1073169-23-9Relevant academic research and scientific papers
Turn-on fluorescence detection of H2O2 and TATP
Germain, Meaghan E.,Knapp, Michael J.
, p. 9748 - 9750 (2008)
Peroxide-based explosives, like triacetone triperoxide (TATP), are important targets for detection because of their broad use in improvised explosives but pose challenges. We report a highly sensitive turn-on fluorescence detection for H2O2 and organic peroxides, including TATP. The detection strategy relies on oxidative deboronation to unmask H2Salen, which subsequently binds Zn2+ to form fluorescent Zn(Salen). Sensitivity is excellent, with detection limits below 10 nM for H2O2, TATP, and benzoyl peroxide. In addition, acid treatment is necessary to sense TATP, suggesting the potential to discriminate between H2O2 and TATP based upon minimal sample pretreatment.
A Double Prodrug with Improved Membrane Permeability over the Parent Chelator HBED Provides Superior Cytoprotection against Hydrogen Peroxide
Thiele, Nikki A.,Sloan, Kenneth B.
, p. 1596 - 1599 (2016)
The clinical use of N,N′-bis(2-hydroxybenzyl)ethylenediamine-N,N′-diacetic acid (HBED) has been hindered by its lack of bioavailability. N,N′-bis(2-boronic pinacol ester benzyl)ethylenediamine-N,N′-diacetic acid methyl, ethyl, and isopropyl esters 7 a–c, respectively, and their dimesylate salts 8 a–c, are double prodrugs that mask the two phenolate and two carboxylate donors of HBED as boronic esters and carboxylate esters, respectively. Their activation by chemical hydrolysis and oxidation, their passive diffusivity, and their cytoprotective capabilities have been investigated here. 8 a–c hydrolyzed in minimum essential medium at 37 °C with half-lives of 0.69, 0.81, and 2.28 h, respectively. The intermediate formed, 9 [N,N′-bis(2-boronic acid benzyl)ethylenediamine-N,N′-diacetic acid], then underwent oxidative deboronation by H2O2to give HBED (k=1.82 m?1min?1). Solubility measurements in mineral oil and in phosphate buffer indicated that 7 a had a better balance between lipid and aqueous solubilities than did HBED. 7 a was also able to passively diffuse across a lipid-like silicone membrane (log flux=?0.36), whereas HBED-HCl was not. 8 c provided better protection to retinal cells than did HBED against a lethal dose of H2O2(84 % vs. 28 % protection, respectively, at 44 μm). These results suggest that the double prodrugs have better membrane permeability than does HBED, and therefore could be therapeutically useful for improving the delivery of HBED.
Preparation of a novel group of hybrid compounds N-benzyl aminoboronbenzylphosphonic and N,N′-ethylenedi(aminoboronbenzylphosphonic) acids
M?ynarz, Piotr,Rydzewska, Agata,Pok?adek, Ziemowit
experimental part, p. 457 - 460 (2011/02/28)
Two groups of new boronic acids containing aminophosphonate functions were synthesized and characterized by NMR spectroscopy and ESI-MS. Both groups of compounds were obtained by simple reactions of prepared in situ tris(trimethylsilyl) phosphite with a corresponding imine. The synthesized compounds may serve as a potential new class of building blocks, BNCT agents and supramolecular host molecules.
