scholarly journals Synthesis and Guest-Binding Behavior of Water-Soluble Cyclophanes Bearing PEG Residues

2014 ◽  
Vol 04 (04) ◽  
pp. 409-416 ◽  
Author(s):  
Osamu Hayashida ◽  
Yuki Nakamura ◽  
Takuya Sato
Keyword(s):  
Water Soluble ◽  
Binding Behavior ◽  
Guest Binding

scholarly journals Synthesis and Guest-Binding Properties of pH/Reduction Dual-Responsive Cyclophane Dimer

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3097
Author(s):  
Osamu Hayashida ◽  
Yudai Tanaka ◽  
Takaaki Miyazaki
Keyword(s):  
Electrostatic Interaction ◽  
Disulfide Bonds ◽  
Water Soluble ◽  
Guest Molecules ◽  
Binding Behavior ◽  
Dual Responsive ◽  
Guest Binding ◽  
Basic Solutions ◽  
Ph Conditions ◽  
Almost All

A water-soluble cyclophane dimer having two disulfide groups as a reduction-responsive cleavable bond as well as several acidic and basic functional groups as a pH-responsive ionizable group 1 was successfully synthesized. It was found that 1 showed pH-dependent guest-binding behavior. That is, 1 strongly bound an anionic guest, 6-p-toluidinonaphthalene-2-sulfonate (TNS) with binding constant (K/M−1) for 1:1 host-guest complexes of 9.6 × 104 M−1 at pH 3.8, which was larger than those at pH 7.4 and 10.7 (6.0 × 104 and 2.4 × 104 M−1, respectively), indicating a favorable electrostatic interaction between anionic guest and net cationic 1. What is more, release of the entrapped guest molecules by 1 was easily controlled by pH stimulus. Large favorable enthalpies (ΔH) for formation of host-guest complexes were obtained under the pH conditions employed, suggesting that electrostatic interaction between anionic TNS and 1 was the most important driving force for host-guest complexation. Such contributions of ΔH for formation of host-guest complexes decreased along with increased pH values from acidic to basic solutions. Upon addition of dithiothreitol (DTT) as a reducing reagent to an aqueous PBS buffer (pH 7.4) containing 1 and TNS, the fluorescence intensity originating from the bound guest molecules decreased gradually. A treatment of 1 with DTT gave 2, having less guest-binding affinity by the cleavage of disulfide bonds of 1. Consequently, almost all entrapped guest molecules by 1 were released from the host. Moreover, such reduction-responsive cleavage of 1 and release of bound guest molecules was performed more rapidly in aqueous buffer at pH 10.7.

Synthesis of Water-Soluble Cyclophane Hexamers Having a Triphenylene Core and Their Enhanced Guest-Binding Behavior

2016 ◽  
Vol 81 (10) ◽  
pp. 4196-4201 ◽  
Author(s):  
Osamu Hayashida ◽  
Toshikazu Matsuo ◽  
Kazuhiro Nakamura ◽  
Shuhei Kusano
Keyword(s):  
Water Soluble ◽  
Binding Behavior ◽  
Guest Binding

The effects of hexafluoroisopropanol on guest binding by water-soluble capsule and cavitand hosts

2015 ◽  
Vol 51 (99) ◽  
pp. 17604-17606 ◽  
Author(s):  
Jesse V. Gavette ◽  
Ioannis D. Petsalakis ◽  
Giannoula Theodorakopoulos ◽  
Kang-Da Zhang ◽  
Yang Yu ◽  
...  
Keyword(s):  
Water Soluble ◽  
Guest Binding

Molecular binding behavior of bipyridium derivatives by water-soluble carboxylato-biphen[3]arene

2015 ◽  
Vol 51 (30) ◽  
pp. 6621-6624 ◽  
Author(s):  
Junwei Ma ◽  
Hongmei Deng ◽  
Suxiang Ma ◽  
Jian Li ◽  
Xueshun Jia ◽  
...  
Keyword(s):  
Water Soluble ◽  
Molecular Binding ◽  
Binding Behavior

Complexation of paraquat derivatives and bis(N-mono-substituted bipyridine) cations by a negatively charged carboxylato-biphen[3]arene in water is described.

Synthesis, Guest-Binding, and Reduction-Responsive Degradation Properties of Water-Soluble Cyclophanes Having Disulfide Moieties

2013 ◽  
Vol 78 (11) ◽  
pp. 5463-5469 ◽  
Author(s):  
Osamu Hayashida ◽  
Kazuaki Ichimura ◽  
Daisuke Sato ◽  
Terutaka Yasunaga
Keyword(s):  
Water Soluble ◽  
Guest Binding ◽  
Degradation Properties

Spectrophotometric study of the selective binding behavior of aliphatic oligopeptides by bridged bis(β-cyclodextrin) linked by a 4,4′-diaminodiphenyl disulfide tether

2010 ◽  
Vol 88 (12) ◽  
pp. 1205-1212 ◽  
Author(s):  
Yang Yong-Cun ◽  
Chi Shao-Ming ◽  
Liu Ming-Hua ◽  
Huang Rong ◽  
Wang Yu-Fei ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Fluorescence Enhancement ◽  
Fluorescent Sensor ◽  
Binding Constants ◽  
2D Nmr ◽  
Binding Mode ◽  
Spectrophotometric Study ◽  
2D Nmr Spectroscopy ◽  
Binding Behavior ◽  
Guest Binding

The conformation and binding behavior of 4,4′-diaminodiphenyl disulfide bridged bis(β-cyclodextrin) (1) towards representative aliphatic oligopeptides, i.e., Leu-Gly, Gly-Leu, Glu-Glu, Met-Met, Gly-Gly, Gly-Gly-Gly, and Gly-Pro, were investigated by circular dichroism, fluorescence, and 1H and 2D NMR spectroscopy at 25 °C in phosphate buffer (pH 7.20). The results indicated that 1 acts as an efficient fluorescent sensor and displays remarkable fluorescence enhancement upon addition of optically inert oligopeptides. Owing to the cooperative host–linker–guest binding mode in which the linker and guest are coincluded in the two cyclodextrin cavities, the bis(β-cyclodextrin) 1 gives high binding constants of up to 103–104 (mol/L)–1 for oligopeptides. The bis(β-cyclodextrin) 1 can recognize not only the size and shape of oligopeptides but also the hydrophobicity, giving an exciting residue selectivity of up to 61.3 for the Gly-Leu/Glu-Glu pair. These phenomena are discussed from the viewpoints of multiple recognition and induce-fit interactions between host and guest.

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