Abstract:
:2'-Deoxyoxanosine (dOxo) is a novel DNA lesion produced from dGuo by reaction with nitrous acid or nitric oxide [Suzuki, T., Yamaoka, R., Nishi, M., Ide, H., and Makino, K. (1996) J. Am. Chem. Soc. 118, 2515-2516]. We investigated the reaction of dOxo with glycine (Gly) under physiological conditions. When 5 mM dOxo was incubated with 500 mM Gly in 100 mM sodium phosphate buffer (pH 7.4) at 37 degrees C, an unknown product was formed exclusively. The yield of the product was 86% at an incubation time of 3 h. Using spectrometric data, it was identified as a ring-opened adduct containing an amide bond between the carbonyl group of dOxo and the amino group of Gly. The adduct was very stable (t(1/2) = 1280 h) under physiological conditions. Furthermore, dOxo in oligodeoxynucleotide reacted with Gly, yielding the same adduct. These results suggest that dOxo formed in DNA may react with Gly present in cells, resulting in adduct formation in vivo.
journal_name
Chem Res Toxicoljournal_title
Chemical research in toxicologyauthors
Suzuki T,Yamada M,Ide H,Kanaori K,Tajima K,Morii T,Makino Kdoi
10.1021/tx990164xsubject
Has Abstractpub_date
2000-04-01 00:00:00pages
227-30issue
4eissn
0893-228Xissn
1520-5010pii
tx990164xjournal_volume
13pub_type
杂志文章abstract::1-Hydroxypyrene (HOP), a metabolite found in the urine of humans and laboratory animals exposed to polycyclic aromatic hydrocarbons (PAHs), is known to be both acutely toxic and genotoxic. It has been widely used as a biomarker for studying PAH exposure. In this research, we have found that, upon UVA irradiation, HOP ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx990199x
更新日期:2000-07-01 00:00:00
abstract::Marine toxins such as brevetoxins and ciguatoxins are produced by dinoflagellates and can accumulate in seafood. These toxins affect humans through seafood consumption. Intoxication is mainly characterized by gastrointestinal and neurological disorders and, in most severe cases, by cardiovascular problems. To prevent ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx0342262
更新日期:2004-04-01 00:00:00
abstract::The two diastereomeric forms (5'S) and (5'R) of 5',8-cyclo-2'-deoxyguanosine have been synthesized and fully characterized. They have been used as references for the investigation of gamma-irradiation of 2'-deoxyguanosine and photolysis of 8-bromo-2'-deoxyguanosine in aqueous solutions. The observed (5'R)/(5'S) ratio ...
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
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
abstract::Overexposure to biphenyl amine compounds, which are found in smoke and azo-dyes, is linked to the occurrence of bladder cancer. However, the molecular mechanisms of biphenyl amine compound-induced bladder cancer are still unclear. Many studies have demonstrated that overexpression of cyclooxygenase-2 (COX-2) in neopla...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx2004689
更新日期:2012-03-19 00:00:00
abstract::Diabetes mellitus is a metabolic disorder constituting a major health problem whose prevalence has gradually increased worldwide over the past few decades. Type 2 diabetes mellitus (T2DM) remains more complex and heterogeneous and arises as a combination of insulin resistance and inadequate functional β-cell mass and ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章,评审
doi:10.1021/acs.chemrestox.5b00171
更新日期:2015-09-21 00:00:00
abstract::1-{4-[(4-Phenyl-5-trifluoromethyl-2-thienyl)methoxy]benzyl}azetidine-3-carboxylic acid (MRL-A) is a potent sphingosine-1-phosphate-1 receptor agonist, with potential application as an immunosuppressant in organ transplantation or for the treatment of autoimmune diseases. When administered orally to rats, radiolabeled ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx300017s
更新日期:2012-07-16 00:00:00
abstract::Metabolically formed dihydrodiol epoxides in the bay-region of polycyclic aromatic hydrocarbons are thought to be responsible for the genotoxic properties of these environmental pollutants. The hexacyclic aromatic hydrocarbon dibenzo[def,mno]chrysene (anthanthrene), although lacking this structural feature, was found ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx010131t
更新日期:2002-03-01 00:00:00
abstract::The efficacy of DNA-damaging anticancer drugs is highly influenced by cellular DNA repair capacity, and by inhibiting the relevant DNA repair pathway, efficacy of alkylating agents may be increased. Therefore, combining DNA repair inhibitors with anticancer agents that selectively target tumor tissue should improve ca...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx400255f
更新日期:2013-11-18 00:00:00
abstract::Mouse cytochrome P450 2A5 (CYP2A5) is upregulated in various pathophysiological liver diseases and induced by structurally variable hepatotoxic chemicals. A putative common feature for all of these conditions is altered cellular redox status. Nuclear factor erythroid 2-like 2 (Nrf2) is a transcription factor that is p...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx100084c
更新日期:2010-05-17 00:00:00
abstract::A newly developed recombinant yeast strain, in which the human estrogen receptor has been stably integrated into the genome of the yeast, was used to gain information on the estrogenic activity of a large series of dietary flavonoids. Among 23 flavonoids investigated, 8 were found to markedly stimulate the transcripti...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx970170y
更新日期:1998-06-01 00:00:00
abstract::Chemically reactive species formed from the metabolism of carboxylic acid-containing compounds have been proposed as mediators of their toxic side-effects. Two alternative metabolic pathways known to be involved in the generation of reactive acylating metabolites of carboxylic acids are acyl glucuronidation and acyl-C...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx020013l
更新日期:2002-10-01 00:00:00
abstract::Hydrophobic and volatile chemicals have proven to be difficult to dose in cell assays. Cosolvents are often needed to dissolve these chemicals in cell culture medium. Moreover, the free concentration of these chemicals in culture medium may diminish over time due to metabolism, evaporation, and nonspecific binding to ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx1002595
更新日期:2010-11-15 00:00:00
abstract::Oxidation of the tris(p-carboxyltetrathiaaryl)methyl (TAM) EPR radical probe, TAMa(•), by rat liver microsomes (RLM) + NADPH, or horseradish peroxidase (HRP) + H2O2, or K2IrCl6, led to an intermediate cation, TAMa(+), which was treated with glutathione (GSH), with formation of an adduct, TAMa-SG(•), resulting from the...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx400467p
更新日期:2014-04-21 00:00:00
abstract::Two hemorrhagic proteases, Lachesis hemorrhagic toxins a and b (LHTa and LHTb), were isolated from the venom of Lachesis muta, which is distributed in Central and South America. One protease showed strong hemorrhagic action, while the other showed weak hemorrhagic activity even though the two enzymes are very similar ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx00006a003
更新日期:1988-11-01 00:00:00
abstract::One possible mechanism linking inflammation with cancer involves the generation of reactive oxygen, nitrogen, and halogen species by activated macrophages and neutrophils infiltrating sites of infection or tissue damage, with these chemical mediators causing damage that ultimately leads to cell death and mutation. To ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx300473n
更新日期:2013-04-15 00:00:00
abstract::The trichothecene mycotoxin T-2 toxin, which is produced by fungi of the Fusarium species, is a worldwide occurring contaminant of cereal based food and feed. The cytotoxic properties of T-2 toxin are already well described with apoptosis being a major mechanism of action in various cell lines as well as in primary ce...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx3004664
更新日期:2013-03-18 00:00:00
abstract::Catalase is an important antioxidant enzyme, which has been shown to provide cardiac protection from acute toxicity induced by doxorubicin, a most effective anticancer agent. Because cumulative dose-dependent chronic cardiomyopathy due to a long-term administration of doxorubicin is a significant clinical problem, the...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx015532n
更新日期:2002-01-01 00:00:00
abstract::alpha-Sulfate trans-tamoxifen and alpha-sulfate cis-tamoxifen were synthesized as proposed active metabolites of tamoxifen that react with DNA. alpha-Acetoxytamoxifen was prepared as a model-activated form to produce a reactive carbocation. Calf thymus DNA was reacted with alpha-hydroxytamoxifen or the activated forms...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx960114h
更新日期:1997-02-01 00:00:00
abstract::Acrolein, a known mutagen, undergoes reaction in vitro under physiological conditions with both 2'-deoxyguanosine and native DNA to give rise to exocyclic adducts of the 5,6,7,8-tetrahydropyrimido[1,2-a]purine-10(3H)-one class having a hydroxyl group at either the 6 or the 8 position (these positions are respectively ...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx015568f
更新日期:2002-02-01 00:00:00
abstract::It is vital that methylated trivalent arsenicals [MA(III) and DMA(III)] are described and characterized unequivocally due to their high toxicity. Two different ways of generating the methylated trivalent arsenicals have been practiced-reduction of the methylated pentavalent arsenical either by the sodium-metabisulfite...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx049978q
更新日期:2004-08-01 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::Cytochrome P450 enzymes (CYPs) metabolize alkyl- and arylamines, generating several different products. For the primary and secondary amines, some of these reactions result in hydroxylated amines, which may be toxic. Thus, when designing new drugs containing amine groups, it is important to be able to predict if a giv...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx500371a
更新日期:2015-04-20 00:00:00
abstract::Cr(VI) genotoxicity is caused by products of its reductive metabolism inside the cells. Reactive oxygen species (ROS) and Cr(V,IV) intermediates are potential sources of oxidative damage by Cr(VI). Here, we investigated seven fluorescent probes for the detection of ROS and non-ROS oxidants in Cr(VI) reactions with its...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx500028x
更新日期:2014-05-19 00:00:00
abstract::This work reveals a novel mechanism for triplet carbonyl formation (and hence chemiluminescence) during lipid peroxidation, whose chemiluminescence has been attributed to both triplet carbonyls and singlet oxygen. As a model for polyunsaturated fatty acid hydroperoxides, we have synthesized 3-hydroperoxy-2,3-dimethyl-...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx970075p
更新日期:1997-10-01 00:00:00
abstract::In recent years, there has been an increase in the production of shellfish and in global demand for seafood as nutritious and healthy food. Unfortunately, a significant number of incidences of shellfish poisoning occur worldwide, and microalgae that produce phycotoxins are responsible for most of these. Phycotoxins in...
journal_title:Chemical research in toxicology
pub_type: 杂志文章,评审
doi:10.1021/tx200182m
更新日期:2011-11-21 00:00:00
abstract::Reaction of lysine with estrone 3,4-o-quinone gave a complex mixture of products. Six compounds were isolated and identified using spectroscopic techniques. Among the reaction products isolated were 4-hydroxyestrone (2), 3-aminoisoestrone (3), 3-(N-pentyl-5-amino)-isoestrone (4), 1-lysylestrone 3,4-o-iminoquinone (5),...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx00041a016
更新日期:1994-09-01 00:00:00
abstract::Butadiene monoxide, a toxic metabolite of 1,3-butadiene, is a substrate for the human placental glutathione (GSH) S-transferase. The products have been identified as S-(2-hydroxy-3-buten-1-yl)glutathione (I) and S-(1-hydroxy-3-buten-2-yl)glutathione (II). S-(4-hydroxy-2-buten-1-yl)glutathione (III), which was formed c...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx00022a006
更新日期:1991-07-01 00:00:00
abstract::The monoamine oxidase B (MAO-B) catalyzed oxidation of amines has been proposed to proceed via a polar pathway, an initial single-electron transfer pathway and an initial hydrogen atom transfer pathway. Results from previous studies on selected N-cyclopropyl-4-substituted-1,2,3,6-tetrahydropyridine derivatives have le...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx960063o
更新日期:1996-09-01 00:00:00
abstract::The antitumor agent N,N'-bis(2-chloroethyl)-N-nitrosourea (BCNU) is known to be unstable in aqueous solution, and to degrade spontaneously to reactive alkylating and carbamoylating intermediates. Whereas the alkylating component is believed to be responsible for the antitumor effects of this drug, it has been speculat...
journal_title:Chemical research in toxicology
pub_type: 杂志文章
doi:10.1021/tx00033a020
更新日期:1993-05-01 00:00:00