Switching the Solubility of PMMA Bearing Attached Cyclodextrin‐Moieties by Supramolecular Interactions with Ionic Liquids

Amajjahe, Sadik; Munteanu, Maricica; Ritter, Helmut

doi:10.1002/marc.200900007

Cited by 17 publications

(5 citation statements)

References 37 publications

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“…In contrast, after reaction with 6I-azido-6I-deoxy-β-cyclodextrin, the LCST increased to temperatures of well above the LCST of PNIPAAM. The LCST of the statistical copolymer increases with increasing fraction of β-cyclodextrin in agreement with earlier studies. ,, Interesting is the behavior of the prepared block copolymers. Block copolymers with a low content of β-cyclodextrin still show similar curves to the statistical block copolymer as depicted in Figure .…”

Section: Resultssupporting

confidence: 90%

“…The synthesis of cyclodextrin polymers using cyclodextrin monomers was first reported by Furue and co-workers in 1975 . Although most of the polymers produced were homopolymers, in some cases copolymerizations were examined. ,− Alternatively, postfunctionalization of a reactive linear polymer with monofunctional cyclodextrin was investigated . Seo et al were among the first to use the two-step polymer analogous reaction.…”

Section: Introductionmentioning

confidence: 99%

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Development of Micellar Novel Drug Carrier Utilizing Temperature-Sensitive Block Copolymers Containing Cyclodextrin Moieties

et al. 2011

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A drug-delivery system for albendazole (ABZ) based on β-cyclodextrin has been synthesized. Well-defined statistical copolymers, composed of N-isopropylacrylamide (NIPAAM) and trimethylsilylpropargyl acrylate (TMSPA), have been prepared by reversible additionÀfragmentation chain transfer (RAFT) polymerization. The reactivity ratios were determined to be r TMSPA = 1.12 and r NIPAAm = 0.49, in the absence of RAFT agent, and r TMSPA = 1.35 and r NIPAAm = 0.35, in the presence of RAFT agent using the average of different techniques. Block copolymers were prepared using a POEGMEA 40 macro-RAFT agent chain extended with NIPAAm and TMSPA in various feed ratios. After deprotection, the polymers were reacted with 6I-azido-6I-deoxy-β-cyclodextrin via Huisgen azideÀalkyne 1,3dipolar cycloaddition, resulting in thermo-responsive block copolymers with pendant β-cyclodextrin groups, which were then acetylated to modify the polarity and inclusion-complex formation of β-cyclodextrin with the drug albendazole (ABZ). Only block copolymers with small amounts of cyclodextrin were observed to have an LCST while the copolymers containing higher β-cyclodextrin fractions increased the LCST of PNIPAAm beyond measurable temperature ranges. Encapsulation of ABZ increased the LCST. The loading efficiency increased in the polymer β-cyclodextrin conjugate compared to native β-cyclodextrin with the highest loading observed in the block copolymer after all remaining cyclodextrin hydroxyl groups had been acetylated. While β-cyclodextrin is toxic, attachment of a polymer lowered the toxicity to nontoxic levels. The ABZ-loaded polymers were all observed to be highly toxic to OVCAR-3 ovarian cancer cell lines with the acetylated polymer showing the highest toxicity.

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Development of Micellar Novel Drug Carrier Utilizing Temperature-Sensitive Block Copolymers Containing Cyclodextrin Moieties

et al. 2011

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“…They could either directly participate in the assembly of supramolecular organizations or influence the assembly of various supramolecular structures . The combination of CDs and ILs is interesting and has been applied in supramolecular systems with novel structures and properties, − in catalysis, in separations, − etc. As a result, the interaction between CD and IL is of great importance and there are some reports on this subject. − …”

Section: Introductionmentioning

confidence: 99%

Multiple Equilibria Interaction Pattern between the Ionic Liquids C_nmimPF₆ and β-Cyclodextrin in Aqueous Solutions

Zhang

Shen

2011

J. Phys. Chem. B

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The interactions of ionic liquids (ILs) 1-alkyl-3-methylimidazolium hexafluorophosphate (C(n)mimPF(6), n = 2, 4, 6, 8) with β-cyclodextrin (β-CD) in aqueous solutions are investigated in this article. The stoichiometry and apparent association constants were obtained by the competitive fluorescence method, NMR measurements, and isothermal titration calorimetry (ITC). The results showed that C(2)mimPF(6), C(4)mimPF(6), and C(6)mimPF(6) form 1:1 (guest:host) inclusion complexes with β-CD whereas the 1:2 inclusion complex can be formed between C(8)mimPF(6) and β-CD. We studied the existence state of the ILs and found that they exist mainly as separated ions with a minor percentage existing as associated ion pairs within the concentration studied. By ESI/HRMS, the coexistence of different complexes including C(n)mim(+)·PF(6)(-)-β-CD, C(n)mim(+)-β-CD (or C(n)mim(+)-β-CD(2)), and PF(6)(-)-β-CD was observed. It is also deduced that the intermediate complex, (β-CD-cation)·(anion-β-CD), may dissociate into cation-β-CD and anion-β-CD complexes. Thermodynamic parameters determined by ITC indicate that, while the inclusion process for C(6)mimPF(6)/β-CD complex is entropy and enthalpy driven, the interactions of other C(n)mimPF(6) (n = 2, 4, 8) with β-CD are enthalpy controlled. Based on these results, a more comprehensive pattern involving multiple equilibria on the interaction between C(n)mimPF(6) and β-CD in aqueous solutions is presented herein.

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“…Because the choice of compatible monomer pairs in terms of reactivity ratios is difficult, the preparation of PMMA‐based copolymers with randomly dispersed supramolecular associative units is limited to a few example. [ 25,26 ] In particular, the preparation of dual supramolecular associative PMMA‐based materials with randomly dispersed associative units has rarely been reported so far.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Synthesis of Dual Supramolecular Associative PMMA‐Based Copolymers and the Precise Thermal Property Tuning

Hayashi

Kimura

Oba

et al. 2020

Macro Chemistry & Physics

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Dual supramolecular associative polymers have attracted attention for efficient physical property modification. Herein, a one‐pot synthesis of dual supramolecular associative poly(methyl methacrylate)‐based copolymers via reversible addition fragmentation chain transfer (RAFT) copolymerization using a novel methacrylate‐type monomer (coded as UP‐MA) bearing a urea bond and a pendant pyridine group is demonstrated. UP‐MA is synthesized by reacting 4‐picolylamine and 2‐isocyanatoethyl methacrylate. The subsequent RAFT copolymerization of UP‐MA and methyl methacrylate (MMA) can be performed by directly adding MMA, a chain transfer agent, and a radical initiator into the reaction solution of UP‐MA. The estimated values of radical reactivity ratio (r) for UP‐MA and MMA are close to unity, attaining a nearly ideal random sequence of the dual supramolecular associative units in the copolymer chain. By blending a metal salt into the random copolymer, coordination bonds between the salt and the pyridine groups are formed, and the urea groups simultaneously form hydrogen bonds, generating a dual supramolecular associative network. Precise tuning of the thermal property is realized by changing the fraction of the metal salt and associative groups in the copolymers.

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Switching the Solubility of PMMA Bearing Attached Cyclodextrin‐Moieties by Supramolecular Interactions with Ionic Liquids

Cited by 17 publications

References 37 publications

Development of Micellar Novel Drug Carrier Utilizing Temperature-Sensitive Block Copolymers Containing Cyclodextrin Moieties

Development of Micellar Novel Drug Carrier Utilizing Temperature-Sensitive Block Copolymers Containing Cyclodextrin Moieties

Multiple Equilibria Interaction Pattern between the Ionic Liquids C_nmimPF₆ and β-Cyclodextrin in Aqueous Solutions

One‐Pot Synthesis of Dual Supramolecular Associative PMMA‐Based Copolymers and the Precise Thermal Property Tuning

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Switching the Solubility of PMMA Bearing Attached Cyclodextrin‐Moieties by Supramolecular Interactions with Ionic Liquids

Cited by 17 publications

References 37 publications

Development of Micellar Novel Drug Carrier Utilizing Temperature-Sensitive Block Copolymers Containing Cyclodextrin Moieties

Development of Micellar Novel Drug Carrier Utilizing Temperature-Sensitive Block Copolymers Containing Cyclodextrin Moieties

Multiple Equilibria Interaction Pattern between the Ionic Liquids CnmimPF6 and β-Cyclodextrin in Aqueous Solutions

One‐Pot Synthesis of Dual Supramolecular Associative PMMA‐Based Copolymers and the Precise Thermal Property Tuning

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Multiple Equilibria Interaction Pattern between the Ionic Liquids C_nmimPF₆ and β-Cyclodextrin in Aqueous Solutions