Chiral ionic liquid interface as a chiral selector for recognition of propranolol enantiomers: A molecular dynamics simulations study

Sedghamiz, Tahereh; Bahrami, Maryam

doi:10.1016/j.molliq.2019.111441

Cited by 14 publications

(10 citation statements)

References 30 publications

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Section: Introductionmentioning

confidence: 99%

“…The bis(mandelato)borate ([BMB]) anion based ILs are used as selectors for chiral discrimination of propranolol enantiomers [27,28]. Both experimental [26] and computational studies [27,28] showed that [BMB] anions contribute to distinct hydrogen bonding (HB) and π-π stacking interactions with propranolol enantiomers, leading to the formation of propranolol-[BMB] complexes with varied molecular stabilities depending on specific chiralities of [BMB] anions. In another work, Wong and coworkers presented experimental evidences that [BMB] anions are effective resolving agents for resolution of a chemically diverse range of racemic cations via metathesis crystallization [29][30][31].…”

Section: Introductionmentioning

confidence: 99%

“…Besides variations in cation structures, molecular chiralities of spiroborate anions have a significant effect on microstructures and dynamics, mesoscopic liquid morphologies, and macroscopic functionalities of these ILs in tribology, electrochemistry, and pharmaceutical chemistry [25][26][27]. The bis(mandelato)borate ([BMB]) anion based ILs are used as selectors for chiral discrimination of propranolol enantiomers [27,28]. Both experimental [26] and computational studies [27,28] showed that [BMB] anions contribute to distinct hydrogen bonding (HB) and π-π stacking interactions with propranolol enantiomers, leading to the formation of propranolol-[BMB] complexes with varied molecular stabilities depending on specific chiralities of [BMB] anions.…”

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confidence: 99%

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How Molecular Chiralities of Bis(mandelato)borate Anions Affect Their Binding Structures With Alkali Metal Ions and Microstructural Properties in Tetraalkylphosphonium Ionic Liquids

Pei

Laaksonen

et al. 2020

Front. Chem.

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Spiroborate anions based inorganic electrolytes and ionic liquids (ILs) have fascinating electrochemical and tribological properties, and have received widespread ers owing to preferential cation-π interactions. Furthermore, effects of molecular chiralities of [BMB] anions on thermodynamics and microstructural properties of tetraalkylphosphonium [BMB] ILs were studied by performing extensive atomistic interactions. Oxygen atoms in [BMB] anions have competitive hydrogen bonding interactions with hydrogen atoms in cations depending on molecular chiralities and steric hindrance effects of [BMB] anions. However, molecular chiralities of [BMB] anions have negligible effect on liquid densities of tetraalkylphosphonium [BMB] ILs and spatial distributions of boron atoms in anions around phosphorous atoms in cations. Enlarging tetraalkylphosphonium cation sizes leads to enhanced cationanion intermolecular hydrogen bonding and Coulombic interactions due to enhanced segregation of polar groups in apolar networks in heterogeneous IL matrices as verified from scattering structural functions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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How Molecular Chiralities of Bis(mandelato)borate Anions Affect Their Binding Structures With Alkali Metal Ions and Microstructural Properties in Tetraalkylphosphonium Ionic Liquids

Pei

Laaksonen

et al. 2020

Front. Chem.

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“…With the development of industry and the needs of the society, chiral ILs have also achieved considerable development [21]. Chiral ILs have been used in optical resolution, asymmetric synthesis, chiral stationary phase in chromatography, and chiral selectors [22]. To date, most of the reported chiral ILs were those based on chiral cations, only a very limited number of chiral ILs contained chiral anions [23].…”

mentioning

confidence: 99%

New Insight Regarding the Relationship Between Enantioselective Toxicity Difference and Enantiomeric Toxicity Interaction from Chiral Ionic Liquids

Zhou

et al. 2019

IJMS

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Chirality is an important property of molecules. The study of biological activity and toxicity of chiral molecules has important theoretical and practical significance for toxicology, pharmacology, and environmental science. The toxicological significance of chiral ionic liquids (ILs) has not been well revealed. In the present study, the enantiomeric joint toxicities of four pairs of chiral ILs 1-alkyl-3-methylimidazolium lactate to Allivibrio fischeri were systematically investigated by using a comprehensive approach including the co-toxicity coefficient (CTC) integrated with confidence interval (CI) method (CTCICI), concentration-response curve (CRC), and isobole analysis. The direct equipartition ray (EquRay) design was used to design five binary mixtures of enantiomers according to molar ratios of 1:5, 2:4, 3:3, 4:2, and 5:1. The toxicities of chiral ILs and their mixtures were determined using the microplate toxicity analysis (MTA) method. Concentration addition (CA) and independent action (IA) were used as the additive reference models to construct the predicted CRC and isobole of mixtures. On the whole, there was an enantioselective toxicity difference between [BMIM]D-Lac and [BMIM]L-Lac, and [HMIM]D-Lac and [HMIM]L-Lac, while no enantioselective toxicity difference was observed for [EMIM]D-Lac and [EMIM]L-Lac, and [OMIM]D-Lac and [OMIM]L-Lac. Thereinto, the enantiomer mixtures of [BMIM]D-Lac and [BMIM]L-Lac, and [HMIM]D-Lac and [HMIM]L-Lac presented antagonistic action, and the enantiomer mixtures of [EMIM]D-Lac and [EMIM]L-Lac, and [OMIM]D-Lac and [OMIM]L-Lac overall presented additive action. Moreover, the greatest antagonistic toxicity interaction occurred at the equimolar ratio of enantiomers. Based on these results, we proposed two hypotheses, (1) chiral molecules with enantioselective toxicity difference tended to produce toxicity interactions, (2) the highest or lowest toxicity was usually at the equimolar ratio and its adjacent ratio for the enantiomer mixture. These hypotheses will need to be further validated by other enantiomer mixtures.

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“…However, S - and R -enantiomers of propranolol show different efficacy in blocking β receptors. , Chiral discrimination of enantiomers is always a challenging task due to the similarity in the physical properties, such as water solubility, density, and melting and boiling points. Although chiral discrimination technology has made some progress in the past few decades, − the design of a simple system with effective ability in enantioselective sensing of drug molecules still needs further exploration.…”

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confidence: 99%

Efficient Chiral Nanosenor Based on Tip-Modified Nanochannels

et al. 2021

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Enantiomers of various drug molecules have a specific effect on living organisms. Accordingly, developing a sample method for the efficient and rapid recognition of chiral drug enantiomers is of great industrial value and physiological significance. Here, inspired by the structure of ion channels in living organisms, we developed a chiral nanosensor based on an artificial tip-modified nanochannel system that allows efficient selective recognition of chiral drugs. In this system, l-alanine-pillar[5]arenes as selective receptors were introduced on the tip side of conical nanochannels to form an enantioselective “gate”. The selective coefficient of our system toward R-propranolol is 4.96, which is higher than the traditional fully modified nanochannels in this work.

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Chiral ionic liquid interface as a chiral selector for recognition of propranolol enantiomers: A molecular dynamics simulations study

Cited by 14 publications

References 30 publications

How Molecular Chiralities of Bis(mandelato)borate Anions Affect Their Binding Structures With Alkali Metal Ions and Microstructural Properties in Tetraalkylphosphonium Ionic Liquids

How Molecular Chiralities of Bis(mandelato)borate Anions Affect Their Binding Structures With Alkali Metal Ions and Microstructural Properties in Tetraalkylphosphonium Ionic Liquids

New Insight Regarding the Relationship Between Enantioselective Toxicity Difference and Enantiomeric Toxicity Interaction from Chiral Ionic Liquids

Efficient Chiral Nanosenor Based on Tip-Modified Nanochannels

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