Abstract：
:Vinyl chloride and acrolein are important industrial chemicals. Both form DNA adducts, vinyl chloride after enzymatic oxidation to chlorooxirane and acrolein by direct reaction. Reaction at the N(2) position of guanine is a major pathway. The resulting 2-oxoethyl and 3-oxopropyl adducts cyclize spontaneously to hydroxyethano and hydroxypropano derivatives, respectively. The two cyclic adducts have been detected in DNA exposed to these mutagens. A new method has been developed for the synthesis of deoxyguanosine adducts of chlorooxirane and acrolein, as well as oligonucleotides containing these adducts. Reaction of O(6)-[(trimethylsilyl)ethyl]-2-fluoro-2'-deoxyinosine with the appropriate aminodiol followed by oxidative cleavage of the diol with NaIO(4) gave the adducts in excellent yields. Reaction of oligonucleotides containing the halonucleoside with the aminodiols followed by NaIO(4) efficiently created the nucleosides in the oligonucleotides. Deoxyadenosine adducts were created similarly using 6-chloropurine 9-(2'-deoxyriboside).
journal_name
Chem Res Toxicoljournal_title
Chemical research in toxicologyauthors
Nechev LV,Harris CM,Harris TMdoi
10.1021/tx990167+subject
Has Abstractpub_date
2000-05-01 00:00:00pages
421-9issue
5eissn
0893-228Xissn
1520-5010pii
tx990167+journal_volume
13pub_type
杂志文章abstract：:The hydroperoxide of linoleic acid (13-HPODE) degrades to 9,12-dioxo-10(E)-dodecenoic acid (DODE), which readily modifies proteins. This study identified the major proteins in MCF7 cells modified by DODE. To reduce false positives, three methods were used to identify DODE-modified proteins. First, cells were treated w...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx9002808
更新日期：2010-03-15 00:00:00
abstract：:N,N-Bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil, 1) is an orally administrated drug widely used in the chemotherapy of chronic lymphocytic leukemia. We have recently described a new metabolic path for the decomposition of 1 in human gastric juice based on its reactions with saliva-derived thiocyanate io...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx980122t
更新日期：1998-11-01 00:00:00
abstract：:High-throughput screening (HTPS) assays to detect inhibitors of thyroperoxidase (TPO), the enzymatic catalyst for thyroid hormone (TH) synthesis, are not currently available. Herein, we describe the development of a HTPS TPO inhibition assay. Rat thyroid microsomes and a fluorescent peroxidase substrate, Amplex UltraR...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx400310w
更新日期：2014-03-17 00:00:00
abstract：:Methylglyoxal is a mutagenic bis-electrophile that is produced endogenously from carbohydrate precursors. Methylglyoxal has been reported to induce DNA-protein cross-links (DPCs) in vitro and in cultured cells. Previous work suggests that these cross-links are formed between guanine and either lysine or cysteine side ...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx500068v
更新日期：2014-06-16 00:00:00
abstract：:Divicine is an unstable aglycon metabolite of the fava bean pyrimidine beta-glucoside vicine. Divicine has long been thought to be a mediator of an acute hemolytic crisis, known as favism, in susceptible individuals who ingest fava beans (Vicia faba). However, a recent report has questioned the chemical identity of th...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx00034a009
更新日期：1993-07-01 00:00:00
abstract：:Bisphenol A (BPA) is used in the production of polycarbonate plastics and epoxy resins for baby bottles, liners of canned food, and many other consumer products. Previously, BPA has been shown to reduce the activity of several antioxidant enzymes, which may contribute to oxidative stress. However, the underlying mecha...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx400036v
更新日期：2013-03-18 00:00:00
abstract：:Spin adducts are observed when the unfiltered smoke produced during the aerobic pyrolysis of perfluoro polymers (PFP) is bubbled through a solution of the ESR spin trap alpha-phenyl-N-tert-butylnitrone (PBN). The spin adducts include those from an oxy radical and the fluorine atom, and in addition the spin trap is oxi...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx00009a009
更新日期：1989-05-01 00:00:00
abstract：:Interstrand cross-links are minor components of the collection of products formed in DNA by ionizing radiation. Through their formation by other damaging agents, it is known that interstrand cross-links exert significant effects on replication and transcription. The structures of DNA interstrand cross-links produced a...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx7002307
更新日期：2007-11-01 00:00:00
abstract：:S-(1,2-Dichlorovinyl)-L-cysteine (DCVC), a mutagenic and nephrotoxic metabolite of trichloroethylene, is bioactivated to S-(1,2-dichlorovinyl)-L-cysteine sulfoxide (DCVCS) and chlorothioketene and/or 2-chlorothionoacetyl chloride by cysteine conjugate S-oxidase (S-oxidase) and cysteine conjugate beta-lyase (beta-lyase...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx900219x
更新日期：2009-09-01 00:00:00
abstract：:Smokeless tobacco products, such as moist snuff or chewing tobacco, contain many of the same carcinogens as tobacco smoke; however, the impact on children of indirect exposure to tobacco constituents via parental smokeless tobacco use is unknown. As part of the California Childhood Leukemia Study, dust samples were co...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/acs.chemrestox.5b00040
更新日期：2015-05-18 00:00:00
abstract：:N-Methyl-N-nitrosourea (MNU) is a reactive, mutagenic methylating agent. MNU methylates DNA at various sites, including guanine N7, guanine O6, and adenine N3. Dixit and Gold [(1986) Proc. Natl. Acad. Sci. U.S.A. 83, 8039-8043] reported that ellagic acid, a phenolic natural product, inhibited the mutagenicity of MNU i...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx00015a002
更新日期：1990-05-01 00:00:00
abstract：:Cancer-associated mutations often lead to perturbed cellular energy metabolism and accumulation of potentially harmful oncometabolites. One example is the chiral molecule 2-hydroxyglutarate (2HG); its two stereoisomers (d- and l-2HG) have been found at abnormally high concentrations in tumors featuring anomalous metab...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/acs.chemrestox.7b00009
更新日期：2017-04-17 00:00:00
abstract：:Protein-xenobiotic adducts are byproducts of xenobiotic metabolism. While there is a correlation between protein adduction and target organ toxicity, a cause and effect relationship is not often clear. Naphthoquinone (NQ) and monocrotaline pyrrole (MCTP) are two pneumotoxic electrophiles that form covalent adducts wit...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx1002436
更新日期：2010-09-20 00:00:00
abstract：:2,4-Dichlorophenol (2,4-DCP), an environmental pollutant, was reported to cause hepatotoxicity. The biochemical mechanisms of 2,4-DCP induced liver injury remain unknown. The present study showed that 2,4-DCP is chemically reactive and spontaneously reacts with GSH and bovine serum albumin to form GSH conjugates and B...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/acs.chemrestox.0c00118
更新日期：2020-09-21 00:00:00
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journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx00013a004
更新日期：1990-01-01 00:00:00
abstract：:Pyridoxamine (PM) is an effective inhibitor of the formation of the carcinogen acrylamide (AA) from its precursors in low-moisture model systems. Although AA is widely assumed to act by scavenging carbonyl compounds, no alternative pathways have to date been explored. In this work, we found AA to directly react with P...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx100293y
更新日期：2011-03-21 00:00:00
abstract：:N(6)-(2-Hydroxy-3-buten-1-yl)-2'-deoxyadenosine (N(6)-HB-dA I) and N(6),N(6)-(2,3-dihydroxybutan-1,4-diyl)-2'-deoxyadenosine (N(6),N(6)-DHB-dA) are exocyclic DNA adducts formed upon alkylation of the N(6) position of adenine in DNA by epoxide metabolites of 1,3-butadiene (BD), a common industrial and environmental che...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/acs.chemrestox.5b00166
更新日期：2015-07-20 00:00:00
abstract：:A series of 13 cyclopenta polycyclic aromatic hydrocarbons have been studied using quantum mechanical methods. The three-dimensional molecular structure of each carbocation that might result from the opening of a protonated epoxide ring formed between the carbon atoms completing the cyclopenta ring was computed with A...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx00026a022
更新日期：1992-03-01 00:00:00
abstract：:Nicking of the DNA strand immediately upstream of an internal abasic (AP) site produces 5'-terminal abasic (dRp) DNA. Both the intact and the nicked abasic species are reactive intermediates along the DNA base excision repair (BER) pathway and can be derailed by side reactions. Aberrant accumulation of the 5'-terminal...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/acs.chemrestox.7b00057
更新日期：2017-06-19 00:00:00
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journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx0600604
更新日期：2006-08-01 00:00:00
abstract：:Previous reports indicate that 4-benzyl-1-methyl-1,2,3,6-tetrahydropyridine (BMTP), the benzyl analogue of the Parkinsonian inducing neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), is not neurotoxic in the C-57 black mouse even when administered at a dose 10 times greater than the dose of MPTP required...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx00014a008
更新日期：1990-03-01 00:00:00
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journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx990098z
更新日期：1999-11-01 00:00:00
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journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx970021f
更新日期：1997-07-01 00:00:00
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journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx700282x
更新日期：2007-12-01 00:00:00
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journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx500255r
更新日期：2014-10-20 00:00:00
abstract：:Nuclear magnetic resonance (NMR) spectroscopy has traditionally been considered as an indispensable tool in elucidating structures of metabolites. With the advent of Fourier transform (FT) spectrometers, along with improvements in software and hardware (such as high-field magnets, cryoprobes, versatile pulse sequences...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx800251p
更新日期：2009-02-01 00:00:00
abstract：:Topoisomerase II is an essential nuclear enzyme involved in regulating DNA topology to facilitate replication and cell division. Disruption of topoisomerase II function by chemotherapeutic agents is in use as an effective strategy to fight cancer. Etoposide is an anticancer therapeutic that disrupts the catalytic cycl...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/acs.chemrestox.6b00209
更新日期：2016-09-19 00:00:00
abstract：:We propose here a combined gas chromatography/mass spectrometry (GC/MS) and liquid chromatography/mass spectrometry (LC/MS) metabolic profiling strategy to elucidate the toxicity in rats induced by orally administered multiglycosides of Tripterygium wilfordii Hook. f. (GTW) in multiple organs including the kidney, liv...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx7002905
更新日期：2008-02-01 00:00:00
abstract：:Peroxynitrite (ONOO-), the reaction product of superoxide (O2.-) and nitric oxide (.NO), nitrates tyrosine and other phenolics. We report herein that tryptophan is also nitrated by peroxynitrite in the absence of transition metals to one predominant isomer of nitrotryptophan, as determined from spectral characteristic...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx950133b
更新日期：1996-03-01 00:00:00
abstract：:Five major products (adducts A(1a), A(1b), A(2), A(3,) and B) from the reaction of guanosine (Guo) with 4-oxo-2(E)-nonenal (ONE) were detected by liquid chromatography-mass spectrometry (LC-MS). Tandem MS (MS/MS) analysis of these compounds suggested that modifications to the nucleoside had been introduced. Adducts A(...
journal_title：Chemical research in toxicology
pub_type： 杂志文章
doi：10.1021/tx0600189
更新日期：2006-06-01 00:00:00
