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


: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 techniques were used to investigate the interactions between N-methyl-N'-(7-chloro-4-quinolyl)-1,3-diaminopropane (QD), an achiral, bicyclic compound similar to previously investigated antimalarial drugs, and heparin, a complex GAG that is frequently used as a clinical anticoagulant. Relatively intense heparin-induced CD features were observed for QD and were noted to be radically different from previous studies using related chiral drugs, underscoring the importance of the Pfieffer effect on this and similar heparin research. Additionally, the induced CD for QD was observed to be highly dependent upon drug concentration, heparin concentration, system pH, equilibration time, and ionic strength. These results, in connection with recent work, provide new insight into the nature of the association between GAGs and antimalarial species.






Stanley FE,Warner AM,McWilliams KM,Stalcup AM




Has Abstract


2011-01-01 00:00:00












  • Enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral Lewis bases.

    abstract::The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model su...


    pub_type: 杂志文章


    authors: Guizzetti S,Benaglia M,Cozzi F,Rossi S,Celentano G

    更新日期:2009-01-01 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...


    pub_type: 杂志文章


    authors: Aboul-Enein HY,Hefnawy MM

    更新日期:2004-03-01 00:00:00

  • Evaluation of the chiral recognition properties and the column performances of three chiral stationary phases based on cellulose for the enantioseparation of six dihydropyridines by high-performance liquid chromatography.

    abstract::Separations of six dihydropyridine enantiomers on three commercially available cellulose-based chiral stationary phases (Chiralcel OD-RH, Chiralpak IB, and Chiralpak IC) were evaluated with high-performance liquid chromatography (HPLC). The best enantioseparation of the six chiral drugs was obtained with a Chiralpak I...


    pub_type: 杂志文章


    authors: Yu J,Tang J,Yuan X,Guo X,Zhao L

    更新日期:2017-03-01 00:00:00

  • Enantioselectivity in the metabolism of mexiletine by conjugation in female patients with the arrhythmic form of chronic Chagas' heart disease.

    abstract::The phenomenon of enantioselectivity in the metabolism of mexiletine (MEX) conjugation was investigated in eight female patients with the arrhythmic form of chronic Chagas' heart disease treated with racemic mexiletine hydrochloride (two 100 mg capsules every 8 hr). Blood samples were collected up to 24 hr after the a...


    pub_type: 临床试验,杂志文章


    authors: Lanchote VL,Cesarino EJ,Santos VJ,Mere Júnior Y,Santos SR

    更新日期:1999-01-01 00:00:00

  • Computational simulation of vibrationally resolved spectra for spin-forbidden transitions.

    abstract::In this computational study, we illustrate a method for computing phosphorescence and circularly polarized phosphorescence spectra of molecular systems, which takes into account vibronic effects including both Franck-Condon and Herzberg-Teller contributions. The singlet and triplet states involved in the phosphorescen...


    pub_type: 杂志文章


    authors: Egidi F,Fusè M,Baiardi A,Bloino J,Li X,Barone V

    更新日期:2018-07-01 00:00:00

  • Capillary electrophoresis of herbicides. III. Evaluation of octylmaltopyranoside chiral surfactant in the enantiomeric separation of phenoxy acid herbicides.

    abstract::A chiral alkylglucoside surfactant, namely n-octyl-beta-D-maltopyranoside (OM), was evaluated in the enantiomeric separation of phenoxy acid herbicides. The enantiomeric resolution of the phenoxy acid herbicides could be manipulated readily by adjusting the surfactant concentration, ionic strength, pH, the percent org...


    pub_type: 杂志文章


    authors: Mechref Y,el Rassi Z

    更新日期:1996-01-01 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

  • 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

  • A new water soluble Zn-salophen derivative as a receptor for alpha-aminoacids: unexpected chiral discrimination.

    abstract::A new water soluble zinc-salophen complex with appended D-glucose moieties was synthesized and characterized. Its binding properties toward six aminoacids were investigated by UV-vis spectrophotometric titrations. Association constants showed to be unfavorably affected by increasing steric hindrance of the side chain....


    pub_type: 杂志文章


    authors: Dalla Cort A,De Bernardin P,Schiaffino L

    更新日期:2009-01-01 00:00:00

  • Separation and quantitation of (R)- and (S)-atenolol in human plasma and urine using an alpha 1-AGP column.

    abstract::A method for the determination of (R)- and (S)-atenolol in human plasma and urine is described. The enantiomers of atenolol are extracted into dichloromethane containing 3% heptafluorobutanol followed by acetylation with acetic anhydride at 60 degrees C for 2 h. The acetylated enantiomers were separated on a chiral al...


    pub_type: 杂志文章


    authors: Enquist M,Hermansson J

    更新日期:1989-01-01 00:00:00

  • Resolution of enantiomers of novel C2 -symmetric aminobisphosphinic acids via diastereomeric salt formation with quinine.

    abstract::C2 -symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2 -symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation wi...


    pub_type: 杂志文章


    authors: Kaboudin B,Faghihi MR,Kazemi F,Yokomatsu T

    更新日期:2015-01-01 00:00:00

  • Two-dimensional separation of [7]helicene enantiomers on Cu(111).

    abstract::The adsorption of heptahelicene, a helically shaped polyaromatic hydrocarbon (C(30)H(18)), on a Cu(111) surface was studied by means of thermal desorption mass spectrometry (TDMS) and low energy electron diffraction (LEED) at temperatures between 130-1,000 K under ultrahigh vacuum (UHV) conditions. The molecule in the...


    pub_type: 杂志文章


    authors: Ernst KH,Kuster Y,Fasel R,Müller M,Ellerbeck U

    更新日期:2001-01-01 00:00:00

  • Strategic use of preparative chiral chromatography for the synthesis of a preclinical pharmaceutical candidate.

    abstract::The modern use of preparative chromatography in pharmaceutical development is illustrated by the case of a recent preclinical candidate from these laboratories. The synthesis of the candidate employed a coupling of two enantiopure intermediates, each of which could be resolved using preparative chiral chromatography. ...


    pub_type: 杂志文章


    authors: Leonard WR Jr,Henderson DW,Miller RA,Spencer GA,Sudah OS,Biba M,Welch CJ

    更新日期:2007-09-01 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

  • Successful use of a novel lux® i-Amylose-1 chiral column for enantioseparation of "legal highs" by HPLC.

    abstract::Bath salts, fumigations, cleaners and air fresheners, behind these terms substances are hidden, which count as "Legal Highs". These fancy names are used to pretend Legal Highs as harmless compounds, to circumvent legal regulations for marketing as well as to increase the sales. Besides classic illicit drugs of synthet...


    pub_type: 杂志文章


    authors: Kadkhodaei K,Kadisch M,Schmid MG

    更新日期:2020-01-01 00:00:00

  • Influence of endotoxin on the stereoselective pharmacokinetics of oxprenolol, propranolol, and verapamil in the rat.

    abstract::The influence of endotoxin-induced inflammation on the enantioselective pharmacokinetics of propranolol, oxprenolol, and verapamil, which bind to alpha 1-acid glycoprotein, was studied in the rat. The racemic mixtures were given orally. In the control animals, for propranolol and oxprenolol, the plasma concentrations ...


    pub_type: 杂志文章


    authors: Laethem ME,Belpaire FM,Wijnant P,Rosseel MT,Bogaert MG

    更新日期:1994-01-01 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

  • Resolution of 1-n-butyl-3-methyl-3-phospholene 1-oxide with TADDOL derivatives and calcium salts of O,O'-Dibenzoyl-(2R,3R)- or O,O'-di-p-toluoyl-(2R,3R)-tartaric acid.

    abstract::The resolution methods applying (-)-(4R,5R)-4,5-bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane ("TADDOL"), (-)-(2R,3R)-α,α,α',α'-tetraphenyl-1,4-dioxaspiro[4.5]decan-2,3-dimethanol ("spiro-TADDOL"), as well as the acidic and neutral Ca(2+) salts of (-)-O,O'-dibenzoyl- and (-)-O,O'-di-p-toluoyl-(2R,3R)-tartaric acid ...


    pub_type: 杂志文章


    authors: Bagi P,Fekete A,Kállay M,Hessz D,Kubinyi M,Holczbauer T,Czugler M,Fogassy E,Keglevich G

    更新日期:2014-03-01 00:00:00

  • Stereolability of chiral ruthenium catalysts with frozen NHC ligand conformations investigated by dynamic-HPLC.

    abstract::The stereolability of chiral Hoveyda-Grubbs II type ruthenium complexes bearing N-heterocyclic carbene (NHC) ligands with Syn-phenyl groups on the backbone and Syn- or Anti-oriented o-tolyl N-substituents was studied by resorting to dynamic high-performance liquid chromatography (D-HPLC). A complete chromatographic pi...


    pub_type: 杂志文章


    authors: Menta S,Pierini M,Cirilli R,Grisi F,Perfetto A,Ciogli A

    更新日期:2015-10-01 00:00:00

  • Asymmetric Diels-Alder reaction involving chiral benzimidazoles as organocatalysts.

    abstract::(S)-(-)-2-(α-hydroxyethyl)-benzimidazole and (S)-(+)-2-(α-hydroxybenzyl)-benzimidazole work as chiral Brønsted bases (BBs) in Diels-Alder reaction between anthrone and maleimides under mild reaction condition. These chiral BBs cause asymmetric induction. ...


    pub_type: 杂志文章


    authors: Mirgane NA,Karnik AV

    更新日期:2011-05-01 00:00:00

  • Enantioseparation and determination of the chiral fungicide furametpyr enantiomers in rice, soil, and water by high-performance liquid chromatography.

    abstract::The chiral fungicide furametpyr is widely used in the rice field to control rice sheath blight; however, furametpyr enantiomers are treated as just one compound in traditional achiral analysis, which gives only partial information. An effective chiral analytical method was developed for the resolution and determinatio...


    pub_type: 杂志文章


    authors: Dong F,Chen X,Xu J,Liu X,Chen Z,Li Y,Zhang H,Zheng Y

    更新日期:2013-12-01 00:00:00

  • Chiral counter-current chromatography: A survey of its instrument, mechanism, procedure, and applications.

    abstract::The chiral separation by counter-current chromatography has made great progress in the past three decades. It has become increasingly popular in the field of chiral separation, and many applications have been introduced during the last years. This review mainly focuses on the current topics, applications, and trends i...


    pub_type: 杂志文章,评审


    authors: Duan WD,Huang XY,Di DL

    更新日期:2020-10-01 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

  • Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid-liquid extraction.

    abstract::Flurbiprofen is a kind of nonsteroidal anti-inflammatory drug, which has been widely used in clinic for treatment of rheumatoid arthritis and osteoarthritis. It has been reported that S-flurbiprofen shows good performance on clinic anti-inflammatory treatment, while R-enantiomer almost has no pharmacological activitie...


    pub_type: 杂志文章


    authors: Cui X,Ding Q,Shan RN,He CH,Wu KJ

    更新日期:2019-06-01 00:00:00

  • Metabolic chiral inversion of ibuprofen in isolated rat hepatocytes.

    abstract::Ibuprofen was used to demonstrate that isolated rat hepatocytes offer a suitable in vitro model to investigate the metabolic chiral inversion of anti-inflammatory 2-arylpropionic acids (profens). The inversion of the pharmacologically inactive (-)-(R)-ibuprofen to the active (+)-(S)-ibuprofen was shown to obey apparen...


    pub_type: 杂志文章


    authors: Müller S,Mayer JM,Etter JC,Testa B

    更新日期:1990-01-01 00:00:00

  • Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.

    abstract::Synthetic pyrethroid insecticides are chiral compounds with multiple asymmetric positions. In this study, isomers of four commonly used pyrethroids were separated at the enantiomeric level by enantioselective high-performance liquid chromatography (HPLC), and differences between enantiomers in aquatic toxicity were ch...


    pub_type: 杂志文章


    authors: Liu W,Gan JJ,Qin S

    更新日期:2005-01-01 00:00:00

  • Enantioselective determination of isradipine in human serum using chiral stationary phase liquid chromatography and gas chromatography with nitrogen selective detection.

    abstract::rac-Isradipine is a dihydropyridine type calcium antagonist. Its calcium entry blocking effect is due primarily to the (+)-(S)-enantiomer. This study describes a sensitive enantioselective method for the determination of isradipine in human serum. Following alkaline extraction into hexane, the enantiomers of isradipin...


    pub_type: 杂志文章


    authors: Rask HS,Angelo HR,Christensen HR

    更新日期:1998-01-01 00:00:00

  • Determination of enantiomeric excess of ethyl 3,5-dihydroxy-6-benzyloxy hexanoate by chiral reverse phase high performance liquid chromatography.

    abstract::A simple and reliable chiral HPLC method was developed for the determination of enantiomeric excess of a chiral dihydroxy intermediate for the chemoenzymatic synthesis of side chain of statin drugs. After evaluating different columns and conditions, the four stereoisomers of ethyl 3,5-dihydroxy-6-benzyloxy hexanoate w...


    pub_type: 杂志文章


    authors: Liu JH,Yu BY,Chen YJ

    更新日期:2008-01-01 00:00:00

  • Spontaneous resolution of 2,3-bis-fluoren-9-ylidenesuccinic acid induced by achiral guest inclusion.

    abstract::The racemic title host compound (1) formed homochiral inclusion crystals (conglomerate) of 1 with acetone, while heterochiral inclusion crystals (racemate) were obtained when complexed with ethyl acetate. Upon treatment of the homochiral inclusion crystals of 1 with gaseous acetyl chloride in the solid state, opticall...


    pub_type: 杂志文章


    authors: Tanaka K,Iwamoto T,Wada S,Frelek J,Caira MR

    更新日期:2006-08-01 00:00:00

  • Enantioselective and diastereoselective Michael addition of ketone/aldehyde to trans-nitroolefins catalyzed by a novel chiral pyrrolidine-thiourea.

    abstract::The direct Michael addition reaction of cyclohexanone/aliphatic aldehydes with nitroolefins, catalyzed by a novel chiral pyrrolidine-thiourea catalyst 1a, is described. The desired 1,4-adducts were obtained in moderate yields with enantioselectivities up to 99% ee and dr up to 99:1 of the syn product. ...


    pub_type: 杂志文章


    authors: Shen Z,Zhang Y,Jiao C,Li B,Ding J,Zhang Y

    更新日期:2007-05-05 00:00:00