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

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.

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

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

Guest Binding, Cellular Uptake, and Molecular Delivery of Water-soluble Cyclophanes Having a Pyrene Moiety

2010 ◽  
Vol 39 (12) ◽  
pp. 1321-1322 ◽  
Author(s):  
Osamu Hayashida ◽  
Chika Eguchi ◽  
Keiichiro Kimura ◽  
Yu Oyama ◽  
Tomomi Nakashima ◽  
...  
Keyword(s):  
Cellular Uptake ◽  
Water Soluble ◽  
Molecular Delivery ◽  
Guest Binding

A new water-soluble cavitand with deeper guest binding properties

2019 ◽  
Vol 6 (7) ◽  
pp. 998-1001 ◽  
Author(s):  
Faiz-Ur Rahman ◽  
Hai-Na Feng ◽  
Yang Yu
Keyword(s):  
Aqueous Solution ◽  
Water Soluble ◽  
Binding Properties ◽  
Amphiphilic Molecules ◽  
Guest Binding

A new water-soluble cavitand captured hydrophobic or amphiphilic molecules in an aqueous solution owing to its deep aromatic pocket.

scholarly journals Fabrication of Aliphatic Water-Soluble Polyurethane Composites with Silane Treated CaCO3

Polymers ◽  
2020 ◽  
Vol 12 (4) ◽  
pp. 747 ◽  
Author(s):  
Eyob Wondu ◽  
Zelalem Chernet Lule ◽  
Jooheon Kim
Keyword(s):  
Thermal Degradation ◽  
Water Solubility ◽  
Soft Segment ◽  
Average Molecular Weight ◽  
Water Soluble ◽  
Chemical Structures ◽  
Degradation Temperature ◽  
Surface Modified ◽  
Polyurethane Composites ◽  
Degradation Properties

In the present study, composites of water-soluble polyurethane/calcium carbonate (CaCO3) were prepared from a soft segment of hydroxyl-terminated polybutadiene (HTPB) and polyethylene glycol (PEG, average molecular weight = 4000) with aliphatic diisocyanates. The functionality of CaCO3 particles was modified using aminopropyltriethoxysilane (APTES), and was confirmed by Fourier-transform infrared spectroscopy (FTIR). The solubility, hydrophilic properties, and chemical structures of the composites were analyzed by water-solubility tests, contact angle measurements, and FTIR, respectively, and the successful production of the hydrophilic water-soluble polyurethane (WSPU) structure was demonstrated. The adhesion of surface-modified CaCO3 particles to the WSPU matrix and the thermal degradation properties of the neat WSPU and WSPU/CaCO3 composites were studied using field emission scanning electron microscopy (FE-SEM) and thermogravimetric analysis (TGA). The results demonstrated good adhesion of the surface-modified CaCO3 particles along with an improved thermal degradation temperature with the addition of CaCO3 particles to the WSPU matrix.

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
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