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Journal articles on the topic 'Mercapturic acid pathway'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Hanna, Patrick E., and M. W. Anders. "The mercapturic acid pathway." Critical Reviews in Toxicology 49, no. 10 (2019): 819–929. http://dx.doi.org/10.1080/10408444.2019.1692191.

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2

Kharasch, Evan D., and Carole Jubert. "Compound A Uptake and Metabolism to Mercapturic Acids and 3,3,3-Trifluoro-2-fluoromethoxypropanoic Acid during Low-flow Sevoflurane Anesthesia." Anesthesiology 91, no. 5 (1999): 1267. http://dx.doi.org/10.1097/00000542-199911000-00017.

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Background Sevoflurane is degraded during low-flow anesthesia to fluoromethyl-2,2-difluoro-1-(trifluoromethyl)vinyl ether ("compound A"), which causes renal necrosis in rats but is not known to cause nephrotoxicity in surgical patients. Compound A is metabolized to glutathione S-conjugates and then to cysteine S-conjugates, which are N-acetylated to mercapturic acids (detoxication pathway), or metabolized by renal beta-lyase to reactive intermediates (toxification pathway) and excreted as 3,3,3-trifluoro-2-fluoromethoxypropanoic acid. This investigation quantified compound A metabolites in uri

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3

Goyal, R., R. Tardif, and J. Brodeur. "Influence of a cysteine prodrug, L-2-oxothiazolidine-4-carboxylic acid, on the urinary elimination of mercapturic acids of ethylene oxide, dibromoethane, and acrylonitrile: a dose–effect study." Canadian Journal of Physiology and Pharmacology 67, no. 3 (1989): 207–12. http://dx.doi.org/10.1139/y89-035.

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Metabolic disposition of ethylene oxide, dibromoethane, and acrylonitrile in rats after acute exposure was studied by examining the relationship between dose and urinary metabolites, and by establishing the influence of a glutathione precursor, L-2-oxothiazolidine-4-carboxylic acid (OTCA), on the above relationship. Respective urinary metabolites, hydroxyethylmercapturic acid, cyanoethylmercapturic acid, thiocyanate, and ethylene glycol, were quantified to estimate the extent to which each compound was metabolized. The animals were given either ethylene oxide (0.34, 0.68, or 1.36 mmol/kg), dib

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Tierbach, Alena, Ksenia J. Groh, René Schönenberger, Kristin Schirmer, and Marc J. F. Suter. "Biotransformation Capacity of Zebrafish (Danio rerio) Early Life Stages: Functionality of the Mercapturic Acid Pathway." Toxicological Sciences 176, no. 2 (2020): 355–65. http://dx.doi.org/10.1093/toxsci/kfaa073.

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Abstract Zebrafish (Danio rerio) early life stages offer a versatile model system to study the efficacy and safety of drugs or other chemicals with regard to human and environmental health. This is because, aside from the well-characterized genome of zebrafish and the availability of a broad range of experimental and computational research tools, they are exceptionally well suited for high-throughput approaches. Yet, one important pharmacokinetic aspect is thus far only poorly understood in zebrafish embryo and early larvae: their biotransformation capacity. Especially, biotransformation of el

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5

Iwata, Shuzo, and Takami Maesato. "Studies on the mercapturic acid pathway in the rabbit lens." Experimental Eye Research 47, no. 3 (1988): 479–88. http://dx.doi.org/10.1016/0014-4835(88)90058-9.

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6

Singhal, Sharad S., Saumya Srivastava, Tamara Mirzapoiazova, David Horne, Sanjay Awasthi, and Ravi Salgia. "Targeting the mercapturic acid pathway for the treatment of melanoma." Cancer Letters 518 (October 2021): 10–22. http://dx.doi.org/10.1016/j.canlet.2021.06.004.

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7

Ou, Yueh‐Hsing, and Jen‐Kun Lin. "Biotransformation of butachlor through mercapturic acid pathway in rat tissue homogenates." Journal of Toxicology and Environmental Health 35, no. 1 (1992): 19–28. http://dx.doi.org/10.1080/15287399209531590.

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8

Moss, Elizabeth J., G. E. Neal, and D. J. Judah. "The mercapturic acid pathway metabolites of a glutathione conjugate of aflatoxin B1." Chemico-Biological Interactions 55 (1985): 139–55. http://dx.doi.org/10.1016/s0009-2797(85)80124-1.

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9

Yang, Y., J. Rafter, J. Å. Gustafsson, J. Sjövall, and W. Griffiths. "Letter: Differentiation of isomeric mercapturic acid pathway metabolites of benzo[a]pyrene." European Journal of Mass Spectrometry 3, no. 1 (1997): 396. http://dx.doi.org/10.1255/ejms.172.

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10

Singhal, Sharad S., Divya Jain, Preeti Singhal, Sanjay Awasthi, Jyotsana Singhal, and David Horne. "Targeting the mercapturic acid pathway and vicenin-2 for prevention of prostate cancer." Biochimica et Biophysica Acta (BBA) - Reviews on Cancer 1868, no. 1 (2017): 167–75. http://dx.doi.org/10.1016/j.bbcan.2017.03.009.

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11

Hanschen, Baldermann, Brobrowski, et al. "Identification Of N-Acetyl-S-(3-Cyano-2-(Methylsulfanyl)Propyl-Cysteine as a Major Human Urine Metabolite from the Epithionitrile 1-Cyano-2,3-Epithiopropane, the Main Glucosinolate Hydrolysis Product from Cabbage." Nutrients 11, no. 4 (2019): 908. http://dx.doi.org/10.3390/nu11040908.

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Brassica vegetables such as cabbage or pak choi contain alkenyl glucosinolates which can release epithionitriles and to a lesser degree isothiocyanates upon enzymatic hydrolysis. Here, for the first time, the metabolism of an epithionitrile was investigated in humans, namely 1-cyano-2,3-epithiopropane (CETP). After consumption of Brassica oleracea var. capitata f. alba and Brassica carinata sprouts, the main urinary metabolite of CETP was identified as N-acetyl-S-(3-cyano-2-(methylsulfanyl)propyl-cysteine using an UHPLC-ESI-QToF-MS approach and synthesis of the metabolite. This urinary epithio

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12

Tsikas, Dimitrios, Alexander A. Zoerner, Frank-Mathias Gutzki, and Ranieri Rossi. "On the mercapturic acid pathway of nitric oxide: is S-nitrosoglutathione present in the bile?" Hepatology 52, no. 5 (2010): 1858–59. http://dx.doi.org/10.1002/hep.23926.

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13

Monks, Terrence J., та Serrine S. Lau. "Glutathione, γ-glutamyl transpeptidase, and the mercapturic acid pathway as modulators of 2-bromohydroquinone oxidation". Toxicology and Applied Pharmacology 103, № 3 (1990): 557–63. http://dx.doi.org/10.1016/0041-008x(90)90328-r.

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14

Buckberry, Lorraine D., Ian S. Blagbrough, and P. Nicholas Shaw. "Cysteine Conjugate Toxicity in a Human Cell Line: Correlation with C-S Lyase Activity in Human Hepatic Tissue." Human & Experimental Toxicology 12, no. 4 (1993): 329–35. http://dx.doi.org/10.1177/096032719301200412.

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C-S lyase enzymes catalyse the generation of mutagenic and/or cytotoxic thiols from cysteine conjugated xenobiotics. These cysteine conjugates are produced subsequent to glutathione conjugations as a metabolic step in the mercapturic acid pathway, traditionally thought of as a pathway solely associated with detoxification. Human Chang liver (HCL) cells were challenged with a range of cysteine conjugates demonstrated to be substrates for human hepatic C-S lyases. The cellular toxicity of these compounds was determined and it was observed that the rank order of substrate toxicity obtained for th

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15

Klasson-wehler, E., Å. Bergman, B. Kowalski, and I. Brandt. "Metabolism of 2,3,4′,6-tetrachlorobiphenyl: formation and tissue localization of mercapturic acid pathway metabolites in mice." Xenobiotica 17, no. 4 (1987): 477–86. http://dx.doi.org/10.3109/00498258709043954.

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16

Goeptar, Arnold R., Jan N. M. Commandeur, Ben van Ommen, Peter J. van Bladeren, and Nico P. E. Vermeulen. "Metabolism and Kinetics of Trichloroethylene in Relation to Toxicity and Carcinogenicity. Relevance of the Mercapturic Acid Pathway." Chemical Research in Toxicology 8, no. 1 (1995): 3–21. http://dx.doi.org/10.1021/tx00043a001.

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17

Tierbach, Alena, Ksenia J. Groh, René Schoenenberger, Kristin Schirmer, and Marc J. F. Suter. "Characterization of the Mercapturic Acid Pathway, an Important Phase II Biotransformation Route, in a Zebrafish Embryo Cell Line." Chemical Research in Toxicology 33, no. 11 (2020): 2863–71. http://dx.doi.org/10.1021/acs.chemrestox.0c00315.

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18

Trevisan, Andrea, Paola Meneghetti, Stefano Maso, and Ornella Troso. "In-Vitro Mechanisms of 1,2-Dichloropropane Nephrotoxicity using the Renal Cortical Slice Model." Human & Experimental Toxicology 12, no. 2 (1993): 117–21. http://dx.doi.org/10.1177/096032719301200204.

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1 Renal cortical slices isolated from the kidneys of male Wistar rats were used as an experimental model for studying the nephrotoxicity induced by 1,2-dichloropropane. 2 The solvent causes a depletion of renal reduced glutathione content and slight, but significant, lipid peroxidation. The block of the oxidative pathway with carbon monoxide prevents glutathione content depletion, and shows that this conjugation is the major step in 1,2-dichloropropane metabolism. 3 Loss of organic anion accumulation and release into the incubation medium of tubular enzymes, mainly from the soluble fraction, a

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19

Feng, Paul C. C., and James E. Patanella. "Identification of mercapturic acid pathway metabolites of alachlor formed by liver and kidney homogenates of rats, mice, and monkeys." Pesticide Biochemistry and Physiology 31, no. 1 (1988): 84–90. http://dx.doi.org/10.1016/0048-3575(88)90032-6.

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20

Egner, Patricia A., Thomas W. Kensler, Jian-Guo Chen, Stephen J. Gange, John D. Groopman, and Marlin D. Friesen. "Quantification of Sulforaphane Mercapturic Acid Pathway Conjugates in Human Urine by High-Performance Liquid Chromatography and Isotope-Dilution Tandem Mass Spectrometry." Chemical Research in Toxicology 21, no. 10 (2008): 1991–96. http://dx.doi.org/10.1021/tx800210k.

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21

Yang, Yang, Joseph Rafter, Jan-Åke Gustafsson, Jan Sjövall, and William J. Griffiths. "Analysis of the major mercapturic acid pathway metabolites of benzo[a]pyrene found in rat urine by nano-electrospray mass spectrometry." Rapid Communications in Mass Spectrometry 12, no. 8 (1998): 465–71. http://dx.doi.org/10.1002/(sici)1097-0231(19980430)12:8<465::aid-rcm180>3.0.co;2-f.

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22

Uttamsingh, Vinita, Iyer A. Ramswamy, Raymond B. Baggs, and M. W. Anders. "Fate and Toxicity of 2-(Fluoromethoxy)-1,1,3,3,3-pentafluoro-1-propene (Compound A)-derived Mercapturates in Male, Fischer 344 Rats." Anesthesiology 89, no. 5 (1998): 1174–83. http://dx.doi.org/10.1097/00000542-199811000-00018.

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Background 2-(Fluoromethoxy)-1,1,3,3,3-pentafluoro-1-propene (compound A) is formed in the anesthesia circuit by the degradation of sevoflurane. Compound A is nephrotoxic in rats and undergoes metabolism by the mercapturic acid pathway in rats and humans to yield the mercapturates S-[2-(fluoromethoxy)-1,1,3,3,3-pentafluoropropyl]-N-acetyl-L -cysteine (compound 3) and S-[2(fluoromethoxy)-1,3,3,3-tetrafluoro-1-propenyl]-N-acetyl-L-cys teine (compound 5). These experiments were designed to examine the fate and nephrotoxicity of compound A-derived mercapturates in rats. Methods The deacetylation o

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23

Vamvakas, S., F. J. Kordowich, W. Dekant, T. Neudecker, and D. Henschler. "Mutagenicity of hexachloro-1,3-butadiene and its S-conjugates in the Ames test—role of activation by the mercapturic acid pathway in its nephrocarcinogenicity." Carcinogenesis 9, no. 6 (1988): 907–10. http://dx.doi.org/10.1093/carcin/9.6.907.

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24

Janobi, Ahmed A. Al, Richard F. Mithen, Amy V. Gasper, et al. "Quantitative measurement of sulforaphane, iberin and their mercapturic acid pathway metabolites in human plasma and urine using liquid chromatography–tandem electrospray ionisation mass spectrometry." Journal of Chromatography B 844, no. 2 (2006): 223–34. http://dx.doi.org/10.1016/j.jchromb.2006.07.007.

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25

Michielsen, C., S. Boeren, I. Rietjens, F. van Mil, J. Vos, and N. Bloksma. "The mercapturic acid biotransformation pathway of hexachlorobenzene is not involved in the induction of splenomegaly, or skin and lung lesions in the Brown Norway rat." Archives of Toxicology 74, no. 10 (2000): 609–17. http://dx.doi.org/10.1007/s002040000166.

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26

Shanshal, Mohamed, Lukman Aderoju Tijani, Fred L. Hardwicke, et al. "Effect of amplification of xenobiotic detoxification pathways genes on survival in lung adenocarcinoma versus squamous cell carcinoma bases on the Cancer Genome Atlas provisional database." Journal of Clinical Oncology 35, no. 15_suppl (2017): e14093-e14093. http://dx.doi.org/10.1200/jco.2017.35.15_suppl.e14093.

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e14093 Background: Ral interacting protein (RLIP76) is a stress-responsive anti-apoptotic efflux transporter of the mercapturic acid pathway (MPy). The MPy enzymes are an essential component of the broader xenobiotic detoxification pathways (XDP) that are regulated by p53 (TP53) in response to xenobiotic/oxidative stress. Homozygous Rlip knockout (Rlip-/-) mice are resistant to benzopyrene induced adenocarcinoma and have constitutive activation of p53. The cancer-resistant phenotype of Rlip-/- mice is the diametric opposite of p53 homozygous knockout mice (p53-/-) mice, which die before the ag

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Duncan, A. J., T. Acamovic, and I. I. Onaga. "Urinary mercapturic acids as markers for the estimation of isothiocyanate release in the digestive tract of rats following oral adminstration of glucosinolates." Proceedings of the British Society of Animal Science 1995 (March 1995): 181. http://dx.doi.org/10.1017/s0308229600029470.

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Glucosinolates are a group of plant thioglucosides, found in a range of plant genera, notably theBrassicae. Glucosinolates assume agricultural importance because of their presence in rapeseed meal and forage brassica crops whose nutritional value they may limit. Glucosinolates are hydrolysed under the action of plant or microbial myrosinase to release a range of toxic metabolites (see Duncan, 1991). For example, sinigrin, a commonly found glucosinolate, breaks down to allyl isothiocyanate (AITC) and allyl cyanide as well as a number of lesser components. The course of hydrolysis is influenced

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Awasthi, Sanjay, Joshua Tompkins, Jyotsana Singhal, et al. "Rlip depletion prevents spontaneous neoplasia in TP53 null mice." Proceedings of the National Academy of Sciences 115, no. 15 (2018): 3918–23. http://dx.doi.org/10.1073/pnas.1719586115.

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TP53 (p53) is a tumor suppressor whose functions are lost or altered in most malignancies. p53 homozygous knockout (p53−/−) mice uniformly die of spontaneous malignancy, typically T-cell lymphoma. RALBP1 (RLIP76, Rlip) is a stress-protective, mercapturic acid pathway transporter protein that also functions as a Ral effector involved in clathrin-dependent endocytosis. In stark contrast to p53−/− mice, Rlip−/− mice are highly resistant to carcinogenesis. We report here that partial Rlip deficiency induced by weekly administration of an Rlip-specific phosphorothioate antisense oligonucleotide, R5

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Bose, Chhanda, Sushma Yadav, Sharad S. Singhal, et al. "Rlip Depletion Suppresses Growth of Breast Cancer." Cancers 12, no. 6 (2020): 1446. http://dx.doi.org/10.3390/cancers12061446.

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RLIP76 (RAL-binding protein-1, Rlip) is a stress-protective mercapturic-acid-pathway transporter protein that also plays a key role in regulating clathrin-dependent endocytosis as a Ral effector. Targeted inhibition or depletion of Rlip causes regression of xenografts of many cancers and is capable of abrogating tumor formation in p53-null mice. This is associated with the reversion of the abnormal methylomic profile of p53-null mice to wild-type. In a query of The Cancer Genome Atlas (TCGA) databases, we found that Rlip expression was associated with poor survival and with significant differe

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Zhang, Yuesheng, Song Yao, and Jun Li. "Vegetable-derived isothiocyanates: anti-proliferative activity and mechanism of action." Proceedings of the Nutrition Society 65, no. 1 (2006): 68–75. http://dx.doi.org/10.1079/pns2005475.

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Many isothiocyanates (ITC), which are available to human subjects mainly through consumption of cruciferous vegetables, demonstrate strong cancer-preventive activity in animal models. Human studies also show an inverse association between consumption of ITC and risk of cancer in several organs. Whereas earlier studies primarily focused on the ability of ITC to inhibit carcinogen-activating enzymes and induce carcinogen-detoxifying enzymes, more recent investigations have shown that ITC inhibit the proliferation of tumour cells both in vitro and in vivo by inducing apoptosis and arresting cell

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Pushkin, Alexander, Gerardo Carpenito, Natalia Abuladze, et al. "Structural characterization, tissue distribution, and functional expression of murine aminoacylase III." American Journal of Physiology-Cell Physiology 286, no. 4 (2004): C848—C856. http://dx.doi.org/10.1152/ajpcell.00192.2003.

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Many xenobiotics are detoxified through the mercapturate metabolic pathway. The final product of the pathway, mercapturic acids ( N-acetylcysteine S-conjugates), are secreted predominantly by renal proximal tubules. Mercapturic acids may undergo a transformation mediated by aminoacylases and cysteine S-conjugate β-lyases that leads to nephrotoxic reactive thiol formation. The deacetylation of cysteine S-conjugates of N-acyl aromatic amino acids is thought to be mediated by an aminoacylase whose molecular identity has not been determined. In the present study, we cloned aminoacylase III, which

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32

Oliveri, Douglas, Qiwei Liang, and Mohamadi Sarkar. "Real-World Evidence of Differences in Biomarkers of Exposure to Select Harmful and Potentially Harmful Constituents and Biomarkers of Potential Harm Between Adult E-Vapor Users and Adult Cigarette Smokers." Nicotine & Tobacco Research 22, no. 7 (2019): 1114–22. http://dx.doi.org/10.1093/ntr/ntz185.

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Abstract Introduction Real-world evidence regarding likely long-term health effects of e-vapor products (EVP) under actual use conditions relative to cigarette smoking is not well studied. Methods In this cross-sectional, observational study, biomarkers of exposure (BOE) to select harmful and potentially harmful constituents and biomarkers of potential harm (BOPH) relevant to smoking-related diseases were measured in exclusive adult EVP users (AEVP, n = 144) and exclusive adult cigarette smokers (AS, n = 73). AEVP used their own brand of EVP for 6+ months following 10+ years of cigarette smoki

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Gunn, Joshua. "An Analysis of Biomarkers in Patients with Chronic Pain." Pain Physician 1;23, no. 1;1 (2020): E41—E49. http://dx.doi.org/10.36076/ppj.2020/23/e41.

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Background: Because of the subjective nature of current pain assessments, limited efficacy of treatment options and risks associated with opioid abuse and diversion, the need for objective data to assist with chronic pain management has never been greater. Successful identification of mechanistic biomarkers would not only improve our understanding and ability to accurately diagnose pain disorders but would also facilitate the development of disease-modifying pain drugs. Objectives: The objective of this study was to determine and evaluate the prevalence of abnormal biomarker findings in a popu

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34

Fang, Zhong, Alexandra A. Roberts, Karissa Weidman, et al. "Cross-functionalities of Bacillus deacetylases involved in bacillithiol biosynthesis and bacillithiol-S-conjugate detoxification pathways." Biochemical Journal 454, no. 2 (2013): 239–47. http://dx.doi.org/10.1042/bj20130415.

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BshB, a key enzyme in bacillithiol biosynthesis, hydrolyses the acetyl group from N-acetylglucosamine malate to generate glucosamine malate. In Bacillus anthracis, BA1557 has been identified as the N-acetylglucosamine malate deacetylase (BshB); however, a high content of bacillithiol (~70%) was still observed in the B. anthracis ∆BA1557 strain. Genomic analysis led to the proposal that another deacetylase could exhibit cross-functionality in bacillithiol biosynthesis. In the present study, BA1557, its paralogue BA3888 and orthologous Bacillus cereus enzymes BC1534 and BC3461 have been characte

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35

Poli, Diana, Roberta Andreoli, Lucia Moscato, et al. "The Relationship Between Widespread Pollution Exposure and Oxidized Products of Nucleic Acids in Seminal Plasma and Urine in Males Attending a Fertility Center." International Journal of Environmental Research and Public Health 17, no. 6 (2020): 1880. http://dx.doi.org/10.3390/ijerph17061880.

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Background: In recent decades, there has been an increase in male infertility, and in many cases, the etiology remains unclear. Several studies relate male hypo-fertility to xenobiotic exposure, even if no data exist about multiple exposure at the environmental level. Methods: The study involved 86 males with diagnosis of idiopathic male infertility (IMI), and 46 controls with no alteration in sperm characteristics. Seminal plasma (SP) and urine samples were analyzed by liquid chromatography tandem mass spectrometry (LC-MS/MS) to quantify biomarkers of exposure (the main metabolites of benzene

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Newton, Gerald L., Nancy Buchmeier, and Robert C. Fahey. "Biosynthesis and Functions of Mycothiol, the Unique Protective Thiol of Actinobacteria." Microbiology and Molecular Biology Reviews 72, no. 3 (2008): 471–94. http://dx.doi.org/10.1128/mmbr.00008-08.

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SUMMARY Mycothiol (MSH; AcCys-GlcN-Ins) is the major thiol found in Actinobacteria and has many of the functions of glutathione, which is the dominant thiol in other bacteria and eukaryotes but is absent in Actinobacteria. MSH functions as a protected reserve of cysteine and in the detoxification of alkylating agents, reactive oxygen and nitrogen species, and antibiotics. MSH also acts as a thiol buffer which is important in maintaining the highly reducing environment within the cell and protecting against disulfide stress. The pathway of MSH biosynthesis involves production of GlcNAc-Ins-P by

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Roser, Marie, David Béal, Camille Eldin, et al. "Glutathione conjugates of the mercapturic acid pathway and guanine adduct as biomarkers of exposure to CEES, a sulfur mustard analog." Analytical and Bioanalytical Chemistry, January 7, 2021. http://dx.doi.org/10.1007/s00216-020-03096-4.

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Jóhannsson, Freyr, Paulina Cherek, Maonian Xu, Óttar Rolfsson, and Helga M. Ögmundsdóttir. "The Anti-Proliferative Lichen-Compound Protolichesterinic Acid Inhibits Oxidative Phosphorylation and Is Processed via the Mercapturic Pathway in Cancer Cells." Planta Medica, September 14, 2021. http://dx.doi.org/10.1055/a-1579-6454.

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AbstractThe lichen compound protolichesterinic acid (PA) has an anti-proliferative effect against several cancer cell lines of different origin. This effect cannot be explained by the known inhibitory activity of PA against 5- and 12-lipoxygenases. The aim was therefore to search for mechanisms for the anti-proliferative activity of PA. Two cancer cell lines of different origin, both sensitive to anti-proliferative effects of PA, were selected for this study, T-47D from breast cancer and AsPC-1 from pancreatic cancer. Morphological changes were assessed by transmission electron microscopy, HPL

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Admin, Admin, and Dr Mustafa Arslan. "Effect of dexmedetomidine on ischemia-reperfusion injury of liver and kidney tissues in experimental diabetes and hepatic ischemia-reperfusion injury induced rats." Anaesthesia, Pain & Intensive Care, May 9, 2019, 143–49. http://dx.doi.org/10.35975/apic.v0i0.641.

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Background: Reperfusion following ischemia can lead to more injuries than ischemia itself especially in diabetic patients. The aim of this study was to evaluate the effect of dexmedetomidine on ischemia-reperfusion injury (IRI) in rats with have hepatic IRI and diabetes mellitus. Methodology: Twenty-eight Wistar Albino rats were randomised into four groups as control (C), diabetic (DC), diabetic with hepatic ischemia-reperfusion injury (DIR), and diabetic but administered dexmedetomidine followed by hepatic IRI (DIRD) groups. Hepatic tissue samples were evaluated histopathologically by s

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