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PH-Sensitive Chiral Hydrogels Consisting Of Poly(N-acryloyl-l-alanine) And β-Cyclodextrin: Preparation And Enantiodifferentiating Adsorption And Release Ability

P. Xie, X. Liu, Ru Cheng, Y. Wu, Jianping Deng
Published 2014 · Chemistry

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Both chiral hydrogels and pH-sensitive hydrogels have received considerable attention in recent years. In the present study, we combined the two intriguing concepts, i.e., chirality and pH sensitivity, in one single hydrogel. Such hydrogels were prepared via free radical copolymerization using chiral N-acryloyl-l-alanine (NAA) as monomer, the inclusion complex of glycidyl methacrylate (GMA) and hydroxypropyl-β-cyclodextrin (HP-β-CD) as comonomer, N,N′-methylenebis(acrylamide) as cross-linking agent, and K2S2O8 as initiator. The hydrogels were successfully obtained and exhibited remarkable swelling in water and pH responsivity. The hydrogels were characterized by circular dichroism and UV–vis absorption spectroscopies, demonstrating the optical activity of the hydrogels. The hydrogels performed chiral recognition and enantiodifferentiating release abilities toward proline enantiomers, in which l-proline was preferentially adsorbed whereas d-proline was preferentially released. The present study established...
This paper references
10.1016/j.jhazmat.2010.07.055
The removal of heavy metal ions from aqueous solutions by novel pH-sensitive hydrogels.
U. Yildiz (2010)
10.1021/la303388s
Salt-induced control of supramolecular order in biocatalytic hydrogelation.
S. Roy (2012)
10.1039/B602279K
Hydrogel behavior of a sugar-based gelator by introduction of an unsaturated moiety as a hydrophobic group.
J. Jung (2006)
10.1016/j.biomaterials.2012.09.018
Controlled delivery of recombinant adeno-associated virus serotype 2 using pH-sensitive poly(ethylene glycol)-poly-L-histidine hydrogels.
Y. Zeng (2012)
10.1016/j.jcis.2011.02.006
Simple chiral urea gelators, (R)- and (S)-2-heptylurea: their gelling ability enhanced by chirality.
Jong-Uk Kim (2011)
10.1021/MA400276U
Chiral Packing of Cholesteryl Group as an Effective Strategy To Get Low Molecular Weight Supramolecular Hydrogels in the Absence of Intermolecular Hydrogen Bond
F. Xu (2013)
10.1039/C1SM05907F
Multicomponent hydrogels from enantiomeric amino acid derivatives: helical nanofibers, handedness and self-sorting
Bimalendu Adhikari (2011)
10.1016/j.ijbiomac.2012.09.018
Controlled release of 5-aminosalicylicacid from chitosan based pH and temperature sensitive hydrogels.
M. S. Bostan (2013)
10.1016/S0731-7085(02)00527-7
Investigation of chromatographic performances and binding characteristics of BSA-encapsulated capillary column prepared by the sol-gel method.
Masaru Kato (2003)
10.1002/chem.201200707
Self-assembly studies of a chiral bisurea-based superhydrogelator.
Francisco Rodríguez-Llansola (2012)
10.1039/C2SM26442K
Novel pH responsive hydrogels for controlled cell adhesion and triggered surface detachment
Xiaoqiu Dou (2012)
10.1039/B916310G
Temperature- and pH-sensitive hydrogels to immobilize heparin-modified PEI/DNA complexes for sustained gene delivery
Chaohua Hu (2009)
10.1016/J.POLYMER.2013.01.050
Biodegradable pH-responsive polyacrylic acid derivative hydrogels with tunable swelling behavior for oral delivery of insulin
Xiaoye Gao (2013)
10.1021/la904540x
A smart supramolecular hydrogel of N(alpha)-(4-n-alkyloxybenzoyl)-L-histidine exhibiting pH-modulated properties.
Trilochan Patra (2010)
10.1021/la034694b
Inter/Intramolecular Interaction and Chiral Recognition of Water-Soluble Copolymers and Their Hydrogels Containing an Optically Active Group
D. Nakayama (2003)
10.1016/J.REACTFUNCTPOLYM.2011.06.006
Synthesis of optically active macroporous poly(N-isopropylacrylamide) hydrogels with helical poly(N-propargylamide) for chiral recognition of amino acids
L. Li (2011)
10.1039/C2PY20546G
Chiral polymeric microspheres grafted with optically active helical polymer chains: a new class of materials for chiral recognition and chirally controlled release
C. Song (2013)
10.1021/bm301844u
Self-healing mussel-inspired multi-pH-responsive hydrogels.
M. Krogsgaard (2013)
10.1021/ja908721t
Amino acid based metal-organic nanofibers.
I. Imaz (2009)
10.1002/chem.201201217
Dramatic specific-ion effect in supramolecular hydrogels.
S. Roy (2012)
10.1016/J.CARBPOL.2009.08.024
Synthesis and characteristics of pH-sensitive semi-interpenetrating polymer network hydrogels based on konjac glucomannan and poly(aspartic acid) for in vitro drug delivery
C. Liu (2010)
10.1021/la301541d
Functionalization of multiwalled carbon nanotubes and their pH-responsive hydrogels with amyloid fibrils.
C. Li (2012)
10.1021/la300098q
Helical assembly of azobenzene-conjugated carbohydrate hydrogelators with specific affinity for lectins.
Y. Ogawa (2012)
10.1021/MA035272B
Liquid Crystalline Hydrogels: Mesomorphic Behavior of Amphiphilic Polyacrylates Bearing Cholesterol Mesogen
T. Kaneko (2004)
10.1002/POLA.22766
Synthesis and chiral recognition properties of poly(N‐propargylamide) gels derived from ornithine and lysine
Ruiyuan Liu (2008)
10.1016/j.biortech.2012.10.157
Preparation and application of abietic acid-derived optically active helical polymers and their chiral hydrogels.
F. Yao (2013)
10.1002/ADFM.200700527
Ultrasensitive Specific Stimulant Assay Based on Molecularly Imprinted Photonic Hydrogels
X. Hu (2008)
10.1021/JA029036C
Chiral stimuli-responsive gels: helicity induction in poly(phenylacetylene) gels bearing a carboxyl group with chiral amines.
Hidetoshi Goto (2003)
10.1021/JA042840+
A [2]rotaxane capped by a cyclodextrin and a guest: formation of supramolecular [2]rotaxane polymer.
M. Miyauchi (2005)
10.1002/MACP.200800254
Assembled Structures and Chiroptical Properties of Amphiphilic Block Copolymers Synthesized by RAFT Polymerization of N‐Acryloyl‐L‐alanine
Hideharu Mori (2008)
10.1016/J.MATCHEMPHYS.2009.03.005
Radiation synthesis of pH-sensitive hydrogels from β-cyclodextrin-grafted PEG and acrylic acid for drug delivery
J. Chen (2009)
10.1021/MA301250U
Chiral Microspheres Consisting Purely of Optically Active Helical Substituted Polyacetylene: The First Preparation via Precipitation Polymerization and Application in Enantioselective Crystallization
Dongyue Zhang (2012)
10.1002/marc.201100557
Microspheres consisting of optically active helical substituted polyacetylenes: preparation via suspension polymerization and their chiral recognition/release properties.
Bo Chen (2011)
10.1039/C3TC31802H
Optically active, magnetic gels consisting of helical substituted polyacetylene and Fe3O4 nanoparticles: preparation and chiral recognition ability
D. Liu (2013)
10.1002/chir.22040
Chiral chemical absorption property of a cross-linked poly(N-isopropyl acrylamide-co-sodium acrylate) thermoresponsive smart gel.
D. S. Bag (2012)
10.1039/C2RA21506C
Maltose-based gelators having azobenzene as light-sensitive unit
M. Clemente (2012)
10.1002/POLA.22554
Using glycidyl methacrylate as cross‐linking agent to prepare thermosensitive hydrogels by a novel one‐step method
J. Deng (2008)
10.1021/MA0300950
Stumuli-responsive organogel based on poly(N-propargylamide)
R. Nomura (2003)
10.1039/C0PY00028K
Synthesis and chiral recognition of optically active hydrogels containing helical polymer chains
X. Du (2010)
10.1039/C2TB00021K
Polyol induced interpenetrating networks: chitosan-methylmethacrylate based biocompatible and pH responsive hydrogels for drug delivery system.
A. Vashist (2013)
10.1016/J.JCIS.2007.06.013
Formation mechanism of supramolecular hydrogels in the presence of L-phenylalanine derivative as a hydrogelator.
X. Fu (2007)
10.1039/C2PY20086D
Biodegradable, pH-sensitive P(CL-Pluronic-CL-co-MAA-MEG) hydrogel for 5-aminosalicylic acid delivery
K. Wang (2012)
10.1002/ADMA.200600040
Transduction of Volume Change in pH-Sensitive Hydrogels with Resonance Energy Transfer†
J. Mao (2006)
10.1039/C0SM00094A
Tuning responsiveness and structural integrity of a pH responsive hydrogel using a poly(ethylene glycol) cross-linker
J. H. Jeong (2010)
10.1039/b800409a
Lost in translation? Chirality effects in the self-assembly of nanostructured gel-phase materials.
D. Smith (2009)
10.1039/c0cc00891e
Creating chirality in the inner walls of silica nanotubes through a hydrogel template: chiral transcription and chiroptical switch.
J. Jiang (2010)
10.1021/JP073275A
A new pH and thermo-responsive chiral hydrogel for stimulated release.
B. V. Shankar (2007)
10.1021/bm301598g
Enhancing biocompatibility of D-oligopeptide hydrogels by negative charges.
Laura L Hyland (2013)
10.1021/JA036817K
Supramolecular hydrogels respond to ligand-receptor interaction.
Y. Zhang (2003)
10.1021/nl2011627
"Nanohybrids" based on pH-responsive hydrogels and inorganic nanoparticles for drug delivery and sensor applications.
A. Riedinger (2011)
10.1002/MACP.201200729
Chiral pH-Responsive Amphiphilic Polymer Co-networks: Preparation, Chiral Recognition, and Release Abilities
Lu Shi (2013)
10.1039/B908755A
Highly selective iodide-responsive gel–sol state transition in supramolecular hydrogels
Jiang-Shan Shen (2009)
10.1016/J.SYNTHMET.2009.08.002
Nanocomposite hydrogels—Controlled synthesis of chiral polyaniline nanofibers and their inclusion in agarose
X. Zhang (2009)



This paper is referenced by
10.1021/ACS.IECR.6B01031
Materials Established for Enantioselective Release of Chiral Compounds
Huli Yu (2016)
10.1016/j.jconrel.2020.05.019
Recent advances, challenges and perspectives in enantioselective release.
Lujie Song (2020)
10.1039/C6RA04762A
Hydrophobic association hydrogels based on N-acryloyl-alanine and stearyl acrylate using gelatin as emulsifier
Z. Cui (2016)
10.1002/PAT.3615
Chiral, pH responsive hydrogels constructed by N‐Acryloyl‐alanine and PEGDA/α‐CD inclusion complex: preparation and chiral release ability
J. Liu (2016)
10.1016/J.CEJ.2018.03.076
Polylactide-based chiral particles with enantio-differentiating release ability
J. Liang (2018)
10.1021/jo502451k
Pd-catalyzed direct C-H bond sulfonylation of azobenzenes with arylsulfonyl chlorides.
Duo Zhang (2015)
10.1016/J.POLYMER.2015.05.034
Chiral, pH-sensitive polyacrylamide hydrogels: Preparation and enantio-differentiating release ability
R. Cheng (2015)
10.1021/acsami.8b09999
HP-β-CD Functionalized Fe3O4/CNPs-Based Theranostic Nanoplatform for pH/NIR Responsive Drug Release and MR/NIRFL Imaging-Guided Synergetic Chemo/Photothermal Therapy of Tumor.
Saijie Song (2018)
10.1002/APP.48034
Chiral phosphoric triamide‐based polymers for enantioseparation
F. K. Ahmadabad (2019)
10.1039/C7PY02014G
Amino acid-derived stimuli-responsive polymers and their applications
Kamal Bauri (2018)
10.1039/C6TB01757F
Chiral porous hybrid particles constructed by helical substituted polyacetylene covalently bonded organosilica for enantioselective release.
J. Liang (2016)
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