Reversibility of disulfide formation. Comparison of chemical and enzyme-mediated reduction of penicillamine and captopril disulfides.

Abstract:

:The reduction of penicillamine disulfide by reductants in aqueous solutions has been studied and compared with that for captopril disulfide. Whereas near quantitative reduction for captopril disulfide was achieved with tributyl phosphine (200 mM), no detectable penicillamine was formed from penicillamine disulfide. Thiol reductants (25 mM) were, however, partially able to reduce penicillamine disulfide with the most effective agent being glutathione (15% reduction) following by dithioerythritol (8%) and cysteine (5.1%). The reduction of penicillamine-cysteine disulfide by glutathione was 6-fold higher than for penicillamine disulfide. Kinetic analysis showed that the initial rate of reduction and equilibrium constant for the reduction of penicillamine disulfides by glutathione were 267- and 875-fold less than for captopril disulfide at pH 7.4. Biotransformation studies in the cytosol fraction of rat blood cells demonstrated that whereas 48% of the reduction of captopril disulfide was enzyme-mediated only 19% of the penicillamine formed was enzyme-mediated for penicillamine disulfide. Accumulation of disulfides of penicillamine in patients taking penicillamine may therefore be a problem during chronic therapy.

journal_name

Biochem Pharmacol

journal_title

Biochemical pharmacology

authors

Drummer OH,Routley L,Christophidis N

doi

10.1016/0006-2952(87)90070-0

subject

Has Abstract

pub_date

1987-04-15 00:00:00

pages

1197-201

issue

8

eissn

0006-2952

issn

1873-2968

pii

0006-2952(87)90070-0

journal_volume

36

pub_type

杂志文章
  • The in vitro and in vivo depigmenting activity of Coenzyme Q10 through the down-regulation of α-MSH signaling pathways and induction of Nrf2/ARE-mediated antioxidant genes in UVA-irradiated skin keratinocytes.

    abstract::Coenzyme CoQ10 (CoQ10), a ubiquinone compound, has been reported to inhibit tyrosinase activity and melanin production in melanoma B16F10 cells. However, the molecular mechanism underlying this inhibitory effect is poorly understood. In this paper we aimed to investigate the molecular mechanisms involved in the anti-m...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2019.04.015

    authors: Hseu YC,Ho YG,Mathew DC,Yen HR,Chen XZ,Yang HL

    更新日期:2019-06-01 00:00:00

  • Inhibition of indoleamine 2,3-dioxygenase activity in IFN-gamma stimulated astroglioma cells decreases intracellular NAD levels.

    abstract::Astroglia provide essential metabolic and neurotropic support to cells within the CNS and participate in the cellular immune response with microglia/macrophages following activation by the pro-inflammatory cytokine IFN-gamma. Activation of glial cells results in local oxidative stress and induction of a number of prot...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(03)00464-7

    authors: Grant R,Kapoor V

    更新日期:2003-09-15 00:00:00

  • The bone marrow microenvironment as a sanctuary for minimal residual disease in CML.

    abstract::Bcr-abl kinase inhibitors have provided proof of principal that targeted therapy holds great promise for the treatment of cancer. However, despite the success of these agents in treating chronic myelogenous leukemia (CML), the majority of patients continue to present with minimal residual disease contained within the ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2010.04.003

    authors: Nair RR,Tolentino J,Hazlehurst LA

    更新日期:2010-09-01 00:00:00

  • Studies on microsomal azoreduction. N,N-dimethyl-4-aminoazobenzene (DAB) and its derivatives.

    abstract::The azoreduction of N,N-dimethyl-4-aminoazobenzene (DAB) and N-methyl-4-amino-azobenzene (MAB) by rat liver microsomes was investigated. It was shown that measurement of azoreduction of DAB and structurally related azo dyes by the conventional method of substrate disappearance required an anaerobic environment since N...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(85)90343-0

    authors: Levine WG

    更新日期:1985-09-15 00:00:00

  • Catecholamines and the kinetics of lipolysis in isolated rat adipocytes. Statistical analysis and handling of day-to-day variability in dose-response curves: a general procedure for assessing and manipulating dose-response data.

    abstract::(1) As a first step in studying the kinetics of the lipolytic system of rat adipocytes, the day-to-day variation between dose-response curves has been analysed. (2) Methods are described for the evaluation of large quantities of data relating noradrenaline to lipolysis. (3) A 'clustering' technique is presented which ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(82)90455-5

    authors: Davies JI,Cooper DM,Everett D

    更新日期:1982-03-01 00:00:00

  • A human small cell lung carcinoma cell line, resistant to 4'-(9-acridinylamino)-methanesulfon-m-anisidide and cross-resistant to camptothecin with a high level of topoisomerase I.

    abstract::N417/AMSA cells, about 80-fold resistant to mAMSA [4'-(9-acridinylamino)-methanesulfon-m-anisidide], were obtained by serial passages of the parental human small cell lung carcinoma NCI-N417 (N417/p) in stepwise drug concentrations. The N417/AMSA cells were found to be 114-, 100-, and 9-fold cross-resistant to the top...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(94)90368-9

    authors: Prost S,Riou G

    更新日期:1994-08-30 00:00:00

  • Evidence for ryanodine receptors in Schistosoma mansoni.

    abstract::The present study investigated the presence of ryanodine receptors in the trematode Schistosoma mansoni. [3H]Ryanodine specific binding sites were found in the four subcellular fractions of S. mansoni; however, more binding sites were recovered in the heterogeneous fraction P1 and the microsomal fraction P4, as was th...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(98)00219-6

    authors: Silva CL,Cunha VM,Mendonça-Silva DL,Noël F

    更新日期:1998-10-15 00:00:00

  • Methotrexate analogues--XVII. Antitumor activity of 4-amino-4-deoxy-N10-methylpteroyl-D,L-homocysteic acid and its dual inhibition of dihydrofolate reductase and folyl polyglutamate synthetase.

    abstract::A new analogue of methotrexate was synthesized from 4-amino-4-deoxy-N10-methylpteroic acid and D,L-homocysteic acid. The product (mAPA-HCysA) was bound tightly to L1210 mouse leukemia dihydrofolate reductase (IC50 = 1 nM), inhibited L1210 cell proliferation in culture (IC50 = 0.3 microM), and prolonged the survival of...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(84)90383-6

    authors: Rosowsky A,Moran RG,Forsch R,Colman P,Uren J,Wick M

    更新日期:1984-01-01 00:00:00

  • Inhibition of IgE-mediated release of histamine and peptide leukotriene from human basophils and mast cells by forskolin.

    abstract::Forskolin, a diterpene compound isolated from the roots of Coleus forskohlii, activates adenylate cyclase in membranes from a variety of mammalian tissues. We found that forskolin (10(-7) to 3 X 10(-5) M) caused a concentration-related inhibition of IgE-mediated release of histamine and peptide leukotriene C4 (LTC4) f...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(87)90377-7

    authors: Marone G,Columbo M,Triggiani M,Cirillo R,Genovese A,Formisano S

    更新日期:1987-01-01 00:00:00

  • Targeting the epidermal growth factor receptor for therapy of carcinomas.

    abstract::As a group, the carcinomas represent a substantial proportion of all human malignancies, but, with relatively few exceptions, current treatments are ineffective. Modification of existing chemotherapeutic agents has not led to significant improvements in the survival of carcinoma patients, and development of new therap...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/0006-2952(95)02232-5

    authors: Davies DE,Chamberlin SG

    更新日期:1996-05-03 00:00:00

  • Melatonin protects against methotrexate-induced memory deficit and hippocampal neurogenesis impairment in a rat model.

    abstract::Methotrexate (MTX) is a chemotherapy agent linked to cognitive deficits in cancer patients received chemotherapy treatment. MTX decreases cell proliferation in the hippocampus, which is concomitant with cognitive deficits in animal models. The present study aimed to investigate the disadvantages of MTX on cognition as...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2019.02.010

    authors: Sirichoat A,Krutsri S,Suwannakot K,Aranarochana A,Chaisawang P,Pannangrong W,Wigmore P,Welbat JU

    更新日期:2019-05-01 00:00:00

  • LPS-induced dissociation of multidrug resistance-associated protein 2 (Mrp2) and radixin is associated with Mrp2 selective internalization in rats.

    abstract::Multidrug resistance-associated protein 2 (Mrp2) is an ATP-dependent export pump that mediates the formation of bile-salt-independent bile flow. Disruption of the canalicular localization of Mrp2, without changes in its expression, is observed in chronic liver failure and is accompanied by oxidative stress. We reporte...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2010.09.016

    authors: Saeki J,Sekine S,Horie T

    更新日期:2011-01-01 00:00:00

  • Repeated administration of N-methyl-4-phenyl 1,2,5,6-tetrahydropyridine to rats is not toxic to striatal dopamine neurones.

    abstract::N-Methyl-4-phenyl-1,2,5,6-tetrahydropyridine ( MPTP ) (10 mg/kg/day i.p.) was administered to rats for 16 days, which were then observed for a further 9-11 days. MPTP administration did not alter spontaneous locomotor activity or amphetamine (2.5 mg/kg ip)-induced locomotion. Apomorphine (0.25 mg/kg sc) did not alter ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(84)90344-7

    authors: Boyce S,Kelly E,Reavill C,Jenner P,Marsden CD

    更新日期:1984-06-01 00:00:00

  • Selective inhibition of potassium-stimulated rat adrenal glomerulosa cells by ruthenium red.

    abstract::The effect of the cationic dye, ruthenium red (RR), on ionic fluxes, Ca2+ signal generation, and stimulation of aldosterone production was studied in isolated rat adrenal glomerulosa cells. In these cells, increased extracellular [K+] as well as angiotensin II (Ang II) elevate cytoplasmic Ca2+ concentration and thereu...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(98)00285-8

    authors: Szabadkai G,Várnai P,Enyedi P

    更新日期:1999-01-15 00:00:00

  • Liposomal incorporation changes the effect of 1.25-dihydroxyvitamin D3 on the phospholipase C signal transduction pathway and the eicosanoid cascade on keratinocytes in vitro.

    abstract::1.25-dihydroxyvitamin D3 is of clinical importance (e.g. in the treatment of psoriasis) given its ability to regulate the proliferation and differentiation of human keratinocytes. 1.25-Dihydroxyvitamin D3 mediates its action via genomic and nongenomic pathways. The nongenomic actions begin with the activation of phosp...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(96)02130-2

    authors: Prüfer K,Jirikowski GF

    更新日期:1996-02-09 00:00:00

  • Inactivation by acivicin of carbamoyl-phosphate synthetase II of human colon carcinoma.

    abstract::The effect of the anti-tumor, anti-glutamine drug acivicin, L-(alpha S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid, was determined on the activity of the rate-limiting enzyme of de novo pyrimidine biosynthesis, carbamoyl-phosphate synthetase II (glutamine-hydrolyzing) (EC 6.3.5.5), in human colon carci...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(85)90106-6

    authors: Sebolt JS,Aoki T,Eble JN,Glover JL,Weber G

    更新日期:1985-01-01 00:00:00

  • Peroxide-dependent amino acid oxidation and chemiluminescence catalysed by magnesium-pyridoxal phosphate-glutamate complex.

    abstract::Magnesium-pyridoxal-5'-phosphate-glutamate (MPPG) has been shown to ameliorate atherosclerotic symptoms in rabbits. In vitro, MPPG in the presence of peroxides such as cholesterolhydroperoxide or cumene hydroperoxide and Mn2+ ions produces "excited states" measurable as chemiluminescence or ethylene release from 1-ami...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90442-l

    authors: Meyer BU,Schneider W,Elstner EF

    更新日期:1992-08-04 00:00:00

  • Effect of enzyme induction on Sandimmun (cyclosporin A) biotransformation and hepatotoxicity in cultured rat hepatocytes and in vivo.

    abstract::This study was designed to examine the relationship between the extent of Sandimmun (cyclosporin A, SIM) metabolism and SIM-induced hepatotoxicity both in vivo and in primary cultures of rat hepatocytes. Firstly, SIM (50 mg/kg p.o.) was administered daily to male Wistar rats for 10 days with or without co-administrati...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(90)90024-f

    authors: Bouis P,Brouillard JF,Fischer V,Donatsch P,Boelsterli UA

    更新日期:1990-01-15 00:00:00

  • Methionine restriction selectively targets thymidylate synthase in prostate cancer cells.

    abstract::Tumor cells are more sensitive to methionine restriction than normal tissues, a phenomenon known as methionine auxotrophy. Previous studies showed that 5-fluorouracil and methionine restriction act synergistically against a variety of tumors. The purpose of the current studies was to determine the molecular mechanism(...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(03)00406-4

    authors: Lu S,Chen GL,Ren C,Kwabi-Addo B,Epner DE

    更新日期:2003-09-01 00:00:00

  • Jingzhaotoxin-II, a novel tarantula toxin preferentially targets rat cardiac sodium channel.

    abstract::Naturally occurring toxins are invaluable tools for exploration of the structure and function relationships of voltage-gated sodium channels (VGSCs). In this study, we isolated and characterized a novel VGSC toxin named jingzhaotoxin-II (JZTX-II) from the tarantula Chilobrachys jingzhao venom. JZTX-II consists of 32 a...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2008.09.008

    authors: Wang M,Liu Q,Luo H,Li J,Tang J,Xiao Y,Liang S

    更新日期:2008-12-15 00:00:00

  • Lipocortin 1 and the control of cPLA2 activity in A549 cells. Glucocorticoids block EGF stimulation of cPLA2 phosphorylation.

    abstract::Epidermal growth factor (EGF) rapidly stimulates the release of arachidonic acid in A549 cells by a mechanism that is sensitive to pertussis toxin [1]. We show that EGF treatment of A549 cells stimulates phosphorylation of cytosolic phospholipase A2 (cPLA2) through a mechanism that is similarly inhibited by pertussis ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(95)02442-5

    authors: Croxtall JD,Choudhury Q,Newman S,Flower RJ

    更新日期:1996-07-26 00:00:00

  • Antitumor 1-nitroacridine derivative C-1748, induces apoptosis, necrosis or senescence in human colon carcinoma HCT8 and HT29 cells.

    abstract::C-1748 is a DNA-binding agent with potent antitumor activity, especially towards prostate and colon carcinoma xenografts in mice. Here, we elucidated the nature of cellular response of human colon carcinoma HCT8 and HT29 cells to C-1748 treatment, at biologically relevant concentrations (EC(90) and their multiplicity)...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2009.12.012

    authors: Augustin E,Moś-Rompa A,Nowak-Ziatyk D,Konopa J

    更新日期:2010-05-01 00:00:00

  • Comparisons of ESR and HPLC methods for the detection of OH. radicals in ischemic/reperfused hearts. A relationship between the genesis of free radicals and reperfusion arrhythmias.

    abstract::In this study we compared two methods, electron spin resonance (ESR) spectroscopy and high performance liquid chromatography (HPLC), which are currently used to detect directly hydroxyl radical (OH.) formation in the ischemic and reperfused heart. Isolated buffer-perfused rat hearts were subjected to 30 min of normoth...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(93)90182-v

    authors: Tosaki A,Bagchi D,Pali T,Cordis GA,Das DK

    更新日期:1993-02-24 00:00:00

  • Activation of human leukemia protein kinase C by tumor promoters and its inhibition by N-trifluoroacetyladriamycin-14-valerate (AD 32).

    abstract::N-Trifluoroacetyladriamycin-14-valerate (AD 32), a lipophilic, DNA non-binding analog of Adriamycin (ADR), was found to be a potent inhibitor of the membrane-bound enzyme, protein kinase C (PKC). PKC was isolated and purified from human leukemia ML-1 cells, and the enzyme activity was shown to be activated by the tumo...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90254-g

    authors: Chuang LF,Kung HF,Israel M,Chuang RY

    更新日期:1992-02-18 00:00:00

  • Hydrolysis of ibuprofenoyl-CoA and other 2-APA-CoA esters by human acyl-CoA thioesterases-1 and -2 and their possible role in the chiral inversion of profens.

    abstract::Ibuprofen and related 2-arylpropanoic acid (2-APA) drugs are often given as a racemic mixture and the R-enantiomers undergo activation in vivo by metabolic chiral inversion. The chiral inversion pathway consists of conversion of the drug to the coenzyme A ester (by an acyl-CoA synthetase) followed by chiral inversion ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2013.08.067

    authors: Qu X,Allan A,Chui G,Hutchings TJ,Jiao P,Johnson L,Leung WY,Li PK,Steel GR,Thompson AS,Threadgill MD,Woodman TJ,Lloyd MD

    更新日期:2013-12-01 00:00:00

  • Sulfasalazine alters microglia phenotype by competing endogenous RNA effect of miR-136-5p and long non-coding RNA HOTAIR in cuprizone-induced demyelination.

    abstract::Sulfasalazine (SF) promotes remyelination and improves the outcome of multiple sclerosis (MS) patients. However, the underlining mechanism remains elusive. Here, we examined whether SF blocks microglia switching to a pro-inflammatory M1-like phenotype through a competing endogenous RNA (ceRNA) effects in cuprizone-ind...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2018.06.028

    authors: Duan C,Liu Y,Li Y,Chen H,Liu X,Chen X,Yue J,Zhou X,Yang J

    更新日期:2018-09-01 00:00:00

  • P2X7 receptor and the NLRP3 inflammasome: Partners in crime.

    abstract::Adenosine triphosphate (ATP) is a molecule that on one hand plays a central role in cellular energetics and which on the other is a ubiquitous signaling molecule when released into the extracellular media. Extracellular ATP accumulates in inflammatory environments where it acts as a damage-associated molecular pattern...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2020.114385

    authors: Pelegrin P

    更新日期:2020-12-20 00:00:00

  • Flt3 is a target of coumestrol in protecting against UVB-induced skin photoaging.

    abstract::While skin aging is a naturally occurring process by senescence, exposure to ultraviolet (UV) radiation accelerates wrinkle formation and sagging of skin. UV induces skin aging by degrading collagen via activating matrix metalloproteinases (MMPs). In this study, we show that coumestrol, a metabolite of the soybean iso...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2015.08.104

    authors: Park G,Baek S,Kim JE,Lim TG,Lee CC,Yang H,Kang YG,Park JS,Augustin M,Mrosek M,Lee CY,Dong Z,Huber R,Lee KW

    更新日期:2015-12-01 00:00:00

  • Correlation [corrected] of salinity with flavin-containing monooxygenase activity but not cytochrome P450 activity in the euryhaline fish (Platichthys flesus)

    abstract::To test the association between flavin-containing monooxygenases (FMOs) and osmoregulation, saltwater-adapted euryhaline flounder (Platichthys flesus) were statically exposed to 34 (ambient), 25, and 15 parts per thousand (/1000) salinity for 1 or 2 weeks. FMO activity (thiourea S-oxidase) was assayed in gill and live...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(96)00358-9

    authors: Schlenk D,Peters LD,Livingstone DR

    更新日期:1996-09-13 00:00:00

  • Dexamethasone and etoposide induce apoptosis in rat thymocytes from different phases of the cell cycle.

    abstract::Dexamethasone and etoposide both induce apoptosis in immature rat thymocytes. We investigated the dependence of apoptosis on the phase of the cell cycle after incubation with these drugs. Cell cycle progression was followed by a combination of pulse labelling with 5-bromo-2'-deoxyuridine (BrdU), labelling fixed cells ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(94)90142-2

    authors: Fearnhead HO,Chwalinski M,Snowden RT,Ormerod MG,Cohen GM

    更新日期:1994-09-15 00:00:00