916661-26-2Relevant academic research and scientific papers
Cationic dialkylarylphosphates: A new family of bio-inspired cationic lipids for gene delivery
Le Corre, Stphanie S.,Belmadi, Nawal,Berchel, Mathieu,Le Gall, Tony,Haelters, Jean-Pierre,Lehn, Pierre,Montier, Tristan,Jaffrs, Paul-Alain
, p. 1122 - 1132 (2015)
In this work that aims to synthesize and evaluate new cationic lipids as vectors for gene delivery, we report the synthesis of a series of cationic lipids in which a phosphate functional group acts as a linker to assemble on a molecular scale, two lipid chains and one cationic polar head. The mono or dicationic moiety is connected to the phosphate group by an aryl spacer. In this work, two synthesis strategies were evaluated. The first used the Atherton-Todd coupling reaction to introduce a phenolic derivative to dioleylphosphite. The second strategy used a sequential addition of lipid alcohol and a phenolic derivative on POCl3. The two methods are efficient, but the latter allows larger yields. Different polar head groups were introduced, thus producing amphiphilic compounds possessing either one permanent (N-methyl-imidazolium, pyridinium, trimethylammonium) or two permanent cationic charges. All these cationic lipids were formulated as liposomal solutions and characterized (size and zeta potential). They formed stable liposomal solutions both in water (at pH 7.0) and in a weakly acidic medium (at pH 5.5). Finally, this new generation of cationic lipids was used to deliver DNA into various human-derived epithelial cells cultured in vitro. Compared with Lipofectamine used as a reference commercial lipofection reagent, some cationic dialkylarylphosphates were able to demonstrate potent gene transfer abilities, and noteworthily, monocationic derivatives were much more efficient than dicationic analogues. This journal is
Quinone Methide-Based Organophosphate Hydrolases Inhibitors: Trans Proximity Labelers versus Cis Labeling Activity-Based Probes
Dubovetskyi, Artem,Cherukuri, Kesava Phaneendra,Ashani, Yacov,Meshcheriakova, Anna,Reuveny, Eitan,Ben-Nissan, Gili,Sharon, Michal,Fumagalli, Laura,Tawfik, Dan S.
, p. 894 - 903 (2020/12/09)
Quinone methide (QM) chemistry is widely applied including in enzyme inhibitors. Typically, enzyme-mediated bond breaking releases a phenol product that rearranges into an electrophilic QM that in turn covalently modifies protein side chains. However, the factors that govern the reactivity of QM-based inhibitors and their mode of inhibition have not been systematically explored. Foremost, enzyme inactivation might occur in cis, whereby a QM molecule inactivates the very same enzyme molecule that released it, or by trans if the released QMs diffuse away and inactivate other enzyme molecules. We examined QM-based inhibitors for enzymes exhibiting phosphoester hydrolase activity. We tested different phenolic substituents and benzylic leaving groups, thereby modulating the rates of enzymatic hydrolysis, phenolate-to-QM rearrangement, and the electrophilicity of the resulting QM. By developing assays that distinguish between cis and trans inhibition, we have identified certain combinations of leaving groups and phenyl substituents that lead to inhibition in the cis mode, while other combinations gave trans inhibition. Our results suggest that cis-acting QM-based substrates could be used as activity-based probes to identify various phospho- and phosphono-ester hydrolases, and potentially other hydrolases.
Aggregation-induced emission compound, preparation method thereof, and application thereof for detecting immune-related target analytes
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, (2020/01/08)
The invention provides a multifunctional aggregation-induced emission (AIE) compound that can be used to detect an immune-related target analyte, a preparation method thereof, and an application thereof for detecting the target analyte. The compound can b
NEAR-INFRARED FLUORESCENT PROBE FOR DETECTING ALKALINE PHOSPHATASE AND MANUFACTURING METHOD THEREOF
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Paragraph 0094; 0095; 0096; 0097; 0098; 0099, (2018/06/09)
A near-infrared fluorescent probe for detecting ALP is represented by Chemical 1. The fluorescent probe capable of detecting ALP can selectively detect ALP only quickly and accurately. In addition, the fluorescent probe allows monitoring of a biological p
Luminogenic and fluorogenic compounds and methods to detect molecules or conditions
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Paragraph 0375; 0378, (2016/07/27)
A method to detect the presence or amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided.
An improved fluorogenic substrate for the detection of alkaline phosphatase activity
Park, Jeesook,Kim, Youngmi
, p. 2332 - 2335 (2013/05/21)
We designed a new alkaline phosphatase (ALP)-sensitive fluorogenic probe in which a self-immolative spacer group, p-hydroxybenzyl alcohol, is linked to a profluorogenic compound to improve substrate specificity. Enzymatic hydrolysis converts the fluorogenic substrate 1 to a highly fluorescent reporter 3, thus allowing for the fast and quantitative analysis of ALP activity with greatly increased affinity for the enzyme.
