On the nature of the irreversible inhibition of histidine ammonia lyase by cysteine and dioxygen.

Abstract:

:The irreversible inhibition of histidine ammonia lyase by L-cysteine and dioxygen has been reexamined. After denaturation and consecutive digestion of the inhibited enzyme by trypsin and endoproteinase Glu-C, the generated chromophoric system (lambda max = 340 nm) remained intact and was isolated in an octapeptide containing amino acids 138-145, as previously described (Hernandez, D.; Stroh, J.G.; Phillips, A. T. Arch. Biochem. Biophys. 1993, 307, 126). Conducting the inhibition in the presence of 18O2 did not result in the incorporation of the heavy isotope into the isolated octapeptide. Total hydrolysis followed by amino acid analysis of the octapeptide revealed the presence of one arginine in addition to those expected from the deduced sequence (G3SVAD). 1H NMR spectroscopy of the octapeptide confirmed the presence of the amino acids GSVAD and showed no signals for olefinic or aromatic protons. To account for the excess mass of the octapeptide, we propose an oxidative degradation of the dehydroalanine prosthetic group, followed by reaction of the resulting dicarbonyl system with a nearby arginine residue.

journal_name

Bioorg Med Chem

authors

Weber K,Rétey J

doi

10.1016/0968-0896(96)00091-0

subject

Has Abstract

pub_date

1996-07-01 00:00:00

pages

1001-6

issue

7

eissn

0968-0896

issn

1464-3391

pii

0968089696000910

journal_volume

4

pub_type

杂志文章
  • Evaluation of histone deacetylase inhibitors (HDACi) as therapeutic leads for human African trypanosomiasis (HAT).

    abstract::Two of the histone deacetylases, TbDAC1 and TbDAC3, have been reported to be essential genes in trypanosomes. Therefore, we tested the activity of a panel of human histone deacetylase inhibitors (HDACi) for their ability to block proliferation of Trypanosoma brucei brucei. Among the HDACi's, the hydroxamic acid deriva...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.12.066

    authors: Carrillo AK,Guiguemde WA,Guy RK

    更新日期:2015-08-15 00:00:00

  • Isolation and characterization of a monoamine oxidase B selective inhibitor from tobacco smoke.

    abstract::It is well established that tobacco smokers have reduced levels of monoamine oxidase activities both in the brain and peripheral organs. Furthermore, extensive evidence suggests that smokers are less prone to develop Parkinson's disease. These facts, plus the observation that inhibition of monoamine oxidase B protects...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.12.057

    authors: Khalil AA,Davies B,Castagnoli N Jr

    更新日期:2006-05-15 00:00:00

  • Synthesis, stability and in vitro dermal evaluation of aminocarbonyloxymethyl esters as prodrugs of carboxylic acid agents.

    abstract::Aminocarbonyloxymethyl esters based on (S)-amino acid carriers were synthesised and evaluated as potential prodrugs of carboxylic acid agents. In addition, the compounds were evaluated as topical prodrugs with the aim of improving the dermal delivery of two non-steroidal anti-inflammatory agents: naproxen and flufenam...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00336-4

    authors: Mendes E,Furtado T,Neres J,Iley J,Jarvinen T,Rautio J,Moreira R

    更新日期:2002-03-01 00:00:00

  • Synthesis and characterization of modified nucleotides in the 970 hairpin loop of Escherichia coli 16S ribosomal RNA.

    abstract::The synthesis of the 6-O-DPC-2-N-methylguanosine (m(2)G) nucleoside and the corresponding 5'-O-DMT-2'-O-TOM-protected 6-O-DPC-2-N-methylguanosine phosphoramidite is reported [DPC, diphenyl carbamoyl; DMT, 4,4'-dimethoxytrityl; TOM, [(triisopropylsilyl)oxy]methyl]. The availability of the phosphoramidite allows for syn...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.07.008

    authors: Abeydeera ND,Chow CS

    更新日期:2009-08-15 00:00:00

  • Discovery of novel 4-(2-fluorophenoxy)quinoline derivatives bearing 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety as c-Met kinase inhibitors.

    abstract::A series of novel 4-(2-fluorophenoxy)quinoline derivatives containing 4-oxo-1,4-dihydrocinnoline-3-carboxamide moiety were designed, synthesized and evaluated for their in vitro biological activities against c-Met kinase and six typical cancer cell lines (A549, H460, HT-29, MKN-45, U87MG and SMMC-7721). All the prepar...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.04.013

    authors: Li S,Zhao Y,Wang K,Gao Y,Han J,Cui B,Gong P

    更新日期:2013-06-01 00:00:00

  • Direct PCR amplification of various modified DNAs having amino acids: convenient preparation of DNA libraries with high-potential activities for in vitro selection.

    abstract::We synthesized modified 2'-deoxyuridine triphosphates bearing amino acids at the C5 position and investigated their substrate properties for KOD Dash DNA polymerase during polymerase chain reaction (PCR). PCR using C5-modified dUTP having an amino acyl group (arginyl, histidyl, lysyl, phenylalanyl, tryptophanyl, leucy...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.11.030

    authors: Kuwahara M,Hanawa K,Ohsawa K,Kitagata R,Ozaki H,Sawai H

    更新日期:2006-04-15 00:00:00

  • Switchable MRI contrast agents based on morphological changes of pH-responsive polymers.

    abstract::Magnetic resonance imaging (MRI) contrast agents are effective tools in both medical diagnosis and life science research. Various smart contrast agents have been developed for the visualization of biological phenomena. These contrast agents have molecular switches that increase or reduce MRI signal intensity in respon...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.005

    authors: Okada S,Mizukami S,Kikuchi K

    更新日期:2012-01-15 00:00:00

  • Synthesis and antitumor activity of 20-O-linked nitrogen-based camptothecin ester derivatives.

    abstract::A series of nitrogen-based 20S-hydroxyl camptothecin ester derivatives were prepared. 3-Aminopropionate of camptothecin was found more cytotoxic in vitro on several human tumor cell lines than 3-amidopropionate of camptothecin. Ester 16 showed best antitumor activity in vivo and in vitro in all esters we prepared. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.04.023

    authors: Wang CY,Pan XD,Liu HY,Fu ZD,Wei XY,Yang LX

    更新日期:2004-07-01 00:00:00

  • Synthesis, structural investigations and biological evaluation of novel hexahydropyridazine-1-carboximidamides, -carbothioamides and -carbothioimidic acid esters as inducible nitric oxide synthase inhibitors.

    abstract::Local excess of nitric oxide (NO) has been implicated in beta-cell damage, thus, a possible approach to the treatment of autoimmune IDDM is the selective inhibition of inducible nitric oxide synthase (iNOS). A series of variously substituted hexahydropyridazine-1-carbothioamides, -carbothioimidic acid esters and -carb...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2003.12.007

    authors: Morgenstern O,Wanka H,Röser I,Steveling A,Kuttler B

    更新日期:2004-03-01 00:00:00

  • New potent antibacterials against Gram-positive multiresistant pathogens: effects of side chain modification and chirality in linezolid-like 1,2,4-oxadiazoles.

    abstract::The effects of side chain modification and chirality in linezolid-like 1,2,4-oxadiazoles have been studied to design new potent antibacterials against Gram-positive multidrug-resistant pathogens. The adopted strategy involved a molecular modelling approach, the synthesis and biological evaluation of new designed compo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.10.037

    authors: Fortuna CG,Berardozzi R,Bonaccorso C,Caltabiano G,Di Bari L,Goracci L,Guarcello A,Pace A,Palumbo Piccionello A,Pescitelli G,Pierro P,Lonati E,Bulbarelli A,Cocuzza CE,Musumarra G,Musumeci R

    更新日期:2014-12-15 00:00:00

  • Ratiometric nanoprobe for circulating tumor cell detection and intracellular hydrogen peroxide evaluation in colorectal cancer patients.

    abstract::The application of intensity-based H2O2-responsive fluorescence nanoprobe for circulating tumor cell detection was limited by the complex background and the nanoprobe uptake in each CTC. In this context, we developed a ratiometric fluorescence nanoprobe, on which a H2O2-responsive subunit and a stable subunit grafted ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115930

    authors: Pan R,Lu X,Ju J,Guan Q,Su Y,Li C,Li P

    更新日期:2021-01-15 00:00:00

  • Crop plants versus energy plants--on the international food crisis.

    abstract::The recent price explosion of important agricultural commodities has lead to an international food crisis. The price rise is attributed to fundamental factors, such as the rising demand for dairy and meat products in China and the development of the bioenergy branch as well as on short-term factors such as the behavio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.11.041

    authors: Schmitz PM,Kavallari A

    更新日期:2009-06-15 00:00:00

  • Mechanism of influence of phosphorylation on serine 124 on a decrease of catalytic activity of human thymidylate synthase.

    abstract::Regulation by phosphorylation is a well-established mechanism for controlling biological activity of proteins. Recently, phosphorylation of serine 124 in human thymidylate synthase (hTS) has been shown to lower the catalytic activity of the enzyme. To clarify a possible mechanism of the observed influence, molecular d...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.04.019

    authors: Jarmuła A,Fraczyk T,Cieplak P,Rode W

    更新日期:2010-05-15 00:00:00

  • The discovery of UK-369003, a novel PDE5 inhibitor with the potential for oral bioavailability and dose-proportional pharmacokinetics.

    abstract::This paper describes our recent efforts to design and synthesise potent and selective PDE5 inhibitors and the use of in vitro predictors of clearance, absorption and permeability to maximise the potential for dose-proportional pharmacokinetics and good oral bioavailability in man. Optimisation of the preclinical profi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.10.022

    authors: Rawson DJ,Ballard S,Barber C,Barker L,Beaumont K,Bunnage M,Cole S,Corless M,Denton S,Ellis D,Floc'h M,Foster L,Gosset J,Holmwood F,Lane C,Leahy D,Mathias J,Maw G,Million W,Poinsard C,Price J,Russel R,Street S

    更新日期:2012-01-01 00:00:00

  • Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors.

    abstract::A series of 1,2,3-triazolylsalicylamide derivatives has been developed from the antiproliferative agent 7 and was evaluated for their Aurora kinase inhibitory activity. The novel 1,2,3-triazolylsalicylamide scaffold could be readily assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition, allowing rapid ac...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.06.047

    authors: Song D,Park Y,Yoon J,Aman W,Hah JM,Ryu JS

    更新日期:2014-09-01 00:00:00

  • Synthesis, biological activity and docking study of imidazol-5-one as novel non-nucleoside HIV-1 reverse transcriptase inhibitors.

    abstract::A novel series of substituted imidazol-5-ones were designed, synthesized and evaluated for in vitro reverse transcriptase (RT) inhibition activity using reverse transcriptase assay kit (Roche, Colorimetric). It has been observed from in vitro screening that newly synthesized compounds possess RT inhibitory activity. D...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.02.037

    authors: Mokale SN,Lokwani D,Shinde DB

    更新日期:2012-05-01 00:00:00

  • Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines.

    abstract::A series of aryloxypropanolamines (5a-r) of different chalcones (3a-e) were synthesized and evaluated for antihyperglycemic activity in sucrose loaded (SLM) and streptozotocin (STZ) induced diabetic animal models. Among them compounds 5a, g, m, o, p and r showed significant reduction in blood glucose levels in both SL...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2003.12.026

    authors: Satyanarayana M,Tiwari P,Tripathi BK,Srivastava AK,Pratap R

    更新日期:2004-03-01 00:00:00

  • Novel steroidal vinyl fluorides as inhibitors of steroid C17(20) lyase.

    abstract::20-fluoro-17(20)-pregnenolone derivatives were designed as enol mimics of pregnenolone. All of the targeted, novel fluoroolefins were potent inhibitors of C17(20) lyase. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00354-6

    authors: Burkhart JP,Weintraub PM,Gates CA,Resvick RJ,Vaz RJ,Friedrich D,Angelastro MR,Bey P,Peet NP

    更新日期:2002-04-01 00:00:00

  • Assessing the physiological relevance of alternate architectures of the p7 protein of hepatitis C virus in different environments.

    abstract::The viroporin p7 of the hepatitis C virus forms multimeric channels eligible for ion transport across the endoplasmic reticulum membrane. Currently the subject of many studies and discussion, the molecular assembly of the ion channel and the structural characteristics of the p7 monomer are not yet fully understood. St...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.07.063

    authors: Holzmann N,Chipot C,Penin F,Dehez F

    更新日期:2016-10-15 00:00:00

  • Multi-receptor drug design: Haloperidol as a scaffold for the design and synthesis of atypical antipsychotic agents.

    abstract::Using haloperidol as a scaffold, new agents were designed to investigate the structural contributions of various groups to binding at CNS receptors associated with atypical antipsychotic pharmacology. It is clear that each pharmacophoric group, the butyrophenone, the piperidine and the 4-chlorophenyl moieties contribu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.019

    authors: Peprah K,Zhu XY,Eyunni SV,Setola V,Roth BL,Ablordeppey SY

    更新日期:2012-02-01 00:00:00

  • Chemical and microbial semi-synthesis of tetrahydroprotoberberines as inhibitors on tissue factor procoagulant activity.

    abstract::To discover new inhibitors on tissue factor procoagulant activity, 21 tetrahydroprotoberberines were screened on the model of human THP-1 cells stimulated by lipopolysaccharide. Among these tetrahydroprotoberberines, several unique compounds were synthesized through microbial transformation: compound 6 (l-corydalmine)...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.11.002

    authors: Ge HX,Zhang J,Chen L,Kou JP,Yu BY

    更新日期:2013-01-01 00:00:00

  • Phenylhydrazides as inhibitors of Leishmania amazonensis arginase and antileishmanial activity.

    abstract::Searching for new substances with antileishmanial activity, we synthesized and evaluated a series of α,α-difluorohydrazide and α,α-difluoramides against Leishmania amazonensis arginase (LaArg). Four α,α-difluorohydrazide derivatives showed activity against LaArg with Ki in the range of 1.3-26 μM. The study of the kine...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.07.022

    authors: Crizanto de Lima E,Castelo-Branco FS,Maquiaveli CC,Farias AB,Rennó MN,Boechat N,Silva ER

    更新日期:2019-09-01 00:00:00

  • Simple molecular engineering of glycol nucleic acid: progression from self-pairing to cross-pairing with cDNA and RNA.

    abstract::The acyclic chiral nucleic acid analogue, Glycol Nucleic Acid (GNA), displayed exceptional structural simplicity and atom economy while forming self-paired duplexes, using canonical Watson-Crick base pairing. We disclose here that the replacement of phosphodiester linker in GNA with somewhat rigid and shorter carbamat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.022

    authors: Bose T,Kumar VA

    更新日期:2014-11-01 00:00:00

  • A quantitative structure-activity relationship study on some HIV-1 protease inhibitors using molecular connectivity index.

    abstract::A quantitative structure-activity relationship (QSAR) study has been made on two different series of tetrahydropyrimidinones acting as HIV-1 protease inhibitors. A structural parameter, the first order valence molecular connectivity index ((1)chi(v)), has been used to account for the variation in the activity. The pro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00210-3

    authors: Gayathri P,Pande V,Sivakumar R,Gupta SP

    更新日期:2001-11-01 00:00:00

  • 2-O-substituted cyclodextrins as reversal agents for the neuromuscular blocker rocuronium bromide.

    abstract::A series of secondary face modified cyclodextrins (CDs) were synthesised with the aim of constructing host molecules capable of forming host-guest complexes with neuromuscular blockers, especially with rocuronium bromide. Perfacial 2-O-substitution of gamma-CD with 4-carboxybenzyl resulted in a CD host molecule 1 that...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00026-3

    authors: Tarver GJ,Grove SJ,Buchanan K,Bom A,Cooke A,Rutherford SJ,Zhang MQ

    更新日期:2002-06-01 00:00:00

  • Synthesis and biological evaluation of di-aryl urea derivatives as c-Kit inhibitors.

    abstract::Inhibition of receptor tyrosine kinases (RTKs) continued to be a successful approach for the treatment of many types of human cancers and many potent small molecules kinase inhibitors have been discovered the last decade. In the present study, we describe the synthesis of thienopyrimidine derivatives and their pharmac...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.10.035

    authors: Ravez S,Arsenlis S,Barczyk A,Dupont A,Frédérick R,Hesse S,Kirsch G,Depreux P,Goossens L

    更新日期:2015-11-15 00:00:00

  • Discovery of novel phenoxazinone derivatives as DKK1/LRP6 interaction inhibitors: Synthesis, biological evaluation and structure-activity relationships.

    abstract::Amino derivatives of NCI8642 were synthesized and evaluated as inhibitors of DKK1/LRP6 interactions. The new inhibitors were able to activate the Wnt signaling pathway as indicated by the increased levels of β-catenin, and decrease the DKK1-induced Tau phosphorylation at serine 396. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.01.025

    authors: Thysiadis S,Mpousis S,Avramidis N,Katsamakas S,Balomenos A,Remelli R,Efthimiopoulos S,Sarli V

    更新日期:2016-03-01 00:00:00

  • Expanding the recognition of the minor groove of DNA by incorporation of beta-alanine in hairpin polyamides.

    abstract::In order to expand the recognition code by hairpin polyamides to include DNA sequences of the type 5'-CWWC-3' two polyamides, PyPyPyPy-(R)(H2N)gamma-ImPyPyIm-beta-Dp (1) and PyPyPyPy-(R)(H2N)gamma-ImPy-beta-Im-beta-Dp (2) were synthesized which have in common an Py/Im pair in the terminal position for targeting C x G ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00282-0

    authors: Wang CC,Ellervik U,Dervan PB

    更新日期:2001-03-01 00:00:00

  • 2-Phenylimidazo[2,1-i]purin-5-ones: structure-activity relationships and characterization of potent and selective inverse agonists at Human A3 adenosine receptors.

    abstract::Structure-activity relationships of 2-phenyl-imidazo[2,1-i]purin-5-ones as ligands for human A(3) adenosine receptors (ARs) were investigated. An ethyl group in the 8-position of the imidazoline ring of 4-methyl-2-phenyl-imidazopurinone leading to chiral compounds was found to increase affinity for human A(3) ARs by s...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00456-x

    authors: Ozola V,Thorand M,Diekmann M,Qurishi R,Schumacher B,Jacobson KA,Müller CE

    更新日期:2003-02-06 00:00:00

  • Chemical studies on antioxidant mechanism of tea catechins: analysis of radical reaction products of catechin and epicatechin with 2,2-diphenyl-1-picrylhydrazyl.

    abstract::Tea catechins, an important class of polyphenols, have been shown to have wide spectrum of antitumor activity believed to be due mainly to their antioxidative effect. In this study, the radical scavenging behavior of catechins on 2,2-diphenyl-1-picrylhydrazyl (DPPH) was studied. Two reaction products of (+)-catechin, ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00089-5

    authors: Sang S,Cheng X,Stark RE,Rosen RT,Yang CS,Ho CT

    更新日期:2002-07-01 00:00:00