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


: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. Stereoselectivity may not be a constant factor and may change according to channel state as determined by stimulus mode or experimental conditions. Selected examples are cited for Na+ and Ca2+ channels.






Triggle DJ




Has Abstract


1996-01-01 00:00:00














  • In vitro stereoselective degradation of carprofen glucuronide by human serum albumin. Characterization of sites and reactive amino acids.

    abstract::Acyl glucuronides formed from carboxylic acids can undergo hydrolysis, acyl migration, and covalent binding to proteins. In buffers at physiological pH, the degradation of acylglucuronide of a chiral NSAID, carprofen, consisted mainly of acyl migration. Acidic pH reduced hydrolysis and acyl migration, thus stabilizing...


    pub_type: 杂志文章


    authors: Georges H,Presle N,Buronfosse T,Fournel-Gigleux S,Netter P,Magdalou J,Lapicque F

    更新日期:2000-02-01 00:00:00

  • Effect of the mobile phase on the retention behavior of optical isomers of the mandelic acid derivative methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate by chiral HPLC.

    abstract::Conditions for separation of enantiomers of a mandelic acid derivative, methyl 2-phenyl-2-(tetrahydropyranyloxy) acetate (the analyte) were studied. Because of the presence of two chiral carbons, the analyte consists of four stereoisomers stable at ambient temperature. Chiral HPLC of the analyte resulted in four peaks...


    pub_type: 杂志文章


    authors: Shen B,Xu X,Chen J,Zhang X,Xu B

    更新日期:2006-09-01 00:00:00

  • Investigation of the stability of Chiralpak AD chiral stationary phase under various solvent conditions and development of a method to identify stationary phase-derived polymer contamination.

    abstract::The stability of Chiralpak AD chiral stationary phase under various solvent conditions was investigated. An analytical method for the detection of the presence of solubilized Chiralpak AD coating was developed using CD spectroscopy (CD signal at 245 nm). In addition, NMR analysis of the solubilized polymer revealed a ...


    pub_type: 杂志文章


    authors: Welch CJ,Fairchild J,Sajonz P

    更新日期:2007-08-01 00:00:00

  • Enantioselectivity of inhibition of cytochrome P450 3A4 (CYP3A4) by ketoconazole: Testosterone and methadone as substrates.

    abstract::Racemic ketoconazole (KTZ) was the first orally active azole antifungal agent used in clinical practice and has become widely used in the treatment of mucosal fungal infections associated with AIDS immunosuppression and cancer chemotherapy. However, the use of KTZ has been limited because of adverse drug-drug interact...


    pub_type: 杂志文章


    authors: Dilmaghanian S,Gerber JG,Filler SG,Sanchez A,Gal J

    更新日期:2004-02-01 00:00:00

  • Simultaneous chiral analysis of amphetamine-type stimulants and ephedrine by capillary electrophoresis coupled to time-of-flight mass spectrometry.

    abstract::This study focused on the chiral characteristics of methamphetamine seizures in Shanghai for inferring the synthetic pathways of drugs. Capillary electrophoresis coupled to time-of-flight mass spectrometry was used for simultaneous chiral separation of amphetamine-type stimulants and ephedrine, including S(+)-amphetam...


    pub_type: 杂志文章


    authors: Cui X,Liang C,Gong F,Wang R,Ni C,Wu Y,Chen G,Zhang Y

    更新日期:2018-09-01 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...


    pub_type: 杂志文章,评审


    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

  • Chemoenzymatic approach to optically active 4-hydroxy-5-alkylcyclopent-2-en-1-one derivatives: an application of a combined circular dichroism spectroscopy and DFT calculations to assignment of absolute configuration.

    abstract::A series of representative optically active derivatives of 4-hydroxy-5-alkylcyclopent-2-en-1-one were prepared from the respective 2-furyl methyl carbinols via the Piancatelli rearrangement followed by the enzymatic kinetic resolution of racemates. Applicability of chiroptical methods (experimental and calculated elec...


    pub_type: 杂志文章


    authors: Frelek J,Karchier M,Madej D,Michalak K,Różański P,Wicha J

    更新日期:2014-06-01 00:00:00

  • Theoretical study of N-heterocyclic carbenes-catalyzed cascade annulation of benzodienones and enals.

    abstract::Growing attention in developing new N-heterocyclic carbene (NHC)-mediated reactions involving homoenolate intermediates has prompted our interest in exploring the mechanistic details of the related reactions. In this work, we carried out a detailed theoretical study for the NHC-catalyzed annulation reaction of cinnama...


    pub_type: 杂志文章


    authors: Sun H,Fang X,Chi YR,Li G

    更新日期:2013-09-01 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

  • 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...


    pub_type: 杂志文章


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

    更新日期:2015-08-01 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

  • Heparin-induced circular dichroism of an achiral, bicyclic species.

    abstract::Antimalarial drugs have shown potential in suppressing the role of glycosaminoglycans (GAGs) in the pathology of prion protein conformational disorders (e.g. "Mad Cow" disease) by competing for sites of electrostatic interaction. In this study, circular dichroism (CD) and UV/Visible (UV/Vis) absorption spectroscopy te...


    pub_type: 杂志文章


    authors: Stanley FE,Warner AM,McWilliams KM,Stalcup AM

    更新日期:2011-01-01 00:00:00

  • Stereoselective pharmacokinetics of (R)-(+)- and (S)-(-)-rabeprazole in human using chiral LC-MS/MS after administration of rabeprazole sodium enteric-coated tablet.

    abstract::Rabeprazole is an effective proton pump inhibitor to treat acid-related diseases. To achieve the simultaneous determination of rabeprazole enantiomers in human plasma, a chiral LC-MS/MS method was developed and validated. Acetonitrile including 0.1% ammonium were used as protein precipitating agent. Analytes were sepa...


    pub_type: 杂志文章


    authors: Sun LN,Shen YW,Ying YW,Li D,Li TF,Zhang XH,Zhao P,Ding L,Wang YQ

    更新日期:2018-12-01 00:00:00

  • The biological activities of prothioconazole enantiomers and their toxicity assessment on aquatic organisms.

    abstract::Chiral fungicide prothioconazole has a wide range of antifungal spectrum; however, little research has been conducted to evaluate prothioconazole on an enantiomeric level. Five target pathogens and three common aquatic organisms were tested for the enantioselective bioactivity and toxicity of prothioconazole in this w...


    pub_type: 杂志文章


    authors: Zhai W,Zhang L,Cui J,Wei Y,Wang P,Liu D,Zhou Z

    更新日期:2019-06-01 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 LC/ESI-MS/MS analysis and pharmacokinetic and tissue distribution study of (2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)-propan-2-ol in rats.

    abstract::A sensitive and stereospecific liquid chromatography-tandem mass spectrometry method for the quantitative determination of TWo8 enantiomers ((2RS)-1-(7-methoxy-1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)-propan-2-ol) was developed and validated in rat serum and some tissues. Racemic TWo8 is a new chemical ent...


    pub_type: 杂志文章


    authors: Walczak M,Szymura-Oleksia J,Groszek G

    更新日期:2012-08-01 00:00:00

  • Three-Dimensional Chemical Structure Search Using the Conformational Code for Organic Molecules (CCOM) Program.

    abstract::Searching the 3D structural fragments of organic molecules is challenging because of structural differences between X-ray and theoretically calculated geometries and the conformational flexibility of substituents. The codification program called Conformational Code for Organic Molecules (CCOM) can be used to unambiguo...


    pub_type: 杂志文章


    authors: Izumi H,Nafie LA,Dukor RK

    更新日期:2016-05-01 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....


    pub_type: 杂志文章


    authors: Jintoku H,Ihara H

    更新日期:2020-05-01 00:00:00

  • Stereoselective pharmacokinetics and metabolism of flobufen in guinea pigs.

    abstract::Stereoselective aspects of pharmacokinetics and metabolism of a chiral nonsteroidal antiinflammatory drug, flobufen, 4-(2', 4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid, were studied in male guinea pigs after p.o. administration of racemic flobufen (rac-flobufen) at a dose of 10 mg/kg. Blood samples were coll...


    pub_type: 杂志文章


    authors: Trejtnar F,Král R,Pávek P,Wsól V

    更新日期:2003-10-01 00:00:00

  • Structure-retention relationship for enantioseparation of selected fluoroquinolones.

    abstract::Fluoroquinolones are popular class of antibiotics with distinct chemical functionality. Most of them are ampholytes with one chiral center. Stereogeneic center is located either in the side ring of Gatifloxacin (GFLX) or in the quinolone core of Ofloxacin (OFLX). These two amphoteric fluoroquinolones have terminal ami...


    pub_type: 杂志文章


    authors: Hassan RM,Yehia AM,Saleh OA,El-Azzouny AA,Aboul-Enein HY

    更新日期:2018-06-01 00:00:00

  • Theoretical Modeling of Surface Confined Chiral Nanoporous Networks: Cruciform Molecules as Versatile Building Blocks.

    abstract::Patterning of solid surfaces with functional organic molecules has been a convenient route to fabricate two-dimensional materials with programmed architecture and activities. One example is the chiral nanoporous networks that can be created via controlled self-assembly of star-shaped molecules under 2D confinement. In...


    pub_type: 杂志文章


    authors: Kasperski A,Szabelski P

    更新日期:2015-07-01 00:00:00

  • Paramagnetic 1H-NMR relaxation probes of stereoselectivity in metalloporphyrin catalyzed olefin epoxidation.

    abstract::Enantioselective catalytic epoxidation of olefins is an important problem from both practical and mechanistic points of view. The origins of chiral induction by asymmetric porphyrin and salen complexes were investigated by FT-NMR T1 relaxation techniques. A new chiral vaulted porphyrin (1) that carries (S)-binaphthyl-...


    pub_type: 杂志文章


    authors: Groves JT,Crowley SJ,Shalyaev KV

    更新日期:1998-01-01 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 ...


    pub_type: 杂志文章


    authors: King RB

    更新日期:2001-08-01 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

  • 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...


    pub_type: 杂志文章


    authors: Schneiderheinze JM,Armstrong DW,Berthod A

    更新日期:1999-01-01 00:00:00

  • Absolute configuration and conformational analysis of a degradation product of inhalation anesthetic Sevoflurane: A vibrational circular dichroism study.

    abstract::1,1,1,3,3-pentafluoro-2-(fluoromethoxy)-3-methoxypropane, compound B, is a product obtained in the degradation of the anesthetic Sevoflurane. Enantiopure (+)-B was investigated using vibrational circular dichroism (VCD). Experimental absorption and VCD spectra of (+)-B in CDCl(3) solution in the 2,000-900 cm(-1) regio...


    pub_type: 杂志文章


    authors: Wang F,Polavarapu PL,Schurig V,Schmidt R

    更新日期:2002-08-01 00:00:00

  • Parallel kinetic resolution of an oxazolidinone using a quasi-enantiomeric combination of [D,13C]-isotopomers of pentafluorophenyl 2-phenyl propionate.

    abstract::Parallel kinetic resolution of Evans' phenylglycine derived oxazolidinone using an equimolar combination of quasi-enantiomeric active esters (derived from [D,13C]-labeled 2-phenylpropionic acid) was achieved. The levels of stereocontrol were high, leading to products with predictable configurations. ...


    pub_type: 杂志文章


    authors: Coumbarides GS,Dingjan M,Eames J,Flinn A,Northen J

    更新日期:2007-05-05 00:00:00

  • Bi-directional chiral inversion of ketoprofen in CD-1 mice.

    abstract::The R enantiomers of some of the 2-arylpropionic acid non-steroidal antiinflammatory drugs (NSAIDs) are known to undergo metabolic chiral inversion to their more pharmacologically active antipodes. This process is drug and species dependent and usually unidirectional. The S to R chiral inversion, on the other hand, is...


    pub_type: 杂志文章


    authors: Jamali F,Lovlin R,Aberg G

    更新日期:1997-01-01 00:00:00

  • A Simple ¹³C NMR Method for the Discrimination of Complex Mixtures of Stereoisomers: All Eight Stereoisomers of α-Tocopherol Resolved.

    abstract::A simple one-dimensional (13)C NMR method is presented to discriminate between stereoisomers of organic compounds with more than one chiral center. By means of this method it is possible to discriminate between all eight stereoisomers of α-tocopherol. To achieve this the chiral solvating agent (S)-(+)-1-(9-anthryl)-2,...


    pub_type: 杂志文章


    authors: Lankhorst PP,Netscher T,Duchateau AL

    更新日期:2015-11-01 00:00:00

  • Absolute configuration and enantiodifferentiation of a hemicryptophane incorporating an azaphosphatrane moiety.

    abstract::The hemicryptophane racemate (±)-1 was optically resolved by semipreparative HPLC on Chiralpak IC column. The absolute configuration of each isolated enantiomer was established from the analysis of their electronic circular dichroism spectra. Enantiodifferentiation of the chiral cationic cage (±)-1 was evidenced in so...


    pub_type: 杂志文章


    authors: Payet E,Dimitrov-Raytchev P,Chatelet B,Guy L,Grass S,Lacour J,Dutasta JP,Martinez A

    更新日期:2012-12-01 00:00:00