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 border membrane vesicles prepared from rabbit kidneys. The transport of CBPC by the organic anion transporter into the basolateral membrane vesicles (BLMV) was not stereoselective. In contrast, a distinct stereoselectivity was observed in the transport of CBPC by the organic anion transporter into the brush border membrane vesicles (BBMV), with the transport of the S-epimer being more favorable. Significant epimer-epimer interactions were also observed in the transport into BBMV. The stereoselectivity of the transport of CBPC was calculated from the kinetic parameters with consideration of epimer-epimer interactions and was similar to that observed in vivo. It was concluded that the observed stereoselectivity in the renal secretion of CBPC in vivo reflected that of transport via the organic anion transporter located at the brush border membrane.

journal_name

Chirality

journal_title

Chirality

authors

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

doi

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

subject

Has Abstract

pub_date

1998-01-01 00:00:00

pages

349-57

issue

4

eissn

0899-0042

issn

1520-636X

pii

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

journal_volume

10

pub_type

杂志文章
  • Chiral aggregates and asymmetric induction of the reduction of prochiral ketones.

    abstract::The aim of this work was to establish structure-reactivity relationships between chiral aggregates (micelles, vesicles, and "pseudo-micelles" of amphiphilic dendrimers) and asymmetric induction. In water, micelles or vesicles formed with sugar-headed surfactants gave less than 10% ee in the reduction of prochiral keto...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2001)13:1<24::AID-CHIR5>3.0.CO;2

    authors: Rico-Lattes I I,Schmitzer A,Perez E,Lattes A

    更新日期:2001-01-01 00:00:00

  • High-performance liquid chromatographic enantioseparation of Betti base analogs on a newly developed isopropyl carbamate-cyclofructan6-based chiral stationary phase.

    abstract::The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1-naphthol analogs, and 2-(1-amino-2-methylpropyl)-1-naphthol) was performed on a newly developed chiral stationary phase containing isopropyl carbamate-cyclofructan6 as chiral selector, wit...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20968

    authors: Aranyi A,Ilisz I,Pataj Z,Szatmári I,Fülöp F,Armstrong DW,Péter A

    更新日期:2011-08-01 00:00:00

  • Chiroptical properties of diamino carboxylic acids.

    abstract::Diamino carboxylic acids have recently come to the attention of scientists working in the field of early life and its development. These are the monomers of a hypothetic early form of genetic material, the so-called Peptide Nucleic Acid (PNA) (Nielson et al., Proc Natl Acad Sci USA 2000;97:3868-3871). Since all biopol...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20422

    authors: Bredehöft JH,Breme K,Meierhenrich UJ,Hoffmann SV,Thiemann WH

    更新日期:2007-07-01 00:00:00

  • Enantiopurity determination of the enantiomers of the triple reuptake inhibitor indatraline.

    abstract::The present study describes the development of two approaches for the determination of the enantiopurity of both enantiomers of indatraline. Initially, a method was developed using different chiral solvating agents (CSAs) for diastereomeric discrimination regarding signal separation in (1)H nuclear magnetic resonance ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22235

    authors: Grimm SH,Allmendinger L,Höfner G,Wanner KT

    更新日期:2013-12-01 00:00:00

  • Chemoenzymatic and microbial dynamic kinetic resolutions.

    abstract::This review tracks a decade of dynamic kinetic resolution developments with a biocatalytic inclination using enzymatic/microbial means for the resolution part followed by the racemization reactions either by means of enzymatic or chemocatalyst. These fast developments are due to the ability of the biocatalysts to sign...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20619

    authors: Kamaruddin AH,Uzir MH,Aboul-Enein HY,Halim HN

    更新日期:2009-04-01 00:00:00

  • CHIRBASE, a graphical molecular database on the separation of enantiomers by liquid-, supercritical fluid-, and gas chromatography.

    abstract::In order to cope with the increasing number of publications on the separation of enantiomers by chromatography on a chiral stationary phase, the graphical molecular database CHIRBASE was created. In the present state, the database package covers information (structural, bibliographic, and chromatographic data) on liqu...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530050404

    authors: Koppenhoefer B,Nothdurft A,Pierrot-Sanders J,Piras P,Popescu C,Roussel C,Stiebler M,Trettin U

    更新日期:1993-01-01 00:00:00

  • (R,R)-N,N'-dimethylcyclohexyl-1,2-diazaseleno-phospholidine as a chiral derivatizing agent for the evaluation of chiral alcohols.

    abstract::Previously, a diazaphospholidine has been synthesized and evaluated as a chiral derivatizing reagent for the determination of the optical purity of chiral alcohols via 31P NMR spectroscopy (Alexakis et al., J. Org. Chem. 57:1224-1237, 1992). Our laboratory is interested in the advantageous and practical applications o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530060306

    authors: House KL,O'Connor MJ,Silks LA 3rd,Dunlap RB,Odom JD

    更新日期:1994-01-01 00:00:00

  • Channel-like crystal structure of cinchoninium L-O-phosphoserine salt dihydrate.

    abstract::Studies on the interactions between L-O- phosphoserine, as one of the simplest fragments of membrane components, and the Cinchona alkaloid cinchonine, in the crystalline state were performed. Cinchoninium L-O-phosposerine salt dihydrate (PhSerCin) crystallizes in a monoclinic crystal system, space group P2(1), with un...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20784

    authors: Wesełucha-Birczyńska A,Oleksyn BJ,Watroba J

    更新日期:2010-06-01 00:00:00

  • Highly enantioselective asymmetric autocatalysis of 2-alkenyl- and 2-vinyl-5-pyrimidyl alkanols with significant amplification of enantiomeric excess.

    abstract::2-Alkenyl- and 2-vinyl-5-pyrimidyl alkanols are highly enantioselective asymmetric autocatalysts with significant amplification of enantiomeric excess in the enantioselective addition of diisopropylzinc to 2-alkenyl- and 2-vinylpyrimidine-5-carbaldehydes. Consecutive asymmetric autocatalysis starting from 7% ee increa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10068

    authors: Sato I,Yanagi T,Soai K

    更新日期:2002-02-01 00:00:00

  • Synthesis of a new enantiomerically pure P-chiral phosphine and its use in probing the mechanism of the Mitsunobu reaction.

    abstract::A new enantiomerically pure P-chiral phosphine, (S)-cyclohexylmethyl- (1-naphthyl)phosphine (1) was prepared by phosphine-borane methodology and used in a mechanistic study of the Mitsunobu reaction. Enantiomerically enriched (S)-cyclo- hexylmethyl(1-naphtyl)phosphine oxide (8) is obtained if the reaction proceeds thr...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<346::AID-CHIR8

    authors: Watanabe T,Gridnev ID,Imamoto T

    更新日期:2000-06-01 00:00:00

  • An integrating sphere to measure CD from difficult samples

    abstract::Integrating spheres are widely used with UV-Vis and occasionally with infrared spectrophotometers to measure different types of samples, either in transmission mode (scattered transmission accessories) or in total/diffuse reflectance mode. We built a prototype sphere of the demountable type, which fits easily the samp...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:4<291::AID-CHIR16>

    authors: Castiglioni E,Albertini P

    更新日期:2000-05-01 00:00:00

  • New atropisomeric amino alcohol ligands for enantioselective addition of diethylzinc to aldehydes.

    abstract::Efficient synthesis of several new atropisomeric amino alcohols having 1-phenyl-1H-pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single-crystal X-ray measurement. The consequences of the size of the N-substituents on enantioinduction were examined by employing the enantioselect...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22415

    authors: Faigl F,Deák S,Erdélyi Z,Holczbauer T,Czugler M,Nyerges M,Mátravölgyi B

    更新日期:2015-03-01 00:00:00

  • Spectroscopic, Structural, and Computational Characterization of Three Bispidinone Derivatives, as Ligands for Enantioselective Metal Catalyzed Reactions.

    abstract::Three chiral derivatives of the alkaloid sparteine (bispidines), characterized by the 3,7-diazabicyclo[3.3.1]nonane moiety, were designed as efficient ligands in a number of enantioselective reactions due to their metal coordination properties. A full evaluation of the 3D properties of the compounds was carried out, a...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22586

    authors: Castellano C,Sacchetti A,Meneghetti F

    更新日期:2016-04-01 00:00:00

  • Plasmonic nanoparticles assemblies templated by helical bacteria and resulting optical activity.

    abstract::Plasmonic nanoparticles (NPs) adsorbing onto helical bacteria can lead to formation of NP helicoids with micron scale pitch. Associated chiroptical effects can be utilized as bioanalytical tool for bacterial detection and better understanding of the spectral behavior of helical self-assembled structures with different...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23225

    authors: Feng W,Kadiyala U,Yan J,Wang Y,DiRita VJ,VanEpps JS,Kotov NA

    更新日期:2020-07-01 00:00:00

  • Synthesis of epimers of L-cyclopentenylglycine using enzymatic resolution.

    abstract::Both epimers of the naturally occurring nonproteinogenic amino acid L-cyclopentenylglycine, (2S,1'S)- and (2S, 1'R)-2-(cyclopent-2'-enyl)glycine, were obtained via a procedure involving condensation of 3-chlorocyclopentene with diethyl acetylaminomalonate, deethoxycarbonylation, chromatographic separation of the resul...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;

    authors: Andersen L,Nielsen B,Jaroszewski JW

    更新日期:2000-10-01 00:00:00

  • Catalytic asymmetric synthesis of 19,20-dihydroakuammicine.

    abstract::An enantiocontrolled total synthesis of 19,20-dihydroakuammicine using a catalytic asymmetric Michael addition of dimethyl malonate to cyclohexenone as the key step is described. The above catalytic asymmetric Michael addition proceeds quite efficiently in the presence of a heterobimetalic asymmetric catalyst (ALB-KO-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:5/6<400::AID-CHIR1

    authors: Ohori K,Shimizu S,Ohshima T,Shibasaki M

    更新日期:2000-06-01 00:00:00

  • Chiral analysis of butaclamol enantiomers in human plasma by HPLC using a macrocyclic antibiotic (vancomycin) chiral stationary phase and solid phase extraction.

    abstract::An enantioseparation of the antipsychotic drug butaclamol in human plasma by high-performance liquid chromatography (HPLC) with solid phase extraction is presented. The separation was achieved on the vancomycin macrocyclic antibiotic chiral stationary phase (CSP) Chirobiotic V with a polar ionic mobile phase (PIM) con...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20001

    authors: Aboul-Enein HY,Hefnawy MM

    更新日期:2004-03-01 00:00:00

  • Chiroptical studies on supramolecular chirality of molecular aggregates.

    abstract::The attempts of applying chiroptical spectroscopy to supramolecular chirality are reviewed with a focus on vibrational circular dichroism (VCD). Examples were taken from gels, solids, and monolayers formed by low-molecular mass weight chiral gelators. Particular attention was paid to a group of gelators with perfluoro...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22482

    authors: Sato H,Yajima T,Yamagishi A

    更新日期:2015-10-01 00:00:00

  • Circular dichroism eigenspectra of polyproline II and β-strand conformers of trialanine in water: Singular value decomposition analysis.

    abstract::Despite that a number of experimental and theoretical investigations have been carried out to determine the structure of trialanine in water, the reported populations of polyproline II (PPII) and β-strand conformers vary and were found to be dependent on which spectroscopic method was used. Such discrepancies are due ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20870

    authors: Oh KI,Lee KK,Park EK,Yoo DG,Hwang GS,Cho M

    更新日期:2010-01-01 00:00:00

  • Enantioselective electrochemical oxidation of enol acetates using a chiral supporting electrolyte.

    abstract::Anodic oxidation of 1-acetoxy-3,4-dihydronaphthalene (1) and alpha-acetoxy-beta-alkylstyrenes (3) at -78 degrees C in a mixed solvent of acetonitrile (CH(3)CN), tetrahydrofuran (THF), and acetic acid (AcOH) containing (S)-tetraethylammonium camphorsulfonate as a chiral supporting electrolyte brought about enantioselec...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10165

    authors: Maekawa H,Itoh K,Goda S,Nishiguchi I

    更新日期:2003-01-01 00:00:00

  • Unusual temperature-induced retention behavior of constrained β-amino acid enantiomers on the zwitterionic chiral stationary phases ZWIX(+) and ZWIX(-).

    abstract::The effects of temperature on the chiral recognition of cyclic β-amino acid enantiomers on zwitterionic [Chiralpak ZWIX(+) and ZWIX(-)] chiral stationary phases were investigated. Experiments were performed at different mobile phase compositions and under 10°C column temperature increments in the temperature range 10-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22333

    authors: Ilisz I,Pataj Z,Gecse Z,Szakonyi Z,Fülöp F,Lindner W,Péter A

    更新日期:2014-08-01 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 ...

    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

  • HPLC enantioseparation and absolute configuration of novel anti-inflammatory pyrrole derivatives.

    abstract::The assignment of the absolute configuration of novel anti-inflammatory pyrrole derivatives has been accomplished by a combined strategy based on independent physical methods. The key step of our stereochemical characterization approach is the production at mg-scale of enantiomerically pure forms by HPLC on Chiralpak ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20518

    authors: Biava M,Cirilli R,Fares V,Ferretti R,Gallinella B,La Torre F,Poce G,Porretta GC,Supino S,Villani C

    更新日期:2008-06-01 00:00:00

  • Optical resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline by supercritical fluid extraction.

    abstract::6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ) enantiomers were separated by supercritical fluid extraction using carbon dioxide. Diastereoisomeric salts were formed from the racemic base with less than one equivalent of O,O'-di-(4-toluoyl)-(2R,3R)-tartaric acid (DPTTA). Further purification was achieved by part...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1178

    authors: Kmecz I,Simándi B,Bálint J,Székely E,Fogassy E,Kemény S

    更新日期:2001-01-01 00:00:00

  • Spirobipyridopyrans and indolinospiropyridopyrans: Synthesis, X-ray crystal structure, separation of enantiomers, and barriers to thermal cleavage of the C(sp(3))-O bond.

    abstract::The novel chiral spirobipyridopyrans 1 and 2 were synthesized by the acid catalyzed aldol type condensation of 5-deoxypyridoxal with the appropriate ketone and subsequent reaction of the resulting pyrylium salt with base. The indolinospiropyridopyrans 3-5, which contain the modified B(6) unit, were prepared by aldol r...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/1520-636X(2001)13:2<81::AID-CHIR1002>3.0.C

    authors: Loncar-Tomaskovic L,Pustet N,Mrvos-Sermek D,Nagl A,Mintas M,Mannschreck A

    更新日期:2001-02-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22607

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

    更新日期:2016-06-01 00:00:00

  • Heterogeneous asymmetric reactions. Part 24. Heterogeneous catalytic enantioselective hydrogenation of the C==N group over cinchona alkaloid modified palladium catalyst.

    abstract::The enantioselective hydrogenation of C==N-C group containing compounds over modified metal catalysts is as yet an uninvestigated research area. This work contains results obtained on the hydrogenation of 1-pyrroline-2-carboxylate esters and sodium salt over cinchona alkaloid-modified alumina-supported Pd catalyst. Th...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10001

    authors: Szöllösi G,Kun I,Bartók M

    更新日期:2001-01-01 00:00:00

  • Spectroscopic studies on nicotine and nornicotine in the UV region.

    abstract::The UV absorption and electronic circular dichroism (ECD) spectra of (R)- and (S)-nicotine and (S)-nornicotine in aqueous solution were measured to a significantly lower wavelength range than previously reported, allowing the identification of four previously unobserved electronic transitions. The ECD spectra of the t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22141

    authors: Clayton PM,Vas CA,Bui TT,Drake AF,McAdam K

    更新日期:2013-05-01 00:00:00

  • Chiral 1,1'-binaphthyl-2,2'-dithiol-stabilized gold clusters: size separation and optical activity in the UV-vis.

    abstract::Gold particles covered with 1,1'-binaphthyl-2,2'-dithiol (BINAS) were prepared. Using size exclusion chromatography, it was possible for the first time to separate the sample into fractions with different sizes and colors. Transmission electron microscopy shows that the particles are very small, in the order of 1 nm o...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20488

    authors: Gautier C,Taras R,Gladiali S,Bürgi T

    更新日期:2008-03-01 00:00:00

  • Nonhanded chirality in octahedral metal complexes.

    abstract::Chiral molecules can either be handed (i.e., "shoes") or nonhanded ("potatoes"). The only chiral ligand partition for tetrahedral metal complexes (or for a tetrahedral carbon atom such as that found in amino acids and other chiral biological molecules) is the fully unsymmetrical degree 6 partition (1(4)), which leads ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.1063

    authors: King RB

    更新日期:2001-08-01 00:00:00