Enantioseparation of flinderoles and borreverines by HPLC on Chirobiotic V and V2 stationary phases and by CE using cyclodextrin selectors

Abstract

Racemic mixtures of the promising anti-malarial bisindole alkoids, flinderole A-C, desmethyl flinderole C, borreverine and isoborreverine, are baseline-separated for the first time by HPLC using vancomycin-based stationary phases and partially separated by capillary electrophoresis (CE) using cyclodextrin selectors. The HPLC results compare the performance of Chirobiotic V and V2 in the polar organic and reversed phase modes and their complementary selectivity is discussed. The performance of the cyclodextrin selectors in CE, while less effective, are discussed in terms of their selectivity in normal and reversed polarity modes.

Application of cyclodextrins in chiral capillary electrophoresis

“…This also implies that the number of substituents on each glucose unit is unknown. Nevertheless, these randomly substituted CDs can be very useful in enantioseparations because their separation ability [218]; binaphthol and its mono derivatives [174,209]; ANDA-CC-penicillamine [204]; trimipramine [205]; tryptophan [121]; vincamine, vinpocetine, and vincadifformine [122]; Tic-hydantoin derivatives [208]; modified pregabalins [119] 2-Hydroxypropylated ␤-CD (9-Anthryl)methoxyacetic acid and (9-anthryl)hydroxyacetic acid [253]; four triadimenols [149]; amlodipine [254][255][256]; naphthalene-2,3-dicarboxaldehyde-aspartic acid [257]; chlorpheniramine [258]; etodolac [87]; flinderoles and borreverine [259]; fluvastatin [215]; imazethapyr [260]; ketoconazole and terconazole [107]; four tetrahydrobenzimidazoles [236]; lamivudine [261]; methadone [158]; methamphetamine [262]; three naphthalene-2,3-dicarboxaldehyde amino acids [263]; binaphthol and its mono derivatives [174,209]; 6,6 -dibromo-1,1 -binaphthyl-2,2 -diol [218]; naproxen, warfarin, and pranoprofen [247]; ofloxacin, omeprazole [88]; threo-methylphenidate [265]; pheniramine [266,267]; propranolol and brompheniramine maleate [268]; vincamine, vinpocetine, and vincadifformine [122]; vinpocetine [269]; zolmitriptan [270]; five ␤-agonists…”

“…Carboxyethylated ␤-CD Four drugs [325], modified pregabalins [119] Carboxymethylated ␣-CD Vincamine, vinpocetine, and vincadifformine [122]; nine dipeptides [240]; five antimalarial drugs [280]; two ␤-lactams [281] Carboxymethylated ␤-CD Twenty triadimenols [149]; anisodamine, atenolol, and metoprolol [282]; 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol [283]; fluvastatin [215]; matairesinol [284]; mirtazapine and its metabolites [81]; nateglinide [285]; ofloxacin [286]; trihexyphenidyl [287]; pramipexole [85]; propranolol and 4-hydroxypropranolol [288]; sibutramine [249]; vincamine, vinpocetine, and vincadifformine [122]; five ␤-agonists [227]; five ␤-adrenergic antagonists [289]; five ␤-blockers [290]; four basic compounds [61]; six antimalarial drugs [280]; five ␤-lactams [281]; 10 dipeptides and three tripeptides [240]; ruthenium(II) complexes [291]; stimulants [292] Carboxymethylated ␥-CD Vincamine, vinpocetine, and vincadifformine [122]; four antimalarial drugs [280]; two ␤-lactams [281]; five dipeptides and one tripeptide [240]; ruthenium(II) complexes [ [259], helquats [293], ornidazole [98], tolterodine and methoxytolterodine [89], verapamil [92], benzoxazolinonic aminoalcohols [294], two basic drugs [295], five basic drugs [296], seve...…”

“…Sulfated ␤-CD Amlodipine [241], Betti bases [300], borreverine [259], bupivacaine [178], 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone [283], cetirizine [91,301], citalopram [97], hydroxyflavanones [324], fluoxetine [302], helquats [293,303], 4,5-disubstituted imidazoles [304], lorazepam [108,162], 3-hydroxymexiletine [305], modafinil [134,306], nicotine and its related compounds [307], nicotine butyric acid [90], ofloxacin and ornidazole [132], 3,4-dihydroxyphenylalanine [238,[308][309][310], phenylalanine [308], isoprenaline [92], rotigotine and related chiral impurities [252], thioridazine [311], tolterodine and methoxytolterodine [89], tryptophan [312], tyrosine [238,308], benzoxazolinonic aminoalcohols [294], 13 new amphetamine-like designer drugs [313], 12 basic analytes [314], 19 cathinone derivatives [315], impurity of clopidogrel [316], four antimalarial drugs [280], four basic drugs [295], five basic drugs [296], six basic drugs…”

A novel in situ strategy for the preparation of a β‐cyclodextrin/polydopamine‐coated capillary column for capillary electrochromatography enantioseparations

“…In most CE and CEC studies, enantioseparation has been carried out with chiral selectors such as cyclodextrins (CDs) , chiral crown ethers, chiral calixarenes, chiral ligand exchange complexes , macrocyclic antibiotics, protein , chiral surfactants, or chiral metal–organic frameworks . Among these chiral selectors, α‐, β‐, γ‐CDs, and their derivatives have been used extensively in chiral separations .…”

“…The mechanism is based on the inclusion or incorporation of analytes, or at least a part of the analytes, in a hydrophobic basket of the various CDs. Some remaining interactions such as hydrogen bonding, steric interactions, and electrostatic interactions for charged CDs also contribute to chiral recognition . However, CDs often need to be modified into thiolated CDs , sulfated CDs , carboxymethyl‐CDs , or azide‐CDs , so that, during the stationary phase, they will be immobile on the pretreated capillary inner wall.…”