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

Water-soluble amphiphilic ruthenium(ii) polypyridyl complexes as potential light-activated therapeutic agents

2020 ◽  
Vol 56 (65) ◽  
pp. 9332-9335
Author(s):  
Sandra Estalayo-Adrián ◽  
Salvador Blasco ◽  
Sandra A. Bright ◽  
Gavin J. McManus ◽  
Guillermo Orellana ◽  
...  
Keyword(s):  
Cervical Cancer ◽  
Cancer Cells ◽  
Cellular Uptake ◽  
Therapeutic Agents ◽  
Water Soluble ◽  
Polypyridyl Complexes ◽  
Cervical Cancer Cells

Two new water-soluble amphiphilic Ru(ii) polypyridyl complexes were synthesised and their photophysical and photobiological properties evaluated; both complexes showed a rapid cellular uptake and phototoxicity against HeLa cervical cancer cells.

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 Epigallocatechin Gallate-Gold Nanoparticles Exhibit Superior Antitumor Activity Compared to Conventional Gold Nanoparticles: Potential Synergistic Interactions

Nanomaterials ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 396 ◽  
Author(s):  
Suhash Chavva ◽  
Sachin Deshmukh ◽  
Rajashekhar Kanchanapally ◽  
Nikhil Tyagi ◽  
Jason Coym ◽  
...  
Keyword(s):  
Gold Nanoparticles ◽  
Antitumor Activity ◽  
Cancer Cells ◽  
Cellular Uptake ◽  
Nuclear Translocation ◽  
Epigallocatechin Gallate ◽  
Drug Carriers ◽  
Water Soluble ◽  
Tetrazolium Salt ◽  
Uptake Studies

Epigallocatechin gallate (EGCG) possesses significant antitumor activity and binds to laminin receptors, overexpressed on cancer cells, with high affinity. Gold nanoparticles (GNPs) serve as excellent drug carriers and protect the conjugated drug from enzymatic metabolization. Citrate-gold nanoparticles (C-GNPs) and EGCG-gold nanoparticles (E-GNPs) were synthesized by reduction methods and characterized with UV-visible spectroscopy, transmission electron microscopy (TEM), and dynamic light scattering (DLS). Cytotoxicity of citrate, EGCG, C-GNPs, and E-GNPs was evaluated by the water-soluble tetrazolium salt (WST-1) assay. Nanoparticle cellular uptake studies were performed by TEM and atomic absorption spectroscopy (AAS). Dialysis method was employed to assess drug release. Cell viability studies showed greater growth inhibition by E-GNPs compared to EGCG or C-GNPs. Cellular uptake studies revealed that, unlike C-GNPs, E-GNPs were taken up more efficiently by cancerous cells than noncancerous cells. We found that E-GNP nanoformulation releases EGCG in a sustained fashion. Furthermore, data showed that E-GNPs induced more apoptosis in cancer cells compared to EGCG and C-GNPs. From the mechanistic standpoint, we observed that E-GNPs inhibited the nuclear translocation and transcriptional activity of nuclear factor-kappaB (NF-κB) with greater potency than EGCG, whereas C-GNPs were only minimally effective. Altogether, our data suggest that E-GNPs can serve as potent tumor-selective chemotoxic agents.

scholarly journals Nano-Bio Interaction between Blood Plasma Proteins and Water-Soluble Silicon Quantum Dots with Enabled Cellular Uptake and Minimal Cytotoxicity

Nanomaterials ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 2250
Author(s):  
Shanmugavel Chinnathambi ◽  
Nobutaka Hanagata ◽  
Tomohiko Yamazaki ◽  
Naoto Shirahata
Keyword(s):  
Quantum Dots ◽  
Blood Plasma ◽  
Cellular Uptake ◽  
Plasma Proteins ◽  
Protein Corona ◽  
Water Soluble ◽  
Pluronic F127 ◽  
Infrared Light ◽  
Spectral Window ◽  
Blood Plasma Proteins

A better understanding of the compatibility of water-soluble semiconductor quantum dots (QDs) upon contact with the bloodstream is important for biological applications, including biomarkers working in the first therapeutic spectral window for deep tissue imaging. Herein, we investigated the conformational changes of blood plasma proteins during the interaction with near-infrared light-emitting nanoparticles, consisting of Pluronic F127 shells and cores comprised of assembled silicon QDs terminated with decane monolayers. Albumin and transferrin have high quenching constants and form a hard protein corona on the nanoparticle. In contrast, fibrinogen has low quenching constants and forms a soft protein corona. A circular dichroism (CD) spectrometric study investigates changes in the protein’s secondary and tertiary structures with incremental changes in the nanoparticle concentrations. As expected, the addition of nanoparticles causes the denaturation of the plasma proteins. However, it is noteworthy that the conformational recovery phenomena are observed for fibrinogen and transferrin, suggesting that the nanoparticle does not influence the ordered structure of proteins in the bloodstream. In addition, we observed enabled cellular uptake (NIH3T3 Fibroblasts) and minimal cytotoxicity using different cell lines (HeLa, A549, and NIH3T3). This study offers a basis to design QDs without altering the biomacromolecule’s original conformation with enabled cellular uptake with minimal cytotoxicity.

Synthesis of Water-Soluble Thioglycosylated trans-A2B2 Type Porphyrins: Cellular Uptake Studies and Photodynamic Efficiency

2020 ◽  
Vol 85 (10) ◽  
pp. 6309-6322 ◽  
Author(s):  
Vijayalakshmi Pandey ◽  
Md Kausar Raza ◽  
Pooja Joshi ◽  
Iti Gupta
Keyword(s):  
Cellular Uptake ◽  
Water Soluble ◽  
Uptake Studies

scholarly journals Shear Stress-Dependent Targeting Efficiency Using Self-Assembled Gelatin–Oleic Nanoparticles in a Biomimetic Microfluidic System

Pharmaceutics ◽  
2020 ◽  
Vol 12 (6) ◽  
pp. 555
Author(s):  
Taehee Kang ◽  
Chulhun Park ◽  
Nileshkumar Meghani ◽  
Thao T.D. Tran ◽  
Phuong H.L. Tran ◽  
...  
Keyword(s):  
Shear Stress ◽  
Fluid Flow ◽  
Cellular Uptake ◽  
Static Condition ◽  
Microfluidic System ◽  
Water Soluble ◽  
Cellular Behaviors ◽  
Self Assembled ◽  
Stress Dependent ◽  
Coumarin 6

Cellular properties and microenvironments, as well as the characteristics of nanoparticles (NPs), affect the cellular uptake and cytotoxic effects of drug-loaded NPs. Since there is fluid flow in the human blood system, fluid flow also affects the drug delivery efficiency of NPs. This study aimed to evaluate the cellular behaviors of drug-loaded soft NPs on A549 cancer cells under different levels of shear stress (0.5, 5, and 50 dynes/cm2) in the biomimetic microfluidic system. The soft self-assembled NPs were formed by the gelatin–oleic conjugate (GOC). The poorly water-soluble coumarin-6 or paclitaxel (PTX) were used as model markers for encapsulation within self-assembled NPs (C-GONs or PTX-GONs, respectively). The cellular uptake of C-GONs was found to be improved with shear-stress dependence. The inhibitory concentration (IC50) of PTX-GONs at 0.5, 5, and 50 dynes/cm2 was 0.106 µg/mL, 0.108 µg/mL, and 0.091 µg/mL, respectively, as compared to 0.138 µg/mL in a static condition. The cell killing efficiency of PTX-GONs was increased in the highest shear stress of 50 dynes/cm2 in the static condition, and other levels of shear stress in dynamic conditions.

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
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