FOOD AND CHEMICAL TOXICOLOGY
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2023
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IF 4.3
Xin Wang,Guangyun Ran,Yufen Liao,Bowen Gong,Chutian Wu,Rong Tan,Ying Liu,Shiyu Zhang,Ying Peng,Weiwei Li,Jiang Zheng
Safrole (SFL) is an IARC class 2B carcinogen. To better understand the mechanism involved in SFL toxicity, we explored the potential interactions between SFL metabolites and RNA. Three guanosine adducts (G1-G3), two adenosine adducts (A1-A2), and two cytosine adducts (C1–C2) were detected by LC-MS/MS in mouse liver S9 incubations, cultured mouse primary hepatocytes, and liver tissues of mice after exposure to SFL. These adducts were chemically synthesized, and one of the guanosine adducts was structurally characterized by 1 H-NMR. Studies in vitro and in vivo showed that SFL was oxidized by cytochrome P450 enzymes to the corresponding 1′-hydroxyl metabolite which was further metabolized by sulfotransferases to form allylic sulfate esters. The formed reactive intermediate(s) subsequently reacted with bases of RNA, leading to RNA adduction, which could play a partial role in the toxicities of SFL through the alteration of RNA biochemical properties and interruption of RNA functions.
研究领域:
毒理学
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药理学
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分子生物学
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生物化学
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DOI
PubMed
高影响因子
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS
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2019
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IF 2.983
Yu Tang,Zhe Wang,Menglin Li,Ruiping Zhang,Jinlan Zhang
A rapid, sensitive and wide coverage ultra-high-performance liquid chromatography with tandem mass spectrometry (UHPLC-MS/MS) method has been developed and validated for the simultaneous quantitation of 14 alkylation DNA adducts in cell genomic DNA, RNA and cell contents isolated from the in vitro cultured human kidney cell line 293 T and the human liver cell line L02 exposed to 3 genotoxic reagents: N -methyl -N- nitrosourea (MNU), methyl methanesulfonate (MMS) and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). After exposure, DNA was isolated and directly hydrolysed under acid conditions or digested by enzymes to obtain the hydrolysates containing DNA alkylation adducts followed by optimization of the pretreatment method and chromatographic separation conditions. Quantification was performed on a Waters ACQUITY UPLC BEH Amide column (1.7 μm, 2.1 × 150 mm) using an electrospray ionization (ESI) source in positive mode by selective reaction monitoring (SRM) at the precursor to product ion transitions of 14 analytes. The method showed selectivity, good linearity (r＞0.9950), accuracy (82.1%–115%), and intra-day (RSD%＜14%) and inter-day (RSD%＜15%) precision for 14 analytes. The recoveries of two pretreatment methods were all more than 50.5%, and no relative matrix effects were observed. Additionally, the samples were stable after short-term storage at 20 ℃ for 2 h, at 4 ℃ for 48 h or one cycle of freeze-thaw at −80 ℃. The established UHPLC-MS/MS method was used to evaluate the changes in alkylation DNA adducts and epigenetic modification-related methylcytosine after exposure to genotoxic reagents. For the first time, the results demonstrated that 3 genotoxic reagents induced different total amounts of adducts in the following sequence: MMS ＞ NNK ＞ MNU, and showed significant differences in the ratios of 7MeG to 1MeA and 1MeG to 1MeA in the 293 T cell model. Meanwhile, 293 T and L02 cells revealed significantly different DNA adduct formation characteristics in the contents of 1MeG and 1MeA. The DNA adduct formation relationships between DNA, RNA, and cell contents were probed to predict cancer risk and potential genotoxic exposure. This approach could be used to investigate the DNA adducts, their formation and the relationship to the mutagenicity or carcinogenicity of genotoxic reagents in future studies.
研究领域:
毒理学
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分析化学
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分子生物学
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DOI
PubMed
高影响因子
JOURNAL OF APPLIED POLYMER SCIENCE
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2016
·Vol. 133
·期 39
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IF 1.866
Pengfei Du,Haiyan Jia,Qinghua Chen,Zhen Zheng,Xinling Wang,Denglong Chen
Diels–Alder (DA) reactions between furan and maleimide have been widely applied in thermally remendable polymeric materials. Crosslinked polyurethane with DA adducts exhibited much better mechanical properties than linear polyurethane with DA adducts. However, the highly crosslinked polyurethane needs a higher temperature and a longer healing time. This will increase the possibility of side reactions proceeding during the healing procedure. In this paper, slightly crosslinked polyurethane with DA adducts was synthesized by incorporating trimethylolpropane into linear polyurethane with DA adducts. The structure of the intermediate and final products was characterized by Fourier transform infrared spectroscopy, 1 H-NMR, and differential scanning calorimetry, confirming that the synthesizing process proceeded successfully. The images from the polarizing optical microscope demonstrated that the final product with slight crosslinking needed less time and a lower healing temperature to complete the healing procedure. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016 , 133 , 43971.
研究领域:
材料科学
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化学工程
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产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2024
·
IF 5.7
Yan He,Zihao Cheng,Jingyu Zhang,Yu Chen,Guode Zhao,Hong Tang,Yufen Liao,Tingmin Ye,Ying Peng,Weiwei Li,Jiang Zheng
Myristicin (MYR) mainly occurs in nutmeg and belongs to alkoxy-substituted allylbenzenes, a class of potentially toxic natural chemicals. RNA interaction with MYR metabolites in vitro and in vivo has been investigated in order to gain a better understanding of MYR toxicities. We detected two guanosine adducts (GA1 and GA2), two adenosine adducts (AA1 and AA2), and two cytosine adducts (CA1 and CA2) by LC-MS/MS analysis of total RNA extracts from cultured primary mouse hepatocytes and liver tissues of mice after exposure to MYR. An order of nucleoside adductions was found to be GAs > AAs > CAs, and the result of density functional theory calculations was in agreement with that detected by the LC-MS/MS-based approach. In vitro and in vivo studies have shown that MYR was oxidized by cytochrome P450 enzymes to 1′-hydroxyl and 3′-hydroxyl metabolites, which were then sulfated by sulfotransferases (SULTs) to form sulfate esters. The resulting sulfates would react with the nucleosides by SN1 and/or SN2 reactions, resulting in RNA adduction. The modification may alter the biochemical properties of RNA and disrupt RNA functions, perhaps partially contributing to the toxicities of MYR.
研究领域:
毒理学
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药理学
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分子生物学
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分析化学
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产品关联
DOI
PubMed
高影响因子
ACS Applied Energy Materials
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2020
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IF 4.473
Xiuwei Sun,Shumei Liu,Shan Zhang,Tianyi Dang,Hongrui Tian,Ying Lu,Shuxia Liu
Almost all proton-conducting materials display poor conductivity at subzero temperatures, which significantly limits their application in cold regions. Thus, effective strategies to achieve high proton conductivity in a wide range from subzero to medium temperatures (−40 to 85 °C) need to be developed. Herein, we prepared proton-conductive materials by encapsulating the acid–base adduct based on Keggin-type H3PW12O40 (HPW) and aminoethanesulfonic acid (C2H7O3NS, HSN) in the linear channels of SBA-15 (named HPW-HSN@SBA-15). The result is the same as we expected: HPW-HSN@SBA-15 exhibits high proton conductivity over a wide temperature range (−40 to 85 °C). The proton conductivity of 75 wt % HPW-HSN@SBA-15 (3HPW-HSN@SBA-15) reaches 0.16 S cm–1 at 85 °C, 97% relative humidity (RH), and 6.8 × 10–5 S cm–1 at −40 °C. The excellent proton conductivity at subzero temperature of HPW-HSN@SBA-15 is mainly attributed to the ultrafast proton transfer with low energy barrier between proton donor (acid group) and proton acceptor (base group) in acid–base adduct without the attendance of water. Furthermore, the proton conductivity cycle test of 3HPW-HSN@SBA-15 demonstrates its good durability and stability.
研究领域:
材料科学
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化学
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DOI
高影响因子
ACS Applied Energy Materials
·
2022
·
IF 6.959
Xiuwei Sun,Xue Bai,Qian Wang,Ying Lu,Shuxia Liu
Most reported proton-conducting materials use water molecules as media for proton transport, but their low operating temperatures (below the boiling point of water) and humidity-dependent conductivity limit their extensive applications. This motivated researchers to explore high-temperature proton-conducting materials employing nonaqueous media. The acid–base adduct HPW-SA formed by Keggin-type phosphotungstic acid (H3PW12O40, abbreviated as HPW) and sulfamic acid (SA) shows high proton conductivity in the high-temperature region (160–190 °C), owing to its proton mobility remarkably enhanced by its solid–liquid transition. Inspired by this, we encapsulated the HPW-SA adduct into the cages of MIL-101 by the postsynthetic method to prepare the composite HPW-SA@MIL-101, aiming at taking full advantage of the proton conduction feature of the HPW-SA adduct while avoiding the problems of flowing away and corrosion caused by the independent use of HPW-SA adduct. As expected, HPW-SA@MIL-101 exhibits high proton conductivity (0.85 × 10–3–1.1 × 10–3 S cm–1) in the range of 160–190 °C. Its proton transfer activation energy (Ea) is 0.58 eV in the range of 160–190 °C, which indicates that proton migration is dominated by the diffusion effect following a vehicle mechanism. In addition, the proton conductivity of HPW-SA@MIL-101 did not decrease after six cycles of heating and cooling tests, showing good repeatability and stability.
研究领域:
材料科学
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化学
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产品关联
DOI
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2020
·
IF 4.192
Xiaoyun Jiang,Dingmin Zhang,Yongling Lu,Lishuang Lv
Increasing evidence has identified the unsaturated aldehyde acrolein (ACR) as the potential factor that causes deoxyribonucleic acid cross-linking and the development of chronic diseases. The objective of this study was to investigate the mechanism by which theophylline (TP) scavenges ACR for the first time. TP efficiently scavenged ACR through forming adducts, which was demonstrated in a system in which TP was incubated with ACR at different ratios for different times for liquid chromatography with tandem mass spectrometry. Then, the mono- and di-ACR-TP adducts were purified, and their structures were elucidated by high-resolution mass spectrometry and nuclear magnetic resonance analysis. We found that the ACR residue on mono-ACR-TP further trapped one more ACR and formed di-ACR-TP adducts. Furthermore, mono- and di-ACR-TP had similar time-dependent ACR-scavenging activity to TP. Finally, we demonstrated that green tea, coffee, and cocoa inhibited ACR by trapping ACR to form mono- and di-ACR-TP adducts during the incubation of green tea, coffee, and cocoa with ACR.
研究领域:
食品科学
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毒理学
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生物化学
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DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2020
·
IF 4.192
Xiaoyun Jiang,Huifang Lv,Yang Lu,Yongling Lu,Lishuang Lv
Acrolein (ACR) is a toxic unsaturated aldehyde that is formed during different steps of thermal food processing. Here, we explored the kinetics of curcumin and ACR and elucidated the pathway of curcumin trapping ACR by preparing a mono-adduct of ACR (CMA-1) conjugated with curcumin. The synergistic scavenging effect and mechanism of curcumin combined with quercetin on ACR was analyzed by liquid chromatography–tandem mass spectrometry (LC–MS/MS). Comparing the uses of curcumin and quercetin both individually and in combination, we found that quercetin in combination resulted in more curcumin being transformed into CMA-2, while curcumin in combination made the amount of di-ACR conjugated to quercetin (QDA) increase. We also added combined curcumin and quercetin into grilled chicken wings to demonstrate that curcumin and quercetin could scavenge ACR by forming their own ACR adducts and antioxidant activity during the process. Our results have noted a new strategy, in which some combinations of dietary polyphenols might contribute to the removal of toxic ACR produced during thermal food processing.
研究领域:
食品科学
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生物化学
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毒理学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2025
·
IF 6.2
Yating Gu,Shujingwen Wang,Bo Si,Chun Chang,Hao Ma,Yonglin Lu,Lishuang Lv
Acrolein (ACR) present in vivo and in vitro can damage proteins and DNA, linking it to various chronic diseases. In this paper, ergothioneine (EGT), abundant in edible mushrooms, has been studied for its ability to trap ACR and its reaction pathway with ACR at high temperatures using ultraperformance liquid chromatography–mass spectrometry (UPLC–MS/MS). We synthesized the adducts (EGT-ACR-1 and EGT-ACR-2), elucidating their structure and reaction site through HRMS and nuclear magnetic resonance. Subsequently, we proved the synergistic trapping effect on ACR of EGT when combined with γ-aminobutyric (GABA) and disodium 5′-guanylate (GMP) in binary or ternary employing the Chou–Talalay methods. Quantitative analysis of the ACR adducts revealed that GABA and GMP enhanced EGT’s ability to form additional ACR adducts. Moreover, Boletus eduli and Volvariella volvacea, as the carriers of EGT, GABA, and GMP, show a marked effect on trapping ACR generated during the baking of cookies/cakes. Our finding suggested that EGT, whether as a standalone compound or derived from mushrooms, could act as a potential ACR capturer (including single and multiple uses) in baked food.
研究领域:
生物化学
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食品科学
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医学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2020
·
IF 4.192
Xiaojing Yang,Yukun Feng,Zhengyu Zhang,Hui Wang,Weiwei Li,Dan Ohtan Wang,Ying Peng,Jiang Zheng
Methyleugenol (ME) is a ubiquitous component in spices and other culinary herbal products. A prevailing theory in ME toxicity is its ability to be metabolically activated by P450 enzymes and sulfotransferases, which initiates sequential reactions of the resulting metabolites with functional biomolecules. The present study aimed at a potential interaction between the reactive metabolites of ME and RNA. Cultured mouse primary hepatocytes were incubated with ME followed by RNA extraction and NaOH and alkaline phosphatase-based RNA hydrolysis. Three adenosine adducts were detected in the hydrolytic mixture by LC–MS/MS. The same adenosine adducts were also detected in hepatic tissues harvested from ME-treated mice. These three adducts were chemically synthesized and structurally characterized by 1H NMR. Additionally, two guanosine adducts and one cytidine adduct were detected in the in vivo samples. These results provided solid evidence that the reactive metabolites of ME attacked RNA, resulting in RNA adduction.
研究领域:
毒理学
·
分子生物学
✓ 已验证
DOI
PubMed
高影响因子
LANGMUIR
·
2018
·
IF 3.789
Haiquan Zhao,Dongsheng Wang,Yue Fan,Mingrui Ren,Shumin Dong,Yonghao Zheng
In this report, we designed surfaces with reversible green-light-switched wettability via donor–acceptor Stenhouse adducts (DASAs). Photoresponsive micro/nanoparticles were prepared by coating the surfaces of silica micro/nanoparticles with polydopamine and then postmodifying with DASA molecules. Then, the particles were immobilized on a glass substrate surfaces either with double-sided adhesive tape or cross-linking poly(dimethylsiloxane). Silica micro/nanoparticles with various diameters (0.2, 2.5, and 85 μm) were used to fabricate the photoresponsive surface. Green light irradiation switches the hydrophobic linear DASA to a hydrophilic cyclic isomer, which further increases the wettability and contact angle hysteresis on the surface. On the other hand, heating (100 °C) induces the cyclic-to-linear isomerization of DASA molecules and switches the surface back to hydrophobic. The wettability of the DASA-modified surface is reversible under alternate green light irradiation and heating.
研究领域:
材料科学
·
表面化学
✓ 已验证
DOI
PubMed
高影响因子
MUTAGENESIS
·
2025
·
IF 4.3
Hu Yushi,Lei Yuyang,Gao Zhenna,Cao Yiyi,Xi Jing,Ma Yuning,Gao Qinwen,Fu Jian,Zhang Xinyu,Luan Yang
Aristolochic acid I (AAI) is a carcinogen associated with various human cancers. However, its causal relationship with hepatocellular carcinoma remains controversial, and inconsistent results from rodent studies have suggested species-specific differences. Here we evaluated AAI genotoxicity using functional human-induced hepatocyte-like cells (hiHep cells), a model that closely mimics primary human hepatocytes in gene expression and function, thereby shedding light on its potential hepatocarcinogenic risk in humans. First, we assessed AAI genotoxicity by evaluating AAI-DNA adducts and micronucleus frequency. In hiHep cells, AAI (0.7–2.5 µM) induced up to 105 adducts per 108 nucleotides, indicating high metabolic activation of AAI. A concentration-dependent increase in micronucleus frequency indicated a significant increase in chromosomal aberrations in hiHep cells. Considering the evidence of AAI inducing oxidative stress, we assessed 8-hydroxy-2′-deoxyguanosine and reactive oxygen species levels to evaluate DNA oxidative damage. For both indicators, significantly elevated levels were observed. A mechanism involving oxidative damage was further supported by observations of mitochondrial dysfunction, including changes in mitochondrial membrane potential and mitochondrial complex activity. Ascorbate treatment decreased AAI-induced oxidative DNA damage and DNA adduct formation, providing direct cellular evidence for free radical intermediates in AAI metabolic activation—a mechanism previously hypothesized but not experimentally validated in a human-relevant hepatocyte model. Our study findings revealed the genotoxic effects of AAI on hiHep cells and implicated oxidative stress as the key mechanism. These findings strengthen the association between AAI exposure and liver disease and highlight the potential role of antioxidant therapies in mitigating AAI-associated carcinogenesis.
研究领域:
毒理学
·
肝脏生物学
·
癌症研究
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产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）