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 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.

journal_name

Chirality

journal_title

Chirality

authors

Stanley FE,Warner AM,McWilliams KM,Stalcup AM

doi

10.1002/chir.20873

subject

Has Abstract

pub_date

2011-01-01 00:00:00

pages

84-92

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

23

pub_type

杂志文章
  • Conformation change of hornet silk proteins in the solid phase in response to external stimulation.

    abstract::Hornet silks adopt a variety of morphology such as fibers, sponge, films, and gels depending on the preparation methods. We have studied the conformation change of hornet silk proteins (Vespa mandarina) as regenerated films, using chiroptical spectrophotometer universal chiroptical spectrophotometer 1, which can measu...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22824

    authors: Kuroda R,Kameda T

    更新日期:2018-05-01 00:00:00

  • Measurements of concentration dependence and enantiomeric purity of terpene solutions as a test of a new commercial VCD spectrometer

    abstract::Vibrational circular dichroism (VCD) spectra of (+)-alpha-pinene solutions in carbon tetrachloride have been measured in the range of volume fractions 5-100% (v/v) in the mid-infrared region. The concentration dependence measured was statistically analyzed with the aim of obtaining a reliable correlation between the V...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:4<199::AID-CHIR6>3

    authors: Urbanova M,Setnicka V V,Volka K

    更新日期:2000-05-01 00:00:00

  • Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush-type chiral stationary phases.

    abstract::The chiral discrimination ability of two recently prepared chiral stationary phases (CSP 1 and CSP 2), based on a leucine derived chiral selector, was tested for the enantiomers of dihydropyrimidone (DHPM) derivatives and compared with the commercially available Hyun-leucine CSP 3 and classical Pirkle-leucine CSP 4. B...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20396

    authors: Forjan DM,Gazić I,Vinković V

    更新日期:2007-06-01 00:00:00

  • The first preparation of enantiopure 1-methyl-7-oxabicyclo[2.2.1]heptan-2-one, a versatile chiral building block for terpenoids.

    abstract::Methods for the resolution of (+/-)-1-methyl-7-oxabicyclo[2.2.1]heptan-2-one 1, a versatile chiral building block for terpenoids, have been investigated. While no efficient result was obtained with kinetic resolution methods, both enantiomers of 1 were prepared optically pure for the first time via esterification of t...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20095

    authors: Guan YK,Li YL

    更新日期:2005-02-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20059

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

    更新日期:2004-08-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:2<53::AID-CHIR1>3.

    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

  • Conformational and Chiral Properties of Cyclic-tri(N-methyl-meta-benzamide) Bearing Amidino Groups.

    abstract::Cyclic triamides bearing amidino groups at the meta position of the phenyl rings were synthesized, and their conformational properties in the crystal and in solution were examined. Compound exists as a capsule-type dimer of the enantiomers with a bowl-shaped syn conformation in the crystal state. Compound exists mainl...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22476

    authors: Nishiyama S,Urushibara K,Masu H,Azumaya I,Kagechika H,Tanatani A

    更新日期:2015-08-01 00:00:00

  • R2PI Study of intermolecular hydrogen bond in solvent-free chiral complexes.

    abstract::One- and two-color, mass selected R2PI spectra of the S(1)<--S(0) transitions in the bare (+)-(R)-1-phenyl-1-ethanol (E(R)) and its complexes with different solvent molecules (solv) (-)-(R)-2-butanol (B(R)) or (+)-(S)-2-butanol (B(S)) and (-)-(R)-2-butylamine (A(R)) or (+)-(S)-2-butylamine (A(S)), have been recorded a...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10010

    authors: Giardini Guidoni A,Piccirillo S,Scuderi D,Satta M,Di Palma TM,Speranza M,Filippi A,Paladini A

    更新日期:2001-01-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22011

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

    更新日期:2012-08-01 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22487

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

    更新日期:2015-10-01 00:00:00

  • Improvement of enantioselective syntheses and chiral high resolution gas chromatographic analyses of (+)-2-allyl-2-carboethoxy-cyclopentanol.

    abstract::The improvement of the biocatalytic reduction of 2-allyl-carboethoxy-cyclopentanone (2) to the corresponding cyclopentanol derivative (+)-(1R,2R)-(1) was accomplished employing baker's yeast in organic media. This chiral cyclopentanol derivative (1), analyzed by high resolution gas chromatography performed over beta-c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:4<321::AID-CHIR1>3.

    authors: Fraga CA,Barreiro EJ,da Silva EF,dos Santos AR,KV Ramos MdaC,de Aquino Neto FR

    更新日期:1997-01-01 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

  • Glutathione conjugation and pharmacokinetics of 2-bromo-3-phenylpropionic acid in vitro and in the rat in vivo.

    abstract::Glutathione (GSH) conjugation of the chiral compound 2-bromo-3-phenylpropionic acid (BPP) was studied in vitro and in the rat in vivo. GSH conjugation of BPP, catalyzed by a mixture of glutathione-S-transferases (GST's) from rat liver cytosol in vitro, was stereoselective: at a substrate concentration of 250 microM, (...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040702

    authors: Snel CA,Mahadevan S,Polhuijs M,Mulder GJ

    更新日期:1992-01-01 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. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20942

    authors: Mirgane NA,Karnik AV

    更新日期:2011-05-01 00:00:00

  • Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids.

    abstract::The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3-yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20982

    authors: Borkin DA,Landge SM,Török B

    更新日期:2011-09-01 00:00:00

  • Chiral doping of nematic phases and its application to the determination of absolute configuration.

    abstract::Doping nematic liquid crystals with nonracemic chiral compounds induces a twisted nematic (cholesteric) phase. The ability of solutes to twist the nematic phase may be related to the overall shape of the chiral dopant and consequently to its absolute configuration. The cholesteric induction is therefore a powerful too...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20482

    authors: Pieraccini S,Ferrarini A,Spada GP

    更新日期:2008-05-15 00:00:00

  • Polarization in France.

    abstract::The special relationship between France and the polarization of light from the beginning of the 19th century until the present day is reviewed in the lives and works of Étienne Louis Malus, François Arago, Jean-Baptiste Biot, Augustin Fresnel, Louis Pasteur, Frédéric Wallerant, Aimé Cotton, Francis Perrin, and Alain A...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22818

    authors: Kahr B

    更新日期:2018-04-01 00:00:00

  • Enantioselective reduction of ketones with borane catalyzed by tridentate amino alcohols derived from salicylaldehyde.

    abstract::In the presence of tridentate chiral ligand 4e, 99% e.e. value was obtained by asymmetric reduction of ethyl benzoylacetate with borane in toluene at 25 degrees C. Various ligands and reaction conditions were investigated to develop a reasonable mechanism that explains the experimental outcomes. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20344

    authors: Lee DS

    更新日期:2007-02-01 00:00:00

  • Stereoselective kinetics of warfarin binding to human serum albumin: effect of an allosteric interaction.

    abstract::Kinetic and equilibrium binding studies were performed on the interaction of warfarin enantiomers with human serum albumin (HSA) in the absence and presence of lorazepam acetate (LoAc) enantiomers. Binding kinetics were followed by recording changes in the fluorescence of warfarin upon binding to HSA using the stopped...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10113

    authors: Fitos I,Visy J,Kardos J

    更新日期:2002-05-15 00:00:00

  • The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water.

    abstract::(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro-acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild con...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20728

    authors: Huang L,Liu J,Shan W,Liu B,Shi A,Li X

    更新日期:2010-02-01 00:00:00

  • Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent.

    abstract::Midodrine hydrochloride is a peripheral alpha(1)-adrenoreceptor agonist that induces venous and arterial vasoconstriction. Midodrine, after oral or intravenous administration, undergoes enzymatic hydrolysis and releases deglymidodrine, a pharmacologically active metabolite. Midodrine and deglymidodrine have a chiral c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20041

    authors: Quaglia MG,Farina A,Palmery M,Desideri N,Donati E,Bossù E,Strano S

    更新日期:2004-07-01 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

  • 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...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23125

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

    更新日期:2019-11-01 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

  • Chiral bioanalytical methods in bioequivalence studies of intravenous vs. oral formulations of ibuprofen.

    abstract::According to the Ibuprofen Product-Specific Bioequivalence Guidance of the European Medicines Agency, achiral bioanalytical methods are considered acceptable for demonstration of bioequivalence of ibuprofen-containing products. The aim of this investigation is to compare the bioequivalence outcomes obtained with indiv...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23258

    authors: González-Rojano E,Marcotegui J,Laredo L,Gwaza L,Gordon J,Portolés A,Vargas E,Morales-Alcelay S,García-Arieta A

    更新日期:2020-09-01 00:00:00

  • Liquid chromatographic resolution of 3-amino-1,4-benzodiazepin-2-one derivatives on various Pirkle-type chiral stationary phases.

    abstract::The two enantiomers of N-acyl amide and N-ureide derivatives of 3-amino-5-phenyl-1,4-benzodiazepin-2-ones, which have been known to show anti-respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle-type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mob...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20944

    authors: Park JY,Cho HS,Hyun MH

    更新日期:2011-01-01 00:00:00

  • Species differences in the generation of the chiral sulfoxide metabolite of albendazole in sheep and rats.

    abstract::The prochiral anthelmintic drug albendazole was administered orally to sheep and rats. Blood samples were taken at standardized intervals during the time course of the plasma kinetics: 18 h in rats and 48 h in sheep. The enantiomeric ratio of the sulfoxide metabolite was determined by means of HPLC on a chiral station...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530020306

    authors: Delatour P,Benoit E,Caude M,Tambute A

    更新日期:1990-01-01 00:00:00

  • Chiroptical properties of cation complexes of chiral phenazino-18-crown-6 ether-type hosts.

    abstract::Herein we report CD spectroscopic studies on complexes of (R,R)-dimethyl-, (R,R)-diisobutyl-, and (S,S)-di-sec-butyl-phenazino-18-crown-6 ligands (Scheme 1) with selected alkali (Na+, K+), alkaline earth (Mg2+, Ca2+), and transition-metal (Ag+, Zn2+, Ni2+, Cd2+, Pb2+) cations. The complexation was monitored in the 300...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20162

    authors: Szarvas S,Szalay L,Vass E,Hollósi M,Samu E,Huszthy P

    更新日期:2005-06-01 00:00:00

  • Surface-enhanced chiroptical spectroscopy with superchiral surface waves.

    abstract::We study the chiroptical properties of one-dimensional photonic crystals supporting superchiral surface waves by introducing a simple formalism based on the Fresnel reflection matrix. We show that the proposed framework provides useful insights on the behavior of all the relevant chiroptical quantities, allowing for a...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22971

    authors: Pellegrini G,Finazzi M,Celebrano M,Duò L,Biagioni P

    更新日期:2018-07-01 00:00:00

  • Stereochemical preference of 2'-deoxycytidine for chiral bis(diamido)-bridged basket resorcin[4]arenes.

    abstract::Bis(diamido)-bridged basket resorcin[4]arene (all-S)-1 and its (all-R)-1 enantiomer proved able to interact with 2'-deoxycytidine (2) and pyrimidine nucleoside analogs in dimethyl sulfoxide (DMSO) solution. In such a solvent, the resorcinarene hosts adopt a preferential 1,3-alternate-like conformation, with a larger c...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22224

    authors: D'Acquarica I,Calcaterra A,Sacco F,Balzano F,Aiello F,Tafi A,Pesci N,Uccello-Barretta G,Botta B

    更新日期:2013-12-01 00:00:00