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Bisulfite adducts

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https://www.readbyqxmd.com/read/27572263/estrogen-receptor-expression-and-gene-promoter-methylation-in-non-small-cell-lung-cancer-a-short-report
#1
Xavier Tekpli, Vidar Skaug, Rita Bæra, David H Phillips, Aage Haugen, Steen Mollerup
PURPOSE: In the past, anomalous estrogen receptor (ER) regulation has been associated with various lung pathologies, but so far its involvement in lung cancer initiation and/or progression has remained unclear. Here, we aimed at assessing in vivo and in vitro ER expression and its possible epigenetic regulation in non-small cell lung cancer (NSCLC) samples and their corresponding normal tissues and cells. METHODS: ERα and ERβ gene expression levels were assessed using real time quantitative PCR (RT-qPCR), whereas ERα and ERβ gene promoter methylation levels were assessed using DNA bisulfite conversion followed by pyrosequencing...
August 29, 2016: Cellular Oncology (Dordrecht)
https://www.readbyqxmd.com/read/27348130/aberrant-epigenetic-alterations-of-glutathione-s-transferase-p1-in-age-related-nuclear-cataract
#2
Jia Chen, Jing Zhou, Jian Wu, Guowei Zhang, Lihua Kang, Jindong Ben, Yong Wang, Bai Qin, Huaijin Guan
PURPOSE: Oxidative damage of lens tissue contributes to the formation of age-related cataract. Pi-class glutathione-S-transferase (GSTP1) plays a role in the removal of oxidative adducts by transferring them to glutathione. To assess epigenetic regulation of GSTP1 and its potential role in age-related nuclear cataract (ARNC) pathogenesis, we evaluated GSTP1 mRNA expression, methylation, and chromatin modifications in lenses from ARNC patients. METHODS: The mRNA and protein of lens GSTP1 were assayed by relative quantitative real-time polymerase chain reaction (qRT-PCR) and Western blots...
June 27, 2016: Current Eye Research
https://www.readbyqxmd.com/read/26776028/identification-of-s-3-hexanal-glutathione-and-its-bisulfite-adduct-in-grape-juice-from-vitis-vinifera-l-cv-sauvignon-blanc-as-new-potential-precursors-of-3sh
#3
Cécile Thibon, Caroline Böcker, Svitlana Shinkaruk, Virginie Moine, Philippe Darriet, Denis Dubourdieu
Two main precursors (S-3-(hexan-1-ol)-l-cysteine and S-3-(hexan-1-ol)-l-glutathione) of 3-sulfanylhexanol (3SH, formerly named 3-mercaptohexanol) have been identified so far in grape juice but a correlation between precursor concentrations in grape juices and 3SH concentrations in wines is not always observed. This suggests that there may be other compounds associated with the aromatic potential. In this work, S-3-(hexanal)-glutathione (Glut-3SH-Al) and its bisulfite (Glut-3SH-SO3) adduct were identified in Sauvignon blanc grape juice by liquid chromatography coupled to Fourier transform mass spectrometry experiments...
May 15, 2016: Food Chemistry
https://www.readbyqxmd.com/read/24241969/existence-of-the-sugar-bisulfite-adducts-and-its-inhibiting-effect-on-degradation-of-monosaccharide-in-acid-system
#4
Yan Shi
Degradation of fermentable monosaccharides is one of the primary concerns for acid prehydrolysis of lignocellulosic biomass. Recently, in our research on degradation of pure monosaccharides in aqueous SO₂ solution by gas chromatography (GC) analysis, we found that detected yield was not actual yield of each monosaccharide due to the existence of sugar-bisulfite adducts, and a new method was developed by ourselves which led to accurate detection of recovery yield of each monosaccharide in aqueous SO₂ solution by GC analysis...
February 2014: Applied Biochemistry and Biotechnology
https://www.readbyqxmd.com/read/24197477/modification-of-polyuridylic-acid-by-bisulfite-ii-studies-on-ribosomal-binding-and-enzymatic-hydrolysis
#5
R Shapiro, B Braverman, W Szer
The reaction of polyuridylic acid with sodium bisulfite produces modified polymers in which up to 95% of the uracil residues have been converted to uracil-6-sulfonate residues. A 91.6% bisulfite-saturated polymer was found to resist hydrolysis by spleen phosphodiesterase and phosphorolysis by polynucleotide phosphorylase. Digestion by pancreatic ribonuclease was successful and gave the bisulfite adduct of uridine-3'-phosphate. Treatment of this nucleotide adduct with acid phosphatase afforded the bisulfite adduct of uridine...
August 1973: Molecular Biology Reports
https://www.readbyqxmd.com/read/24154486/aberrant-methylation-of-hypermethylated-in-cancer-1-and-exocyclic-dna-adducts-in-tobacco-smokers
#6
Marco E M Peluso, Armelle Munnia, Valentina Bollati, Petcharin Srivatanakul, Adisorn Jedpiyawongse, Suleeporn Sangrajrang, Marcello Ceppi, Roger W Giese, Paolo Boffetta, Andrea A Baccarelli
Tobacco smoke has been shown to produce both DNA damage and epigenetic alterations. However, the potential role of DNA damage in generating epigenetic changes is largely underinvestigated in human studies. We examined the effects of smoking on the levels of DNA methylation in genes for tumor protein p53, cyclin-dependent kinase inhibitor2A, hypermethylated-in-cancer-1 (HIC1), interleukin-6, Long Interspersed Nuclear Element type1, and Alu retrotransposons in blood of 177 residents in Thailand using bisulfite-PCR andpyrosequencing...
January 2014: Toxicological Sciences: An Official Journal of the Society of Toxicology
https://www.readbyqxmd.com/read/24125888/design-synthesis-and-bioevaluation-of-viral-3c-and-3c-like-protease-inhibitors
#7
Allan M Prior, Yunjeong Kim, Sahani Weerasekara, Meghan Moroze, Kevin R Alliston, Roxanne Adeline Z Uy, William C Groutas, Kyeong-Ok Chang, Duy H Hua
A class of tripeptidyl transition state inhibitors containing a P1 glutamine surrogate, a P2 leucine, and a P3 arylalanines, was found to potently inhibit Norwalk virus replication in enzyme and cell based assays. An array of warheads, including aldehyde, α-ketoamide, bisulfite adduct, and α-hydroxyphosphonate transition state mimic, was also investigated. Tripeptidyls 2 and 6 possess antiviral activities against noroviruses, human rhinovirus, severe acute respiratory syndrome coronavirus, and coronavirus 229E, suggesting a broad range of antiviral activities...
December 1, 2013: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/23719540/o-demethylations-catalyzed-by-rieske-nonheme-iron-monooxygenases-involve-the-difficult-oxidation-of-a-saturated-c-h-bond
#8
Wenzhi Jiang, Mark A Wilson, Donald P Weeks
Dicamba monooxygenase (DMO) catalyzes the O-demethylation of dicamba (3,6-dichloro-2-methoxybenzoate) to produce 3,6-dichlorosalicylate and formaldehyde. Recent crystallographic studies suggest that DMO catalyzes the challenging oxidation of a saturated C-H bond within the methyl group of dicamba to form a hemiacetal intermediate. Testing of this hypothesis was made possible by our development of two new independent techniques. As a novel method to allow use of (18)O2 to follow reaction products, bisulfite was used to trap newly formed (18)O-formaldehyde in the stable adduct, hydroxymethanesulfonate (HMS(-)), and thereby prevent the rapid exchange of (18)O in formaldehyde with (16)O in water...
August 16, 2013: ACS Chemical Biology
https://www.readbyqxmd.com/read/23543013/global-and-mgmt-promoter-hypomethylation-independently-associated-with-genomic-instability-of-lymphocytes-in-subjects-exposed-to-high-dose-polycyclic-aromatic-hydrocarbon
#9
Huawei Duan, Zhini He, Junxiang Ma, Bo Zhang, Zhiguo Sheng, Ping Bin, Juan Cheng, Yong Niu, Haiyan Dong, Han Lin, Yufei Dai, Benzhan Zhu, Wen Chen, Yongmei Xiao, Yuxin Zheng
Global hypomethylation, gene-specific methylation, and genome instability are common events in tumorigenesis. To date, few studies have examined the aberrant DNA methylation patterns in coke oven workers, who are highly at risk of lung cancer by occupational exposure to polycyclic aromatic hydrocarbons (PAHs). We recruited 82 PAH-exposed workers and 62 unexposed controls, assessed exposure levels by urinary 1-hydroxypyrene, and measured genetic damages by comet assay, bleomycin sensitivity, and micronucleus assay...
November 2013: Archives of Toxicology
https://www.readbyqxmd.com/read/23308360/direct-reductive-amination-of-aldehyde-bisulfite-adducts-induced-by-2-picoline-borane-application-to-the-synthesis-of-a-dpp-iv-inhibitor
#10
Margaret Faul, Rob Larsen, Adam Levinson, Jason Tedrow, Filisaty Vounatsos
Aldehyde-bisulfite adducts dervied from unstable parent aldehydes were reductively alkylated in a direct fashion with a variety of amines. This approach features the use of 2-picoline borane as the reducing agent and a protic solvent for the reaction media and has been successfully applied to the synthesis of a DPP-IV inhibitor and a variety of other amines.
February 15, 2013: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/23218713/inhibition-of-norovirus-3cl-protease-by-bisulfite-adducts-of-transition-state-inhibitors
#11
Sivakoteswara Rao Mandadapu, Mallikarjuna Reddy Gunnam, Kok-Chuan Tiew, Roxanne Adeline Z Uy, Allan M Prior, Kevin R Alliston, Duy H Hua, Yunjeong Kim, Kyeong-Ok Chang, William C Groutas
Noroviruses are the most common cause of acute viral gastroenteritis, accounting for >21 million cases annually in the US alone. Norovirus infections constitute an important health problem for which there are no specific antiviral therapeutics or vaccines. In this study, a series of bisulfite adducts derived from representative transition state inhibitors (dipeptidyl aldehydes and α-ketoamides) was synthesized and shown to exhibit anti-norovirus activity in a cell-based replicon system. The ED(50) of the most effective inhibitor was 60 nM...
January 1, 2013: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/23148603/on-the-origin-of-free-and-bound-staling-aldehydes-in-beer
#12
REVIEW
Jeroen J Baert, Jessika De Clippeleer, Paul S Hughes, Luc De Cooman, Guido Aerts
The chemistry of beer flavor instability remains shrouded in mystery, despite decades of extensive research. It is, however, certain that aldehydes play a crucial role because their concentration increase coincides with the appearance and intensity of "aged flavors". Several pathways give rise to a variety of key flavor-active aldehydes during beer production, but it remains unclear as to what extent they develop after bottling. There are indications that aldehydes, formed during beer production, are bound to other compounds, obscuring them from instrumental and sensory detection...
November 21, 2012: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/22915796/broad-spectrum-antivirals-against-3c-or-3c-like-proteases-of-picornaviruses-noroviruses-and-coronaviruses
#13
Yunjeong Kim, Scott Lovell, Kok-Chuan Tiew, Sivakoteswara Rao Mandadapu, Kevin R Alliston, Kevin P Battaile, William C Groutas, Kyeong-Ok Chang
Phylogenetic analysis has demonstrated that some positive-sense RNA viruses can be classified into the picornavirus-like supercluster, which includes picornaviruses, caliciviruses, and coronaviruses. These viruses possess 3C or 3C-like proteases (3Cpro or 3CLpro, respectively), which contain a typical chymotrypsin-like fold and a catalytic triad (or dyad) with a Cys residue as a nucleophile. The conserved key sites of 3Cpro or 3CLpro may serve as attractive targets for the design of broad-spectrum antivirals for multiple viruses in the supercluster...
November 2012: Journal of Virology
https://www.readbyqxmd.com/read/22213191/dna-methylation-of-the-cyp1a1-enhancer-is-associated-with-smoking-induced-genetic-alterations-in-human-lung
#14
Xavier Tekpli, Shanbeh Zienolddiny, Vidar Skaug, Lodve Stangeland, Aage Haugen, Steen Mollerup
CYP1A1 (cytochrome P4501A1) catalyze the conversion of polycyclic aromatic hydrocarbons into reactive metabolites, which may induce DNA damage. We hypothesized that DNA methylation of the CYP1A1 enhancer could be involved in inter-individual differences in mRNA levels of CYP1A1 or affect the smoking-induced DNA damage in human lung. Using DNA bisulfite conversion and pyrosequencing, we show that DNA methylation of the CYP1A1 enhancer is affected by smoking. In adjacent histologically normal lung from lung cancer patients (n = 120), low levels of DNA methylation of the CYP1A1 enhancer were related to high levels of smoking-induced hydrophobic DNA adduct (p < 0...
October 1, 2012: International Journal of Cancer. Journal International du Cancer
https://www.readbyqxmd.com/read/22195515/aldehyde-bisulfite-adducts-prediction-of-some-of-their-thermodynamic-and-kinetic-properties
#15
E A Betterton, Y Erel, M R Hoffmann
No abstract text is available yet for this article.
January 1, 1988: Environmental Science & Technology
https://www.readbyqxmd.com/read/21692937/correlation-between-promoter-methylation-of-glutathione-s-tranferase-p1-and-oxidative-stress-in-acute-on-chronic-hepatitis-b-liver-failure
#16
T Li, Q H Meng, Z Q Zou, Y C Fan, B Long, Y M Guo, W Hou, J Zhao, J Li, H W Yu, Y K Zhu, K Wang
Promoter methylation of glutathione-S-transferase P1 (GSTP1) may be involved in liver damage caused by oxidative stress in acute-on-chronic hepatitis B-induced liver failure (ACHBLF). This study aimed to explore GSTP1 promoter methylation status and oxidative stress in such patients. DNA was extracted from peripheral blood mononuclear cells (PBMCs) of patients with acute-on-chronic liver hepatitis B-induced liver failure, chronic hepatitis B (CHB) and normal controls, followed by sodium-bisulfite treatment and methylation-specific PCR (MSP) analysis...
July 2011: Journal of Viral Hepatitis
https://www.readbyqxmd.com/read/21287394/a-distinct-region-of-the-mgmt-cpg-island-critical-for-transcriptional-regulation-is-preferentially-methylated-in-glioblastoma-cells-and-xenografts
#17
COMPARATIVE STUDY
Deborah S Malley, Rifat A Hamoudi, Sylvia Kocialkowski, Danita M Pearson, Vincent Peter Collins, Koichi Ichimura
O(6)-Methylguanine-DNA methyltransferase (MGMT) is a DNA repair protein that removes alkyl DNA adducts such as those induced by alkylating agents. Loss of MGMT expression through transcriptional silencing by hypermethylation of its CpG island (CGI) is found in diverse human cancers including glioblastomas. Glioblastomas that have MGMT methylation respond to temozolomide, an alkylating agent, resulting in improved survival. Consequently, assessment of MGMT methylation has become a therapy response and prognostic indicator...
May 2011: Acta Neuropathologica
https://www.readbyqxmd.com/read/20813757/chemical-discrimination-between-dc-and-5medc-via-their-hydroxylamine-adducts
#18
Martin Münzel, Lukas Lercher, Markus Müller, Thomas Carell
The presence of the methylated nucleobase (5Me)dC in CpG islands is a key factor that determines gene silencing. False methylation patterns are responsible for deteriorated cellular development and are a hallmark of many cancers. Today genes can be sequenced for the content of (5Me)dC only with the help of the bisulfite reagent, which is based exclusively on chemical reactivity differences established by the additional methyl group. Despite intensive optimization of the bisulfite protocol, the method still has specificity problems...
November 2010: Nucleic Acids Research
https://www.readbyqxmd.com/read/20707310/physico-chemical-and-chromatic-characterization-of-malvidin-3-glucoside-vinylcatechol-and-malvidin-3-glucoside-vinylguaiacol-wine-pigments
#19
Natalia Quijada-Morín, Olivier Dangles, Julián C Rivas-Gonzalo, M Teresa Escribano-Bailón
The physicochemical and chromatic features of malvidin 3-glucoside-vinylcatechol (PA1) and malvidin 3-glucoside-vinylguaiacol (PA2) adducts were investigated. Important differences between both pigments were observed. In the investigated pH range (2.0-4.5), our results suggest that PA1 could be considered as a noncovalent dimer of two pyranoflavylium ions (AH)2 which undergo a hydration reaction in two successive steps, with no proton transfer. In contrast, only proton transfer equilibrium between the pyranoflavylium ion and the quinonoid bases was observed for PA2...
September 8, 2010: Journal of Agricultural and Food Chemistry
https://www.readbyqxmd.com/read/20608023/development-and-application-of-a-sensitive-method-to-determine-concentrations-of-acrolein-and-other-carbonyls-in-ambient-air
#20
COMPARATIVE STUDY
Thomas M Cahill, M Judith Charles, Vincent Y Seaman
Acrolein, an unsaturated aldehyde, has been identified as one of the most important toxic air pollutants in recent assessments of ambient air quality. Current methods for determining acrolein concentrations, however, suffer from poor sensitivity, selectivity, and reproducibility. The collection and analysis of unsaturated carbonyls, and acrolein in particular, is complicated by unstable derivatives, coelution of similar compounds, and ozone interference. The primary objective of this research was to develop an analytical method to measure acrolein and other volatile carbonyls present in low part-per-trillion concentrations in ambient air samples obtained over short sampling periods...
May 2010: Research Report (Res Rep Health Eff Inst)
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