The possible role of enantiodiscrimination in bilirubin toxicity.

Abstract:

: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.

journal_name

Chirality

journal_title

Chirality

authors

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

doi

10.1002/chir.20610

subject

Has Abstract

pub_date

2009-01-01 00:00:00

pages

87-91

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

21

pub_type

杂志文章
  • 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 ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.21017

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

    更新日期:2011-11-01 00:00:00

  • Experimental methods for measuring optical rotatory dispersion: survey and outlook.

    abstract::The measurement of optical rotation (OR) and optical rotatory dispersion has been finding renewed interest for some years, because of advancement in computational methods and in the performance of new experiments. Here, we shortly review the traditional and most-used experimental methods. We define and discuss the two...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.20981

    authors: Castiglioni E,Abbate S,Longhi G

    更新日期:2011-10-01 00:00:00

  • Chiroptical property tuning of supramolecular assemblies in polymer matrices.

    abstract::Chiroptical materials have received much attention in diverse fields for applications such as displays, sensors, smart memory devices, and catalysis. Here, we develop a simple fabrication method for polymer films with tunable chiroptical properties using small amounts of self-assembling fluorescent dye as an additive....

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23201

    authors: Jintoku H,Ihara H

    更新日期:2020-05-01 00:00:00

  • Deracemization of an axially chiral biphenylic derivative as a tool for investigating chiral recognition in self-assemblies.

    abstract::Two diastereomeric cationic surfactants derived from L-proline, in which the second chiral center is a quaternary nitrogen, have been separated and fully characterized. The recognition properties of the aggregates formed by the two diastereomeric surfactants have been investigated by circular dichroism and (1)H NMR th...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10230

    authors: Borocci S,Ceccacci F,Galantini L,Mancini G,Monti D,Scipioni A,Venanzi M

    更新日期:2003-05-15 00:00:00

  • Stereochemical analysis of β-keto sulfoxides by circular dichroism.

    abstract::Three β-keto sulfoxides (1-3) were synthesized in enantiopure form and investigated by means of circular dichroism (CD) spectroscopy, both in electronic and vibrational range (ECD, VCD), in combination with quantum chemical calculations. For compound 2, the X-ray structure was available; thus, the ECD in the solid sta...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22773

    authors: Górecki M,Capozzi MAM,Albano G,Cardellicchio C,Di Bari L,Pescitelli G

    更新日期:2018-01-01 00:00:00

  • Enantioselectivity in the steady-state pharmacokinetics and transplacental distribution of pindolol at delivery in pregnancy-induced hypertension.

    abstract::Nine patients taking oral doses of 10 mg/12 h rac-pindolol as part of their treatment for hypertension in pregnancy were recruited for the study. Maternal and fetal gestational age ranged from 20-38 years and 28-41 weeks, respectively. Blood was collected from the umbilical cord vein and from the mother from zero to 1...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10124

    authors: Gonçalves PV,Matthes Ado C,Da Cunha SP,Lanchote VL

    更新日期:2002-08-01 00:00:00

  • Enantioseparation of nine indanone and tetralone derivatives by HPLC using carboxymethyl-β-cyclodextrin as the mobile phase additive.

    abstract::High-performance liquid chromatography (HPLC) is a powerful method in the area of chiral separation. In this study, a method of HPLC using carboxymethyl-β-cyclodextrin (CM-β-CD) as chiral selector was developed for enantioseparation of nine indanone and tetralone derivatives. The separation was performed on a conventi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22665

    authors: Hu X,Guo X,Sun S,Zhu B,Yu J,Guo X

    更新日期:2017-01-01 00:00:00

  • Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism.

    abstract::Compound A, a novel disubstituted pyrrolidine acid, is a member of a new class of agents that are potentially useful for the treatment of diabetes and dyslipidemia. The absolute configuration of this compound was determined by using vibrational circular dichroism (VCD). The results are in agreement with the assignment...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20316

    authors: Freedman TB,Cao X,Phillips LM,Cheng PT,Dalterio R,Shu YZ,Zhang H,Zhao N,Shukla RB,Tymiak A,Gozo SK,Nafie LA,Gougoutas JZ

    更新日期:2006-09-01 00:00:00

  • Asymmetric Borane Reduction of Prochiral Ketones Catalyzed By Helical Poly[(S)-3-vinyl-2,2'-dihydroxy-1,1'-binaphthyl].

    abstract::The application of helical poly[(S)-3-vinyl-2,2'-dihydroxy-1, 1'-binaphthyl] (L*) in the asymmetric borane reduction of prochiral ketones was studied. The results showed that L* had excellent catalytic activity as well as enantioselectivity, giving up to 96% yield and up to 99% enantiomeric excess (ee) of the correspo...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22459

    authors: Qin G,Chen Y,Yang L,Yang N,Yang Z

    更新日期:2015-07-01 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:...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20187

    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

  • Programmed assembly of rigid-rod beta-barrel pores: thermal inversion of chirality.

    abstract::The programmed assembly of p-octiphenyl rods carrying six complementary tripeptide strands was studied in the presence of bilayer membranes using circular dichroism (CD) spectroscopy. Thermal CD experiments demonstrated programmed assembly of anionic and cationic rods into supramolecules at low temperature that irreve...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20034

    authors: Sakai N,Matile S

    更新日期:2004-01-01 00:00:00

  • N,N-dimethylcarbamyl derivatives of oxazepam.

    abstract::Three N,N-dimethylcarbamyl derivatives of oxazepam (1-(N,N-dimethylcarbamyl)oxazepam, 3-O-(N,N-dimethylcarbamyl)oxazepam, and 1,3-O-bis(N,N-dimethylcarbamyl) oxazepam) and a 3-O-acyl-1-(N,N-dimethylcarbamyl)-oxazepam were synthesized from either oxazepam or demoxepam. Enantiomeric pairs of these derivatives and of cam...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530030313

    authors: Yang SK,Lu XL

    更新日期:1991-01-01 00:00:00

  • Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative.

    abstract::Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dica...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20377

    authors: Schindler J,Egressy M,Bereczki L,Pokol G,Fogassy E,Marthi K

    更新日期:2007-03-01 00:00:00

  • Variable stereochemistry in highly branched isoprenoids from diatoms.

    abstract::C(25) highly branched isoprenoid (HBI) alkenes are ubiquitous lipids found in geochemical samples around the globe. The origins of these widespread geochemicals are believed to be restricted to a limited number of diatoms, including Haslea ostrearia (and related species), Rhizosolenia setigera, and Pleurosigma interme...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1053

    authors: Belt ST,Allard WG,Johns L,König WA,Massé G,Robert JM,Rowland S

    更新日期:2001-08-01 00:00:00

  • How do reaction conditions affect the enantiopure synthesis of 2-substituted-1,4-benzodioxane derivatives?

    abstract::Several biologically active compounds structurally include the enantiopure 2-substituted-1,4-benzodioxane scaffold. The straightforward racemization that affects reactions involving most of the common chemical reactives is thus a crucial issue. The developing of a completely stereo-controlled synthetic route that does...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22968

    authors: Straniero V,Casiraghi A,Fumagalli L,Valoti E

    更新日期:2018-07-01 00:00:00

  • Enantiospecific analysis of 8-prenylnaringenin in biological fluids by liquid-chromatography-electrospray ionization mass spectrometry: application to preclinical pharmacokinetic investigations.

    abstract::8-Prenylnaringenin (8PN) is a naturally occurring bioactive chiral prenylflavonoid found most commonly in the female flowers of hops (Humulus lupulus L.). A stereospecific method of analysis for 8PN in biological fluids is necessary to study the pharmacokinetic disposition of each enantiomer. A novel and simple liquid...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22343

    authors: Martinez SE,Lakowski TM,Davies NM

    更新日期:2014-08-01 00:00:00

  • From cosmic chirality to protein structure: Lord Kelvin's legacy.

    abstract::A selection of my work on chirality is sketched in two distinct parts of this lecture. Symmetry and Chirality explains how the discrete symmetries of parity P, time reversal T, and charge conjugation C may be used to characterize the properties of chiral systems. The concepts of true chirality (time-invariant enantiom...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22017

    authors: Barron LD

    更新日期:2012-11-01 00:00:00

  • Stereospecific pH-dependent degradation kinetics of R- and S-naproxen-beta-l-O-acyl-glucuronide.

    abstract::The hydrolysis and acyl migration of biosynthetic S-naproxen-beta-l-O-acyl glucuronide (I) and R-naproxen-beta-l-O-acyl glucuronide (II) was followed by HPLC. Nine first-order kinetic rate constants for the hydrolysis and acyl migration between the beta-l-O-acyl glucuronide, its alpha/beta-2, alpha/beta-3-, alpha/beta...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10047

    authors: Mortensen RW,Sidelmann UG,Tjørnelund J,Hansen SH

    更新日期:2002-05-05 00:00:00

  • Structural Features and Asymmetric Environment of i-Pr-SPRIX Ligand.

    abstract::Novel chiral diisopropyl spiro bis(isoxazoline) ligands, anti-i-Pr-SPRIX and syn-i-Pr-SPRIX, were designed and synthesized. Their catalytic utility, X-ray crystallographic analyses, and complexation studies demonstrated the structural features of tetraisopropyl spiro bis(isoxazoline) ligand, i-Pr-SPRIX, which is a pro...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22467

    authors: Takenaka K,Lin X,Takizawa S,Sasai H

    更新日期:2015-08-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2000)12:8<627::AID-CHIR5>3.0.CO;

    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

  • Stereoselective renal secretion of carbenicillin in rabbits: role of the organic anion transporter at the renal brush border membrane.

    abstract::Stereoselectivity in the renal secretion of carbenicillin (CBPC) was studied in rabbits. Significant renal secretion of CBPC was observed in vivo, with the secretion of the S-epimer being greater than that of the R-epimer. Stereoselective transport of CBPC was further studied in vitro using basolateral and brush borde...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1998)10:4<349::AID-CHIR10>

    authors: Itoh T,Nakaura H,Koyano S,Tsuda Y,Yamada H

    更新日期:1998-01-01 00:00:00

  • Chiral lumazines: preparation, properties, enantiomeric separation.

    abstract::Optically active lumazines (biolumazine, dictyolumazine, monalumazine, and neolumazine) are prepared from the corresponding pterins by enzymatic reaction, using pterin deaminase excreted by Dictyostelium discoideum. The fluorescence properties, circular dichroism spectra, and chromatographic behavior of these lumazine...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530060709

    authors: Klein R,Tatischeff I,Tham G,Mano N

    更新日期:1994-01-01 00:00:00

  • Base-catalyzed epimerization of the butenolide in annonaceous acetogenins.

    abstract::The elusive epimerization process in the chiral butenolide moiety of Annonaceous acetogenins was examined under several sets of conditions commonly used for elimination leading to the alpha, beta-unsaturated lactone and the results provide practical guidance in choosing elimination conditions. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:3<127::AID-CHIR4>3

    authors: Yu Q,Wu Y,Wu YL,Xia LJ,Tang MH

    更新日期:2000-03-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1036

    authors: Glówka FK,Strzelecka D,Zapalski S

    更新日期:2001-06-01 00:00:00

  • Unequivocal Enantiomeric Identification and Analysis of 10 Chiral Pesticides in Fruit and Vegetables by QuEChERS Method Combined With Liquid Chromatography-Quadruple/Linear Ion Trap Mass Spectrometry Determination.

    abstract::In this research, 10 chiral pesticides in fruits and vegetables were simultaneously determined using chiral liquid chromatography triple quadrupole-linear ion trap hybrid mass spectrometry (LC-QqLIT). The QuEChERS method was applied for sample preparation, and an enhanced product ion (EPI) scan was used to acquire tan...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22531

    authors: He Z,Peng Y,Wang L,Luo M,Liu X

    更新日期:2015-12-01 00:00:00

  • Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides.

    abstract::The biodegradation of the chiral phenoxyalkanoic herbicides 2-(2,4-dichlorophenoxy)propionic aid (2,4-DP) and 2-(4-chloro-2-methylphenoxy)propionic acid (MCPP) was investigated using enantioselective HPLC and chiroptical detection. Racemic mixtures of 2,4-DP and MCPP were applied to three species of turf grass, four s...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1999)11:4<330::AID-CHIR12>

    authors: Schneiderheinze JM,Armstrong DW,Berthod A

    更新日期:1999-01-01 00:00:00

  • Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity.

    abstract::Plants and fungi are seemingly inexhaustible sources of interesting natural products with remarkable structural and biological diversity. One of the most important groups is the terpenes, ubiquitous natural products that are generated by 2 now well-established biosynthetic pathways: the older mevalonate and the more r...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.23009

    authors: Reveglia P,Cimmino A,Masi M,Nocera P,Berova N,Ellestad G,Evidente A

    更新日期:2018-10-01 00:00:00

  • Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.

    abstract::Polymorphonuclear neutrophils (PMNs) are short-lived leukocytes that die by apoptosis. Although PMNs are crucial in the defense against infection, they have been implicated in the pathogenesis of tissue injury observed in inflammatory diseases. The induction or prevention of PMN apoptosis is currently discussed as a k...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20516

    authors: Zielińska-Przyjemska M,Główka FK,Klaczyńska J

    更新日期:2008-02-01 00:00:00

  • Applications of the Cartesian coordinate tensor transfer technique in the simulations of vibrational circular dichroism spectra of oligonucleotides.

    abstract::The application of the Cartesian coordinate tensor transfer (CCT) technique for simulations of the IR absorption and vibrational circular dichroism (VCD) spectra of relatively large nucleic acid fragments is demonstrated on several case studies. The approach is based on direct ab initio calculations of atomic tensors,...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.20872

    authors: Andrushchenko V,Bouř P

    更新日期:2010-01-01 00:00:00

  • Isothermal titration calorimetry for chiral chemistry.

    abstract::One of the most powerful techniques that are currently available to measure thermodynamic parameters such as enthalpy (ΔH), Gibbs free energy (ΔG), entropy changes (ΔS), and binding affinity in chemical reactions is isothermal titration calorimetry (ITC). Recent advances in instrumentation have facilitated the develop...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22842

    authors: Werber L,Mastai Y

    更新日期:2018-05-01 00:00:00