Amino‐Acid‐Based Chiral Nanoparticles for Enantioselective Crystallization

Preiß, Laura; Werber, Liora; Fischer, Viktor; Hanif, Sadaf; Landfester, Katharina; Mastai, Yitzhak; Muñoz‐Espí, Rafael

doi:10.1002/adma.201405531

Cited by 98 publications

(79 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Taking advantage of the optical activity of the SiO 2 @P1 core/shell particles, we next utilized them as chiral additives for performing enantioselective crystallization (Scheme B), which currently is an indispensable technique for acquiring enantio‐pure compounds . Enantioselective crystallization was conducted by taking threonine as model chiral compound.…”

Section: Resultsmentioning

confidence: 99%

Seed‐Surface Grafting Precipitation Polymerization for Preparing Microsized Optically Active Helical Polymer Core/Shell Particles and Their Application in Enantioselective Crystallization

Zhao

Lin

Deng

et al. 2018

Macromol. Rapid Commun.

View full text Add to dashboard Cite

Core/shell particles constructed by polymer shell and silica core have constituted a significant category of advanced functional materials. However, constructing microsized optically active helical polymer core/shell particles still remains as a big academic challenge due to the lack of effective and universal preparation methods. In this study, a seed-surface grafting precipitation polymerization (SSGPP) strategy is developed for preparing microsized core/shell particles with SiO as core on which helically substituted polyacetylene is covalently bonded as shell. The resulting core/shell particles exhibit fascinating optical activity and efficiently induce enantioselective crystallization of racemic threonine. Taking advantage of the preparation strategy, novel achiral polymeric and hybrid core/shell particles are also expected.

show abstract

Section: Resultsmentioning

confidence: 99%

Seed‐Surface Grafting Precipitation Polymerization for Preparing Microsized Optically Active Helical Polymer Core/Shell Particles and Their Application in Enantioselective Crystallization

Zhao

Lin

Deng

et al. 2018

Macromol. Rapid Commun.

View full text Add to dashboard Cite

show abstract

“…When chiral substituents are regularly arranged, it is unlikely that a short distance between chiral moiety and main chain is always essential to transcript chirality from side chain to the main chain. In addition, researchers have made different chiral polymers carrying amino acid moiety in the side chain by controlled polymerization techniques, and applied those for various applications, such as in enantioselective crystallization, asymmetric organocatalysis …”

Section: Chiroptical Propertiesmentioning

confidence: 99%

Side‐Chain Amino‐Acid‐Derived Cationic Chiral Polymers by Controlled Radical Polymerization

Bauri

Roy

2015

Macro Chemistry & Physics

View full text Add to dashboard Cite

There is an increased interest in incorporation of naturally occurring amino acid/peptide moieties into the synthetic polymeric chain. Because of functional group diversity in amino acids, it is possible to synthesize a large variety of well-defi ned functional amino-acid/peptide-based optically active polymers with varied polymer length, composition, and architectures using available controlled/living polymerization techniques. The amino acid inclusion into the synthetic polymer chains may offer several advantages such as (a) functional group availability which not only results in improved hydrophilicity and possible interactions with proteins and genes but also facilitates further modifi cation with bioactive molecules, (b) introduces chirality, and (c) makes room for noncovalent interactions to form hierarchical superstructures. From the long past, amino acids have been extensively incorporated in the main chain of biodegradable polymers, and their biological importance have been evaluated. Besides, various sidechain amino-acid/peptide-bearing polymers have been synthesized and used for different purposes. In this article, utilization of different controlled/living polymerization methods to prepare various side-chain amino acid/peptide pendant polymers will be discussed, mainly focusing on cationic chiral polymeric architectures and 3D gel networks by reversible addition-fragmentation chain transfer polymerization.

show abstract

“…As nanomedicine often refers to device particles <200 nm, we have developed a polymeric drug delivery system following the size constraints of nanoparticles, that is biocompatible, biodegradable, economical in their design, and competent for enhancing the therapeutic efficiency of drug molecules through sustained delivery approach. A number of synthetic approaches for N‐acryloyl amino acid and ester monomer have been reported for the design of nanocapsules with different sizes . Amino acid derived high‐molecular‐weight polymer contains many functional groups such as OH, NH 2 , and COOH.…”

Section: Introductionmentioning

confidence: 99%

P‐LME polymer nanocapsules stimulate naïve macrophages and protect them from oxidative damage during controlled drug release

Yamala

Nadella

Mastai

et al. 2019

J of Applied Polymer Sci

Self Cite

View full text Add to dashboard Cite

Using polymer‐based nanocapsules as novel drug delivery systems have gained significant importance. In this work, we present poly‐(N‐Acryloyl L‐Leucine methyl ester [pLME]) nanocapsules with hollow core (pLME) of size approximately ~160 nm (dia.) synthesized for the first time through the miniemulsion approach. Our study reveals that pLME are biocompatible and immune stimulatory in nature on macrophages, which are decisive for host immunity. These nanocapsules are effective for encapsulating and sustainable release of drug (SNP; nitric oxide donor) at a high extent ~1.04 μM mg‐. pLME also demonstrated their potential of stimulating naïve macrophages toward the M1 phenotype for extended period of time indicating their adjuvant activity on immune system. Our data also demonstrated their antioxidant potential toward H2O2‐induced oxidative stress in macrophages. These results suggest pLME as an effective drug/vaccine delivery material with immune adjuvant and cytoprotective efficacy warranting its pharmacological application. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020, 137, 48363.

show abstract

Amino‐Acid‐Based Chiral Nanoparticles for Enantioselective Crystallization

Cited by 98 publications

References 27 publications

Seed‐Surface Grafting Precipitation Polymerization for Preparing Microsized Optically Active Helical Polymer Core/Shell Particles and Their Application in Enantioselective Crystallization

Seed‐Surface Grafting Precipitation Polymerization for Preparing Microsized Optically Active Helical Polymer Core/Shell Particles and Their Application in Enantioselective Crystallization

Side‐Chain Amino‐Acid‐Derived Cationic Chiral Polymers by Controlled Radical Polymerization

P‐LME polymer nanocapsules stimulate naïve macrophages and protect them from oxidative damage during controlled drug release

Contact Info

Product

Resources

About