NADPH-cytochrome reductase catalysed redox cycling of 1,4-benzoquinone; hampered at physiological conditions, initiated at increased pH values.

Abstract:

:In the present study the inability of 1,4-benzoquinone to support NADPH-cytochrome reductase catalysed redox cycling was investigated. The results obtained demonstrate that NADPH-cytochrome reductase is able to initiate a rapid two-electron reduction of 1,4-benzoquinone resulting in formation of the hydroquinone. The intermediate one-electron reduced semiquinone form does not pass its electron on to molecular oxygen, i.e. giving rise to redox cycling, but is reduced by a second electron, either by NADPH-cytochrome reductase upon protonation of the semiquinone or through disproportionation, both giving rise to the two-electron reduced hydroquinone. At pH values below the pK alpha of the hydroquinone, the electrons of the hydroquinone are also not passed on to molecular oxygen due to efficient protonation. However, at pH values around or above the pK alpha (9.85) of the two-electron reduced hydroquinone form, significant redox cycling activity is observed in a 1,4-benzoquinone containing incubation. Further experiments demonstrate a similarity in both the concentration and pH dependence of 1,4-benzoquinone or 1,4-hydroquinone supported NADPH-cytochrome reductase catalysed redox cycling. From these observations it is concluded that 1,4-benzoquinone is able to redox cycle from its deprotonated two-electron reduced hydroquinone form, but only at relatively high pH values. Together the data provide an insight into why the NADPH-cytochrome reductase catalysed redox cycling of 1,4-benzoquinone is inhibited at physiological conditions, but initiated at increased pH values.

journal_name

Biochem Pharmacol

journal_title

Biochemical pharmacology

authors

Boersma MG,Balvers WG,Boeren S,Vervoort J,Rietjens IM

doi

10.1016/0006-2952(94)90068-x

subject

Has Abstract

pub_date

1994-06-01 00:00:00

pages

1949-55

issue

11

eissn

0006-2952

issn

1873-2968

pii

0006-2952(94)90068-X

journal_volume

47

pub_type

杂志文章
  • Posttranslationally modified ornithine decarboxylase may regulate RNA polymerase I activity.

    abstract::Purified ornithine decarboxylase (EC 4.1.1.17, ODC) transamidated with four putrescine moieties on four glutamine residues through the action of transglutaminase (EC 2.3.2.13, TGase) purified from guinea pig liver, when added to isolated rat liver nuclei, stoichiometrically increased the activity of RNA polymerase I (...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(82)90614-1

    authors: Russell DH,Manen CA

    更新日期:1982-11-01 00:00:00

  • Comparison of the effects of recently developed alpha 2-adrenergic antagonists with yohimbine and rauwolscine on monoamine synthesis in rat brain.

    abstract::The effects of two recently developed alpha 2-adrenergic antagonists, RX 781094 and WY 26703, on the synthesis of norepinephrine (NE), dopamine (DA) and serotonin (5-HT) in rat brain were compared to those of yohimbine, its diastereoisomer rauwolscine, and mianserin. Intraperitoneal administration of these compounds i...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(85)90614-8

    authors: Pettibone DJ,Pfleuger AB,Totaro JA

    更新日期:1985-04-01 00:00:00

  • Polymerization of the triphosphates of AraC, 2',2'-difluorodeoxycytidine (dFdC) and OSI-7836 (T-araC) by human DNA polymerase alpha and DNA primase.

    abstract::OSI-7836 (4'-thio-araC, T-araC) is a nucleoside analogue that shows efficacy against solid tumor xenograft models. We examined how the triphosphates of OSI-7836 (T-araCTP), cytarabine (araCTP), and gemcitabine (dFdCTP) affected the initiation of new DNA strands by the pol alpha primase complex. Whereas dFdCTP very wea...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2004.07.042

    authors: Richardson KA,Vega TP,Richardson FC,Moore CL,Rohloff JC,Tomkinson B,Bendele RA,Kuchta RD

    更新日期:2004-12-15 00:00:00

  • The two faces of aldehyde oxidase: Oxidative and reductive transformations of 5-nitroquinoline.

    abstract::Aldehyde oxidase (AOX) is a cytosolic enzyme responsible for the metabolism of some drugs and drug candidates. AOX catalyzes the oxidative hydroxylation of substrates including several aliphatic and aromatic aldehydes, and nitrogen-containing heterocyclic compounds. AOX is also reported to catalyze the reductive metab...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2017.09.002

    authors: Paragas EM,Humphreys SC,Min J,Joswig-Jones CA,Jones JP

    更新日期:2017-12-01 00:00:00

  • Identification of psychedelic new psychoactive substances (NPS) showing biased agonism at the 5-HT2AR through simultaneous use of β-arrestin 2 and miniGαq bioassays.

    abstract::Psychedelic new psychoactive substances (NPS), compounds exerting their main pharmacological effects through the activation of the serotonin 2A receptor (5-HT2AR), continuously comprise a substantial portion of the reported NPS. However, these substances and their exact mechanism of action, differentiating them from n...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2020.114251

    authors: Pottie E,Dedecker P,Stove CP

    更新日期:2020-12-01 00:00:00

  • Inhibition of prostaglandin production in the inflammatory tissue by loxoprofen-Na, an anti-inflammatory prodrug.

    abstract::The effect of loxoprofen-Na, a novel non-steroidal anti-inflammatory drug with a prodrug property, on prostaglandin (PG) levels in the inflammatory tissue was investigated with a carrageenin-induced pleurisy model in rats. The intrapleural injection of carrageenin caused a marked increase in the levels of PGE2 and 6-k...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(91)90242-w

    authors: Sugimoto M,Kojima T,Asami M,Iizuka Y,Matsuda K

    更新日期:1991-11-27 00:00:00

  • Nitroblue tetrazolium inhibits oxidation of glyceryl trinitrate to nitric oxide in bovine aortic smooth muscle cells.

    abstract::The effects of nitroblue tetrazolium (NBT), a well-known scavenger of superoxide anions and an inhibitor of nicotinamide adenine dinucleotide (NADPH)-dependent oxidations, were assessed on the metabolism of glyceryl trinitrate (GTN) to nitric oxide (NO) by bovine aortic smooth muscle cells (SMC). The extent of this me...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(94)90300-x

    authors: Pistelli A,Mollace V,Nistico G,Salvemini D,Vane J

    更新日期:1994-05-18 00:00:00

  • The morphogenetically active polymer, inorganic polyphosphate complexed with GdCl3, as an inducer of hydroxyapatite formation in vitro.

    abstract::Inorganic polyphosphate (polyP) is a physiological polymer composed of tens to hundreds of phosphate units linked together via phosphoanhydride bonds. Here we compared the biological activity of polyP (chain length of 40 phosphate units), complexed with Gd(3+) (polyP·Gd), with the one caused by polyP (as calcium salt)...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2015.12.011

    authors: Wang X,Huang J,Wang K,Neufurth M,Schröder HC,Wang S,Müller WEG

    更新日期:2016-02-15 00:00:00

  • Benzylamine metabolism at low O2 concentrations. Relative sensitivities of monoamine oxidase, aldehyde dehydrogenase and hippurate synthesis to hypoxia.

    abstract::The O2 dependence of the metabolism of benzylamine to benzaldehyde, benzoate and hippurate was studied in isolated rat hepatocytes. The initial oxidation to benzaldehyde, catalyzed by monoamine oxidase, had an apparent Kmo2 value of 34 microM in cells and 40 microM in isolated rat liver mitochondria. The conversion of...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(84)90234-x

    authors: Jones DP

    更新日期:1984-02-01 00:00:00

  • Oxidative activation of 2-aminofluorene by human red blood cell cytosol.

    abstract::Purified red blood cell cytosol is able to activate 2-aminofluorene (2AF) to N-hydroxy-2-aminofluorene. Apparent kinetic parameters are determined with and without methylene blue. The latter, which maintains haemoglobin in the reduced form and stimulates NADPH production, increases the affinity of the enzyme for the 2...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90691-b

    authors: Duverger-van Bogaert M,Wiame D,Stecca C

    更新日期:1992-12-15 00:00:00

  • Cross-resistance to antifolates in multidrug resistant cell lines with P-glycoprotein or multidrug resistance protein expression.

    abstract::Resistance to some (lipophilic) antifolates has been associated with P-glycoprotein (P-gp)-mediated multidrug resistance (MDR). A possible relationship with non-P-gp MDR has not been established. We studied resistance to antifolates in SW-1573 human lung carcinoma cells, a P-gp overexpressing variant SW-1573/2R160 and...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(97)82448-3

    authors: van Triest B,Pinedo HM,Telleman F,van der Wilt CL,Jansen G,Peters GJ

    更新日期:1997-06-15 00:00:00

  • Effects of the beta 2-adrenoceptor agonist clenbuterol on tyrosine and tryptophan in plasma and brain of the rat.

    abstract::The beta 2-adrenoceptor agonist, clenbuterol (initially 5 mg/kg), was found to significantly reduce plasma tyrosine and raise brain tryptophan levels (P less than 0.01). By comparison, decreases in plasma tryptophan and increases in brain tyrosine were small and often nonsignificant. Amino acid levels measured in diff...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(89)90003-8

    authors: Edwards DJ,Sorisio DA,Knopf S

    更新日期:1989-09-15 00:00:00

  • Antioxidant and pro-oxidant properties of pyrroloquinoline quinone (PQQ): implications for its function in biological systems.

    abstract::Pyrroloquinoline quinone (PQQ) is a novel redox cofactor recently found in human milk. It has been reported to function as an essential nutrient, antioxidant and redox modulator in cell culture experiments and in animal models of human diseases. As mitochondria are particularly susceptible to oxidative damage we studi...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(02)01453-3

    authors: He K,Nukada H,Urakami T,Murphy MP

    更新日期:2003-01-01 00:00:00

  • Contribution of phosphodiesterase isoenzymes and cyclic nucleotide efflux to the regulation of cyclic GMP levels in aortic smooth muscle cells.

    abstract::Involvement of phosphodiesterase isoenzymes (PDEs) in guanosine-3',5'-cyclic monophosphate (cGMP) hydrolysis was analyzed in aortic smooth muscle cells. Four families of PDEs were separated from pig aorta: PDE1 (calcium-calmodulin-activated), PDE3 (cGMP-inhibited), PDE4 (adenosine 3',5'-cyclic monophosphate [cAMP]-spe...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(99)00252-x

    authors: Mercapide J,Santiago E,Alberdi E,Martinez-Irujo JJ

    更新日期:1999-11-15 00:00:00

  • Production of low molecular weight cadmium-binding proteins in rabbit lung following exposure to cadmium chloride.

    abstract::Low molecular weight cadmium-binding proteins were studed in lung tissue from rabbits exposed to aerosols of CdCl2. Lungs obtained from animals exposed by inhalation to aerosols of 800 or 1600 micrograms/m3 CdCl2 for 2-hr periods/day, every other day for a 5-day period, were found to contain at least three low molecul...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(82)90271-4

    authors: Post CT,Squibb KS,Fowler BA,Gardner DE,Illing J,Hook GE

    更新日期:1982-09-15 00:00:00

  • Mode of action of the new selective leukotriene synthesis inhibitor BAY X 1005 ((R)-2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cyclopentyl acetic acid) and structurally related compounds.

    abstract::BAY X 1005 ((R)-2-[4-(quinolin-2-yl-methoxy)phenyl]-2-cyclopentyl acetic acid) has been demonstrated to be a potent inhibitor of leukotriene B4 (LTB4) and 5-hydroxyeicosatetraenoic acid (5-HETE) synthesis in various in vitro systems. Using mainly human polymorphonuclear leukocytes (PMNL) this study elucidates the mech...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(93)90382-7

    authors: Hatzelmann A,Fruchtmann R,Mohrs KH,Raddatz S,Müller-Peddinghaus R

    更新日期:1993-01-07 00:00:00

  • Cetaben and fibrates both influence the activities of peroxisomal enzymes in different ways.

    abstract::The effects of cetaben and clofibric acid were compared on the activities of peroxisomal enzymes in the liver and kidney of male Wistar rats. Cetaben at 200 mg/kg body wt increased the activities of all of the enzymes in the liver that were studied two to eight times, whereas the changes induced by the same dose of cl...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(94)90183-x

    authors: Chandoga J,Rojeková I,Hampl L,Hocman G

    更新日期:1994-02-09 00:00:00

  • The effect of lipid composition on the metabolism of lignocaine by a reconstituted mixed function oxidase system from rat liver.

    abstract::Hepatic microsomal preparations from male and female rats were delipidated by column chromatography following cholate solubilisation. The enzyme activities were reconstituted using known lipids and the vesicle reconstitution method. Enzyme activity was assayed using lignocaine as the substrate for the mixed function o...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(87)90071-2

    authors: Meftah NM,Skett P

    更新日期:1987-04-15 00:00:00

  • Current perspectives on parathyroid hormone (PTH) and PTH-related protein (PTHrP) as bone anabolic therapies.

    abstract::Osteoporosis is characterized by low bone mineral density and/or poor bone microarchitecture leading to an increased risk of fractures. The skeletal alterations in osteoporosis are a consequence of a relative deficit of bone formation compared to bone resorption. Osteoporosis therapies have mostly relied on antiresorp...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2013.03.002

    authors: Esbrit P,Alcaraz MJ

    更新日期:2013-05-15 00:00:00

  • Dose-dependent regulation of mitochondrial function and cell death pathway by sorafenib in liver cancer cells.

    abstract::Hepatocellular carcinoma (HCC) is the most common type of primary liver cancer and the fourth most frequent cause of cancer-related death worldwide. Sorafenib is the first line recommended therapy for patients with locally advanced/metastatic HCC. The low response rate is attributed to intrinsic resistance of HCC cell...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2020.113902

    authors: Rodríguez-Hernández MA,de la Cruz-Ojeda P,Gallego P,Navarro-Villarán E,Staňková P,Del Campo JA,Kučera O,Elkalaf M,Maseko TE,Červinková Z,Muntané J

    更新日期:2020-06-01 00:00:00

  • Gli family transcription factors are drivers of patupilone resistance in ovarian cancer.

    abstract::Epothilones constitute a novel class of antitubulin agents that are active in patients who relapse after treatment with other chemotherapeutics. This study investigated the molecular mechanisms leading to the onset of epothilone-B (patupilone) resistance in ovarian cancer. Results demonstrated that the Gli family of t...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2012.08.019

    authors: Mozzetti S,Martinelli E,Raspaglio G,Prislei S,De Donato M,Filippetti F,Shahabi S,Scambia G,Ferlini C

    更新日期:2012-12-01 00:00:00

  • Inhibition of MMPs and ADAM/ADAMTS.

    abstract::Matrix metalloproteinases (MMPs), A Disintegrin and Metalloproteinase (ADAM) and A Disintegrin and Metalloproteinase with Thrombospondin Motif (ADAMTS) are zinc-dependent endopeptidases that play a critical role in the destruction of extracellular matrix proteins and, the shedding of membrane-bound receptor molecules ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2019.02.033

    authors: Malemud CJ

    更新日期:2019-07-01 00:00:00

  • Clotrimazole inhibits and modulates heterologous association of the key glycolytic enzyme 6-phosphofructo-1-kinase.

    abstract::Clotrimazole is an antifungal azole derivative recently recognized as a calmodulin antagonist with promising anticancer effects. This property has been correlated with the ability of the drug to decrease the viability of tumor cells by inhibiting their glycolytic flux and consequently decreasing the intracellular conc...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2007.01.018

    authors: Zancan P,Rosas AO,Marcondes MC,Marinho-Carvalho MM,Sola-Penna M

    更新日期:2007-05-15 00:00:00

  • Cytotoxicity of dichloromethane diphosphonate and of 1-hydroxyethane-1,1-diphosphonate in the amoebae of the slime mould Dictyostelium discoideum. A 31P NMR study.

    abstract::Two pyrophosphate analogues, dichloromethane diphosphonate (Cl2MDP), and 1-hydroxyethane-1,1-diphosphonate (EHDP), at concentrations of 0.5-1 mM, efficiently inhibited the growth of amoebae of the slime mould Dictyostelium discoideum. Cell viability decreased markedly upon incubation with the diphosphonates. The mecha...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90342-g

    authors: Pelorgeas S,Martin JB,Satre M

    更新日期:1992-12-01 00:00:00

  • Snake three-finger α-neurotoxins and nicotinic acetylcholine receptors: molecules, mechanisms and medicine.

    abstract::Snake venom three-finger α-neurotoxins (α-3FNTx) act on postsynaptic nicotinic acetylcholine receptors (nAChRs) at the neuromuscular junction (NMJ) to produce skeletal muscle paralysis. The discovery of the archetypal α-bungarotoxin (α-BgTx), almost six decades ago, exponentially expanded our knowledge of membrane rec...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2020.114168

    authors: Nirthanan S

    更新日期:2020-11-01 00:00:00

  • Lidocaine inhibits priming and protein tyrosine phosphorylation of human peripheral neutrophils.

    abstract::The addition of agents, such as tumor necrosis factor-alpha, to human peripheral neutrophils (HPPMN) induces priming, which enhances the receptor-mediated superoxide (O2-) generation and tyrosine phosphorylation of several HPPMN proteins. Lidocaine, a local anesthetic, inhibited both enhanced O2- generation and tyrosi...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(93)90299-c

    authors: Kanbara T,Tomoda MK,Sato EF,Ueda W,Manabe M

    更新日期:1993-04-22 00:00:00

  • Effect of stereo and regiochemistry towards wild and multidrug resistant HIV-1 virus: viral potency of chiral PETT derivatives.

    abstract::Chiral derivatives of several substituted halopyridyl and thiazolyl PETT compounds were synthesized as non-nucleoside inhibitors of the reverse transcriptase (RT) enzyme of the human immunodeficiency virus (HIV-1). Molecular modeling studies indicated that because of the asymmetric geometry of the non-nucleoside inhib...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2004.01.019

    authors: Venkatachalam TK,Mao C,Uckun FM

    更新日期:2004-05-15 00:00:00

  • Debrisoquine 4-monooxygenase and bufuralol 1'-monooxygenase activities in bovine and rabbit tissues.

    abstract::The tissue distributions of debrisoquine 4-monooxygenase and bufuralol 1'-monooxygenase activities in microsomes from bovine and rabbit tissues were analysed. Debrisoquine 4-monooxygenase and bufuralol 1'-monooxygenase activities were found in liver, and at low levels in cerebral cortex, kidney cortex, lung, small int...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90633-t

    authors: Matsuo Y,Iwahashi K,Ichikawa Y

    更新日期:1992-05-08 00:00:00

  • Specific, high-affinity bradykinin binding by purified porcine kidney post-proline cleaving enzyme.

    abstract::Post-proline cleaving enzyme (PPCE) was purified from porcine kidney cytosol. The purified enzyme bound [125I-Tyr5]-bradykinin but neither [125I-Tyr1]-kallidin nor [125I-Tyr8]-bradykinin. Scatchard analysis of the data was consistent with a single class of binding sites with a Kassoc = 1.3 +/- 0.1 X 10(8) M-1. The opt...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(87)90380-7

    authors: Odya CE,Dally RD,Georgiadis KE

    更新日期:1987-01-01 00:00:00

  • Hepatic aldehyde and alcohol dehydrogenases in alcohol-preferring and alcohol-avoiding rat lines.

    abstract::The alcohol-avoiding ANA (Alko, Non-Alcohol) and alcohol-preferring AA (Alko, Alcohol) rat lines are known to differ in their acetaldehyde metabolism and were originally found to differ in hepatic alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) activities in the 1970s. At the beginning of the 1980s, thes...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(94)90199-6

    authors: Koivisto T,Eriksson CJ

    更新日期:1994-10-18 00:00:00