products. In addition, inhibitory mechanism of antioxidants in oil and spices on the formation of HCAs and PAHs in meat system were also discussed. In this work, HCAs and PAHs were extracted by solid-phase extraction and analysed by HPLC- Diode array UV/ Fluorescence detector. For RTE meat in UK, chargrilled chicken had the highest level of HCAs (37.45±4.89ng/g) and PAHs (3.11±0.49ng/g), followed by roasted bacon (HCAs 15.24±1.31ng/g, PAHs 1.75±0.17ng/g) in selected RTE meat products. Increase intake of chargrilled chicken and ham could increase breast cancer and colorectal adenoma risk, but other types of meat had relatively lower health risk. Replacing pork back fat with vegetable oils including sunflower oil, olive oil and grape seed oil could not only improve fatty acids profile in cooked meat products, but also reduce HCAs, which could be attributed to the existence of tocopherols and polyphenol compounds in the vegetable oils. However, antioxidants in the oils could not reduce the total amount of PAHs effectively, while the complexity of oil decomposition and antioxidants performance at high temperature could partially explain the case. All 6 spices powder including garlic, onion, red chilli, paprika, black pepper and ginger reduced the formation of total HCAs, while ginger powder achieved the highest inhibition efficiency compared with all other spices. Antioxidant capacity of spices determined their efficiency in prohibiting formation of HCAs and PAHs in great extent, while meat type only affected the formation of HCAs (p < 0.05), but not PAHs (p > 0.05). Regression model suggested that both diallyl disulfide and gallic acid contributed similar inhibitory efficiency on the formation of HCAs and PAHs. Synergistic effect between diallyl disulfide and gallic acid was observed on reducing HCAs (p < 0.05), but not on PAHs (p > 0.05).
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Scholtka, Bettina, Dana Kühnel, Felicitas Taugner, and Pablo Steinberg. "Inflammation does not precede or accompany the induction of perneoplastic lesions in the colon of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine-fed rats." Universität Potsdam, 2009. http://opus.kobv.de/ubp/volltexte/2010/4457/.

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Heterocyclic aromatic amines (HCAs) are formed in meat cooked at high temperatures for a long time or over an open flame. In this context 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), the most abundant HCA in cooked meat, has been suggested to be involved in colon and prostate carcinogenesis. In the latter case it has been reported that: (1) roughly 50% of Fischer F344 male rats treated with PhIP develop carcinomas in the ventral prostate lobe at 1 year of age; (2) inflammation precedes prostatic intraepithelial neoplasia in PhIP-fed rats; (3) inflammation specifically occurs in the ventral prostate lobe of PhIP-fed rats. To test whether PhIP by itself leads to inflammation in the colon and whether a human-relevant concentration of PhIP is able to induce preneoplastic lesions in the colon, male F344 rats were fed 0.1 or 100 ppm PhIP for up to 10 months and thereafter the colon tissue was analyzed histochemically. In none of the experimental groups signs of acute or chronic colonic inflammation were observed. 0.1 ppm PhIP leads to the development of hyperplastic and dysplastic lesions in the colon of single animals, but the incidence of these lesions does not reach a statistical significance. In contrast, in rats fed 100 ppm PhIP for 10 months hyperplastic and dysplastic colonic lesions were induced in a statistically significant number of animals. It is concluded that: (1) the induction of preneoplastic lesions in rat colon by PhIP is not preceded or accompanied by an inflammatory process; (2) a human-relevant concentration of PhIP alone is not sufficient to initiate colon carcinogenesis in rats.
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Kidd, La Creis R. "Estimation of exposure to two potent heterocyclic aromatic amines in various human populations and their role in colorectal cancer." Thesis, Massachusetts Institute of Technology, 1997. http://hdl.handle.net/1721.1/42653.

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Bellamri, Medjda. "Activation métabolique et génotoxicité des Amines Hétérocycliques Aromatiques (AHA) chez l’Homme." Thesis, Rennes 1, 2016. http://www.theses.fr/2016REN1B033/document.

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Les amines hétérocycliques aromatiques (AHA) sont des contaminants de l'environnement et de l'alimentation, majoritairement formés lors de la cuisson de viande et poisson ainsi que dans la fumée de cigarette et les gaz d'échappements. Les AHA sont mutagènes chez la bactérie, cancérogènes multi-sites chez le rongeur et sont classées comme cancérogènes possibles ou probables chez l'Homme par l'IARC. Il est aujourd'hui indispensable de caractériser des biomarqueurs d'exposition dérivés des AHA (adduits à l'ADN et métabolites) pour améliorer l'estimation du risque chez l'Homme. Des résultats de l'équipe ont démontré que le 2-amino-9H-pyrido[2,3-b]indole (AαC) forme des niveaux d'adduits à l'ADN élevés dans les hépatocytes humains. Ces niveaux sont plus élevés que ceux formés par les autres AHA. L'objectif de cette thèse est de mieux comprendre le potentiel génotoxique d'AαC chez l'Homme. Nos travaux ont démontré que les adduits à l'ADN dérivés d'AαC sont persistants dans les hépatocytes humains et formés à des doses aussi faibles que 1nM. De plus, le CYP1A2 a été confirmé comme enzyme majoritaire dans la bioactivation d'AαC dans le foie humain. Nous avons également caractérisé les métabolites majeurs dérivés d'AαC dans les hépatocytes humains. Cette étude a permis d'établir pour la première fois une corrélation entre l'activité catalytique du CYP1A2, la formation d'AαC-HN2-O-Gl et la formation des adduits à l'ADN dérivés d'AαC. Le métabolite AαC-HN2-O-Gl étant réactif vis-à-vis de l'ADN in vitro, nos travaux confortent l'hypothèse que la voie des UDP-Glucuronosyltransférases (UGTs) est une nouvelle voie de bioactivation d'AαC dans le foie humain. De plus, nous avons montré que les adduits à l'ADN dérivés des AHA sont formés dans les lymphocytes T humains activés et en particulier les adduits en position C8 de la guanine dérivés d'AαC. Au total, ces travaux ont permis l'identification de métabolites stables et des adduits à l'ADN, potentiels biomarqueurs d'exposition à AαC, qui sont indispensables pour une meilleure estimation du risque génotoxique d'AαC chez l'Homme
Heterocyclic aromatic amines (HAA) are environmental and food contaminants, mainly formed during meat and fish cooking, but also in cigarette smoke and exhaust gaz. HAA are mutagenic in bacteria, carcinogenic in rodents and are classified as possible or probable human carcinogens by IARC. Today it is essential to characterize exposure biomarkers i.e. DNA adducts and metabolites, to assess the human risk associated with HAA. The research team has previously demonstrated that 2-amino-9H-pyrido[2,3-b]indole (AαC) form high levels of DNA adducts in human hepatocytes. These levels are greater that those derived from other HAAs. Thus, the aim of this thesis was to better understand the genotoxic potential of AαC in human. We demonstrated that in human hepatocytes, DNA adducts derived from AαC are persistent and formed at doses as low as 1nM. Moreover, we confirmed that CYP1A2 is the major enzyme implicated in the bioactivation of AαC in human liver. We have also characterized the major metabolites derived from AαC formed in human hepatocytes. This study allows, for the first time, the establishment of a correlation between the catalytic activity of CYP1A2, AαC-HN2-O-Gl formation and AαC derived DNA adducts formation. AαC-HN2-O-Gl being reactive toward DNA in vitro, our work reinforces the hypothesis that the UDP-glucuronosyltransferase (UGTs) pathway is a new bioactivation pathway for AαC in human liver. Moreover, we demonstrated the formation of HAA derived DNA adducts, especially those derived from AαC at position C8 of guanine, in activated human T lymphocytes. Taken together, our data lead to the identification of stable metabolites as well as DNA adducts which are potentials AαC exposure biomarkers in human. These biomarkers are essential for a better assessment of the genotoxic risk of AαC in human
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Fuchs, Iris Judith. "Untersuchungen zur chemischen Transformation von intestinalen Epithelzellen der Ratte und des Menschen durch 2-Hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridin." Phd thesis, Universität Potsdam, 2006. http://opus.kobv.de/ubp/volltexte/2007/1180/.

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Lindh, Dillon Beatrice. "Kan marinering av kött reducera uppkomsten av heterocykliska aminer vid tillagning? : En litteraturstudie." Thesis, Linnéuniversitetet, Institutionen för kemi och biomedicin (KOB), 2019. http://urn.kb.se/resolve?urn=urn:nbn:se:lnu:diva-85844.

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Bakgrund: Över 20 mutagena ämnen har detekterats i tillagade livsmedel. Till dessa räknas heterocykliska aminer. Studier har visat att dessa aminer kan orsaka mutationer och därmed öka risken för att utveckla cancer. Heterocykliska aminer bildas under tillagning av kött i höga temperaturer genom Maillardreaktionen. Syfte: Syftet med denna litteraturstudie var att se om marinering med öl, vin eller örtkryddor kan minska bildningen av heterocykliska aminer vid tillagning av kött. Metod: Denna studie är en litteraturstudie med ett urval av artiklar från databaserna PubMed och Web of Science. Totalt inkluderades 6 artiklar varav 3 artiklar studerade marinering med öl/vin och 3 studerade marinering med örtkryddor och örtextrakt. Resultat: Samtliga studier som undersöktes visade att marinering har en reducerande effekt på mängden heterocykliska aminer som bildas vid tillagning. Den mest troliga hypotesen om mekanismen är att effekten beror på den antioxidativa förmågan hos marinaderna. Ett exempel är en marinad med kombinationen gurkmeja och citrongräs som reducerade koncentrationen heterocykliska aminer med 94,8%. Slutsats: Marinering med öl, vin eller örtkryddor visades effektivt reducera mängden heterocykliska aminer. Stora reducerande effekter detekterades i marinader med gurkmeja, citrongräs, ingefära och mörk lager. Mer forskning behövs för att fastställa om reduktionen är kopplad till den antioxidativa effekten hos marinaderna
Background: Over 20 different mutagenic substances has been detected in cooked food. These include heterocyclic amines. Studies have shown that these amines can create mutations and increase the risk of developing cancer. Heterocyclic amines are formed in meat during the Maillard reaction which occours at high temperature cooking. Aim: The aim of this study was to investigate if the effect of marinating with beer, wine and herbs/spices can reduce the formation of heterocyclic amines found in cooked meat. Method: This study is a literature study with a selection of articles from databases PubMed and Web of Science. Six articles were included in this study. 3 articles involved marinade with beer/wine and 3 articles involved marinade with herbs/spices and extract. Results: All studies examined showed that marinating has a reducing effect on the concentration of heterocyclic amines formed during cooking. The most credible hypothesis of the mechanism is that the effect depends on the antioxidativ capacity of the marinades. For example one marinade with the combination of turmeric and lemon grass reduced the concentration of heterocyclic amines by 94,8%. Conclusion: Marinades containing beer, wine or herbs/spices was shown to effectively reduce the amount of heterocyclic amines. Great reducing effects were found using turmeric, lemon grass, ginger and black beer. More scientific research is needed to determine if the reduction is linked to the antioxidant effect in marinades.
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Tatton, Matthew R. "New methods for the synthesis of aromatic compounds." Thesis, University of Oxford, 2014. http://ora.ox.ac.uk/objects/uuid:52a95189-d8ea-432f-aefd-4f9ae7ef996a.

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Introduction The introduction describes the importance of arylamine compounds to society and provides a brief overview of the methods available for their synthesis. The application of metathesis catalysis to the de novo synthesis of heteroaromatic compounds is also described. Results and discussion The first section describes efforts towards the de novo synthesis of arylamines using a cross metathesis/oxidation protocol to form a 1,5-unsaturated dicarbonyl followed by an amine mediated cyclisation. The scope with respect to the 1,5-unsaturated dicarbonyl and amine is covered as well as the utility of some of the products. The section concludes with a modification of the Bohlmann Rahtz pyridine synthesis to furnish arylamines. The next section describes the applications of our methodology to the synthesis of naphthylamines, specifically using the palladium catalysed α-arylation reaction. A discussion of the α-arylation reaction is included as well as our efforts to explore the scope of the reaction. The third section follows our efforts to apply this methodologyy to the synthesis of five benzo[c]phenanthridine alkaloids including the first reported synthesis of maclekarpine B and C. The final section concludes with a discussion of our efforts towards the de novo synthesis of furans bearing a benzylic stereocentre.
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Wend, Korinna. "Konstruktion und toxikologische Nutzung von transgenen Mäusen mit den allelischen Varianten von humanen SULT1A-Genen." Phd thesis, Universität Potsdam, 2009. http://opus.kobv.de/ubp/volltexte/2010/4205/.

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Eine besondere Rolle im Fremdstoffmetabolismus hat die SULT1A1 beim Menschen aufgrund der hohen Expression und breiten Gewebeverteilung. Während die humane SULT1A1 in sehr vielen Geweben exprimiert wird, wurde die murine SULT1A1 vor allem in der Leber, Lunge und Colon gefunden. Neben der Gewebeverteilung spielt auch der Polymorphismus im humanen SULT1A1-Gen eine bedeutende Rolle. Der häufigste Polymorphismus in diesem Gen führt zu einer Aminosäuresubstitution von Arginin zu Histidin an Position 213. Die Genvariante mit Histidin (auch als SULT1A1*2 bezeichnet) codiert für ein Protein mit einer geringen Enzymaktivität und einer reduzierten Enzymmenge in Thrombocyten. Über den Einfluss dieser allelischen Varianten in anderen Geweben ist bislang wenig bekannt. In vorausgegangenen epidemiologischen Studien wurden mögliche Korrelationen zwischen den Genvarianten und der Krebsentstehung in verschiedenen Geweben untersucht. Diese Daten liefern jedoch widersprüchliche Ergebnisse zum Krebsrisiko. Aufgrund der strittigen epidemiologischen Daten sollten Tiermodelle generiert werden, um die häufigsten SULT1A1-Allele hinsichtlich der Empfindlichkeit gegenüber Nahrungs- und Umweltkanzerogenen zu untersuchen. Zur Erzeugung transgener (tg) Mauslinien wurde mittels Mikroinjektion der codierenden Genbereich und große flankierende Humansequenzen stromaufwärts und stromabwärts in das Mausgenom integriert. Es wurden mehrere Mauslinien hergestellt. Zwei davon, die Mauslinie 31 mit dem SULT1A1*1-Allel und die Mauslinie 28 mit dem SULT1A1*2-Allel, wurden eingehend analysiert. In beiden Linien wurde eine identische Kopienzahl des Transgens ermittelt. Proteinbiochemische Charakterisierungen zeigten eine weitgehend dem Menschen entsprechende Gewebeverteilung und zelluläre und subzelluläre Lokalisation der humanen SULT1A1 in der Linie (Li) 28. In Li 31 wurden Unterschiede zu Li 28 sowohl in der Gewebeverteilung als auch in der zellulären Lokalisation des exprimierten humanen Proteins ermittelt. Dabei war die Expression auf Proteinebene in der SULT1A1*2-tg Linie generell stärker als in der SULT1A1*1-Linie. Dieses Ergebnis war überraschend, denn in humanen Thrombocyten führt das SULT1A1*1-Allel zu einem höheren Gehalt an SULT1A1-Protein als das SULT1A1*2-Allel. Zur Analyse der unterschiedlichen Proteinexpressionen in den tg Mauslinien wurde die cDNA und der 5´-flankierende Bereich des SULT1A1-Gens sequenziert. In beiden tg Linien entsprach die Sequenz der cDNA der Referenzsequenz aus der Gendatenbank (Pubmed). In der 5´-flankierenden Region wurden bekannte Polymorphismen analysiert und unterschiedliche Haplotypen in den tg Linien an den Positionen -624 und -396 ermittelt. Dabei wurde in der Li 31 der Haplotyp detektiert, der in der Literatur mit einer höheren SULT1A1-Enzymaktivität beschrieben wird. Der mögliche Zusammenhang zwischen Transkriptionsrate und Proteinexpression wurde in RNA-Expressionsanalysen im codierenden und 5´-nicht codierenden Bereich (mit den alternativen Exons 1B und 1A) untersucht. Im codierenden Bereich und im Exon 1B konnte in den untersuchten Organen eine höhere RNA-Expression in der Li 28 im Vergleich zur Li 31 ermittelt werden. Außer in der Lunge wurde für Exon 1B eine identische RNA-Expression detektiert. RNA, die Exon 1A enthielt, wurde in allen untersuchten Organen der Li 28, aber nur in der Lunge bei der Li 31 gefunden. In beiden tg Linien konnten mit den Exon 1A-Primern jedoch auch größere PCR-Produkte ermittelt werden. Dieser Unterschied im Exon 1A und mögliche Spleißvarianten könnten damit für die unterschiedliche Proteinexpression des humanen SULT1A1-Proteins in den beiden tg Mauslinien sein. Die in dieser Arbeit generierten und charakterisierten tg Mausmodelle wurden in einer toxikologischen Studie eingesetzt. Es wurde das heterozyklische aromatische Amin 2-Amino-1-methyl-6-phenylimidazo-[4,5-b]pyridin (PhIP) verwendet. PhIP wird beim Erhitzen und Braten von Fleisch und Fisch gebildet und könnte mit der erhöhten Krebsentstehung im Colon in der westlichen Welt im Zusammenhang stehen. Mittels 32P-Postlabelling sollte der Einfluss der zusätzlichen Expression der humanen SULT-Proteine auf die PhIP-DNA-Adduktbildung analysiert werden. Dabei wurden mehr DNA-Addukte in den tg Tieren als in den Wildtyp-Mäusen ermittelt. Die Konzentration der gebildeten DNA-Addukte korrelierte mit der Expressionsstärke des humanen SULT1A1-Proteins in den tg Mäusen. An den in dieser Arbeit generierten tg Mauslinien mit den häufigsten allelischen Varianten des SULT1A1-Gens konnten Unterschiede auf RNA- und Protein-Ebene ermittelt werden. Zudem konnte gezeigt werden, dass die Expression der humanen SULT1A1 eine Auswirkung sowohl auf die Stärke als auch das Zielgewebe der DNA-Adduktbildung in vivo hat.
In humans, SULT1A1 and its polymorphic variants play an important role in xenobiotic metabolism and display a broad tissue distribution and high expression level. This enzyme is expressed in almost every human organ whereas in mice SULT1A1 can only be detected in liver, lung and colon. The most common polymorphism of this gene leads to an amino acid substitution from arginine to histidine at the position 213. In platelets, the allele encoding histidine (also designated as SULT1A1*2) is associated with both low activity and low thermal stability of the SULT protein. However, so far only little is known about the significance of these allelic variants in the other tissues with hSULT1A1 expression. Previous epidemiological studies have made attempts to correlate SULT1A1 allelic variants and cancer development, their data, however, have been contradictory for an appropriate cancer risk assessment. In this thesis, we addressed the effect of the hSULT1A1 genetic variability on the susceptibility to nutritional and environmental carcinogens using transgenic (tg) mouse models. We generated tg mice carrying the most common allelic variants of the human SULT1A1 gene. The coding region and large flanking human sequences upstream and downstream of the hSULT1A1 gene were integrated randomly into the mouse genome by microinjection. Several tg mouse lines were generated. Two of them, line (li) 31 with the SULT1A1*1 allele and li 28 with the SULT1A1*2 allele, were analysed in detail. At first, an identical transgene copy number was detected in both lines. Furthermore, biochemical characterization of li 28 showed that the tissue distribution, the cellular and subcellular localisation of the protein were very similar to those in humans. In contrast, li 31 exhibited differences in tissue distribution and cellular localisation of the human protein compared to li 28. The protein expression level in the tg line with SULT1A1*2 (li 28) was generally higher than in SULT1A1*1 (li 31) mice. These results were surprising since the SULT1A1*1 allele in human platelets usually leads to a higher amount of SULT1A1 protein compared to the SULT1A1*2 allele. To investigate these differences, we sequenced the cDNA and 5´-flanking region of the SULT1A1 gene. In both tg mouse lines, the cDNA sequence was identical to the reference sequence from the gene databank (Pubmed). We subsequently analysed the common polymorphisms of the 5´-flanking region, and determined different haplotypes at position -624 and -396 in the tg mouse lines. According to the literature, the haplotype associated with a higher SULT1A1 enzyme activity, we detected in li 31. We analyzed the possible correlation between gene transcription and protein expression by measuring RNA expression levels of the coding and the non-coding region (with alternative exons 1B and 1A). We detected a higher RNA expression level of the coding region and exon 1B in li 28 compared to li 31, whereas RNA for exon 1A was only found in li 28 in all investigated tissues, but only in lung in li 31. Furthermore we detected with exon 1A-primers larger RNA in both lines. These differences in exon 1A expression accompanied by potential splicing variants could be responsible for the different expression and activity of the human SULT1A1 protein in both tg mouse lines. In order to validate our generated and characterized tg mouse models as toxicological in vivo models, we used them for the evaluation of the heterocyclic aromatic amine 2-amino-1-methyl-6-phenylimidazo-[4,5-b]pyridine (PhIP). PhIP is typically generated during heating and roasting of meat and fish and is suggested to be associated with an increased colon cancer incidence in the western world. We measured the impact of the additionally expressed human SULT proteins on the PhIP-DNA adduct level by 32P-postlabelling. We detected significantly higher DNA adduct levels in tg compared to wildtype mice, which correlated positively with the expression pattern of the human SULT1A1 protein in the tg mice. In conclusion, in this thesis, we have successfully generated and validated the transgenic mouse lines carrying the most common allelic variants of the human SULT1A1 gene. Interestingly, these lines exhibited differences in both the SULT1A1 RNA and protein levels. Using these transgenic mouse models as in vivo toxicological tools we have shown that the expression of human SULT1A1 in mice has a decisive impact on the strength and the target tissue of DNA adducts.
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Books on the topic "Heterocyclic aromatic amines"

1

Sin, Han-sŭng. Sikpʻum chung heterocyclic amines monitʻŏring mit wihae pʻyŏngka =: Monitoring and risk analysis for heterocyclic amines in foods. [Seoul]: Sikpʻum Ŭiyakpʻum Anjŏnchʻŏng, 2007.

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Humans, IARC Working Group on the Evaluation of Carcinogenic Risks to. Some naturally occurring substances: Food items and constituents, heterocyclic aromatic amines and mycotoxins. Lyon: Distributed for the International Agency for Research on Cancer by the Secretariat of the World Health Organization, 1993.

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Dolara, Piero, ed. TOX: lezioni di tossicologia. Florence: Firenze University Press, 2006. http://dx.doi.org/10.36253/88-8453-412-7.

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TOX is a manual aimed primarily at the Toxicology courses of the Faculty of Pharmacy and Science, that can also be profitably utilised by students following different degree courses in other Faculties (Medicine, Agriculture, Engineering)and by anyone else looking for a thorough but succinct overview of toxicological questions. TOX covers the principal sectors of general toxicology (acute and chronic toxicity, mutagenesis, teratogenesis, carcinogenesis, reproductive toxicity, oxidative damage, epidemiological methods), specialist toxicology(dietary toxicity, tobacco smoke, pesticides, N-nitroso compounds, heterocyclic amines and aromatic amines toxicity) and environmental toxicology (environmental estrogens, PAH, heavy metals, dioxins and polychlorinated di-benzo-furans, water and air pollution).
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Lednicer, Daniel. The organic chemistry of drug synthesis. New York: Wiley, 1995.

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Lednicer, Daniel. The organic chemistry of drug synthesis. Chichester: Wiley, 1990.

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Minako, Nago, and Sugimura Takashi, eds. Food borne carcinogens: Heterocyclic amines. Chichester: Wiley, 2000.

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Takashi, Sugimura, and Minako Nagao. Food Borne Carcinogens: Heterocyclic Amines. Wiley, 2000.

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(Contributor), WHO, ed. Some Naturally Occurring Substances: Food Items and Constituents, Heterocyclic Aromatic Amines and Mycotoxins (IARC Monographs on the Evaluation of Carcinogenic Risks to H). World Health Organisation, 1993.

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Lednicer, Daniel. Organic Chemistry of Drug Synthesis. Wiley & Sons, Incorporated, John, 2007.

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Lednicer, Daniel, and Lester A. Mitscher. Volume 4, The Organic Chemistry of Drug Synthesis. Wiley-Interscience, 1990.

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Book chapters on the topic "Heterocyclic aromatic amines"

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Turesky, Robert J. "Heterocyclic Aromatic Amines: Potential Human Carcinogens." In Chemical Carcinogenesis, 95–112. Totowa, NJ: Humana Press, 2010. http://dx.doi.org/10.1007/978-1-61737-995-6_5.

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Turesky, Robert J. "Aromatic Amines and Heterocyclic Aromatic Amines: From Tobacco Smoke to Food Mutagens." In The Chemical Biology of DNA Damage, 157–83. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2010. http://dx.doi.org/10.1002/9783527630110.ch7.

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Knize, Mark G., Cynthia P. Salmon, Pilar Pais, and James S. Felton. "Food Heating and the Formation of Heterocyclic Aromatic Amine and Polycyclic Aromatic Hydrocarbon Mutagens/Carcinogens." In Advances in Experimental Medicine and Biology, 179–93. Boston, MA: Springer US, 1999. http://dx.doi.org/10.1007/978-1-4615-4853-9_12.

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Kato, Ryuichi, and Yasushi Yamazoe. "Enzymic Aspects on the Metabolic Activation of Aromatic and Heterocyclic Amine Mutagens in Mammalian and Bacterial Cells." In Mechanisms of Environmental Mutagenesis-Carcinogenesis, 211–21. Boston, MA: Springer US, 1990. http://dx.doi.org/10.1007/978-1-4615-3808-0_17.

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John, K., and S. Beedanagari. "Heterocyclic Aromatic Amines." In Encyclopedia of Toxicology, 855–63. Elsevier, 2014. http://dx.doi.org/10.1016/b978-0-12-386454-3.01127-1.

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"Heterocyclic Aromatic Amines." In Encyclopedia of Cancer, 2072. Berlin, Heidelberg: Springer Berlin Heidelberg, 2017. http://dx.doi.org/10.1007/978-3-662-46875-3_101091.

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Turesky, Robert J. "Heterocyclic Aromatic Amines." In Advances in Molecular Toxicology, 37–83. Elsevier, 2010. http://dx.doi.org/10.1016/s1872-0854(10)04002-6.

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Sabbioni, G., and E. Richter. "Aromatic Amines, Nitroarenes, and Heterocyclic Aromatic Amines." In Toxicology, 729–41. Elsevier, 1999. http://dx.doi.org/10.1016/b978-012473270-4/50089-4.

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Knize, M. G. "Assessing human exposure to heterocyclic aromatic amines." In Acrylamide and Other Hazardous Compounds in Heat-Treated Foods, 231–46. Elsevier, 2006. http://dx.doi.org/10.1533/9781845692018.2.231.

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Knize, M. "Assessing human exposure to heterocyclic aromatic amines." In Acrylamide and other hazardous compounds in heat-treated foods. CRC Press, 2006. http://dx.doi.org/10.1201/9781439824283.ch11.

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Conference papers on the topic "Heterocyclic aromatic amines"

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Hsu, Ray-Wen, Hung-Lun Liao, and Pen-Cheng Wang. "Removal of aqueous metals from wastewater using porous functional heterocyclic aromatic amines." In 2016 IEEE 11th Annual International Conference on Nano/Micro Engineered and Molecular Systems (NEMS). IEEE, 2016. http://dx.doi.org/10.1109/nems.2016.7758280.

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Zamora, Rosario, and Francisco J. Hidalgo. "Lipid Oxidation and the Formation of Processing-induced Toxicants in Foods: Acrylamide and Heterocyclic Aromatic Amines." In Virtual 2021 AOCS Annual Meeting & Expo. American Oil Chemists' Society (AOCS), 2021. http://dx.doi.org/10.21748/am21.320.

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Ho, Vikki, Sarah Peacock, Thomas E. Massey, Roger W. L. Godschalk, Frederik-Jan van Schooten, Jian Chen, and Will D. King. "Abstract A10: Exposure to heterocyclic aromatic amines, genetic susceptibility and bulky DNA adduct levels in blood leukocytes." In Abstracts: Thirteenth Annual AACR International Conference on Frontiers in Cancer Prevention Research; September 27 - October 1, 2014; New Orleans, LA. American Association for Cancer Research, 2015. http://dx.doi.org/10.1158/1940-6215.prev-14-a10.

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Hsu, Ray-Wen, and Pen-Cheng Wang. "Tuning nanostructured morphology in polymers based on heterocyclic aromatic amines using phenyl amines as additive initiators for the construction of porous functional materials." In 2015 10th International Microsystems, Packaging, Assembly and Circuits Technology Conference (IMPACT). IEEE, 2015. http://dx.doi.org/10.1109/impact.2015.7365215.

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Rohrmann, Sabine, Anja Sander, and Jakob Linseisen. "Abstract B105: Intake of heterocyclic aromatic amines and the risk of prostate cancer in the EPIC‐Heidelberg cohort." In Abstracts: AACR International Conference on Frontiers in Cancer Prevention Research‐‐ Dec 6–9, 2009; Houston, TX. American Association for Cancer Research, 2010. http://dx.doi.org/10.1158/1940-6207.prev-09-b105.

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Azeez, Hashim J., and Roshna Bahram. "Synthesis and spectroscopic identification of a new series of 2-iminothia-zolidin-4-one compounds from aromatic heterocyclic primary amines." In 6TH INTERNATIONAL CONFERENCE AND WORKSHOPS ON BASIC AND APPLIED SCIENCES. Author(s), 2017. http://dx.doi.org/10.1063/1.5004296.

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