Bis(pyrrolecarboxamide) linked to intercalating chromophore oxazolopyridocarbazole (OPC): selective binding to DNA and polynucleotides.

Abstract:

:We have investigated some properties related to interaction with DNA and recognition of AT-rich sequences of netropsin-oxazolopyridocarbazole (Net-OPC) (Mrani et al., 1990), which is a hybrid groove-binder-intercalator. The hybrid molecule Net-OPC binds to poly[d(A-T)] at two different sites with Kapp values close to 7 x 10(6) and 6 x 10(8) M-1 (100 mM NaCl, pH 7.0). Data obtained from melting experiments are in agreement with these values and indicate that Net-OPC displays a higher binding constant to poly[d(A-T)] than does netropsin. On the basis of viscometric and energy transfer data, the binding of Net-OPC to poly[d(A-T)] is suggested to involve both intercalation and external binding of the OPC chromophore. In contrast, on poly[d(G-C)], Net-OPC binds to a single type of site composed of two base pairs in which the OPC chromophore appears to be mainly intercalated. The binding constant of Net-OPC to poly[d(G-C)] was found to be about 350-fold lower than that of the high-affinity binding site in poly[d(A-T)]. As evidenced by footprinting data, Net-OPC selectively recognizes TTAA and CTT sequences and strongly protects the 10-bp AT-rich DNA region 3'-TTAAGAACTT-5' containing the EcoRI site. The binding of Net-OPC to this sequence results in a strong and selective inhibition of the activity of the restriction endonuclease EcoRI on the plasmid pBR322 as substrate. The extent of inhibition of the rate constant of the first strand break catalyzed by the enzyme is about 100-fold higher than the one observed in the presence of netropsin under similar experimental conditions.

journal_name

Biochemistry

journal_title

Biochemistry

authors

Subra F,Carteau S,Pager J,Paoletti J,Paoletti C,Auclair C,Mrani D,Gosselin G,Imbach JL

doi

10.1021/bi00220a029

subject

Has Abstract

pub_date

1991-02-12 00:00:00

pages

1642-50

issue

6

eissn

0006-2960

issn

1520-4995

journal_volume

30

pub_type

杂志文章
  • Determinants of high-affinity DNA binding by the glucocorticoid receptor: evaluation of receptor domains outside the DNA-binding domain.

    abstract::In this study, we have investigated the influence of regions outside the DNA-binding domain of the human glucocorticoid receptor on high-affinity DNA binding. We find that the DNA-binding domain shows a 10-fold lower affinity for a palindromic DNA-binding site than the intact receptor. The N-terminal part of the recep...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00152a047

    authors: Dahlman-Wright K,Wright AP,Gustafsson JA

    更新日期:1992-09-22 00:00:00

  • Measurement of spontaneous transfer and transbilayer movement of BODIPY-labeled lipids in lipid vesicles.

    abstract::An assay was developed to study the spontaneous transfer and transbilayer movement (flip-flop) of lipid analogs labeled with the fluorescent fatty acid, 5-(5,7-dimethyl BODIPY)-1-pentanoic acid (C5-DMB-) in large unilamellar lipid vesicles comprised of 1-palmitoyl-2-oleoyl phosphatidylcholine (POPC). The assay is base...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi970145r

    authors: Bai J,Pagano RE

    更新日期:1997-07-22 00:00:00

  • Probing histidine-substrate interactions in tyrosyl-tRNA synthetase using asparagine and glutamine replacements.

    abstract::We have analyzed the interactions of a histidine residue with a substrate using site-directed mutagenesis. Previous studies on tyrosyl-tRNA synthetase from Bacillus stearothermophilus have shown that a histidine residue (His-48) makes an interaction with ATP, which is improved on mutating Thr-51----Pro-51. We find on ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00340a022

    authors: Lowe DM,Fersht AR,Wilkinson AJ,Carter P,Winter G

    更新日期:1985-09-10 00:00:00

  • The amino-terminal tail of glycogen phosphorylase is a switch for controlling phosphorylase conformation, activation, and response to ligands.

    abstract::Glycogen phosphorylase is a muscle enzyme which metabolizes glycogen, producing glucose-1-phosphate, which can be used for the production of ATP. Phosphorylase activity is regulated by phosphorylation/dephosphorylation, and by the allosteric binding of numerous effectors. In this work, we have studied 10 site-directed...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0020372

    authors: Biorn AC,Graves DJ

    更新日期:2001-05-01 00:00:00

  • Tubulin polymerization promoting proteins (TPPPs): members of a new family with distinct structures and functions.

    abstract::TPPP/p25 is a brain-specific protein, which induces tubulin polymerization and microtubule (MT) bundling and is enriched in Lewy bodies characteristic of Parkinson's disease [Tirián et al. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 13976-13981]. We identified two human gene sequences, CG1-38 and p25beta, which encoded ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi061305e

    authors: Vincze O,Tökési N,Oláh J,Hlavanda E,Zotter A,Horváth I,Lehotzky A,Tirián L,Medzihradszky KF,Kovács J,Orosz F,Ovádi J

    更新日期:2006-11-21 00:00:00

  • Structural Characterization of the Hydratase-Aldolases, NahE and PhdJ: Implications for the Specificity, Catalysis, and N-Acetylneuraminate Lyase Subgroup of the Aldolase Superfamily.

    abstract::NahE and PhdJ are bifunctional hydratase-aldolases in bacterial catabolic pathways for naphthalene and phenanthrene, respectively. Bacterial species with these pathways can use polycyclic aromatic hydrocarbons (PAHs) as sole sources of carbon and energy. Because of the harmful properties of PAHs and their widespread d...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.8b00532

    authors: LeVieux JA,Medellin B,Johnson WH Jr,Erwin K,Li W,Johnson IA,Zhang YJ,Whitman CP

    更新日期:2018-06-26 00:00:00

  • Synthesis and study of phosphoenolthiopyruvate.

    abstract::Phosphoenolthiopyruvate, the analogue of phosphoenolpyruvate in which the bridging oxygen of the phosphate ester is replaced by sulfur, has been synthesized from methyl acrylate and dimethyl (chlorothio)phosphonate. The compound is a substrate for alkaline phosphatase, pyruvate kinase, enolase, and phosphoenolpyruvate...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00404a038

    authors: Sikkema KD,O'Leary MH

    更新日期:1988-02-23 00:00:00

  • Evaluation of cooperative interactions between substructures of iso-1-cytochrome c using double mutant cycles.

    abstract::A double mutant cycle has been used to evaluate interaction energies between the global stabilizer mutation asparagine 52 --> isoleucine (N52I) in iso-1-cytochrome c and mutations producing single surface histidines at positions 26, 33, 39, 54, 73, 89, and 100. These histidine mutation sites are distributed through th...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi034958t

    authors: Wandschneider E,Hammack BN,Bowler BE

    更新日期:2003-09-16 00:00:00

  • Identification and characterization of Mg2+ binding sites in isolated alpha and beta subunits of H(+)-ATPase from Bacillus PS3.

    abstract::The properties of the nucleotide binding sites in the isolated beta and alpha subunits of H(+)-ATPase from Bacillus PS3 (TF1) have been examined by studying the EPR properties of bound VO(2+), which is a paramagnetic probe for the native Mg2+ cation cofactor. The amino acid ligands of the VO2+ complexes with the isola...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9910732

    authors: Zimmermann JL,Amano T,Sigalat C

    更新日期:1999-11-16 00:00:00

  • DNA hairpin structures in solution: 500-MHz two-dimensional 1H NMR studies on d(CGCCGCAGC) and d(CGCCGTAGC).

    abstract::A hairpin structure contains two conformationally distinct domains: a double-helical stem with Watson-Crick base pairs and a single-stranded loop that connects the two arms of the stem. By extensive 1D and 2D 500-MHz 1H NMR studies in H2O and D2O, it has been demonstrated that the DNA oligomers d(CGCCGCAGC) and d(CGCC...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00398a027

    authors: Gupta G,Sarma MH,Sarma RH,Bald R,Engelke U,Oei SL,Gessner R,Erdmann VA

    更新日期:1987-12-01 00:00:00

  • Specific photoaffinity labeling of Tyr-49 on the light chain in the steroid-combining site of a mouse monoclonal anti-estradiol antibody using two epimeric 6alpha- and 6beta-(5-azido-2-nitrobenzoyl)amidoestradiol photoreagents.

    abstract::A mouse monoclonal anti-7-(O-carboxymethyl)oximinoestradiol antibody was photoaffinity labeled with two cross-reactive 6alpha- and 6beta-(5-azido-2-nitrobenzoyl)amido[17alpha-3H]estradiol photoreagents (6alpha- and 6beta-ANBA-[17alpha-3H]estradiol). Covalently bound radioactivity was found exclusively on the light cha...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi962645a

    authors: Rousselot P,Mappus E,Blachère T,de Ravel MR,Grenot C,Tonnelle C,Cuilleron CY

    更新日期:1997-06-24 00:00:00

  • Aggregation studies on fluorescein-coupled cobra venom phospholipase A2.

    abstract::Phospholipase A2 from Naja naja naja venom (Indian cobra) undergoes a concentration-dependent aggregation, and at an assay concentration of 1 microgram mL-1, it exists as a monomer. However, there is some evidence that the enzyme is actually active as a dimer or higher order aggregate. Previous attempts to determine t...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00343a018

    authors: Hazlett TL,Dennis EA

    更新日期:1985-10-22 00:00:00

  • A new N-terminal recognition domain in caveolin-1 interacts with sterol carrier protein-2 (SCP-2).

    abstract::Although plasma membrane domains, such as caveolae, provide an organizing principle for signaling pathways and cholesterol homeostasis in the cell, relatively little is known regarding specific mechanisms, whereby intracellular lipid-binding proteins are targeted to caveolae. Therefore, the interaction between caveoli...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi7002636

    authors: Parr RD,Martin GG,Hostetler HA,Schroeder ME,Mir KD,Kier AB,Ball JM,Schroeder F

    更新日期:2007-07-17 00:00:00

  • Cytochrome bo from Escherichia coli: binding of azide to CuB.

    abstract::Azide binds to fast cytochrome bo with a stoichiometry of 1:1, the dissociation constant for this reaction being approximately 2 x 10(-5) M. The changes induced in the electronic absorption are very slight and are consistent with heme o remaining hexacoordinate high-spin, an observation confirmed by room temperature M...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi961221d

    authors: Little RH,Cheesman MR,Thomson AJ,Greenwood C,Watmough NJ

    更新日期:1996-10-29 00:00:00

  • Organization of the human protein S genes.

    abstract::Human genomic clones that span the entire protein S expressed gene (PS alpha) and the 3' two-thirds of the protein S pseudogene (PS beta) have been isolated and characterized. The PS alpha gene is greater than 80 kilobases in length and contains 14 introns and 15 exons, as well as 6 repetitive "Alu" sequences. Exons I...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00486a010

    authors: Schmidel DK,Tatro AV,Phelps LG,Tomczak JA,Long GL

    更新日期:1990-08-28 00:00:00

  • Refolding a disulfide dimer of cytochrome c.

    abstract::A covalent dimer of Saccharomyces cerevisiae iso-1 cytochrome c is stabilized by an interchain disulfide bond involving the cysteine residue penultimate to the C-terminus. The individual chains in the dimer appear to retain the tertiary structural features characteristic for monomeric cytochrome c albeit with some per...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00335a011

    authors: Bryant C,Strottmann JM,Stellwagen E

    更新日期:1985-07-02 00:00:00

  • Ethanol-perturbed amyloidogenic self-assembly of insulin: looking for origins of amyloid strains.

    abstract::A model cosolvent, ethanol, has profound and diversified effects on the amyloidogenic self-assembly of insulin, yielding spectroscopically and morphologically distinguishable forms of beta-aggregates. The alcohol reduces hydrodynamic radii of insulin molecules, decreases enthalpic costs associated with aggregation-pro...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi050281t

    authors: Dzwolak W,Grudzielanek S,Smirnovas V,Ravindra R,Nicolini C,Jansen R,Loksztejn A,Porowski S,Winter R

    更新日期:2005-06-28 00:00:00

  • Calcium-promoted fusion of isolated chromaffin granules detected by resonance energy transfer between labeled lipids embedded in the membrane bilayer.

    abstract::Chromaffin granules isolated from bovine adrenal medulla were labeled with small unilamellar vesicles (SUV) made from N-(7-nitro-2,1,3-benzoxadiazol-4-yl)phosphatidylethanolamine and/or N-(lissamine rhodamine B sulfonyl)phosphatidylethanolamine as donor and acceptor fluorophores. Labeling of granules could be followed...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00315a020

    authors: Morris SJ,Bradley D

    更新日期:1984-09-25 00:00:00

  • Biochemical studies on Mycobacterium tuberculosis UreG and comparative modeling reveal structural and functional conservation among the bacterial UreG family.

    abstract::Nickel is a fundamental micronutrient for cellular life, but it is toxic in soluble form at nonphysiological concentrations. Such potentially contradictory features required living organisms to develop efficient systems for nickel utilization and homeostasis. This is the case for incorporation of nickel into the activ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi6024676

    authors: Zambelli B,Musiani F,Savini M,Tucker P,Ciurli S

    更新日期:2007-03-20 00:00:00

  • Interfering with the Dimerization of the ErbB Receptors by Transmembrane Domain-Derived Peptides Inhibits Tumorigenic Growth in Vitro and in Vivo.

    abstract::The ErbB family of tyrosine kinase receptors is a key element in preserving cell growth homeostasis. This family is comprised of four single-transmembrane domain proteins designated ErbB-1-4. Ligand binding initiates dimerization followed by tyrosine phosphorylation and signaling, which when uncontrolled lead to cance...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.6b00450

    authors: Bublil EM,Cohen T,Arnusch CJ,Peleg A,Pines G,Lavi S,Yarden Y,Shai Y

    更新日期:2016-10-04 00:00:00

  • Substrate recognition determinants for rhodopsin kinase: studies with synthetic peptides, polyanions, and polycations.

    abstract::Rhodopsin kinase phosphorylates serine- and threonine-containing peptides from bovine rhodopsin's carboxyl-terminal sequence. Km's for the peptides decrease as the length of the peptide is increased over the range 12-31 amino acids, reaching 1.7 mM for peptide 318-348 from the rhodopsin sequence. The Km for phosphoryl...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00448a013

    authors: Palczewski K,Arendt A,McDowell JH,Hargrave PA

    更新日期:1989-10-31 00:00:00

  • Analysis of membrane-binding properties of dermaseptin analogues: relationships between binding and cytotoxicity.

    abstract::To understand relationships between membrane-binding properties of cytolytic peptides and resulting cytotoxicity, we investigated interactions of dermaseptin analogues with model bilayers by means of surface plasmon resonance. First, we tested the system by comparing two native dermaseptins, S1 and S4, whose binding p...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi034514x

    authors: Gaidukov L,Fish A,Mor A

    更新日期:2003-11-11 00:00:00

  • Insights into the signal transduction mechanism of RmFixL provided by carbon monoxide recombination kinetics.

    abstract::This report presents evidence for interdomain steps of the ligand-coupled signal transduction mechanism of the oxygen receptor from Rhizobium meliloti, RmFixL. Photolysis of the CO adducts of heme domain (RmFixLN) and heme kinase (RmFixL*) proteins allowed tracking of second-order heme CO recombination reactions by tr...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi011237q

    authors: Rodgers KR,Tang L,Lukat-Rodgers GS,Wengenack NL

    更新日期:2001-10-30 00:00:00

  • Interactions of oleic acid with liver fatty acid binding protein: a carbon-13 NMR study.

    abstract::13C NMR spectroscopy was used to probe the structural interactions between carboxyl-13C-enriched oleic acid (18:1) and rat liver fatty acid binding protein (FABP) and the partitioning of 18:1 between FABP and unilamellar phosphatidylcholine (PC) vesicles. Spectra of systems containing 2-8 mol of 18:1/mol of FABP (but ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00402a033

    authors: Cistola DP,Walsh MT,Corey RP,Hamilton JA,Brecher P

    更新日期:1988-01-26 00:00:00

  • Metal-selective DNA-binding response of Escherichia coli NikR.

    abstract::The NikR transcription factor from Escherichia coli is a Ni(II)-dependent repressor that regulates production of the nickel ion transporter encoded by the nik operon. In the previous paper in this issue (Wang, S. C., Dias, A., Bloom, S. L., and Zamble, D. B. (2004) Selectivity of Metal Binding and Metal-Induced Stabil...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi049404k

    authors: Bloom SL,Zamble DB

    更新日期:2004-08-10 00:00:00

  • O2 activation by non-heme diiron proteins: identification of a symmetric mu-1,2-peroxide in a mutant of ribonucleotide reductase.

    abstract::Non-heme diiron clusters occur in a number of enzymes (e.g., ribonucleotide reductase, methane monooxygenase, and Delta9-stearoyl-ACP desaturase) that activate O2 for chemically difficult oxidation reactions. In each case, a kinetically labile peroxo intermediate is believed to form when O2 reacts with the diferrous e...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi981838q

    authors: Moënne-Loccoz P,Baldwin J,Ley BA,Loehr TM,Bollinger JM Jr

    更新日期:1998-10-20 00:00:00

  • Yeast pol eta holds a cis-syn thymine dimer loosely in the active site during elongation opposite the 3'-T of the dimer, but tightly opposite the 5'-T.

    abstract::Polymerase eta is a member of the Y family of DNA polymerases which is able to bypass thymine dimers efficiently and in a relatively error-free manner. To elucidate the mechanism of dimer bypass, the efficiency of dAMP and pyrene nucleotide insertion opposite the thymine dimer and its N3-methyl derivatives was determi...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0345687

    authors: Sun L,Zhang K,Zhou L,Hohler P,Kool ET,Yuan F,Wang Z,Taylor JS

    更新日期:2003-08-12 00:00:00

  • Carbon-13 nuclear magnetic resonance studies on the interaction of glycophorin with lecithin in reconstituted vesicles.

    abstract::Glycophorin, the MN blood group substance, is a major intrinsic glycoprotein in erythrocyte membranes. The interaction of glycophorin with phosphatidylcholine, 13C-labeled in specific positions in reconstituted unilamellar vesicles, was investigated by using the 13C NMR technique. 1-Palmitoyl-2-([14-13C]linoleoyl)-sn-...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00552a016

    authors: Utsumi H,Tunggal BD,Stoffel W

    更新日期:1980-05-27 00:00:00

  • Introduction of a pi-pi interaction at the active site of a cupredoxin: characterization of the Met16Phe Pseudoazurin mutant.

    abstract::The Met16Phe mutant of the type 1 copper protein pseudoazurin (PACu), in which a phenyl ring is introduced close to the imidazole moiety of the His81 ligand, has been characterized. NMR studies indicate that the introduced phenyl ring is parallel to the imidazole group of His81. The mutation has a subtle effect on the...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi030030p

    authors: Yanagisawa S,Sato K,Kikuchi M,Kohzuma T,Dennison C

    更新日期:2003-06-10 00:00:00

  • Cyclopiazonic acid biosynthesis in Aspergillus sp.: characterization of a reductase-like R* domain in cyclopiazonate synthetase that forms and releases cyclo-acetoacetyl-L-tryptophan.

    abstract::The fungal neurotoxin alpha-cyclopiazonic acid (CPA), a nanomolar inhibitor of Ca2+-ATPase, has a pentacyclic indole tetramic acid scaffold that arises from one molecule of tryptophan, acetyl-CoA, malonyl-CoA, and dimethylallyl pyrophosphate by consecutive action of three enzymes, CpaS, CpaD, and CpaO. CpaS is a hybri...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi901123r

    authors: Liu X,Walsh CT

    更新日期:2009-09-15 00:00:00