The possible role of enantiodiscrimination in bilirubin toxicity.


:The possibility that enantiodiscrimination of bilirubin might be involved in neuronal membrane destabilization, and therefore in bilirubin toxicity, was investigated, by circular dichroism, on model membranes composed of phospholipids. The equilibrium between bilirubin enantiomers is displaced at some extent by the interaction with certain phospholipids. The extent of equilibrium displacement depends on the molecular structure of phospholipids and on the state of charge of bilirubin. The results obtained validate the hypothesis of a possible involvement of chirality in bilirubin toxicity and support a previously suggested model for the molecular mechanism of the interaction of bilirubin with the synaptic membrane.






Bernardini C,D'Arrigo P,Elemento G,Mancini G,Servi S,Sorrenti A




Has Abstract


2009-01-01 00:00:00












  • Chiral recognition ability and solvent versatility of bonded amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase: enantioselective liquid chromatographic resolution of racemic N-alkylated barbiturates and thalidomide analogs.

    abstract::The chiral recognition ability and solvent versatility of a new chiral stationary phase containing amylose 3,5-dimethylphenylcarabamate immobilized onto silica gel (CHIRALPAK IA) is investigated. Thus, the direct enantioselective separation of a set of racemic N-alkylated barbiturates and 3-alkylated analogs of thalid...


    pub_type: 杂志文章


    authors: Ghanem A,Al-Humaidi E

    更新日期:2007-06-01 00:00:00

  • Asymmetric reduction of β-ketoesters and chiral β-iminoesters: impact of a α-quaternary stereocenter.

    abstract::Diastereomeric reduction of nonactivated, hindered β-keto and chiral β-iminoesters are described. The influence of a α-stereocontrolled center on the efficiency and stereoselectivity of the reduction was studied. Reaction conditions were optimized to synthesize β-hydroxy- and β-aminoesters in good yields. In the case ...


    pub_type: 杂志文章


    authors: Almahli H,Hendra F,Troufflard C,Cavé C,Joseph D,Delarue-Cochin S

    更新日期:2011-03-01 00:00:00

  • Ion channels as pharmacologic receptors: the chirality of drug interactions.

    abstract::Ion channels are pharmacologic receptors and as such exhibit stereoselective interactions with drugs. Ion channels are conformationally mobile transmembrane proteins existing in a number of open and closed states. Drug interactions with these different states may differ quantitatively and qualitatively. Stereoselectiv...


    pub_type: 杂志文章,评审


    authors: Triggle DJ

    更新日期:1996-01-01 00:00:00

  • Enantioselectivity of esterases in human brain.

    abstract::Subcellular fractions of three human brain specimens were found to contain esterase activities which hydrolyzed racemic oxazepam 3-acetate (rac-OXA). All three human brain preparations were highly selective toward the S-enantiomer of rac-OXA. ...


    pub_type: 杂志文章


    authors: Yang SK,Huang A,Huang JD

    更新日期:1993-01-01 00:00:00

  • Photo-ionization spectroscopy and mass spectrometry of some molecular and supramolecular asymmetric systems in the isolated state.

    abstract::Asymmetric molecular and supramolecular systems are characterized by: i. the circular dicroism in the angular distribution of valence photoelectrons emitted from randomly oriented chiral molecules by their interaction with circularly polarized VUV light; ii. the different stability and reactivity of diastereomeric agg...


    pub_type: 杂志文章


    authors: Giardini A,Paladini A,Catone D,Piccirillo S,Rondino F,Satta M,Filippi A,Speranza M,Turchini S,Zema N

    更新日期:2006-08-01 00:00:00

  • Screening Approach for Chiral Separation of β-Aminoketones by HPLC on Various Polysaccharide-Based Chiral Stationary Phases.

    abstract::Nine β-aminoketones were synthesized via Mannich reaction when benzaldehyde was condensed with some primary amines and acetophenone. The purified compounds were identified by using spectroscopic methods. The enantiomeric separation of these derivatives was carried out by high-performance liquid chromatography (HPLC) u...


    pub_type: 杂志文章


    authors: Addadi K,Sekkoum K,Belboukhari N,Cheriti A,Aboul-Enein HY

    更新日期:2015-05-01 00:00:00

  • A new definition of life.

    abstract::Chirality is often glossed over in theoretical or experimental discussions concerning the origin of life, but the ubiquity of homochiral building blocks in known biological systems demands explanation. Information theory can provide a quantitative framework for understanding the role of chirality in biology. Here I sh...


    pub_type: 杂志文章


    authors: Carroll JD

    更新日期:2009-03-01 00:00:00

  • Effect of serum lipoproteins on stereoselective halofantrine metabolism by rat hepatocytes.

    abstract::Experimental hyperlipidemia has shown to decrease cytochrome P450 3A4 and 2C11 expression and to increase liver concentrations and the plasma protein binding of halofantrine (HF) enantiomers. The present study examined the effect of hyperlipidemic (HL) serum on the metabolism of HF enantiomers by primary rat hepatocyt...


    pub_type: 杂志文章


    authors: Patel JP,Hamdy DA,El-Kadi AO,Brocks DR

    更新日期:2012-07-01 00:00:00

  • Comparison of mid-infrared Fourier transform vibrational circular dichroism measurements with single and dual polarization modulations.

    abstract::Fourier transform infrared vibrational circular dichroism (FTIR-VCD) measurements have gone through major advances in the last decade. A major thrust in these advances was to find ways that can minimize the VCD spectral artifacts and obtain the VCD signals at enhanced signal quality. However, all these advances are no...


    pub_type: 杂志文章


    authors: Polavarapu PL,Shanmugam G

    更新日期:2011-10-01 00:00:00

  • Organocatalytic aza-Michael/retro-aza-Michael reaction: pronounced chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction.

    abstract::A detailed experimental investigation of an aza-Michael reaction of aniline and chalcone is presented. A series of Cinchona alkaloid-derived organocatalysts with different functional groups were prepared and used in the aza-Michael and retro-aza-Michael reaction. There was an interesting finding that a complete revers...


    pub_type: 杂志文章


    authors: Cai YF,Li L,Luo MX,Yang KF,Lai GQ,Jiang JX,Xu LW

    更新日期:2011-05-01 00:00:00

  • Enantioseparation and determination of flumequine enantiomers in multiple food matrices with chiral liquid chromatography coupled with tandem mass spectrometry.

    abstract::The present work firstly described the enantioseparation and determination of flumequine enantiomers in milk, yogurt, chicken, beef, egg, and honey samples by chiral liquid chromatography-tandem mass spectrometry. The enantioseparation was performed under reversed-phase conditions on a Chiralpak IC column at 20°C. The...


    pub_type: 杂志文章


    authors: Li S,Liu B,Xue M,Yu J,Guo X

    更新日期:2019-11-01 00:00:00

  • Simulated moving columns technique for enantioselective supercritical fluid chromatography.

    abstract::This article describes a very useful extension of an unique column switching technique called "Simulated Moving Columns" (SMC) that was previously reported for chiral high performance liquid chromatography (HPLC) (Zhang and McConnell, Journal of Chromatography A 2004;1028:227-238). SMC uses two or three short chiral c...


    pub_type: 杂志文章


    authors: Zhang Y,Dai J,Wang-Iverson DB,Tymiak AA

    更新日期:2007-09-01 00:00:00

  • Pharmacologic implications of alpha-adrenoreceptor interactive parameters for epinephrine enantiomers in the rat vas deferens.

    abstract::After alkylation of a fraction of the total alpha-adrenoreceptors by phenoxybenzamine in rat vas deferens, the dissociation constants of (-)- and (+)-epinephrine in functional studies were 7 X 10(-7) M and 2 X 10(-5) M, respectively. In the adrenoreceptor-containing tissue fraction, when 3H-labeled WB4101 was used as ...


    pub_type: 杂志文章


    authors: Rice PJ,Miller DD,Sokoloski TD,Patil PN

    更新日期:1989-01-01 00:00:00

  • Synthesis of molecularly imprinted polymers using a functionalized initiator for chiral-selective recognition of propranolol.

    abstract::We present a new concept of synthesis for preparation of molecularly imprinted polymers using a functionalized initiator to replace the traditional functional monomer. Using propranolol as a model template, a carboxyl-functionalized radical initiator was demonstrated to lead to high-selectivity polymer particles prepa...


    pub_type: 杂志文章


    authors: Liu W,Holdsworth C,Ye L

    更新日期:2020-03-01 00:00:00

  • Conformational spaces of Cinchona alkaloids.

    abstract::A systematic and comprehensive study of the conformational spaces of the Cinchona alkaloids quinine, quinidine, cinchonine, cinchonidine, epiquinine, epiquinidine, epicinchonine, and epicinchonidine using the semiempirical PM3 method is described. The results were analyzed in terms of syn/anti and open/closed/hindered...


    pub_type: 杂志文章


    authors: Caner H,Biedermann PU,Agranat I

    更新日期:2003-08-01 00:00:00

  • Asymmetric aldol reactions catalyzed by efficient and recyclable silica-supported proline-based peptides.

    abstract::A series of silica-supported proline-based peptides were synthesized and applied as catalysts for direct asymmetric intermolecular aldol reactions. Among these, a peptide with two L-proline units was found to be the most efficient one for the asymmetric aldol reactions between acetone and aromatic aldehydes. The react...


    pub_type: 杂志文章


    authors: Yan J,Wang L

    更新日期:2009-04-01 00:00:00

  • Spectroscopic properties of the nonplanar amide group: a computational study.

    abstract::Experimental studies suggest that amide bond may significantly deviate from planar arrangement even in linear peptides and proteins. In order to find out the extent to which such deviation may influence principal amide spectroscopic properties, we conducted a computational study of nonplanar N-methylacetamide (NMA) co...


    pub_type: 杂志文章


    authors: Bednárová L,Malon P,Bour P

    更新日期:2007-11-01 00:00:00

  • Structure and unexpected chiroptical properties of chiral 4-pyrrolidinyl substituted 2(5H)-furanones.

    abstract::Planar 2(5H)-furanones substituted at C4 with a chiral pyrrolidinyl group show CD spectra which are apparently due to the distortion of the C4-N1 bond of sp2 character from the plane defined by the 2(5H)-furanone ring atoms and/or due to the presence of substituents in the pyrrolidine ring. This is a new, previously n...


    pub_type: 杂志文章


    authors: Gawroński J,Gawrońska K,Kwit M,Kacprzak K,Rychlewska U

    更新日期:2004-08-01 00:00:00

  • Steady-state pharmacokinetics of indobufen enantiomers in patients with obliterative atherosclerosis.

    abstract::Steady-state pharmacokinetics of indobufen (INDB) enantiomers administered as racemic INDB (rac-INDB) tablets and bleeding time were studied in patients. Two-hundred mg INDB tablets (Ibustrin) were administered twice daily for 7 days to obliterative atherosclerosis patients. Enantiospecific reversed phase (RP) HPLC wi...


    pub_type: 杂志文章


    authors: Glówka FK,Strzelecka D,Zapalski S

    更新日期:2001-06-01 00:00:00

  • A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes.

    abstract::Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the ...


    pub_type: 杂志文章


    authors: Liu CL,Wei CY,Wang SW,Peng YG

    更新日期:2011-11-01 00:00:00

  • Enantiomeric resolution and modeling of DL-alanine-DL-tryptophan dipeptide on amylose stationary phase.

    abstract::The enantiomeric resolution of DL-alanine-DL-tryptophan dipeptide is described on amylose stationary phase. The eluent used was CH3 OH─CH3 COONH4 (10mM)─CH3 CN (50: 40, 10) at 0.8-mL/min flow, 230-nm detection, 25-minute run time, and 25°C ± 1°C temperature. The chiral phase was amylose [AmyCoat RP (15 cm × 0.46 cm × ...


    pub_type: 杂志文章


    authors: Ali I,Khattab RA,Alothman ZA,Badjah AY,Alwarthan A

    更新日期:2018-04-01 00:00:00

  • Enantioselective degradation of warfarin in soils.

    abstract::Environmental enantioselectivity information is important to fate assessment of chiral contaminants. Warfarin, a rodenticide and prescription medicine, is a chiral chemical but used in racemic form. Little is known about its enantioselective behavior in the environment. In this study, enantioselective degradation of w...


    pub_type: 杂志文章


    authors: Lao W,Gan J

    更新日期:2012-01-01 00:00:00

  • Use of the exciton chirality method in the investigation of ligand-gated synthetic ion channels.

    abstract::The objective of this brief highlight is to point out the central role of the exciton chirality method to gain insights on the structural basis of the recently achieved ligand gating of synthetic ion channels. This unprecedented ligand gating was achieved with an equally unprecedented transmembrane rigid-rod pi-stack ...


    pub_type: 杂志文章


    authors: Sakai N,Talukdar P,Matile S

    更新日期:2006-02-01 00:00:00

  • Enantiomer self-disproportionation and chiral stationary phase based selective chiral separation of organic compounds.

    abstract::In modern chromatography, chiral stationary phase (CSP) and enantiomer self-disproportionation (ESD) are new inventions of packing material offer a guarantee for a successful enantiomeric separation. All CSPs were synthesized by chemical bonding of the relevant organic moieties onto a porous parent silica material for...


    pub_type: 杂志文章


    authors: Mayani VJ,Abdi SH,Mayani SV,Kim HC,Park SK

    更新日期:2011-04-01 00:00:00

  • Synthesis, resolution, and chiroptical properties of hemicryptophane cage controlling the chirality of propeller arrangement of a C3 triamide unit.

    abstract::The five-steps synthesis of a hemicryptophane cage combining a benzene-1,3,5-tricarboxamide unit and a cyclotriveratrylene (CTV) moiety is described. Chiral high-performance liquid chromatography (HPLC) was used to resolve the racemic mixture. The absolute configuration of the isolated enantiomers was assigned by comp...


    pub_type: 杂志文章


    authors: Long A,Jean M,Albalat M,Vanthuyne N,Giorgi M,Górecki M,Dutasta JP,Martinez A

    更新日期:2019-11-01 00:00:00

  • Gas chromatographic separation of saturated aliphatic hydrocarbon enantiomers on permethylated beta-cyclodextrin.

    abstract::Enantiomers of chiral aliphatic hydrocarbons are generally difficult to separate because they lack functional groups to be derivatized in order to generate diastereomers. The systematic and quantitative separation of a series of branched hydrocarbon enantiomers using a chiral cyclodextrin stationary phase and a cryost...


    pub_type: 杂志文章


    authors: Meierhenrich UJ,Nguyen MJ,Barbier B,Brack A,Thiemann WH

    更新日期:2003-01-01 00:00:00

  • Separation of amino acid enantiomers by micelle-enhanced ultrafiltration.

    abstract::A Micelle-enhanced ultrafiltration (MEUF) separation process was investigated that can potentially be used for large-scale enantioseparations. Copper(II)-amino acid derivatives dissolved in nonionic surfactant micelles were used as chiral selectors for the separation of dilute racemic amino acids solutions. For the al...


    pub_type: 杂志文章


    authors: De Bruin TJ,Marcelis AT,Zuilhof H,Rodenburg LM,Niederländer HA,Koudijs A,Overdevest PE,Van der Padt A,Sudhölter EJ

    更新日期:2000-08-01 00:00:00

  • Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivatives.

    abstract::The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled (31)P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:...


    pub_type: 杂志文章


    authors: Bui TT,Coles SJ,Davies DB,Drake AF,Eaton RJ,Hursthouse MB,Kiliç A,Shaw RA,Yeşilot S

    更新日期:2005-10-01 00:00:00

  • Synthesis of Novel Chiral Sulfonamide-Bearing 1,2,4-Triazole-3-thione Analogs Derived from D- and L-Phenylalanine Esters as Potential Anti-Influenza Agents.

    abstract::Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR...


    pub_type: 杂志文章


    authors: Başaran E,Karaküçük-Iyidoğan A,Schols D,Oruç-Emre EE

    更新日期:2016-06-01 00:00:00

  • Short step enantioselective synthesis of (-)-swainsonine.

    abstract::Recent discovery of asymmetric desymmetrization of meso-heterocycles using (R,R)-(salen)manganese complex 2 as a catalyst allowed easy access to optically active 2,3,4-trisubstituted pyrrolidines. Taking advantage of this new reaction, we could achieve the short-step synthesis of (-)-swainsonine 1. ...


    pub_type: 杂志文章


    authors: Punniyamurthy T,Irie R,Katsuki T

    更新日期:2000-06-01 00:00:00