60984-63-6Relevant articles and documents
Electrochemical redox responsive polymeric micelles formed from amphiphilic supramolecular brushes
Feng, Anchao,Yan, Qiang,Zhang, Huijuan,Peng, Liao,Yuan, Jinying
, p. 4740 - 4742 (2014)
The end-decorated homopolymer poly(ε-caprolactone)-ferrocene threaded onto a β-cyclodextrin-functionalized main-chain polymer can form a class of amphiphilic noncovalent graft copolymers based on the host-guest interactions of the terminal groups on the side chains. These new supramolecular polymer brushes can further self-assemble into micellar aggregates that exhibit reversible assembly and disassembly behavior under an electrochemical redox trigger, which opens up a new route to building dynamic block copolymer topologies. This journal is the Partner Organisations 2014.
Star polymers with both temperature sensitivity and inclusion functionalities
Liu, Yu-Yang,Zhong, Yao-Bing,Nan, Jiang-Kun,Tian, Wei
, p. 10221 - 10230 (2010)
We designed and synthesized novel star poly(N-isopropylacrylamide) (star-PNIPAm) and star-PNIPAm with cyclodextrin (CD) end groups (star-PNIPAm-CD) by atom transfer radical polymerization (ATRP). In the synthesis, β-CD-core with 21 initiation sites, heptakis[2,3,6-tri-O-(2- chloropropionyl)]-β-cyclodextrin (21Cl-β-CD), was first synthesized by the reaction of β-CD with 2-chloropropionyl chloride (CPC). Then, 21-arm star-PNIPAm (PDI = 1.03) was synthesized by ATRP of N-isopropylacrylamide (NIPAm) initiated via 21Cl-β-CD. Finally, a star-PNIPAm-CD (PDI = 1.02) was synthesized by ATRP of a monovinyl β-CD (GMA-EDA-β-CD) initiated via star-PNIPAm. The obtained star-PNIPAm and star-PNIPAm-CD were characterized by means of SEC/MALLS, NMR, IR, and DSC. By using 8-anilino-1-naphthalenesulfonic acid ammonium salt hydrate (ANS), 1-adamantanamine hydrochloride (ADA-NH 3Cl), and ibuprofen sodium salt (ibuprofen-Na) as guest molecules, thermal sensitivity and inclusion behaviors of the star polymers were investigated by fluorescence spectrophotometer and DLS. It is found that the star polymers can combine both thermal sensitivity of PNIPAm and inclusion behavior of β-CD. Interestingly, the star polymers can self-assembly to form nanosized aggregates in aqueous solution above their LCSTs. The self-assembly behavior shows molecular recognition capability. And formation and dissociation of the nanosized aggregation can change reversibly by changing temperature above and below the LCST.
Thio[2-(benzoylamino)ethylamino]-β-CD fragment modified gold nanoparticles as recycling extractors for [60]fullerene
Liu, Yu,Yang, Ying-Wei,Chen, Yong
, p. 4208 - 4210 (2005)
Gold particles are modified with surface-attached bis(β-cyclodextrin)s bearing S-S bridges to give water-soluble cyclodextrin-modified gold nanoparticles, which are successfully used as recycling extractors for [60]fullerene. The Royal Society of Chemistry 2005.
β-Cyclodextrin-modified hybrid magnetic nanoparticles for catalysis and adsorption
Kang, Yan,Zhou, Lilin,Li, Xia,Yuan, Jinying
, p. 3704 - 3710 (2011)
β-Cyclodextrin-modified hybrid magnetic nanoparticles (Fe 3O4@SiO2-PGMACD) were synthesized via the combination of atom transfer radical polymerization on the surfaces of silica coated iron oxide particles (Fe3O4@SiO2) and ring-opening reaction of epoxy groups. The feasibility of using Fe 3O4@SiO2-PGMACD as separable immobilized catalyst and adsorbent was demonstrated. It was found: (1) the prepared Fe 3O4@SiO2-PGMACD could be used as catalyst in substrate-selective oxidation of alcohols system and the catalytic efficiency was close to pure β-Cyclodextrin of equal quantity; (2) the resulting particles appeared remarkably dominant adsorption capacity compared with poly(glycidyl methacrylate) grafted magnetic nanoparticles (Fe3O 4@SiO2-PGMA) in the removal of bisphenol A from aqueous solutions. The results suggest that the novel fabricated nanoparticles could serve as bifunctional materials in catalysis or adsorption and subsequently become potential multifunctional materials. The Royal Society of Chemistry 2011.
Synthesis of novel indolyl modified β-cyclodextrins and their molecular recognition behavior controlled by the solution's pH value
Liu, Yu,You, Chang-Cheng,He, Song,Chen, Guo-Song,Zhao, Yan-Li
, p. 463 - 469 (2002)
In order to investigate the effects of substituent and tether length in molecular recognition, three novel indolyl-contained β-cyclodextrin derivatives were synthesized by the condensation of indol-3-ylbutyric acid with the corresponding oligo(aminoethylamino)-β-cyclodextrin in the presence of DCC. Their molecular recognition behavior with some representative dye guests, i.e. Acridine Red, Rhodamine B, Neutral Red, Brilliant Green and Methyl Orange, was studied by using absorption, fluorescence and circular dichroism spectrometry. From the results of induced circular dichroism spectra and two-dimensional NMR spectroscopy, it was found that the initial conformations of these compounds are dramatically different in aqueous buffers of pH 2.0 and 7.2, which intrinsically determine the molecular binding ability of the host. It was also revealed that both the guest structure and the host tether length were responsible for the inclusion complexation stability. Therefore, on the one hand the hydrophobicity and substituent effect of the guest simultaneously determine the stability of host-guest complex through hydrophobic, van der Waals, and electrostatic interactions. On the other hand, the size/shape-matching relationship and induced-fit concept working between host and guest also play crucial roles in the selective molecular binding process of cyclodextrin hosts.
Influence of supramolecular layer-crosslinked structure on stability of dual pH-Responsive polymer nanoparticles for doxorubicin delivery
Feng, Hailiang,Sun, Yu,Zhang, Jianhua,Deng, Liandong,Dong, Anjie
, p. 81 - 92 (2018)
Undesired physiological instability remains a major limitation for nanoparticle-based drug delivery. To overcome this issue, a dual pH-responsive supramolecular layer-crosslinked nanoparticles (PCB-b-PCD/PBM-b-PDPA NPs, PDM NPs), which consisted of pH-responsive hydrophobic poly(diisopropylethyl methacrylate) (pKa ≈6.3) as the core, hydrophilic poly((methacrylic acid betaine) methyl methacrylate) as the shell and pH-responsive supramolecular crosslinked layer based on β-cyclodextrin and benzimidazole (pKa 6.0), was prepared. Effects of this supramolecular layer-crosslinked structure on dilution and stored stability, protein adsorption, and pH-responsibility were investigated. PDM NPs exhibited lower critical aggregation concentrations, good unimodal distribution and better dilution stability in comparison with non-crosslinked PCB-PDPA NPs. Moreover this pH-responsive supramolecular layer-crosslinked structure did not only influence the anti-protein adsorption ability, but also reduced the disintegrated pH (from 6.3 to below 6.0) of PDM NPs, which leads to the DOX was released from PDM NPs at the mildly acid condition effectively and sustainably in vitro. Therefore, this pH-responsive layer-crosslinked NPs held promising potentials as a smart nanocarriers for drug delivery.
In vitro dissolution study on inclusion complex of piperine with ethylenediamine-β-cyclodextrin
Liu, Kai,Liu, Huijun,Li, Zhendong,Li, Wei,Li, Liuxing
, p. 233 - 243 (2020)
The co-evaporation method was used to synthesize the EN-β-CD@Piperine inclusion complex with a molar ratio of 1:1. The properties and structures of the inclusion complex were characterized by various methods to investigate the inclusion mode and interactions between host and guest. The results of molecular modeling were theoretically analyzed to determine the inclusion mechanism of inclusion complexes. Finally, the vitro dissolution release studies showed that the water solubility of piperine was significantly enhanced when EN-β-CD was combined with piperine. Therefore, the EN-β-CD@Piperine inclusion complex provides a promising development for the clinical application of piperine in the future.
Synthesis and photodynamic therapy properties of a water-soluble hypocrellin modified by cyclodextrin
Ou, Zhi-Ze,Chen, Jing-Rong,Wang, Xue-Song,Zhang, Bao-Wen,Cao, Yi
, p. 838 - 839 (2001)
For improving water solubility of hypocrellin B (HB), a cyclodextrin modified hypocrellin B (HBCD) was designed and synthesized. Electron spin resonance (ESR) measurement indicated that this HB derivative remained photodynamically active in terms of type I and type II mechanisms. HBCD is water-soluble and possesses stronger photosensitized damage ability to calf thymus DNA than hypocrellin B.
Alizarin yellow-modified β-cyclodextrin as a guest-responsive absorption change sensor
Aoyagi, Taiyo,Nakamura, Asao,Ikeda, Hiroshi,Ikeda, Tsukasa,Mihara, Hisakazu,Ueno, Akihiko
, p. 659 - 663 (1997)
Alizarin yellow-modified β-cyclodextrin (ACD), in which alizarin yellow is linked to β-cyclodextrin via an ethylenediamine spacer, was synthesized as a new absorption change indicator for molecules. Alizarin yellow is a pH indicator mat exhibits absorption peaks at 360 and 480 nm in the neutral region and in the alkaline region, respectively, with pKa = 10.98 for an equilibrium between two forms. ACD has two parts to be deprotonated: one is the phenolic hydroxyl group of alizarin yellow residue and the other is the secondary amine group of the spacer. ACD exhibits pH dependency very different from that of alizarin yellow. We obtained two pKa values, 4.88 (pKa1) and 8.89 (pKa2), for ACD by pH titration of its absorption intensity. The pKa1 and pKa2 values were suggested to be the pKa values of the phenolic hydroxyl group of alizarin yellow residue and the secondary amine group, respectively. Upon addition of guest species, the pKa1 and pKa2 values shifted to 5.11 and 7.56, respectively, indicating a larger shift in the pKa for the amine group than for the hydroxyl group. The guest-induced pKa shift in the alkaline region suggests that deprotonation of the amine group of ACD occurs when the alizarin yellow moiety is excluded from the cyclodextrin cavity associated with guest accommodation and exposed to an alkaline environment The sensitivities of this host to various guests were examined by absorption changes at 475 nm in pH 8.3 phosphate buffer, and the order of the sensitivities was found to be adamantane derivatives > borneol > bile acids. This order is not parallel with that of the binding constants, suggesting that the structural features of the host-guest complexes are important. All these results demonstrate that ACD can be used as an effective chemosensor for molecules.
Interactions of some modified mono- and bis-β-cyclodextrins with bovine serum albumin
Gao, Hui,Wang, Yi-Nong,Fan, Yun-Ge,Ma, Jian-Biao
, p. 131 - 137 (2006)
Two mono-substituted β-cyclodextrins and two bridged bis-β-cyclodextrins, that is, mono(6-(2-aminoethylamino)-6-deoxy)-β- cyclodextrin (1), mono(6-(2-(2-aminoethylamino)ethylamino)-6-deoxy)-β- cyclodextrin (2), ethylene-1,2-diamino bis-6-(6-deoxy-β-cyclodextrin) (3), and iminodiethylene-2,2′-diamino bis-6-(6-deoxy-β-cyclodextrin) (4), were prepared from β-cyclodextrin. Their binding ability with bovine serum albumin as a model protein was investigated through proton magnetic resonance (1H NMR), ultraviolet visible spectroscopy (UV-vis), circular dichroism (CD), and fluorescence spectroscopy. In the 1H NMR spectra of the modified cyclodextrins, the resolution of proton signals decreases after the addition of BSA. From the UV and CD spectra, it is found that both the UV absorption and the α-helix content of BSA increase with the concentration of the modified cyclodextrins. The protein-ligand interactions cause a fluorescence quenching. The quenching constants are determined using the Stern-Volmer equation to provide an observation of the binding affinity between modified cyclodextrins and BSA. All these results indicate that the modified cyclodextrins can interact with BSA and the bridged bis(β-cyclodextrin)s (3 and 4) have much stronger interactions than the mono-substituted β-cyclodextrins (1 and 2). The strong binding stability of bis-cyclodextrins should be attributed to the cooperative effect of two adjacent cyclodextrin moieties. Job's plot shows that the complex stoichiometries of BSA to the modified cyclodextrins were 1:4 for 1 and 2, as well as 1:3 for 3 and 4, respectively.
