betadex and benzeneboronic-acid

The aim of the present paper is to highlight a novel electrochemical assay for an extremely-selective detection of fructose thanks to the use of a supramolecular complex between β-cyclodextrins (β-CDs) and a chemically modified ferrocene with boronic acid named 4-Fc-PB/natural-β-CDs. Another kind of β-CDs, the 4-Fc-PB/3-phenylboronic-β-CDs, is proposed for the detection of glucose. The novel electrochemical probe is fully characterized by

Topics: beta-Cyclodextrins; Boronic Acids; Fructose; Metallocenes

Atherosclerosis is a leading cause of vascular diseases worldwide. Whereas antioxidative therapy has been considered promising for the treatment of atherosclerosis in view of a critical role of reactive oxygen species (ROS) in the pathogenesis of atherosclerosis, currently available antioxidants showed considerably limited clinical outcomes. Herein, we hypothesize that a broad-spectrum ROS-scavenging nanoparticle can serve as an effective therapy for atherosclerosis, taking advantage of its antioxidative stress activity and targeting effects. As a proof of concept, a broad-spectrum ROS-eliminating material was synthesized by covalently conjugating a superoxide dismutase mimetic agent Tempol and a hydrogen-peroxide-eliminating compound of phenylboronic acid pinacol ester onto a cyclic polysaccharide β-cyclodextrin (abbreviated as TPCD). TPCD could be easily processed into a nanoparticle (TPCD NP). The obtained nanotherapy TPCD NP could be efficiently and rapidly internalized by macrophages and vascular smooth muscle cells (VSMCs). TPCD NPs significantly attenuated ROS-induced inflammation and cell apoptosis in macrophages, by eliminating overproduced intracellular ROS. Also, TPCD NPs effectively inhibited foam cell formation in macrophages and VSMCs by decreasing internalization of oxidized low-density lipoprotein. After intravenous (i.v.) administration, TPCD NPs accumulated in atherosclerotic lesions of apolipoprotein E-deficient (ApoE

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Apolipoproteins E; Apoptosis; Atherosclerosis; beta-Cyclodextrins; Boronic Acids; Cyclic N-Oxides; Hydrogen Peroxide; Inflammation; Macrophages; Male; Mice; Mice, Inbred C57BL; Mice, Knockout; Nanoparticles; Polysaccharides; Reactive Oxygen Species; Spin Labels

Complex formation reactions of phenylboronic, phenylphosphonic, phenylarsonic and 4-aminophenyl arsonic acids with β-cyclodextrin (cycloheptaamylose, β-CD) and some simple carbohydrates (mannitol, sorbitol, glucose) have been studied using spectrophotometric, potentiometric methods and solubility measurements, supplemented with HPLC and IR analyses of the solid samples. Equilibrium constants have been determined at ionic strength of 0.2M (NaCl) and 25°C. β-CD forms the most stable complexes with the neutral, undissociated forms of the acids, the stability constants are as follows: phenylboronic acid: 320 ± 36, phenylphosphonic acid: 108 ± 25, phenylarsonic acid: 97 ± 4 and 4-aminophenyl arsonic acid: 107 ± 10. The stability constants for the β-CD-complexes of the ionic forms are much lower. Ternary complexes of low stability could be detected in the case of phenylphosphonic acid and sorbitol with the undissociated form and with glucose and the dianion. In more concentrated solutions phenylboronic acid forms insoluble complexes with mannitol, sorbitol and β-CD. The solid phases obtained in the ternary systems are predominantly mixtures of ester type 3:1 complexes with the carbohydrate and 1:1 inclusion complex with the β-CD. No significant interaction has been found with glucose. The phenomena can be explained by the differences in the structures of the components and by the changes in the H-bonding network of β-CD on the complex formation.

Topics: beta-Cyclodextrins; Boronic Acids; Glucose; Potentiometry; Sorbitol; Spectrophotometry, Infrared

An inclusion complex consisting of a fluorescent phenylboronic acid (C1-APB) and beta-cyclodextrin (beta-CD) acts as a supramolecular saccharide sensor whose response mechanism is based on photoinduced electron transfer (PET). This study evaluated four kinds of cyclodextrins (alpha-CD, beta-CD, gamma-CD, and NH(2)-beta-CD) by comparing their pH profiles, and confirmed that beta-CD was the best host for C1-APB because the C1-APB/beta-CD complex exhibited high affinity for saccharides as well as high fluorescent recovery upon saccharide binding. An investigation of the beta-CD concentration effect revealed the formation of a 1:1 inclusion complex of C1-APB with beta-CD. The observed saccharide selectivity of the C1-APB/beta-CD complex is in the following order: D-fructose (4039 +/- 69 M(-1)) > D-ribose (1083 +/- 26 M(-1)) > L-arabinose (474 +/- 11 M(-1)) > D-galactose (318 +/- 3 M(-1)) > maltotoriose (135 +/- 5 M(-1)) > D-glucose (114 +/- 2 M(-1)) > maltose (81 +/- 2 M(-1)). In addition to monomer emission, dimer emission from pyrene dimers was observed in the spectra for the C1-APB/gamma-CD complex, which allowed a ratiometric analysis. This study shows that the combination of a simple fluorescent probe, C1-APB, with various CDs diversifies the response systems for saccharide recognition.

Topics: beta-Cyclodextrins; Boronic Acids; Carbohydrates; Cyclodextrins; Electrons; Fluorescence; Fluorescent Dyes; Hydrogen-Ion Concentration; Macromolecular Substances; Molecular Structure; Photochemistry; Sensitivity and Specificity; Water

Supramolecular complex formation of phenylboronic-acid-modified beta-cyclodextrin (1) with 1-methyl-4-(4-dimethylaminostyryl)pyridinium (C1SP) in aqueous solutions containing saccharides was fully clarified to gain an insight into the observed D-glucose (D-glc) selectivity of a supramolecular fluorescent probe composed of 1 and the 1-heptyl analogue of C1SP (Chem. Commun., 2006, 4319). At pH 9.6, where 1 was in its anionic form, both the stability and the fluorescence of the 1/C1SP complex were reduced by the formation of boronate esters of 1 with saccharides. Among the saccharides, D-glc had the smallest effect on destabilization of the 1/C1SP complex, almost completely retaining the fluorescence of the 1/C1SP complex that was reduced by other saccharides by approximately 2/3. Under neutral conditions, D-glc enhanced the fluorescence of the 1/C1SP complex by increasing the fraction of anionic 1 while minimally decreasing the stability and fluorescence of the 1/C1SP complex. Although other saccharides also increased the fraction of the anionic 1, their relatively large effects on the destabilization and reduction of fluorescence of the 1/C1SP complex limited the enhancement of the fluorescence of the 1-C1SP system under neutral conditions.

Topics: beta-Cyclodextrins; Boronic Acids; Fluorescence; Glucose; Molecular Structure; Pyridinium Compounds

Pseudorotaxane formed by reacting beta-cyclodextrin bearing a phenylboronic acid residue with 1-heptyl-4-(4'-dimethylaminostyryl)pyridinium functioned as a novel fluorescent saccharide receptor having unique responses.

Topics: beta-Cyclodextrins; Boronic Acids; Carcinogens; Fluorescence; Molecular Structure; Pyridines; Rotaxanes