16645-12-8Relevant articles and documents
Hydrolysis-Based Small-Molecule Hydrogen Selenide (H2Se) Donors for Intracellular H2Se Delivery
Bolton, Sarah G.,Chouinard, Julie E.,Garcia, Arman C.,Golledge, Stephen L.,Newton, Turner D.,Pluth, Michael D.,Zakharov, Lev N.
, p. 19542 - 19550 (2021/11/23)
Hydrogen selenide (H2Se) is a central metabolite in the biological processing of selenium for incorporation into selenoproteins, which play crucial antioxidant roles in biological systems. Despite being integral to proper physiological function, this reactive selenium species (RSeS) has received limited attention. We recently reported an early example of a H2Se donor (TDN1042) that exhibited slow, sustained release through hydrolysis. Here we expand that technology based on the P-Se motif to develop cyclic-PSe compounds with increased rates of hydrolysis and function through well-defined mechanisms as monitored by 31P and 77Se NMR spectroscopy. In addition, we report a colorimetric method based on the reaction of H2Se with NBD-Cl to generate NBD-SeH (λmax = 551 nm), which can be used to detect free H2Se. Furthermore, we use TOF-SIMS (time of flight secondary ion mass spectroscopy) to demonstrate that these H2Se donors are cell permeable and use this technique for spatial mapping of the intracellular Se content after H2Se delivery. Moreover, these H2Se donors reduce endogenous intracellular reactive oxygen species (ROS) levels. Taken together, this work expands the toolbox of H2Se donor technology and sets the stage for future work focused on the biological activity and beneficial applications of H2Se and related bioinorganic RSeS.
Furfuryl Cation Induced Three-Component Reaction to Synthesize Triazole-Substituted Thioesters
Zhong, Ying,Xu, Xiaoming,Xing, Qingzhao,Yang, Song,Gou, Jing,Gao, Ziwei,Yu, Binxun
supporting information, p. 3251 - 3256 (2020/05/25)
A furfuryl cation induced three-component thioesterification reaction between thiols, 5-bromo-2-furylcarbinols and azides is reported. This metal-free method relies on the acetyl chloride/HFIP-mediated cascade formal [3+2] cycloaddition/ring-opening/thioesterification, which allows the efficient construction of a series of complex triazole-thioesters linked with an (Z)-olefin. Selenols are also suitable for this strategy. Further derivatization of thioesters highlighted the potential utility of our method.
A77Se NMR study of elemental selenium reduction using NaBH4
Oliveira, Alfredo Ricardo Marques De,Piovan, Leandro,Simonelli, Fabio,Barison, Anderson,Santos, Maria De Fatima C.,De Mello, Murilo Belini Marcondes
, p. 54 - 59 (2016/07/06)
Alkylation or arylation of selenide or diselenide anions is a well-established method to obtain organoselenium compounds. Nevertheless, detecting inorganic selenium anions using77Se NMR is still a challenge. In a previous work, alkylation of Na2Se was found sometimes to yield a mixture of organyl selenides/diselenides in variable amounts. In the literature, this mixture is sometimes attributed to the oxidation of an intermediate alkyl selenol during the extraction. To understand this process, a series of experiments using77Se NMR were performed. It was clear from the77Se NMR experiments that NaHSe-and Se22- formation was very dependent on the NaBH4stoichiometry used. After alkylation, alkyl selenol and dialkyl diselenide were identified, proving they were not formed during the extraction step. As a result, alkyl selenols, dialkyl selenides or dialkyl diselenides with a high purity degree were obtained. To achieve high purity and selectivity of the organoselenium compound, the stoichiometric ratio between Se0/NaBH4has to be carefully measured.
