Chiral, pH responsive hydrogels constructed by <i>N</i>
-Acryloyl-alanine and PEGDA/<i>α</i>
-CD inclusion complex: preparation and chiral release ability

Liu, Jie; Cheng, Ru; Deng, Jianping; Wu, Youping

doi:10.1002/pat.3615

Cited by 10 publications

(9 citation statements)

References 51 publications

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“…In a later study, Wu found that chiral hydrogels derived from D-or L-N-acryloyl-alanine (NAA) and inclusion complexes between poly(ethylene glycol) diacrylate (PEGDA) and α-CD could show different rates of adsorption and release for both enantiomers of trans-4hydroxyproline (HP). 251 The hydrogel containing L-NAA preferentially adsorbed D-HP, indicated stronger enantioselective interactions between them. On the other hand, the D-NAA-containing hydrogel showed greater uptake of the opposite guest enantiomer.…”

Section: T H I S C O N T E N T Imentioning

confidence: 96%

“…When a racemic hydrogel comprising equal quantities of ( R )- and ( S )-polymers was used for enantioselective guest release, d - and l -mandelic acid were released at the same rate. In a later study, Wu found that chiral hydrogels derived from d - or l - N -acryloyl-alanine (NAA) and inclusion complexes between poly(ethylene glycol) diacrylate (PEGDA) and α-CD could show different rates of adsorption and release for both enantiomers of trans -4-hydroxyproline (HP) . The hydrogel containing l -NAA preferentially adsorbed d -HP, indicated stronger enantioselective interactions between them.…”

Section: Hydrogel Molecular Sensors and Biosensorsmentioning

confidence: 99%

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Bottom-Up Engineering of Responsive Hydrogel Materials for Molecular Detection and Biosensing

Lim

Goh

Loh

2020

ACS Materials Lett.

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Molecular sensors respond to target molecules in their surroundings to detect and sometimes even quantify their concentrations. Traditionally comprised of small organic molecules or metal complexes, these technologies have been essential to biomedical and environmental monitoring, ensuring human health, safety, and general well-being. In the past two decades, analyte-responsive hydrogels have been an emerging technology receiving vast research attention worldwide. Hydrogels capable of detecting a vast array of analytes, including inorganic ions, carbohydrates, thiols, gases, biomolecules (nucleic acids and proteins), and even microorganisms such as bacteria and viruses, have been developed. With the added advantages of bottom-up design at the molecular level and biocompatibility, molecular detection using hydrogel sensors is typically simple to perform, and hydrogels can be integrated with electronic devices to enhance detection sensitivity, or with biomedical devices for in vitro and in vivo studies. Herein, we discuss a range of innovative strategies that have been developed for engineering hydrogel molecular sensors, with emphasis on "bottom-up" molecular engineering to achieve analyte selectivity and sensitivity.

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Section: T H I S C O N T E N T Imentioning

confidence: 96%

Section: Hydrogel Molecular Sensors and Biosensorsmentioning

confidence: 99%

Bottom-Up Engineering of Responsive Hydrogel Materials for Molecular Detection and Biosensing

Lim

Goh

Loh

2020

ACS Materials Lett.

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“…As an emergency field, actuators composed of responsive materials, which convert external stimuli to mechanical deformation or movement, [1] have gained increased interest in the fields of soft robot, [2] drug delivery vehicles, [3,4] tissue engineering, and biological machines. [5][6][7] According to the external stimuli, actuators are divided into hydraulic, [8] pneumatic, [9] electrical, [10] magnetic, [11] light-driven [12] actuators, and so on.…”

Section: Introductionmentioning

confidence: 99%

Construction of biocompatible bilayered light‐driven actuator composed of rGO/PNIPAM and PEGDA hydrogel

Yang

Zhang

Sun

2020

J of Applied Polymer Sci

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To construct an actuator with biocompatibility and potential use in biomedicine field, a light‐driven actuator composed of reduced graphene oxide (rGO)/poly (N‐isopropyl acrylamide) (PNIPAM) and poly (ethylene glycol) diacrylate (PEGDA) hydrogel is constructed. First, rGO/PNIPAM hydrogel is prepared by free radical polymerization and l‐ascorbic acid reduction, of which the surface temperature increases quickly under near‐infrared (NIR) laser indicating the efficient photothermal conversion of rGO. The results of cytotoxicity tests demonstrate that rGO/PNIPAM is biocompatible and has no obvious toxicity to myoblast line C2C12 cells. Second, bilayer hydrogel composed of rGO/PNIPAM and PEGDA is prepared using a similar method layer‐by‐layer. The bilayer strip bends towards rGO/PNIPAM under NIR laser. The bending is improved after reduction. The laser power density has a strong impact on the bending rate and degree. The reversible bending deformation indicates the structural stability. All the above results approve that the bilayer actuator has great potential to be applied in biomedicine fields such as organ‐on‐chip, drug‐carrier, or surgical aid.

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“…Naturally occurring and synthetic, chiral polymers are commercially used as column chromatography packing materials or membranes for chiral resolution of organic racemic mixtures . These polymers can be obtained through the optically functionalization of a polymer or polymerization of an optically active monomer, which leads to higher functionalization and purity. Hydrogels are lightly crosslinked hydrophilic polymer networks with the ability to absorb and retain a large amount of water .…”

Section: Introductionmentioning

confidence: 99%

“…Hydrogels are lightly crosslinked hydrophilic polymer networks with the ability to absorb and retain a large amount of water . Chiral hydrogels have aroused increasing attention in chirality‐responsive polymers and enantio‐differentiating adsorption/release …”

Section: Introductionmentioning

confidence: 99%

Chiral phosphoric triamide‐based polymers for enantioseparation

Ahmadabad

Pourayoubi

Bakhshi

2019

J of Applied Polymer Sci

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Novel optical isomers of phosphoramide-methacrylate monomers were synthesized and used for the preparation of corresponding polymers and hydrogels as chiral absorbents. In order to direct enantioseparation, two simple and inexpensive methods were designed: (a) immobilization of the chiral polymers on glass beads as packing material for the separation columns and (b) filling of chiral hydrogels in tea bags to fabricate separation bags. The specific rotations for R-and S-monomers were + 22.0 and − 21.8 , while those for R-and S-polymers were + 20.8 and − 22.1 , respectively. The enantioseparation of (AE)-α-methylbenzylamine, DL-alanine, DL-valine, DL-tartaric acid, DL-phenylalanine, and omeprazole was evaluated. The maximum enantioseparation (optical purity) of 97% was observed for (AE)-α-methylbenzylamine by S-hydrogel. Chiral hydrogels resulted in enantioseparations with higher purities (up to 97%) comparing to the chiral polymers, but in longer times (2-3 days). The desorption process easily occurred from the absorbed columns or bags.Phosphoramides with a P( O)(N) segment are attractive to study owing to their extensive applications in the coordination chemistry, catalysts, and medicine. [32][33][34] From our previous studies on phosphorus-oxygen, phosphorus-nitrogen, and phosphorus-sulfur compounds, 35-37 the P O group was found as the best hydrogen-bond acceptor with respect to the other possible acceptor groups, which usually exist in the molecules, typically C O, S O, N─O, P S, ester and ether oxygen atoms, nitrogen, and π-system, examined with X-ray diffraction study, statistical analysis based on the data deposited in the Cambridge structural database (CSD) 38 and quantum chemical calculations in some cases. The structures investigated include achiral, racemate, and chiral single-enantiomer phosphorus compounds. 36,37,39,40 According to Reaxys web-based tool (licensed by Elsevier) for chiral polymers, there is no report about an enantiomeric pair of phosphoric triamide-based polymers, and such polymers seem to be good chiral selectors, due to relatively strong interaction of P O with OH and NH units, as was observed in small molecules model compounds.In this work, levo-and dextro-rotatory isomers with two chiral centers, P( O)(NH-R-(−)CH(CH 3 )C 6 H 5 ) 2 (Cl) and P( O)(NH-S-(−)CH(CH 3 )C 6 H 5 ) 2 (Cl) (1 and 2), have been synthesized and reacted with 2-aminoethylmethacrylate (AEMA) to prepare phosphoric triamides monomers (3 and 4) as chiral selectors. The methacrylate moiety brought the opportunity for the radical or ionic polymerization reactions of these monomers. Through radical polymerization of these novel monomers, a pair of singleenantiomer phosphoric triamide-based polymers (P1 and P2) and hydrogels (H1 and H2) were prepared. In order to direct Additional Supporting Information may be found in the online version of this article.

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Chiral, pH responsive hydrogels constructed by N -Acryloyl-alanine and PEGDA/α -CD inclusion complex: preparation and chiral release ability

Cited by 10 publications

References 51 publications

Bottom-Up Engineering of Responsive Hydrogel Materials for Molecular Detection and Biosensing

Bottom-Up Engineering of Responsive Hydrogel Materials for Molecular Detection and Biosensing

Construction of biocompatible bilayered light‐driven actuator composed of rGO/PNIPAM and PEGDA hydrogel

Chiral phosphoric triamide‐based polymers for enantioseparation

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