Surface‐imprinted microspheres prepared by a template‐oriented method for the chiral separation of amlodipine

Lai, Shenzhi; Ouyang, Xiaoli; Cai, Changqun; Xu, Wensheng; Chen, Chunyan; Chen, Xiaoming

doi:10.1002/jssc.201700076

Cited by 11 publications

(7 citation statements)

References 25 publications

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“…In the second stage, the weight of PSMIPs, SMIPT, and Mal‐β‐CD reduced to approximately 50, 30, and 15% of the original weight, respectively. The different weight loss of PSMIPs and SMIPT could be attributed to Mal‐β‐CD imprinted into the surface of functionalized silica particles . Similar results were obtained by Gong et al.…”

Section: Resultssupporting

confidence: 85%

“…In the second stage, the weight of PSMIPs, SMIPT, and Mal-β-CD reduced to approximately 50, 30, and 15% of the original weight, respectively. The different weight loss of PSMIPs and SMIPT could be attributed to Mal-β-CD imprinted into the surface of functionalized silica particles [29]. Similar results were obtained by Gong et al [21], who reported that the weight loss of PSMIPs between 300 and 650 • C was caused by the removal of organic compounds in the surface imprinted layer.…”

Section: Stability and Reusability Of Psmipssupporting

confidence: 78%

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Photoirradiation surface molecularly imprinted polymers for the separation of 6‐O‐α‐d‐maltosyl‐β‐cyclodextrin

Fan

Wang

Meng

et al. 2017

J of Separation Science

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Photoirradiation surface molecularly imprinted polymers for the separation of 6-O-α-d-maltosyl-β-cyclodextrin were synthesized using functionalized silica as a matrix, 4-(phenyldiazenyl)phenol as a light-sensitive monomer, and 6-O-α-d-maltosyl-β-cyclodextrin as a template. Fourier transform infrared spectroscopy results indicated that 4-(phenyldiazenyl)phenol was grafted onto the surface of functionalized silica. The obtained imprinted polymers exhibited specific recognition toward 6-O-α-d-maltosyl-β-cyclodextrin. Equilibrium binding experiments showed that the photoirradiation surface molecularly imprinted polymers obtained the maximum adsorption amount of 6-O-α-d-maltosyl-β-cyclodextrin at 20.5 mg/g. In binding kinetic experiments, the adsorption reached saturation within 2 h with binding capacity of 72.8%. The experimental results showed that the adsorption capacity and selectivity of imprinted polymers were effective for the separation of 6-O-α-d-maltosyl-β-cyclodextrin, indicating that imprinted polymers could be used to isolate 6-O-α-d-maltosyl-β-cyclodextrin from a conversion mixture containing β-cyclodextrin and maltose. The results showed that the imprinted polymers prepared by this method were very promising for the selective separation of 6-O-α-d-maltosyl-β-cyclodextrin.

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Section: Resultssupporting

confidence: 85%

Section: Stability and Reusability Of Psmipssupporting

confidence: 78%

Photoirradiation surface molecularly imprinted polymers for the separation of 6‐O‐α‐d‐maltosyl‐β‐cyclodextrin

Fan

Wang

Meng

et al. 2017

J of Separation Science

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“…Recently, Lai et al . synthesized chiral imprinted microspheres that showed 11.3 % enantiomeric excess (ee) and surface‐imprinted microspheres provided 13.8% ee of the drug (S)‐amlodipine . Another example of chiral separation is enantioselective crystallization on the surface of chiral polymeric microspheres, based on polystyrene, which led to as much as 25 % ee enrichment of L‐valine .…”

Section: The Results Of Optical Rotation and CD Measurementsa At 25 °mentioning

confidence: 99%

A New Approach to Chiral Enrichment by Exposure of Racemates of Amino Acids to Sonochemically‐Prepared BSA Microspheres

et al. 2017

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This preliminary study describes a one-step sonochemical formation of Bovine Serum Albumin (BSA) microspheres and their chiral interaction with several amino acids. Partial separation between enantiomers of various amino acids was accomplished by the interaction of these microspheres with solutions of racemic amino acids. The highest rate of enantiomeric enrichment was attained for D,L-cysteine, where 59% enantiomeric excess (ee) of the L-cysteine was measured. This indicates the preferrential interaction of the BSA microspheres with the D-enantiomer of cystein. No chiral activity was observed for unsonicated BSA molecules. All other D,L-amino acids that were examined provided enrichment of the Denantiomer albeit in lower ee values. D,L-cysteine interacted with the BSA microspheres leading to L-enantioselective enrichment up to 59 % ee at room tempertaure and 72% at 5 8C. Chiral enrichment was also carried out succesfully with other protein microspheres such as Avidin microspheres. In this case up to 41 % ee was acheived on interaction with DLphenylalanine. Our simple and facile method opens a new window for enantiomeric separation of racemic compounds.Enantioselective separation of racemates still presents a significant challenge in multidisciplinary scientific research, and methods to obtain enantiomerically-enriched chiral compounds are important for the development of pharmaceuticals, [1] agrochemicals and food additives. Moreover, such materials can also function as supramolecular helices, [2] chiral sensors, [3][4][5] biomimetic materials, [6] chiral asymmetric catalysts, [7,8] and precursors in the design of bioactive chiral drugs. [1,9] More than half of the drugs currently in use are chiral compounds and yet, a large number of them are marketed as racemates so that chiral enrichment of racemic mixtures is important. However, chiral enrichment still relies in part on chromatographic techniques or selective crystallization. The interaction between proteins and simple racemic molecules leading to chiral enrichment has not yet been reported and is a highly desirable process. We report here the first examples of enantiomeric enrichment of amino acids by exposure of their racemates in solution to the chiral surfaces of microspheres of the protein bovine serum albumin (BSA), prepared by sonication. By contrast, no chiral separation was observed using unsonicated BSA molecules.Chirality is a key factor in many molecular recognition processes of naturally occurring materials, such as proteins, carbohydrates and DNA. [10,11] We envisioned that a readily available natural protein like BSA, which contains several Lamino acids, when transformed into solid microspheres, displaying exposed chiral surfaces, could interact enantioselectively with some D,L-amino acids in solution, resulting in chiral enrichment of one enantiomer by covalent or non-covalent interactions. Asymmetric non-covalent interactions play an important role in biocatalysis in nature. Recently, a great deal of progress has been achieved in exploiting ...

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“…Functional polymeric microspheres, which are often used in chemical catalysis and adsorption, have some special advantages, including a large specific surface area, strong adsorption capacity, surface reaction ability, and ease of modification [1,2], tumor embolization [3,4], information transfer [5], chromatographic separation [6], and biomedicine [7]. Transcatheter arterial embolization (TAE) was first reported by Yamamoto et al [8] in 1991, which was an effective technique for the insertion of a catheter into a target tissue or organ.…”

Section: Introductionmentioning

confidence: 99%

Surface Modification of Poly(lactic-co-glycolic acid) Microspheres with Enhanced Hydrophilicity and Dispersibility for Arterial Embolization

Wang

Ren

2019

Materials

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In this study, a series of poly(lactic-co-glycolic acid) (PLGA) microspheres with different particle sizes for arterial embolization surgery were prepared. The polydopamine (PDA) and polydopamine/polyethyleneimine (PDA/PEI) were respectively coated on the PLGA microspheres as shells, in order to improve the hydrophilicity and dispersibility of PLGA embolization microspheres. After modification, with the introduction of PDA and PEI, many hydrophilic hydroxyl and amine groups appeared on the surface of the PLGA@PDA and PLGA@PDA/PEI microspheres. SEM images showed the morphologies, sizes, and changes of the as-prepared microspheres. Meanwhile, the XPS and FT-IR spectra demonstrated the successful modification of the PDA and PEI. Water contact angles (WCAs) of the PLGA@PDA and PLGA@PDA/PEI microspheres became smaller, indicating a certain improvement in surface hydrophilicity. In addition, the results of in vitro cytotoxicity showed that modification had little effect on the biosafety of the microspheres. The modified PLGA microspheres suggest a promising prospective application in biomedical field, as the modified microspheres can reduce difficulties in embolization surgery.

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Surface‐imprinted microspheres prepared by a template‐oriented method for the chiral separation of amlodipine

Cited by 11 publications

References 25 publications

Photoirradiation surface molecularly imprinted polymers for the separation of 6‐O‐α‐d‐maltosyl‐β‐cyclodextrin

Photoirradiation surface molecularly imprinted polymers for the separation of 6‐O‐α‐d‐maltosyl‐β‐cyclodextrin

A New Approach to Chiral Enrichment by Exposure of Racemates of Amino Acids to Sonochemically‐Prepared BSA Microspheres

Surface Modification of Poly(lactic-co-glycolic acid) Microspheres with Enhanced Hydrophilicity and Dispersibility for Arterial Embolization

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