当前位置： SCI文献检索 > CHEMICAL RESEARCH IN TOXICOLOGY期刊下所有文献 > Molecular recognition between oligopeptides and nucleic acids: DNA binding selectivity of a series of 1,2,4-triazole-containing lexitropsins.

Molecular recognition between oligopeptides and nucleic acids: DNA binding selectivity of a series of 1,2,4-triazole-containing lexitropsins.

Abstract：

:The synthesis of a series of 1,2,4-triazole-containing oligopeptide lexitropsins related to the natural antitumor antibiotic distamycin is described. The binding properties of these new agents to both native DNAs and synthetic polydeoxyribonucleotides were determined by UV absorption and circular dichroism studies. The DNA binding and sequence selectivity of these agents have been determined by complementary strand MPE footprinting on two restriction fragments of pBR322 DNA. The lexitropsins bearing one 1,2,4-triazole moiety bind to AT sequences like distamycin but also tolerate GC sites. However, 3, which contains two contiguous 1,2,4-triazole moieties, appears not to recognize AT stretches and demands two consecutive GC bases in the middle of a four-base recognition site. The triazole lexitropsins avoid ATTT (4264-4267) and AAAA (4273-4276) to which distamycin binds strongly to the EcoRI/Hind III fragment. Determination of pKa values indicates the 1,2,4-triazole units are protonated under physiological conditions. The avoidance of AT stretches and the recognition of GC base sites by 3 suggest molecular recognition in these cases is determined, not by electrostatic effects, but rather by invoking a hydrogen bond between the triazole 4-nitrogen and G-2NH2 in the minor groove.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Rao KE,Krowicki K,Burckhardt G,Zimmer C,Lown JW

doi

10.1021/tx00020a019

subject

Has Abstract

pub_date

1991-03-01 00:00:00

pages

241-52

issue

2

eissn

0893-228X

issn

1520-5010

journal_volume

4

pub_type

杂志文章

相关文献

CHEMICAL RESEARCH IN TOXICOLOGY文献大全
  • DNA Polymerases η and ζ Combine to Bypass O(2)-[4-(3-Pyridyl)-4-oxobutyl]thymine, a DNA Adduct Formed from Tobacco Carcinogens.

    abstract：:4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and N'-nitrosonornicotine (NNN) are important human carcinogens in tobacco products. They are metabolized to produce a variety 4-(3-pyridyl)-4-oxobutyl (POB) DNA adducts including O(2)-[4-(3-pyridyl)-4-oxobut-1-yl]thymidine (O(2)-POB-dT), the most abundant POB adduc...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.5b00468

    authors： Gowda AS,Spratt TE

    更新日期：2016-03-21 00:00:00

  • Use of electrochemical oxidation and model peptides to study nucleophilic biological targets of reactive metabolites: the case of rimonabant.

    abstract：:Electrochemical oxidation of drug molecules is a useful tool to generate several different types of metabolites. In the present study we developed a model system involving electrochemical oxidation followed by characterization of the oxidation products and their propensity to modify peptides. The CB1 antagonist rimona...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx500255r

    authors： Thorsell A,Isin EM,Jurva U

    更新日期：2014-10-20 00:00:00

  • Carbon Disulfide Induces Embryo Implantation Disorder by Disturbing the Polarization of Macrophages in Mice Uteri.

    abstract：:Carbon disulfide (CS2) induces embryo implantation disorders. Macrophages participate in the process of pregnancy. Therefore, we want to explore the effects of CS2 exposure on polarization and immune function of macrophages in pregnant mice uteri. The exposure times were gestation days 3 (GD3), 4 (GD4), and 5 (GD5), a...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.9b00119

    authors： Zhang T,Hu C,Wu Y,Wang S,Liu X,Zhang D,Huang F,Gao H,Wang Z

    更新日期：2019-10-21 00:00:00

  • Common E-Cigarette Flavoring Chemicals Impair Neutrophil Phagocytosis and Oxidative Burst.

    abstract：:E-cigarette flavorings have not been thoroughly evaluated for inhalational toxicity. We have shown that the flavoring chemical cinnamaldehyde impairs human neutrophils, macrophages, and natural killer cells. Here we investigated the effects of other common e-liquid flavoring chemicals on phagocytosis and oxidative bur...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.9b00171

    authors： Hickman E,Herrera CA,Jaspers I

    更新日期：2019-06-17 00:00:00

  • Contrasting effects of metal ions on S-nitrosoglutathione, related to coordination equilibria: GSNO decomposition assisted by Ni(II) vs stability Increase in the presence of Zn(II) and Cd(II).

    abstract：:Complex formation between nitrosoglutathione (GSNO) and Zn(II), Cd(II), and Ni(II) ions was studied by potentiometry and spectroscopic techniques. GSNO forms simple ML and ML2 type complexes (L = GSNO) with these ions. The stability of GSNO in HEPES buffer solution, pH 7.4, increased in the presence of both Zn(II) and...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx034194i

    authors： Krezel A,Bal W

    更新日期：2004-03-01 00:00:00

  • Analysis of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB)-releasing DNA adducts in human exfoliated oral mucosa cells by liquid chromatography-electrospray ionization-tandem mass spectrometry.

    abstract：:Quantitation of DNA adducts could provide critical information on the relationship between exposure to tobacco smoke and cancer risk in smokers. In this study, we developed a robust and sensitive liquid chromatography-tandem mass spectrometry method for the analysis of 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB)-releasin...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx300282k

    authors： Stepanov I,Muzic J,Le CT,Sebero E,Villalta P,Ma B,Jensen J,Hatsukami D,Hecht SS

    更新日期：2013-01-18 00:00:00

  • Quantitative component analysis of mixtures for risk assessment: application to eye irritation.

    abstract：:A methodology called quantitative component analysis of mixtures (QCAM) was used to analyze an existing set of product formulation data to determine if the irritating ingredients in the mixtures could be identified. Eye irritation scores, based on a rat model, for 18 mixtures having a composite total of 37 components,...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx990098z

    authors： Patel HC,Duca JS,Hopfinger AJ,Glendening CD,Thompson ED

    更新日期：1999-11-01 00:00:00

  • Polymerase Bypass of N(6)-Deoxyadenosine Adducts Derived from Epoxide Metabolites of 1,3-Butadiene.

    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

    authors： Kotapati S,Wickramaratne S,Esades A,Boldry EJ,Quirk Dorr D,Pence MG,Guengerich FP,Tretyakova NY

    更新日期：2015-07-20 00:00:00

  • Identification and characterization of deoxyguanosine adducts of methyl vinyl ketone and ethyl vinyl ketone. Genotoxicity of the ketones in the SOS Chromotest.

    abstract：:The reaction of the alpha, beta-unsaturated ketones methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) with nucleosides and 5'-mononucleotides was studied. The genotoxic activity of MVK and EVK in the SOS Chromotest was investigated. Three different types of adducts with deoxyguanosine were found and their structu...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00019a007

    authors： Eder E,Hoffman C,Deininger C

    更新日期：1991-01-01 00:00:00

  • Water-soluble organotellurium compounds: catalytic protection against peroxynitrite and release of zinc from metallothionein.

    abstract：:The antioxidant properties of a number of water-soluble diorganyl tellurides have been investigated. These organotellurium compounds efficiently protect against peroxynitrite-mediated oxidation of dihydrorhodamine 123, hydroxylation of benzoate, and nitration of 4-hydroxyphenyl acetate. The peroxidation of the zinc st...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx990156g

    authors： Jacob C,Arteel GE,Kanda T,Engman L,Sies H

    更新日期：2000-01-01 00:00:00

  • Hypochlorite-induced damage to DNA, RNA, and polynucleotides: formation of chloramines and nitrogen-centered radicals.

    abstract：:Stimulated monocytes and neutrophils generate hypochlorite (HOCl) via the release of the enzyme myeloperoxidase and hydrogen peroxide. HOCl is a key bactericidal agent, but can also damage host tissue. As there is a strong link between chronic inflammation and some cancers, we have investigated HOCl damage to DNA, RNA...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx015548d

    authors： Hawkins CL,Davies MJ

    更新日期：2002-01-01 00:00:00

  • CuO nanoparticle interaction with human epithelial cells: cellular uptake, location, export, and genotoxicity.

    abstract：:The toxicity of CuO nanoparticles (NPs) to human lung epithelial (A549) cells was investigated in this study. CuO NPs (10-100 mg/L) had significant toxicity to A549 cells, whereas CuO bulk particles (BPs) showed much lower toxicity (24 h IC(50), 58 and 15 mg/L for CuO BPs and NPs, respectively). Transmission electron ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx3002093

    authors： Wang Z,Li N,Zhao J,White JC,Qu P,Xing B

    更新日期：2012-07-16 00:00:00

  • Allyl alcohol activation of protein kinase C delta leads to cytotoxicity of rat hepatocytes.

    abstract：:Hepatotoxicity of allyl alcohol involves its bioactivation to acrolein and subsequent protein sulfhydryl loss and lipid peroxidation. However, the links between these events and hepatocellular death are not known. The purpose of these studies was to examine whether specific signal transduction pathways are associated ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx025655n

    authors： Maddox JF,Roth RA,Ganey PE

    更新日期：2003-05-01 00:00:00

  • Metabolic studies on the nigrostriatal toxin MPTP and its MAO B generated dihydropyridinium metabolite MPDP+.

    abstract：:The metabolic fates of the nigrostriatal toxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and its two-electron oxidation product, the 1-methyl-4-phenyl-2,3-dihydropyridinium species (MPDP+), have been examined in mouse brain and liver tissue fractions. Incubations of MPTP (50 microM and 1 mM) with mouse brain...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00003a010

    authors： Wu E,Shinka T,Caldera-Munoz P,Yoshizumi H,Trevor A,Castagnoli N Jr

    更新日期：1988-05-01 00:00:00

  • Ethical guidelines to publication of chemical research. American Chemical Society.

    abstract：:The guidelines embodied in this document were revised by the editors of the Publication Division of the American Chemical Society in January 1994 and endorsed by the Society Committee on Publications. ...

    journal_title：Chemical research in toxicology

    pub_type： 指南,杂志文章

    doi：

    authors：

    更新日期：1994-07-01 00:00:00

  • Covalent Modification of CDK2 by 4-Hydroxynonenal as a Mechanism of Inhibition of Cell Cycle Progression.

    abstract：:Oxidative stress is a contributing factor in a number of chronic diseases, including cancer, atherosclerosis, and neurodegenerative diseases. Lipid peroxidation that occurs during periods of oxidative stress results in the formation of lipid electrophiles, which can modify a multitude of proteins in the cell. 4-Hydrox...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.5b00485

    authors： Camarillo JM,Rose KL,Galligan JJ,Xu S,Marnett LJ

    更新日期：2016-03-21 00:00:00

  • Mechanism-based inactivation of human cytochromes p450s: experimental characterization, reactive intermediates, and clinical implications.

    abstract：:The P450 type cytochromes are responsible for the metabolism of a wide variety of xenobiotics and endogenous compounds. Although P450-catalyzed reactions are generally thought to lead to detoxication of xenobiotics, the reactions can also produce reactive intermediates that can react with cellular macromolecules leadi...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章,评审

    doi：10.1021/tx7002504

    authors： Hollenberg PF,Kent UM,Bumpus NN

    更新日期：2008-01-01 00:00:00

  • Systematic investigation of the physicochemical factors that contribute to the toxicity of ZnO nanoparticles.

    abstract：:ZnO nanoparticles (NPs) are prone to dissolution, and uncertainty remains whether biological/cellular responses to ZnO NPs are solely due to the release of Zn(2+) or whether the NPs themselves have additional toxic effects. We address this by establishing ZnO NP solubility in dispersion media (Dulbecco's modified Eagl...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx4004243

    authors： Mu Q,David CA,Galceran J,Rey-Castro C,Krzemiński L,Wallace R,Bamiduro F,Milne SJ,Hondow NS,Brydson R,Vizcay-Barrena G,Routledge MN,Jeuken LJ,Brown AP

    更新日期：2014-04-21 00:00:00

  • Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.

    abstract：:Structure-function relationships for the inhibition of human cytochrome P450s (P450s) 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives were studied. Thirty-two of the 33 flavonoids tested produced reverse type I binding spectra with P450 1B1, and the potencies of binding were correlated with the abilities to in...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx100286d

    authors： Shimada T,Tanaka K,Takenaka S,Murayama N,Martin MV,Foroozesh MK,Yamazaki H,Guengerich FP,Komori M

    更新日期：2010-12-20 00:00:00

  • Liquid chromatography electrospray-mass spectrometry of urinary aflatoxin biomarkers: characterization and application to dosimetry and chemoprevention in rats.

    abstract：:A liquid chromatography electrospray tandem mass spectrometry (LC-ESI-MS/MS) method for the measurement of aflatoxin biomarkers in urine has been developed and validated. The two major aflatoxin-DNA adducts formed in rat tissues, aflatoxin N(7)-guanine and its imidazole ring opened derivative, 8,9-dihydro-8-(2,6-diami...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx010063a

    authors： Walton M,Egner P,Scholl PF,Walker J,Kensler TW,Groopman JD

    更新日期：2001-07-01 00:00:00

  • A novel pectenotoxin, PTX-12, in Dinophysis spp. and shellfish from Norway.

    abstract：:Two novel pectenotoxins (PTXs) were detected by LC-MS in solid phase extracts of net hauls taken at Flødevigen, Norway, in June 2002 that were dominated by Dinophysis acuminata and Dinophysis norvegica. The new compounds were isolated as minor components from a large collection of a Dinophysis acuta-dominated bloom ob...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx049870a

    authors： Miles CO,Wilkins AL,Samdal IA,Sandvik M,Petersen D,Quilliam MA,Naustvoll LJ,Rundberget T,Torgersen T,Hovgaard P,Jensen DJ,Cooney JM

    更新日期：2004-11-01 00:00:00

  • Interactions of nickel(II) with histones. Stability and solution structure of complexes with CH3CO-Cys-Ala-Ile-His-NH2, a putative metal binding sequence of histone H3.

    abstract：:Nickel(II) compounds are established human carcinogens, but the molecular mechanisms underlying their activity are only partially known. One mechanism may include mediation by nickel of promutagenic oxidative DNA damage that depends on Ni(II) binding to chromatin. To characterize such binding at the histone moiety of ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00047a007

    authors： Bal W,Lukszo J,Jezowska-Bojczuk M,Kasprzak KS

    更新日期：1995-07-01 00:00:00

  • Use of Zebrafish in Drug Discovery Toxicology.

    abstract：:Unpredicted human safety events in clinical trials for new drugs are costly in terms of human health and money. The drug discovery industry attempts to minimize those events with diligent preclinical safety testing. Current standard practices are good at preventing toxic compounds from being tested in the clinic; howe...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章,评审

    doi：10.1021/acs.chemrestox.9b00335

    authors： Cassar S,Adatto I,Freeman JL,Gamse JT,Iturria I,Lawrence C,Muriana A,Peterson RT,Van Cruchten S,Zon LI

    更新日期：2020-01-21 00:00:00

  • Copper-2 Hypothesis for Causation of the Current Alzheimer's Disease Epidemic Together with Dietary Changes That Enhance the Epidemic.

    abstract：:Alzheimer's disease, the most common cause of dementia, is at epidemic proportions (15 to 44% depending on age, of those age 65 to 84) in the U.S. and other developed countries but remains relatively rare in undeveloped countries. Surprisingly, solid historical data reveal the epidemic is a creature of the last centur...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章,评审

    doi：10.1021/acs.chemrestox.6b00373

    authors： Brewer GJ

    更新日期：2017-03-20 00:00:00

  • Reactivity and Cross-Linking of 5'-Terminal Abasic Sites within DNA.

    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

    authors： Admiraal SJ,O'Brien PJ

    更新日期：2017-06-19 00:00:00

  • Diclofenac Sodium Triggers p53-Dependent Apoptosis in Human Corneal Epithelial Cells via ROS-Mediated Crosstalk.

    abstract：:Diclofenac sodium (DFS), a nonsteroidal anti-inflammatory drug, is frequently used in ophthalmology, but it causes negative effects on corneas. The mechanisms underlying the toxicities to corneas remains unclear. The present study was designed to assess the cytotoxicity of DFS to human corneal epithelial (HCEP) cells ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.0c00319

    authors： Li H,Fan TJ,Zou P,Xu B

    更新日期：2021-01-18 00:00:00

  • Bezafibrate induces a mitochondrial derangement in human cell lines: a PPAR-independent mechanism for a peroxisome proliferator.

    abstract：:Bezafibrate is a hypolipidemic drug that belongs to the group of peroxisome proliferators because it binds to peroxisome proliferator-activated receptors type alpha (PPARs). Peroxisome proliferators produce a myriad of extraperoxisomal effects, which are not necessarily dependent on their interaction with PPARs. An in...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx0341052

    authors： Scatena R,Bottoni P,Vincenzoni F,Messana I,Martorana GE,Nocca G,De Sole P,Maggiano N,Castagnola M,Giardina B

    更新日期：2003-11-01 00:00:00

  • Chemical Biology of N5-Substituted Formamidopyrimidine DNA Adducts.

    abstract：:DNA nucleobases are the prime targets for chemical modifications by endogenous and exogenous electrophiles. Alkylation of the N7 position of guanine and adenine in DNA triggers base-catalyzed imidazole ring opening and the formation of N5-substituted formamidopyrimidine (N5-R-FAPy) lesions. Me-FAPy-dG adducts induced ...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.6b00392

    authors： Pujari SS,Tretyakova N

    更新日期：2017-01-17 00:00:00

  • Intracellular activation of cytotoxic agents: kinetic models for methylnitrosoureas and N-methyl-N'-nitro-N-nitrosoguanidine in cell culture.

    abstract：:The cytotoxic activity of N-methyl-N-nitrosourea (MNU), streptozotocin, and N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) was determined in cell culture by using a P388 cell growth rate inhibition assay. These agents appear to have very different activities when inhibition is related to the agent concentration in the cu...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/tx00009a006

    authors： Weinkam RJ,Dolan ME

    更新日期：1989-05-01 00:00:00

  • Impact of Physicochemical Properties on Dose and Hepatotoxicity of Oral Drugs.

    abstract：:A database containing maximum daily doses of 1841 marketed oral drugs was used to examine the influence of physicochemical properties on dose and hepatotoxicity (drug induced liver injury, DILI). Drugs in the highest ∼20% dose range had significantly reduced mean lipophilicity and molecular weight, increased fractiona...

    journal_title：Chemical research in toxicology

    pub_type： 杂志文章

    doi：10.1021/acs.chemrestox.8b00044

    authors： Leeson PD

    更新日期：2018-06-18 00:00:00