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 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, 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 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.

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

A Resorcinol-Formaldehyde Resin as an Embedding Material for Electron Microscopy of Membranes

1969 ◽  
Vol 27 ◽  
pp. 328-329 ◽  
Author(s):  
J. G. Robertson ◽  
D. F. Parsons
Keyword(s):  
Electron Microscopy ◽  
Osmium Tetroxide ◽  
Neutral Lipids ◽  
Lipid Extraction ◽  
Water Soluble ◽  
Formaldehyde Resin ◽  
Electron Microscope Autoradiography ◽  
Resorcinol Formaldehyde ◽  
Major Disadvantage ◽  
Cell Organization

The extraction of lipids from tissues during fixation and embedding for electron microscopy is widely recognized as a source of possible artifact, especially at the membrane level of cell organization. Lipid extraction is also a major disadvantage in electron microscope autoradiography of radioactive lipids, as in studies of the uptake of radioactive fatty acids by intestinal slices. Retention of lipids by fixation with osmium tetroxide is generally limited to glycolipids, phospholipids and highly unsaturated neutral lipids. Saturated neutral lipids and sterols tend to be easily extracted by organic dehydrating reagents prior to embedding. Retention of the more saturated lipids in embedded tissue might be achieved by developing new cross-linking reagents, by the use of highly water soluble embedding materials or by working at very low temperatures.

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