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Bisulfite adducts

Maxwell H Furigay, Maria M Boucher, Nikola A Mizgier, Cheyenne S Brindle
The purification of organic compounds is an essential component of routine synthetic operations. The ability to remove contaminants into an aqueous layer by generating a charged structure provides an opportunity to use extraction as a simple purification technique. By combining the use of a miscible organic solvent with saturated sodium bisulfite, aldehydes and reactive ketones can be successfully transformed into charged bisulfite adducts that can then be separated from other organic components of a mixture by the introduction of an immiscible organic layer...
April 2, 2018: Journal of Visualized Experiments: JoVE
Masahiko Tanaka, Natsuhiko Sugimura, Akio Fujisawa, Yorihiro Yamamoto
Edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one) has been used as a free radical scavenging drug for the treatment of acute ischemic stroke in Japan since 2001. Edaravone is given to patients intravenously; therefore, it is distributed in the form of an aqueous solution. However, aqueous solutions of edaravone are very unstable because it is present as edaravone anion, which is capable of transferring an electron to free radicals including oxygen, and becomes edaravone radical. We observed the formation of hydrogen peroxide and edaravone trimer when aqueous edaravone solution was kept at 60°C for 4 weeks...
November 2017: Journal of Clinical Biochemistry and Nutrition
Anushka C Galasiti Kankanamalage, Yunjeong Kim, Athri D Rathnayake, Kevin R Alliston, Michelle M Butler, Steven C Cardinale, Terry L Bowlin, William C Groutas, Kyeong-Ok Chang
Ester and carbamate prodrugs of aldehyde bisulfite adduct inhibitors were synthesized in order to improve their pharmacokinetic and pharmacodynamic properties. The inhibitory activity of the compounds against norovirus 3C-like protease in enzyme and cell-based assays was determined. The ester and carbamate prodrugs displayed equivalent potency to those of the precursor aldehyde bisulfite adducts and precursor aldehydes. Furthermore, the rate of ester cleavage was found to be dependent on alkyl chain length...
July 27, 2017: Journal of Medicinal Chemistry
M L Shen, Z N He, X Zhang, H W Duan, Y Niu, P Bin, M Ye, T Meng, Y F Dai, S F Yu, W Chen, Y X Zheng
Objective: To investigate the association between etheno-DNA adduct and the promoter of DNA methylation levels of cyclin dependent kinase inhibitor 2A (P16), Ras association domain family 1 (RASSF1A) and O-6-methylguanine-DNA methyltransferase (MGMT) in workers with occupational exposure to diesel engine exhaust (DEE). Methods: We recruited 124 diesel engine testing workers as DEE exposure group and 112 water pump operator in the same area as control group in Henan province in 2012 using cluster sampling. The demographic data were obtained by questionnaire survey; urine after work and venous blood samples were collected from each subject...
June 6, 2017: Zhonghua Yu Fang Yi Xue za Zhi [Chinese Journal of Preventive Medicine]
Anna K Michel, Adam T Zarth, Pramod Upadhyaya, Stephen S Hecht
Metabolic activation of the carcinogenic tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK, 1 ) and N '-nitrosonornicotine (NNN, 2 ) results in the formation of 4-(3-pyridyl)-4-oxobutyl (POB)-DNA adducts, several of which have been previously identified both in vitro and in tissues of laboratory animals treated with NNK or NNN. However, 2'-deoxycytidine adducts formed in this process have been incompletely examined in previous studies. Therefore, in this study we prepared characterized standards for the identification of previously unknown 2'-deoxycytidine and 2'-deoxyuridine adducts that could be produced in these reactions...
March 31, 2017: ACS Omega
Arif Akbar Bhat, Hilal Ahmad Wani, Shiekh Ishaq, Ajaz Ahmad Waza, Rawoof Ahmad Malik, Iram Shabir, Showkat Jeelani, Showkat Kadla, Waseem Qureshie, Akbar Masood, Sabhiya Majid
Epigenetic alterations, in addition to multiple gene abnormalities, are involved in the genesis and progression of human cancers. Gastrointestinal tract (GIT) cancer is a major medical and economic burden worldwide. Aberrant methylation of CpG islands within promoter regions is associated with transcriptional inactivation of various tumor suppressor genes. Although a number of cancer-associated genes have been found to be hypermethylated in GIT cancer, valuable methylation markers for early diagnosis and prognostic evaluation of this cancer remain largely unknown...
February 7, 2017: Cancer Investigation
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...
December 2016: Cellular Oncology (Dordrecht)
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...
March 2017: Current Eye Research
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
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
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
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
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
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
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
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
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
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
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
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
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