Enantiomeric separations of chiral pharmaceuticals using chirally modified tetrahexahedral Au nanoparticles

Shukla, Nisha; Yang, Dian; Gellman, Andrew J.

doi:10.1016/j.susc.2015.10.061

Cited by 16 publications

(21 citation statements)

References 19 publications

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“…In principle, the addition of a racemic probe to the solution should induce no change in optical rotation, unless that probe interacts enantiospecifically with the chiral Au-NPs such that one enantiomer adsorbs preferentially on the Au-NP surface. Detection of this separation by optical polarimetry also requires that the specific optical rotation constant of the adsorbed probe enantiomer differs from its value in solution [ 12 , 13 ].…”

Section: Resultsmentioning

confidence: 99%

“…In previous work, we have shown that L- and D-cysteine (Cys, HO 2 CCH(NH 2 )CH 2 SH) modified surfaces of Au-NPs are capable of enantiospecific adsorption of racemic propylene oxide (PO) [ 11 , 12 ] and the chiral pharmaceutical propranolol hydrochloride [ 13 ]. In these studies, Au-NPs were either spherical or tetrahexahedral (24-sided) in shape.…”

Section: Introductionmentioning

confidence: 99%

“…Different chiral ligands have different optical rotations and different capacities for adsorption and interaction with chiral probe molecules. We have substituted the D-/L-Cys ( Figure 1 a) used as a chiral surface modifier in our past work [ 11 , 12 , 13 ] with D-/L-penicillamine (Pen, HO 2 CCH(NH 2 )C(CH 3 ) 2 SH) ( Figure 1 b). In our notation, D-/L-denotes either pure enantiomer, while DL- denotes use of the racemic mixture.…”

Section: Introductionmentioning

confidence: 99%

“…The second direction in which this work expands on our prior accomplishments is by documenting the effect of adsorption time on enantioselective adsorption of racemic RS-PO on chirally modified Au-NPs. In the past, enantioselective adsorption was studied within one hour of exposure of the chiral NPs to the chiral probe PO [ 11 , 12 , 13 , 14 ]. Here, we find that the equilibration of PO on Pen/Au-NP requires ~18 h of exposure.…”

Section: Introductionmentioning

confidence: 99%

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Chiral Separation of rac-Propylene Oxide on Penicillamine Coated Gold NPs

2020

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The surfaces of chemically synthesized spherical gold NPs (Au-NPs) have been modified using chiral L- or D-penicillamine (Pen) in order to impart enantioselective adsorption properties. These chiral Au-NPs have been used to demonstrate enantioselective adsorption of racemic propylene oxide (PO) from aqueous solution. In the past we have studied enantioselective adsorption of racemic PO on L- or D-cysteine (Cys)-coated Au-NPs. This prior work suggested that adsorption of PO on Cys-coated Au-NPs equilibrates within an hour. In this work, we have studied the effect of time on the enantioselective adsorption of racemic PO from solution onto chiral Pen/Au-NPs. Enantioselective adsorption of PO on chiral Pen/Au-NPs is time-dependent but reaches a steady state after ~18 h at room temperature. More importantly, L- or D-Pen/Au-NPs are shown to adsorb R- or S-PO enantiospecifically and to separate the two PO enantiomers from racemic mixtures of RS-PO.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chiral Separation of rac-Propylene Oxide on Penicillamine Coated Gold NPs

2020

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“…In addition, the potential of metal NPs in separation science has been already well recognized due to their easy synthesis procedure, large s / v ratio, controllable particle size, narrow size distribution, extraordinary biocompatibility, molecular detection properties, etc. [24,89,125].…”

Section: Enantiomeric Separation By Chiral Nanoparticlesmentioning

confidence: 99%

Enantiomeric Recognition and Separation by Chiral Nanoparticles

et al. 2019

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Chiral molecules are stereoselective with regard to specific biological functions. Enantiomers differ considerably in their physiological reactions with the human body. Safeguarding the quality and safety of drugs requires an efficient analytical platform by which to selectively probe chiral compounds to ensure the extraction of single enantiomers. Asymmetric synthesis is a mature approach to the production of single enantiomers; however, it is poorly suited to mass production and allows for only specific enantioselective reactions. Furthermore, it is too expensive and time-consuming for the evaluation of therapeutic drugs in the early stages of development. These limitations have prompted the development of surface-modified nanoparticles using amino acids, chiral organic ligands, or functional groups as chiral selectors applicable to a racemic mixture of chiral molecules. The fact that these combinations can be optimized in terms of sensitivity, specificity, and enantioselectivity makes them ideal for enantiomeric recognition and separation. In chiral resolution, molecules bond selectively to particle surfaces according to homochiral interactions, whereupon an enantiopure compound is extracted from the solution through a simple filtration process. In this review article, we discuss the fabrication of chiral nanoparticles and look at the ways their distinctive surface properties have been adopted in enantiomeric recognition and separation.

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Application of nanoparticles in chiral analysis and chiral separation

et al. 2021

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Chiral molecules in relation to particular biological roles are stereoselective. Enantiomers differ significantly in their biochemical responses in biological environment. Despite the current advancement in drug discovery and pharmaceutical biotechnology, the chiral separation of some racemic mixtures continues to be one of the greatest challenges, because the available techniques are too costly and time consuming for the assessment of therapeutic drugs in the early stages of development worldwide. Various nanoparticles became one of the most investigated and explored nanotechnology‐derived nanostructures especially in chirality where several studies are reported to improve enantiomeric separation of different racemic mixtures. The production of surface‐modified nanoparticles has contributed to these limitations in terms of sensitivity, accuracy, and enantioselectivity that can be optimized and therefore makes these surface‐modified nanoparticles convenient for enantiomeric identification and separation.

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Enantiomeric separations of chiral pharmaceuticals using chirally modified tetrahexahedral Au nanoparticles

Cited by 16 publications

References 19 publications

Chiral Separation of rac-Propylene Oxide on Penicillamine Coated Gold NPs

Chiral Separation of rac-Propylene Oxide on Penicillamine Coated Gold NPs

Enantiomeric Recognition and Separation by Chiral Nanoparticles

Application of nanoparticles in chiral analysis and chiral separation

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