Kinetics of oxidation of aliphatic and aromatic thiols by myeloperoxidase compounds I and II.

Abstract:

:Myeloperoxidase (MPO) is the most abundant protein in neutrophils and plays a central role in microbial killing and inflammatory tissue damage. Because most of the non-steroidal anti-inflammatory drugs and other drugs contain a thiol group, it is necessary to understand how these substrates are oxidized by MPO. We have performed transient kinetic measurements to study the oxidation of 14 aliphatic and aromatic mono- and dithiols by the MPO intermediates, Compound I (k3) and Compound II (k4), using sequential mixing stopped-flow techniques. The one-electron reduction of Compound I by aromatic thiols (e.g. methimidazole, 2-mercaptopurine and 6-mercaptopurine) varied by less than a factor of seven (between 1.39 +/- 0.12 x 10(5) M(-1) s(-1) and 9.16 +/- 1.63 x 10(5) M(-1) s(-1)), whereas reduction by aliphatic thiols was demonstrated to depend on their overall net charge and hydrophobic character and not on the percentage of thiol deprotonation or redox potential. Cysteamine, cysteine methyl ester, cysteine ethyl ester and alpha-lipoic acid showed k3 values comparable to aromatic thiols, whereas a free carboxy group (e.g. cysteine, N-acetylcysteine, glutathione) diminished k3 dramatically. The one-electron reduction of Compound II was far more constrained by the nature of the substrate. Reduction by methimidazole, 2-mercaptopurine and 6-mercaptopurine showed second-order rate constants (k4) of 1.33 +/- 0.08 x 10(5) M(-1) s(-1), 5.25 +/- 0.07 x 10(5) M(-1) s(-1) and 3.03 +/- 0.07 x 10(3) M(-1) s(-1). Even at high concentrations cysteine, penicillamine and glutathione could not reduce Compound II, whereas cysteamine (4.27 +/- 0.05 x 10(3) M(-1) s(-1)), cysteine methyl ester (8.14 +/- 0.08 x 10(3) M(-1) s(-1)), cysteine ethyl ester (3.76 +/- 0.17 x 10(3) M(-1) s(-1)) and alpha-lipoic acid (4.78 +/- 0.07 x 10(4) M(-1) s(-1)) were demonstrated to reduce Compound II and thus could be expected to be oxidized by MPO without co-substrates.

journal_name

FEBS Lett

journal_title

FEBS letters

authors

Burner U,Jantschko W,Obinger C

doi

10.1016/s0014-5793(98)01727-x

keywords:

subject

Has Abstract

pub_date

1999-01-29 00:00:00

pages

290-6

issue

3

eissn

0014-5793

issn

1873-3468

pii

S0014-5793(98)01727-X

journal_volume

443

pub_type

杂志文章
  • The chloride channel blocker 5-nitro-2-(3-phenylpropyl-amino) benzoic acid (NPPB) uncouples mitochondria and increases the proton permeability of the plasma membrane in phagocytic cells.

    abstract::We present evidence that the potent chloride channel blocker NPPB has protonophoric activity in the mitochondria and across the plasma membrane of phagocytic cells. The resting O2 consumption of murine peritoneal macrophages was stimulated up to 2.5-fold in the presence of NPPB, with a K0.5 of 15 microM. The stimulato...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(91)80992-c

    authors: Lukacs GL,Nanda A,Rotstein OD,Grinstein S

    更新日期:1991-08-19 00:00:00

  • Farnesylcysteine analogues inhibit chemotactic peptide receptor-mediated G-protein activation in human HL-60 granulocyte membranes.

    abstract::Analogues of S-prenylated cysteine like N-acetyl-S-trans,trans-farnesyl-L-cysteine (AFC) have previously been shown to inhibit the carboxyl methylation of proteins carrying a C-terminal S-prenylated cysteine residue and to block the endotoxin-activated serum-elicited chemotactic response of mouse macrophages. Here, we...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(93)80047-x

    authors: Scheer A,Gierschik P

    更新日期:1993-03-15 00:00:00

  • Phosphorylation and activation of hormone-sensitive lipase in isolated macrophages.

    abstract::Hormone-sensitive lipase (HSL) is responsible for the neutral cholesterol ester hydrolase activity in macrophages. Incubation of intact WEHI macrophages or mouse peritoneal macrophages leads to phosphorylation of HSL, which is increased by incubation with either dibutyryl cyclic AMP and 3-isobutyl-1-methylxanthine or ...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(91)80179-7

    authors: Small CA,Rogers MP,Goodacre JA,Yeaman SJ

    更新日期:1991-02-25 00:00:00

  • Bovine alpha 2-antiplasmin. N-terminal and reactive site sequence.

    abstract::Bovine alpha 2-antiplasmin (alpha 2AP) has been purified and partially characterized. The amino acid composition is very similar to that of human alpha 2AP, and the N-terminal (23 residues determined) and reactive site loop sequences (42 residues determined) are highly homologous to those of the human protein. Compare...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(92)81419-m

    authors: Christensen S,Sottrup-Jensen L

    更新日期:1992-11-02 00:00:00

  • High-field (94-GHz) EPR spectroscopy on the S(2) multiline signal of Photosystem II.

    abstract::The multiline signal of the S(2) state in Photosystem II was measured both in frozen-solution and single-crystal preparations from the cyanobacterium Thermosynechococcus elongatus. The frozen-solution EPR spectrum shows a gaussian-like line shape without any resolution of Mn hyperfine couplings. This line shape can be...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2006.05.039

    authors: Teutloff C,Kessen S,Kern J,Zouni A,Bittl R

    更新日期:2006-06-26 00:00:00

  • NMR studies of fluorophenylalanine-containing carbonic anhydrase.

    abstract::Rabbits ingesting 4-fluorophenylalanine are known to incorporate small amounts of this fluorinated amino acid into their proteins. Carbonic anhydrase I isolated from the erythrocytes of animals so maintained exhibits a well-resolved fluorine NMR signal for each phenylalanine in the sequence. The chemical shifts of mos...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(86)80216-2

    authors: Gamcsik MP,Gerig JT

    更新日期:1986-02-03 00:00:00

  • The oxidant-responsive diaphorase of Rhodobacter capsulatus is a ferredoxin (flavodoxin)-NADP(H) reductase.

    abstract::Challenge of Rhodobacter capsulatus cells with the superoxide propagator methyl viologen resulted in the induction of a diaphorase activity identified as a member of the ferredoxin (flavodoxin)-(reduced) nicotinamide adenine dinucleotide phosphate (NADP(H)) reductase (FPR) family by N-terminal sequencing. The gene cod...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/s0014-5793(03)01075-5

    authors: Bittel C,Tabares LC,Armesto M,Carrillo N,Cortez N

    更新日期:2003-10-23 00:00:00

  • Solution NMR determination of hydrogen bonding and base pairing between the glyQS T box riboswitch Specifier domain and the anticodon loop of tRNA(Gly).

    abstract::In Gram-positive bacteria the tRNA-dependent T box riboswitch regulates the expression of many amino acid biosynthetic and aminoacyl-tRNA synthetase genes through a transcription attenuation mechanism. The Specifier domain of the T box riboswitch contains the Specifier sequence that is complementary to the tRNA antico...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2013.09.003

    authors: Chang AT,Nikonowicz EP

    更新日期:2013-11-01 00:00:00

  • NPC1L1 and cholesterol transport.

    abstract::The polytopic transmembrane protein, Niemann-Pick C1-Like 1 (NPC1L1), is enriched in the apical membrane of small intestine absorptive enterocytes where it mediates extracellular sterol transport across the brush border membrane. It is essential for intestinal sterol absorption and is the molecular target of ezetimibe...

    journal_title:FEBS letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.febslet.2010.03.030

    authors: Betters JL,Yu L

    更新日期:2010-07-02 00:00:00

  • Aloe emodin glycosides stimulates glucose transport and glycogen storage through PI3K dependent mechanism in L6 myotubes and inhibits adipocyte differentiation in 3T3L1 adipocytes.

    abstract::The present study discusses the efficacy of Aloe emodin-8-O-glycoside (AEG), a plant derived anthroquinone, on alleviating insulin resistance and augmenting glycogen synthesis in L6 myotubes and 3T3L1 adipocytes. Dose-dependent increase in glucose uptake activity (GUA) was observed in both cell lines. Immunoblot analy...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2010.06.004

    authors: Anand S,Muthusamy VS,Sujatha S,Sangeetha KN,Bharathi Raja R,Sudhagar S,Poornima Devi N,Lakshmi BS

    更新日期:2010-07-16 00:00:00

  • Apamin-sensitive potassium channels mediate agonist-induced oscillations of membrane potential in pituitary gonadotrophs.

    abstract::In cultured rat pituitary gonadotrophs, gonadotropin-releasing hormone (GnRH) induces rapid hyperpolarization of the cell membrane and causes cessation of the spontaneous electrical activity present in non-stimulated cells. This initial response to GnRH is followed by slow oscillations of membrane potential (Vm) which...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(92)80201-q

    authors: Kukuljan M,Stojilković SS,Rojas E,Catt KJ

    更新日期:1992-04-13 00:00:00

  • Origin of non-cardiac endothelial cells from an Isl1+ lineage.

    abstract::The cardiovascular system consists of many cell types with distinct embryonic origins. Cells from an Islet1 (Isl1)-expressing progenitor population make a substantial contribution to the developing heart. We reasoned that cells derived from Isl1-expressing progenitors might contribute more widely to the cardiovascular...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2012.05.014

    authors: Keenan ID,Rhee HJ,Chaudhry B,Henderson DJ

    更新日期:2012-06-21 00:00:00

  • Original involvement of antimicrobial peptides in mussel innate immunity.

    abstract::Recently, the existence and extended diversity of antimicrobial peptides has been revealed in two mussel species. These molecules are classified into four groups according to common features of their primary structure: defensins, mytilins, myticins and mytimycin. In Mytilus galloprovincialis, gene structure reveals sy...

    journal_title:FEBS letters

    pub_type: 杂志文章,评审

    doi:10.1016/s0014-5793(00)02192-x

    authors: Mitta G,Vandenbulcke F,Roch P

    更新日期:2000-12-15 00:00:00

  • Occurrence of bifurcated three-center hydrogen bonds in proteins.

    abstract::Analysis of 13 high-resolution protein X-ray crystal structures shows that 1204 (24%) of all the 4974 hydrogen bonds are of the bifurcated three-center type with the donor X-H opposing two acceptors A1, A2. They occur systematically in alpha-helices where 90% of the hydrogen bonds are of this type; the major component...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(91)81032-4

    authors: Preissner R,Egner U,Saenger W

    更新日期:1991-08-19 00:00:00

  • Rate limitation within a single enzyme is directly related to enzyme intermediate levels.

    abstract::The extents to which different rate constants limit the steady-state rate of an isolated enzyme can be quantified as the control coefficients of those constants and elemental steps. We have found that the sum of the control coefficients of rate constants characterising unidirectional rates depleting a particular enzym...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(94)00617-2

    authors: Kholodenko BN,Westerhoff HV,Brown GC

    更新日期:1994-07-25 00:00:00

  • Tubulin and microtubule are potential targets for brain hexokinase binding.

    abstract::The metabolite-modulated association of a fraction of hexokinase to mitochondria in brain is well documented, however, the involvement of other non-mitochondrial components in the binding of the hexokinase is controversial. Now we present evidence that the hexokinase binds both tubulin and microtubules in brain in vit...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/s0014-5793(01)03136-2

    authors: Wágner G,Kovács J,Löw P,Orosz F,Ovádi J

    更新日期:2001-11-30 00:00:00

  • Syndromic and non-syndromic disease-linked Cx43 mutations.

    abstract::There are now at least 14 distinct diseases linked to germ line mutations in the 21 genes that encode the connexin (Cx) family of gap junction proteins. This review focuses on the links between germ-line mutations in the gene encoding Cx43 (GJA1) and the human disease termed oculodentodigital dysplasia (ODDD). This di...

    journal_title:FEBS letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.febslet.2013.12.022

    authors: Laird DW

    更新日期:2014-04-17 00:00:00

  • Endothelin-1 induces hypoxia inducible factor 1α expression in pulmonary artery smooth muscle cells.

    abstract::Endothelin-1 (ET-1) dose-dependently increased HIF1α expression in pulmonary artery smooth muscle cells (PASMCs). Inhibition of protein synthesis did not affect ET-1-induced HIF1α expression. The maximum effect of ET-1 was similar to that caused by proteasome inhibitor MG132. Further study indicates that ET-1 also dos...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2012.08.036

    authors: Li M,Liu Y,Jin F,Sun X,Li Z,Liu Y,Fang P,Shi H,Jiang X

    更新日期:2012-11-02 00:00:00

  • Physico-chemical properties of the hydroxysterol binding protein of human lymphocyte cytosol. Effects of high salt concentrations and molybdate.

    abstract::Side chain-hydroxylated derivatives of cholesterol (OH sterol) inhibiting lymphoblastic transformation bind with high affinity and specificity to a hydroxysterol binding protein (OHSBP) in the cytosol of human lymphocytes. These binding properties of OHSBP suggested some analogies with that of steroid hormone receptor...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(84)80798-x

    authors: Defay R,Astruc M,Beseme F,Descomps B,Crastes de Paulet A

    更新日期:1984-08-06 00:00:00

  • Structure of a large photosystem II supercomplex from Acaryochloris marina.

    abstract::Acaryochloris marina is a prochlorophyte-like cyanobacterium containing both phycobilins and chlorophyll d as light harvesting pigments. We show that the chlorophyll d light harvesting system, composed of Pcb proteins, functionally associates with the photosystem II (PSII) reaction center (RC) core to form a giant sup...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2005.01.023

    authors: Chen M,Bibby TS,Nield J,Larkum AW,Barber J

    更新日期:2005-02-14 00:00:00

  • The enigma of the CLIC proteins: Ion channels, redox proteins, enzymes, scaffolding proteins?

    abstract::Chloride intracellular channel proteins (CLICs) are distinct from most ion channels in that they have both soluble and integral membrane forms. CLICs are highly conserved in chordates, with six vertebrate paralogues. CLIC-like proteins are found in other metazoans. CLICs form channels in artificial bilayers in a proce...

    journal_title:FEBS letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.febslet.2010.01.027

    authors: Littler DR,Harrop SJ,Goodchild SC,Phang JM,Mynott AV,Jiang L,Valenzuela SM,Mazzanti M,Brown LJ,Breit SN,Curmi PM

    更新日期:2010-05-17 00:00:00

  • Does the HIV Nef protein mimic the MHC?

    abstract::The sequence of the HIV Nef protein has no significant homology to other proteins in the SwissProt database, and experimental data concerning its function are sparse and contradictory. Using a novel protein sequence comparison method, we find similarities between different Nef sequences and the alpha chain of human MH...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(93)80655-e

    authors: Hobohm U,Sander C

    更新日期:1993-11-01 00:00:00

  • Is the acetylcholine releasing protein mediatophore present in rat brain?

    abstract::Mediatophore is a protein purified from the nerve terminal membranes of Torpedo electric organ. It confers to artificial membranes a calcium-dependent mechanism that translocates acetylcholine. When similar reconstitution experiments are applied to rat brain synaptosomal membranes they reveal the presence of mediatoph...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(88)80475-7

    authors: Israël M,Lesbats B,Morel N,Manaranche R,Le Gal la Salle G

    更新日期:1988-06-20 00:00:00

  • Nitric oxide reacts with the ferryl-oxo catalytic intermediate of the CuB-lacking cytochrome bd terminal oxidase.

    abstract::Cytochrome bd is a bacterial respiratory oxidase carrying three hemes but no copper. We show that nitric oxide (NO) reacts with the intermediate F of cytochrome bd from Azotobacter vinelandii: (i) with a 1:1 stoichiometry, (ii) rapidly (k=1.2 +/- 0.1 x 10(5)M(-1)s(-1) at 20 degrees C), and (iii) yielding the oxidized ...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2006.07.072

    authors: Borisov VB,Forte E,Sarti P,Brunori M,Konstantinov AA,Giuffrè A

    更新日期:2006-09-04 00:00:00

  • Peroxiredoxin-I is an autoimmunogenic tumor antigen in non-small cell lung cancer.

    abstract::In eukaryotic cells, peroxiredoxins are both antioxidants and regulators of H(2)O(2)-mediated signaling. We previously found that peroxiredoxin-I (Prx-I) was overexpressed in non-small cell lung cancer (NSCLC) tissue. Since overexpressed protein can induce a humoral immune response, we examined whether serum from NSCL...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/j.febslet.2005.04.028

    authors: Chang JW,Lee SH,Jeong JY,Chae HZ,Kim YC,Park ZY,Yoo YJ

    更新日期:2005-05-23 00:00:00

  • Recognizing the pleckstrin homology domain fold in mammalian phospholipase D using hidden Markov models.

    abstract::Phospholipase D was first described in plant tissue but has recently been shown to occur in mammalian cells where it is activated by cell surface receptors. Its mode of activation by receptors in unclear. Biochemical studies suggest that it may occur downstream of other effector proteins and that small GTP-dependent r...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/s0014-5793(99)00366-x

    authors: Holbrook PG,Geetha V,Beaven MA,Munson PJ

    更新日期:1999-04-09 00:00:00

  • Degradation of the yeast MAT alpha 2 transcriptional regulator is mediated by the proteasome.

    abstract::Rapid degradation of specific regulatory proteins plays a role in a wide range of cellular phenomena, including cell cycle progression and the regulation of cell growth and differentiation. A major mechanism of selective protein turnover in vivo involves a large multi-subunit protease known as the proteasome or multi-...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(94)01085-4

    authors: Richter-Ruoff B,Wolf DH,Hochstrasser M

    更新日期:1994-10-31 00:00:00

  • The origin of the sodium-dependent NADH oxidation by the respiratory chain of Klebsiella pneumoniae.

    abstract::Properties of Klebsiella pneumoniae respiratory chain enzymes catalyzing NADH oxidation have been studied. Using constructed K. pneumoniae mutant strains, it was shown that three enzymes belonging to different families of NADH:quinone oxidoreductases operate in this bacterium. The NDH-2-type enzyme is not coupled with...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/S0014-5793(04)00312-6

    authors: Bertsova YV,Bogachev AV

    更新日期:2004-04-09 00:00:00

  • Expression of a p16INK4a-specific ribozyme downmodulates p16INK4a abundance and accelerates cell proliferation.

    abstract::The pl6INK4a tumor suppressor negatively regulates progression through the G1 phase of the mammalian cell cycle. To mimic the downmodulation of p16INK4a commonly seen in cancer, we designed and characterized a hammerhead ribozyme against exon E1alpha of the murine pl6INK4a transcript. Stable expression of the ribozyme...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/s0014-5793(98)01089-8

    authors: Nylandsted J,Rohde M,Bartek J,Strauss M

    更新日期:1998-09-25 00:00:00

  • Conservation of local electric fields in the evolution of Cu,Zn superoxide dismutase.

    abstract::The trend of the electric field and the value of the electric field flux, sensed by the superoxide substrate in the proximity of the active site, were found to be constant in three highly homologous Cu,Zn superoxide dismutases from ox, pig and sheep, which display large differences in net protein charge and distributi...

    journal_title:FEBS letters

    pub_type: 杂志文章

    doi:10.1016/0014-5793(89)80681-7

    authors: Desideri A,Falconi M,Parisi V,Rotilio G

    更新日期:1989-06-19 00:00:00