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A small library of 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one derivatives was prepared in good to excellent yields, involving a Ag[sub.2]CO[sub.3]/TFA-catalyzed intramolecular oxacyclization of N-Boc-2-alkynylbenzimidazole substrates. In all experiments, the 6-endo-dig cyclization was exclusively achieved since the possible 5-exo-dig heterocycle was not observed, indicating the high regioselectivity of this process. The scope and limitations of the silver catalyzed 6-endo-dig cyclization of N-Boc-2-alkynylbenzimidazoles as substrates, bearing various substituents, were investigated. While ZnCl[sub.2] has shown limits for alkynes with an aromatic substituent, Ag[sub.2]CO[sub.3]/TFA demonstrated its effectiveness and compatibility regardless of the nature of the starting alkyne (aliphatic, aromatic or heteroaromatic), providing a practical regioselective access to structurally diverse 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-ones in good yields. Moreover, the rationalization of oxacyclization selectivity in favor of 6-endo-dig over 5-exo-dig was explained by a complementary computational study.

Heterocyclic aromatic amine molecularly imprinted polymer nanospheres with surface-bound dithioester groups (haa-MIP) were firstly synthesized via reversible addition-fragmentation chain transfer (RAFT) precipitation polymerization. Then, a series of core-shell structural heterocyclic aromatic amine molecularly imprinted polymer nanospheres with hydrophilic shells (MIP-HSs) were subsequently prepared by grafting the hydrophilic shells on the surface of haa-MIP via on-particle RAFT polymerization of 2-hydroxyethyl methacrylate (HEMA), itaconic acid (IA), and diethylaminoethyl methacrylate (DEAEMA). The haa-MIP nanospheres showed high affinity and specific recognition toward harmine and its structural analogs in organic solution of acetonitrile, but lost the specific binding ability in aqueous solution. However, after the grafting of the hydrophilic shells on the haa-MIP particles, the surface hydrophilicity and water dispersion stability of the polymer particles of MIP-HSs greatly improved. The binding of harmine by MIP-HSs with hydrophilic shells in aqueous solutions is about two times higher than that of NIP-HSs, showing an efficient molecular recognition of heterocyclic aromatic amines in aqueous solution. The effect of hydrophilic shell structure on the molecular recognition property of MIP-HSs was further compared. MIP-PIA with carboxyl groups containing hydrophilic shells showed the highest selective molecular recognition ability to heterocyclic aromatic amines in aqueous solution.

Thermal processing is the most important and popular domestic cooking method. More than 30 heterocyclic aromatic amines have been identified in cooked meat using various methods. This review highlights preventive potential and mechanism of dietary polyphenols on the formation of heterocyclic amines. Tea, coffee, fruits, vegetable, and spice extracts rich in polyphenols exerted significant inhibition against the formation of heterocyclic aromatic amines. Some polyphenols, such as naringenin and epigallocatechin 3‐O‐gallate, can actively participate into food chemistry reaction to trap Strecker aldehyde and lower the formation of heterocyclic aromatic amines. In addition, some polyphenols can lower the mutagenicity of heterocyclic aromatic amines. More specifically, polyphenols possessing two hydroxyl groups at the meta position of aromatic ring are the most efficient one, but the presence of carboxylic or alkyl groups as substituents in the aromatic ring slightly reduced the inhibitory effect. Some spice/herbs are applied to inhibit heterocyclic aromatic amines (HAAs) formation

This work describes the development of an ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method for the determination of 23 primary aromatic amines (PAAs) that can potentially migrate from food contact materials. The chromatographic separation was performed in a pentafluorophenylpropyl (PFPP) column achieving the separation of all PAAs in less than 6.5 min using water to acetonitrile (0.1% acetic acid in both solvents) as mobile phase and a gradient elution. The feasibility of atmospheric pressure chemical ionization (APCI) and atmospheric pressure photoionization (APPI) was evaluated as alternative to electrospray ionization (ESI) for the analysis of PAAs. Results showed that for most of the compounds, better responses were obtained with APCI, which shows the advantage of being less susceptible to matrix effects. Tandem mass spectrometry (MS/MS) fragmentation studies of [M + H]+ allowed for the selection of the two most characteristic and abundant product ions of the 23 PAAs which led to the development of a selective and sensitive UHPLC-APCI-MS/MS method with limits of detection ranging from 0.2 to 2 μg kg−1. Moreover, intra-day and inter-day precisions of the method in terms of relative standard deviation (RSD%) were lower than 10% and 15%, while trueness as relative error was <15% for most of the compounds. The UHPLC-APCI-MS/MS method was applied to the analysis of twenty black Nylon kitchenware samples that were submitted to migration tests using food simulant B (3% acetic acid, w/v), and the presence of PAAs were detected in eighteen samples at concentrations above the legislated limit (2 μg kg−1 of food or food simulants).

The heating process is a crucial step that can lead to the formation of several harmful chemical compounds in red meat such as heterocyclic aromatic amines, N-Nitrosamines, polycyclic aromatic hydrocarbons and acrylamide. Meat has high nutritional value, providing essential amino acids, bioactive compounds and several important micronutrients which can also be affected by heating processes. This review aims to provide an updated overview of the effects of different heating processes on both the safety and nutritional parameters of cooked red meat. The most-used heating processes practices were taken into consideration in order to develop a risk–benefit scenario for each type of heating process and red meat.

Heterocyclic aromatic amines (HAAs) form during the high-temperature cooking of meats, poultry, and fish. Some HAAs also arise during the combustion of tobacco. HAAs are multisite carcinogens in rodents, inducing cancer of the liver, gastrointestinal tract, pancreas, mammary, and prostate glands. HAAs undergo metabolic activation by N-hydroxylation of the exocyclic amine groups to produce the proposed reactive intermediate, the heteroaryl nitrenium ion, which is the critical metabolite implicated in DNA damage and genotoxicity. Humans efficiently convert HAAs to these reactive intermediates, resulting in HAA protein and DNA adduct formation. Some epidemiologic studies have reported an association between frequent consumption of well-done cooked meats and elevated cancer risk of the colorectum, pancreas, and prostate. However, other studies have reported no associations between cooked meat and these cancer sites. A significant limitation in epidemiology studies assessing the role of HAAs and cooked meat in cancer risk is their reliance on food frequency questionnaires (FFQ) to gauge HAA exposure. FFQs are problematic because of limitations in self-reported dietary history accuracy, and estimating HAA intake formed in cooked meats at the parts-per-billion level is challenging. There is a critical need to establish long-lived biomarkers of HAAs for implementation in molecular epidemiology studies designed to assess the role of HAAs in health risk. This review article highlights the mechanisms of HAA formation, mutagenesis and carcinogenesis, the metabolism of several prominent HAAs, and the impact of critical xenobiotic-metabolizing enzymes on biological effects. The analytical approaches that have successfully biomonitored HAAs and their biomarkers for molecular epidemiology studies are presented.

Herein, the effect of the dipping (static) marination process (at 4 °C for 2 h) with different types of vinegar (balsamic, pomegranate, apple, and grape) on various quality properties, including texture and protein profile of beef steaks and the formation of heterocyclic aromatic amines (HAAs) in beef steaks cooked on a hot plate (at 200 °C for 24 min), were determined. The results showed that 3.12–4.13% of the marinate liquids were absorbed by beef steak as a result of the marination process. No significant differences (p > 0.05) were observed between the marinated and cooked beef steaks in terms of water content, cooking loss, thiobarbituric acid reactive substances (TBARS) value, hardness, cohesiveness, and chewiness. However, significant differences were detected in terms of pH value and color values (L*, a*, and b*) (p < 0.01), and springiness, 2-amino-3,8-dimethylimidazo (4,5-f) quinoxaline (MeIQx) and total HAA content (p < 0.05). The marination with pomegranate vinegar resulted in the formation of darker steak, while a lighter one was obtained when apple vinegar was used in the marination. The use of balsamic and grape vinegar in the marination process decreased the springiness value compared to the control group. The myofibrillar proteins of beef steaks marinated with different types of vinegar generally showed a similar sodium dodecyl-sulfate polyacrylamide gel electrophoresis (SDS-PAGE) profile. However, some differences were observed in the band density of some proteins depending on the trial and the type of marination. In this study, of the nine examined HAAs, only two (2-amino-3-methylimidazo (4,5-f) quinoline (IQ) and MeIQx) could be detected and quantified. IQ was detected only in the control group steak (up to 0.51 ng/g), while MeIQx was detected in all treatment groups (up to 2.22 ng/g). The total HAA content varied between 0.59–2.22 ng/g. It was determined that the marination process with different vinegar types had different effects on the total HAA content of the steaks. Using balsamic and apple vinegar in the marination process decreased the total HAA content compared to the control group, but this decrease was not statistically significant (p > 0.05). On the other hand, using grape and pomegranate vinegar in the marination process increased the total HAA content, but this increase was only significant (p < 0.05) in the marination with pomegranate vinegar.

The International Agency for Research on Cancer has classified the consumption of heat-processed meat as a direct human carcinogen and the consumption of red meat as a probable carcinogen. Mutagenic and carcinogenic compounds present in meat dishes include, among others, polycyclic aromatic hydrocarbons (PAHs) and heterocyclic aromatic amines (HAAs). These compounds can cause the development of gastrointestinal cancer. Oral cancer is one of the world’s research priorities due to the ever-increasing incidence rate. However, the effect of diet on oral cancer is still a poorly recognized issue. The aim of this study was to assess the relationship between the risk of oral cancer and dietary ingredients with a particular emphasis on red meat and thermally processed meat. This study was conducted among patients with oral cancer in 2022 and 2023. The shortened standardized Food Frequency Questionnaire (FFQ) and a multivariate regression statistical analysis were used. The high consumption of red meat in general and thermally processed meat, especially smoked, fried, roasted and boiled, increases the risk of oral cavity cancer. Limiting the consumption of meat products and modifying the methods of preparing meat dishes may reduce exposure to carcinogenic compounds from the diet and thus reduce the risk of developing oral cancer.

Heterocyclic aromatic amines (HAAs) are mutagenic and potentially carcinogenic compounds formed during the thermal processing of protein- and sugar-rich foods, yet their occurrence in plant-based milk alternatives remains largely unexplored. To the best of our knowledge, this is the first study to report on the presence of HAAs in plant-based milk beverages. The aim of this study was to develop a robust and environmentally friendly µSPE–UHPLC–MS/MS method for the quantification of ten HAAs in plant-based milk beverages and to assess the potential health risks associated with their formation under varying thermal treatment conditions. A novel analytical method was applied to both commercially available and homemade beverages prepared from almonds, soy, cashews, and peanuts, including pasteurized and unpasteurized variants with and without added sugar. Chemometric tools were used to optimize retention and enrichment strategies. Detection limits ranged from 0.01 to 0.04 µg L−1, while quantification limits ranged from 0.01 to 0.05 µg L−1. Recovery rates ranged between 84% and 100%, with enrichment factors spanning 43 to 50. HAA concentrations varied from 0.09 to 13.66 µg L−1, with significantly higher levels observed in beverages subjected to thermal treatment, particularly those with added sugar and higher protein content. The health risk assessment indicated that the cumulative incremental lifetime cancer risk (ILCR) values were below the unacceptable threshold (10−4), though some scenarios approached 10−5, suggesting a moderate risk for frequent consumers of plant-based milk alternatives.

In recent times, the research on the synthesis of highly functionalized piperidines has become a challenge and an attractive research field among synthetic chemists because these compounds have many biological, pharmaceutical and industrial applications. In this regard, in this paper we would like to report a green, rapid and efficient method for the synthesis of highly functionalized piperidines based on the use of zinc (II) chloride supported on Fe.sub.3O.sub.4 NPs modified with Dopamine and 5H-Cyclopenta[2,1-b:3,4-b']dipyridin-5-one [Fe.sub.3O.sub.4@Dop/CP-diPy-ZnCl.sub.2 as a novel magnetically reusable catalyst. The structure of Fe.sub.3O.sub.4@Dop/CP-diPy-ZnCl.sub.2 nanocatalyst was well identified by several spectroscopic techniques including: FT-IR, TEM, SEM, EDX, ICP-OES, TGA, XRD, VSM and Elemental mapping technique. One-pot three-component reactions of aromatic amines with different aryl aldehydes and -ketoesters were performed in water and all desired highly functionalized piperidines were synthesized with high to excellent yields, which indicates the high efficiency of this catalytic system. The reusability tests shown that that Fe.sub.3O.sub.4@Dop/CP-diPy-ZnCl.sub.2 catalyst is a reusable and stable catalyst.