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| 2-Naphthol, or β-naphthol, is a fluorescent colorless (or occasionally yellow) crystalline solid with the formula C10H7OH. It is an isomer of 1-naphthol, differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, but more reactive. Both isomers are soluble in simple alcohols, ethers, and chloroform. 2-Naphthol is a widely used intermediate for the production of dyes and other compounds.
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Read full article at Wikipedia
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| InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H |
| JWAZRIHNYRIHIV-UHFFFAOYSA-N |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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Found in
urine
(BTO:0001419).
See:
PubMed
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radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
electron donor
A molecular entity that can transfer an electron to another molecular entity.
(via phenolic donor )
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genotoxin
A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
human urinary metabolite
Any metabolite (endogenous or exogenous) found in human urine samples.
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antinematodal drug
A substance used in the treatment or control of nematode infestations.
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View more via ChEBI Ontology
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2-hydroxynaphthalene
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HMDB
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2-Naftol
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ChemIDplus
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2-naftolo
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ChemIDplus
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2-naphthalenol
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NIST Chemistry WebBook
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2-Naphthol
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KEGG COMPOUND
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2-naphthol
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UniProt
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2-naphtol
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ChemIDplus
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beta-hydroxynaphthalene
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ChemIDplus
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β-hydroxynaphthalene
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NIST Chemistry WebBook
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β-Naftol
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ChemIDplus
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β-naftolo
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ChemIDplus
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beta-Naphthol
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KEGG COMPOUND
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beta-Naphthol
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KEGG COMPOUND
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β-naphthol
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NIST Chemistry WebBook
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β-naphthyl alcohol
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ChemIDplus
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β-naphthyl hydroxide
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ChemIDplus
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β-Naphtol
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ChemIDplus
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Isonaphthol
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ChemIDplus
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Antioxygene BN
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HMDB
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Azogen Developer A
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HMDB
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C.I. Azoic Coupling Component 1
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ChemIDplus
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C.I. Developer 5
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ChemIDplus
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Developer A
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ChemIDplus
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Developer AMS
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ChemIDplus
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Developer BN
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ChemIDplus
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135-19-3
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CAS Registry Number
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KEGG COMPOUND
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135-19-3
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CAS Registry Number
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NIST Chemistry WebBook
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135-19-3
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CAS Registry Number
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ChemIDplus
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27395
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Gmelin Registry Number
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Gmelin
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742134
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Reaxys Registry Number
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Reaxys
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Tao C, Fan Y, Niu R, Li Z, Qian H, Yu H, Xu Q, Xu Q, Lu C (2021)
Urinary polycyclic aromatic hydrocarbons and sex hormones in children and adolescents: Evidence from NHANES.
Ecotoxicology and environmental safety 216, 112215 [PubMed:33862438]
[show Abstract]
BackgroundEvidences showed that polycyclic aromatic hydrocarbons (PAHs) do harm to human body. However, the association between PAHs and sex hormones in children and adolescents remains unclear.ObjectivesThe study aims to investigate the associations between PAHs and sex hormones in the general children and adolescent population.Methods967 participants aged 6-19 with complete data of PAHs exposure biomarkers, covariates and sex hormones [total testosterone (TT), estradiol (E2) and sex hormone binding globulin (SHBG)] were recruited from National Health and Nutrition Examination Survey (NHANES), 2013-2016. Free androgen index (FAI) was calculated with TT/SHBG. Multivariate linear regression models were performed in six subgroups (male children, male adolescents, male late adolescents, female children, female adolescents and female late adolescents) to estimate the associations between sex hormone alterations and PAHs exposure.ResultsIn male puberty adolescents, weighted multivariate linear regression indicated that negative trends for 2-Hydroxynaphthalene, 1-Hydroxyphenanthrene, 2&3-Hydroxyphenanthrene and E2 (2-Hydroxynaphthalene: β: -0.104, 95%CI: -0.180, -0.029, P < 0.01; 1-Hydroxyphenanthrene: β: -0.112, 95%CI: -0.206, -0.018, P = 0.019; 2&3-Hydroxyphenanthrene: β: -0.125, 95%CI: -0.232, -0.018, P = 0.022), while exposure to 2-Hydroxynaphthalene was related to TT reduction (β: -0.099, 95%CI: -0.177, -0.020, P = 0.014). Same pattern between 2&3-Hydroxyphenanthrene and E2 alteration (2&3-Hydroxyphenanthrene: β: -0.139, 95%CI: -0.236, -0.041, P < 0.01) was also observed in male late adolescents. In male children, we determined that 1-Hydroxyphenanthrene was negatively associated with SHBG (β: -0.121, 95%CI: -0.205, -0.037, P < 0.01), while the same patterns were observed in male puberty children. We did not observe any significant result in female subgroups. All these results above were determined to have q value < 0.05.ConclusionPAHs exposure was associated with the alterations of sex hormones in male adolescents and children. Considering the cross-sectional study design, further large-scale epidemiological study is necessary. | Cheng S, Zhang H, Wang P, Zou K, Duan X, Wang S, Yang Y, Shi L, Wang W (2021)
Benchmark dose analysis for PAHs hydroxyl metabolites in urine based on mitochondrial damage of peripheral blood leucocytes in coke oven workers in China.
Environmental toxicology and pharmacology 86, 103675 [PubMed:34033865]
[show Abstract]
ObjectivesThe aim was to explore the dose-response relationship between occupational polycyclic aromatic hydrocarbons (PAHs) exposure and mitochondrial damage in coke oven plants workers.Methods544 workers and 238 healthy people were recruited. The ultra-high performance liquid chromatography was used to determine the level of 1-hydroxypyrene, 1-hydroxynaphthalene, 2-hydroxynaphthalene and 3-hydroxyphenanthrene. The real-time fluorescence quantitative polymerase chain reaction was used to determine the mitochondrial DNA copy number (mtDNAcn). The benchmark dose software was used to analyze the benchmark dose.ResultsThe mtDNAcn in the exposure group was lower than that in the control group. The concentrations of 1-hydroxypyrene, 1-hydroxynaphthalene, 2-hydroxynaphthalene and 3-hydroxyphenanthrene in the exposure group were higher than those in the control group. There is a dose-response relationship between 1-hydroxypyrene, 3-hydroxyphenanthrene and mitochondrial DNA damage. The benchmark dose lower confidence limit (BMDL) of 1-hydroxypyrene were 0.045, 0.004, and 0.058 pg/μg creatinine in the total, male, and female population, respectively. The BMDL of 3-hydroxyphenanthrene were 5.142, 6.099, and 2.807 pg/μg creatinine in the total, male, and female population, respectively.ConclusionsThe BMDL of 1-hydroxypyrene and 3-hydroxyphenanthrene initially explored can provide a reference to establish occupational exposure biological limits. | Chaudhary A (2021)
Recent development in the synthesis of heterocycles by 2-naphthol-based multicomponent reactions.
Molecular diversity 25, 1211-1245 [PubMed:32206945]
[show Abstract]
2-Naphthol or β-naphthol is an important starting material that has drawn great attention in various organic transformations because of its attributes, such as low cost, easy to handle and eco-friendliness. The electron-rich aromatic framework of 2-naphthol with multiple reactive sites allows it to be utilized in several kinds of organic reactions eventuated to several organic molecules with potent biological properties. Multicomponent reaction approach has been tremendously utilized to explore the synthetic utility of 2-naphthol for the construction of diverse N/O-containing heterocyclic framework. In this review, we summarize recent data pertaining to multicomponent reactions, wherein heterocyclic compounds are synthesized utilizing 2-naphthol as one of the starting materials. It is anticipated that this review will stimulate the researchers to design new multicomponent strategies complying with the Green Chemistry principles for the further exploitation of 2-naphthol for the rapid synthesis of versatile biologically relevant heterocycles. This review provides a concise overview of the different 2-naphthol based multicomponent reactions utilized for the construction of diverse bioactive heterocyclic scaffold. | Seidel CM, Brethauer S, Gyenge L, Rudolf von Rohr P, Studer MH (2019)
Two-stage steam explosion pretreatment of softwood with 2-naphthol as carbocation scavenger.
Biotechnology for biofuels 12, 37 [PubMed:30828382]
[show Abstract]
Background Lignocellulosic biomass is considered as a potential source for sustainable biofuels. In the conversion process, a pretreatment step is necessary in order to overcome the biomass recalcitrance and allow for sufficient fermentable sugar yields in enzymatic hydrolysis. Steam explosion is a well known pretreatment method working without additional chemicals and allowing for efficient particle size reduction. However, it is not effective for the pretreatment of softwood and the harsh conditions necessary to achieve a highly digestible cellulose fraction lead to the partial degradation of the hemicellulosic sugars. Previous studies showed that the autohydrolysis pretreatreatment of softwood can benefit from the addition of 2-naphthol. This carbocation scavenger prevents lignin repolymerisation leading to an enhanced glucose yield in the subsequent enzymatic hydrolysis.Results In order to prevent the degradation of the hemicellulose, we investigated in this study a two-stage 2-naphthol steam explosion pretreatment. In the first stage, spruce wood is pretreated at a severity which is optimal for the autocatalytic hydrolysis of the hemicellulose. The hydrolyzate containing the solubilized sugars is withdrawn from the reactor and the remaining solids are pretreated with different amounts of 2-naphthol in a second stage at a severity that allows for high glucose yields in enzymatic hydrolysis. The pretreated spruce was subjected to enzymatic hydrolysis and to simultaneous saccharification and fermentation (SSF). In the first stage, the maximal yield of hemicellulosic sugars was 47.5% at a pretreatment severity of log R 0 = 3.75 at 180 °C. In the second stage, a 2-naphthol dosage of 0.205 mol/mol lignin C9-unit increased the ethanol yield in SSF with a cellulose loading of 1% using the whole second stage pretreatment slurry by 17% from 73.6% for the control without 2-naphthol to 90.4%. At a higher solid loading corresponding to 5% w/w cellulose, the yields decreased due to higher concentrations of residual 2-naphthol in the biomass and the pretreatment liquor, but also due to higher concentrations of potential inhibitors like HMF, furfural and acetic acid. Experiments with washed solids, vacuum filtered solids and the whole slurry showed that residual 2-naphthol can inhibit the fermentation as a single inhibitor but also synergistically together with HMF, furfural and acetic acid.Conclusions This work shows that a two-stage pretreatment greatly enhances the recovery of hemicellulosic sugars from spruce wood. The presence of 2-naphthol in the second pretreatment stage can enhance the ethanol yield in SSF of steam explosion pretreated softwood at low cellulose concentrations of 1% w/w. However, with higher solid loadings of 5% w/w cellulose, the ethanol yields were in general lower due to the solid effect and a synergistic inhibition of HMF, furfural, acetic acid with residual 2-naphthol. The concentration of residual 2-naphthol tolerated by the yeast decreased with increasing concentrations of HMF, furfural, and acetic acid. | Nie J, Li J, Cheng L, Li Y, Deng Y, Yan Z, Duan L, Niu Q, Perera F, Tang D (2018)
Maternal urinary 2-hydroxynaphthalene and birth outcomes in Taiyuan, China.
Environmental health : a global access science source 17, 91 [PubMed:30572877]
[show Abstract]
BackgroundNaphthalene is the simplest polycyclic aromatic hydrocarbon (PAH). It is easily emitted into the atmosphere, posing a significant risk to human health. However, limited studies have described the impact of naphthalene exposure on birth outcomes. In this study, we investigated the association between the maternal urinary metabolites of naphthalene, 2-hydroxynaphthalene (2-OH NAP), and birth outcomes.MethodIn the present study, four urinary PAH metabolites were measured in 263 pregnant women during late pregnancy. Multiple linear regression analysis was used to analyze the relationship between the concentrations of 2-OH NAP and birth outcomes, and restricted cubic spline models were further used to examine the shapes of the dose-response association.ResultGeneral linear models showed that prenatal urinary 2-OH NAP was associated with lower birth weight (BW) (- 4.38% for the high vs. low exposure group of 2-OH NAP; p for trend = 0.049) and higher cephalization index (CI) (4.30% for the high vs. low exposure group of 2-OH NAP; p for trend = 0.038). These associations were linear and significant when 2-OH NAP was modeled as a continuous variable in restricted cubic spline models (P linear = 0.0293 for 2-OH NAP and BW; P linear = 0.0326 for 2-OH NAP and CI). Multiple linear regression data indicated that each 1 ln-unit increase in 2-OH NAP was significantly associated with a 2.09 g/cm increase in the CI. The associations among 2-OH NAP, BW, and CI were also observed in a subset of participants residing close to arterial traffic.ConclusionOur data indicated that prenatal exposure to naphthalene had an adverse effect on fetal birth outcomes, especially the brain development index. Reduced exposure to naphthalene may improve newborn health outcomes. In Taiyuan, naphthalene may result from traffic pollution. | Lin TJ, Guo YL, Hsu JC, Wang IJ (2018)
2-Naphthol Levels and Allergic Disorders in Children.
International journal of environmental research and public health 15, E1449 [PubMed:29987264]
[show Abstract]
BackgroundThe measurement of polycyclic aromatic hydrocarbons (PAH) in ambient air is quite difficult to perform. Using urine biomarkers of PAH such as 2-naphthol is one approach to this problem. This study explored the association between urine 2-naphthol levels and allergic diseases. The associations between 2-naphthol levels and oxidative stress biomarkers for the possible disease pathogenesis were also investigated.MethodA total of 453 kindergarten children from the (Childhood Environment and Allergic Diseases Study) CEAS cohort with urine samples were recruited. Urine 2-naphthol levels were measured by high-performance liquid chromatography mass spectrometry (HPLC-MS/MS) and markers of oxidative stress (8OHdG) were measured by enzyme-linked immunosorbent assays (ELISA). Information on environmental risk factors and allergic diseases were also collected. The association between 2-naphthol levels, 8OHdG levels, IgE, and allergic diseases were evaluated by multivariate linear regression and logistic regression.ResultsLevels of 2-naphthol were positively correlated with 8OHdG levels. A one ln-unit increase in the 2-naphthol level was positively associated to 8OHdG levels (per ln-unit: β = 100.61, p < 0.001). When dividing 2-naphthol levels into quartiles, asthma was significantly associated with 2-naphthol levels at a concentration of >1.60 ng/mL (adjusted OR: 3.14, 95% CI 1.34⁻7.35).ConclusionUrine 2-naphthol levels are associated with markers of oxidative stress and the risk of allergic diseases in young children. | Kapuci M, Ulker Z, Gurkan S, Alpsoy L (2014)
Determination of cytotoxic and genotoxic effects of naphthalene, 1-naphthol and 2-naphthol on human lymphocyte culture.
Toxicology and industrial health 30, 82-89 [PubMed:22740618]
[show Abstract]
Naphthalene, a bicyclic aromatic hydrocarbon, has toxic effects on animals and humans. Although recent studies stressed on the genotoxic and cytotoxic effects of naphthalene and its metabolites on eukaryotic cells, there is a big controversy among the results of these studies. The aim of this study is to investigate the effects of naphthalene and its metabolites on the cytotoxicity and genotoxicity in the human lymphocytes in the culture. The genotoxic and cytotoxic effects of naphthalene and its metabolites, 1-naphthol and 2-naphthol, were studied using cytotoxicity test (lactate dehydrogenase and cell proliferation (WST-1) assays) and DNA fragmentation assay (terminal deoxynucleotidyl transferase dUTP nick end labeling (TUNEL) assay). Naphthalene and its metabolites had no significant cytotoxic effect on treated samples when compared with untreated ones. This result was also confirmed by WST-1 assay. In the TUNEL assay, DNA fragmentation was induced significantly by all concentrations of naphthalene and 2-naphthol and 50 and 100 µM concentrations of 1-naphthol (p < 0.05 or 0.001). In the DNA fragmentation, the most effective dose of 2-naphthol (63%) was 100 µM, when compared with negative control group (13%). These results suggest that naphthalene and its metabolites, 1-naphthol and 2-naphthol, may cause DNA damage on human lymphocytes. | Scott DE, Ehebauer MT, Pukala T, Marsh M, Blundell TL, Venkitaraman AR, Abell C, Hyvönen M (2013)
Using a fragment-based approach to target protein-protein interactions.
Chembiochem : a European journal of chemical biology 14, 332-342 [PubMed:23344974]
[show Abstract]
The ability to identify inhibitors of protein-protein interactions represents a major challenge in modern drug discovery and in the development of tools for chemical biology. In recent years, fragment-based approaches have emerged as a new methodology in drug discovery; however, few examples of small molecules that are active against chemotherapeutic targets have been published. Herein, we describe the fragment-based approach of targeting the interaction between the tumour suppressor BRCA2 and the recombination enzyme RAD51; it makes use of a screening pipeline of biophysical techniques that we expect to be more generally applicable to similar targets. Disruption of this interaction in vivo is hypothesised to give rise to cellular hypersensitivity to radiation and genotoxic drugs. We have used protein engineering to create a monomeric form of RAD51 by humanising a thermostable archaeal orthologue, RadA, and used this protein for fragment screening. The initial fragment hits were thoroughly validated biophysically by isothermal titration calorimetry (ITC) and NMR techniques and observed by X-ray crystallography to bind in a shallow surface pocket that is occupied in the native complex by the side chain of a phenylalanine from the conserved FxxA interaction motif found in BRCA2. This represents the first report of fragments or any small molecule binding at this protein-protein interaction site. | Berger I, Guttman C, Amar D, Zarivach R, Aharoni A (2011)
The molecular basis for the broad substrate specificity of human sulfotransferase 1A1.
PloS one 6, e26794 [PubMed:22069470]
[show Abstract]
Cytosolic sulfotransferases (SULTs) are mammalian enzymes that detoxify a wide variety of chemicals through the addition of a sulfate group. Despite extensive research, the molecular basis for the broad specificity of SULTs is still not understood. Here, structural, protein engineering and kinetic approaches were employed to obtain deep understanding of the molecular basis for the broad specificity, catalytic activity and substrate inhibition of SULT1A1. We have determined five new structures of SULT1A1 in complex with different acceptors, and utilized a directed evolution approach to generate SULT1A1 mutants with enhanced thermostability and increased catalytic activity. We found that active site plasticity enables binding of different acceptors and identified dramatic structural changes in the SULT1A1 active site leading to the binding of a second acceptor molecule in a conserved yet non-productive manner. Our combined approach highlights the dominant role of SULT1A1 structural flexibility in controlling the specificity and activity of this enzyme. | Lee KH, Kang D (2008)
Stability and intra-individual variation of urinary malondialdehyde and 2-naphthol.
Journal of preventive medicine and public health = Yebang Uihakhoe chi 41, 195-199 [PubMed:18515997]
[show Abstract]
ObjectivesMalondialdehyde (MDA), a lipid peroxidation by-product, has been widely used as an indicator of oxidative stress. Urinary 2-naphthol, a urinary PAH metabolite, is used as a marker of ambient particulate exposure and is associated with lung cancer and chronic obstructive pulmonary disease. However, the stability and intra-individual variation associated with urinary MDA and 2-naphthol have not been thoroughly addressed. The objective of this study was to assess the stability and intraindividual variation associated with urinary MDA and 2-naphthol.MethodsUrine samples were collected from 10 healthy volunteers (mean age 34, range 27 approximately 42 years old). Each sample was divided into three aliquots and stored under three different conditions. The levels of urinary MDA and 2-naphthol were analyzed 1) just after sampling, 2) after storage at room temperature (21 degrees C) for 16 hours, and 3) after storage in a -20 degrees C freezer for 16 hours. In addition, an epidemiological study was conducted in 44 Chinese subjects over a period of 3 weeks. The urinary MDA and 2-naphthol were measured by HPLC three times.ResultsThere was no difference in the levels of urinary MDA and 2-naphthol between the triplicate measurements (n=10, p=0.84 and p=0.83, respectively). The intra-class correlation coefficients (ICC) for urinary MDA and 2-naphthol were 0.74 and 0.42, respectively. However, the levels of PM2.5 in the air were well correlated with the levels of both MDA and 2-naphthol in the epidemiological study.ConclusionsThese results suggest that urinary MDA and 2-naphthol remain stable under variable storage conditions, even at room temperature for 16 hours, and indicate that these markers can be used in epidemiological studies involving various sample storage conditions. The intra-CC of urinary 2-naphthol and MDA were acceptable for application to epidemiological studies. | Preuss R, Angerer J (2004)
Simultaneous determination of 1- and 2-naphthol in human urine using on-line clean-up column-switching liquid chromatography-fluorescence detection.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 801, 307-316 [PubMed:14751800]
[show Abstract]
We developed a new 3-D HPLC method for on-line clean-up and simultaneous quantification of two important naphthalene metabolites, 1-naphthol and 2-naphthol, in human urine. Except an enzymatic hydrolysis no further sample pre-treatment is necessary. The metabolites are stripped from urinary matrix by on-line extraction on a restricted access material pre-column (RAM RP-8), transferred in backflush mode onto a silica-based CN-(cyano)phase column for further purification from interfering substances. By another successive column switching step both analytes are transferred with a minimum of overlapping interferences onto a C12 bonded reversed phase column with trimethylsilyl endcapping where the final separation is carried out. The entire arrangement is software controlled. Eluting analytes are quantified by fluorescence detection (227/430 nm) after an external calibration. Within a total run time of 40 min we can selectively quantify both naphthols with detection limits in the lower ppb range (1.5 and 0.5 microg/l for 1- and 2-naphthol, respectively) with excellent reliability (ensured by precision, accuracy, matrix-independency and FIOH quality assurance program participation). First results on a collective of 53 occupationally non exposed subjects showed mean levels of 11.0 microg/l (1-naphthol) and 12.9 microg/l (2-naphthol). Among smokers (n=21) a significantly elevated mean level of urinary naphthols was determined (1-naphthol: 19.2 microg/l and 2-naphthol: 23.7 microg/l) in comparison to non smokers (n=32; 1-naphthol: 5.6 microg/l, 2-naphthol: 5.6 microg/l). | COLOMB D, TISSOT A (1956)
[2nd Case of dermatitis from betanaphthol with reticular reactions].
Lyon medical 88, 423-424 [PubMed:13386410] | PATTERSON SJ, LERRIGO AF (1947)
Betanaphthol in gelatin capsules; its use as a preservative, with a method for its determination.
Quarterly journal of pharmacy and pharmacology 20, 83-86 [PubMed:20260560] | VORONEOV II (1947)
[Effect of temperature in the sulphonating of betanaphtol for production of 2,6,8-naphtaldisulphonic acid].
Zhurnal prikladnoi khimii (Leningrad, R.S.F.S.R.) 20, 464-466 [PubMed:18856458] |
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