19983-15-4Relevant articles and documents
Cysteine-Activated Small-Molecule H2Se Donors Inspired by Synthetic H2S Donors
Cai, Xuekang,Cheng, Longhuai,Dong, Yalun,Huang, Haojie,Jiang, Chenyang,Kang, Xueying,Sang, Yueqian,Sun, Lu,Wen, Xin,Xi, Zhen,Yi, Long
, p. 3957 - 3967 (2022/03/08)
The importance of selenium (Se) in biology and health has become increasingly clear. Hydrogen selenide (H2Se), the biologically available and active form of Se, is suggested to be an emerging nitric oxide (NO)-like signaling molecule. Nevertheless, the research on H2Se chemical biology has technique difficulties due to the lack of well-characterized and controllable H2Se donors under physiological conditions, as well as a robust assay for direct H2Se quantification. Motivated by these needs, here, we demonstrate that selenocyclopropenones and selenoamides are tunable donor motifs that release H2Se upon reaction with cysteine (Cys) at pH 7.4 and that structural modifications enable the rate of Cys-mediated H2Se release to be tuned. We monitored the reaction pathways for the H2Se release and confirmed H2Se generation qualitatively using different methods. We further developed a quantitative assay for direct H2Se trapping and quantitation in an aqueous solution, which should also be operative for investigating future H2Se donor motifs. In addition, we demonstrate that arylselenoamide has the capability of Cys-mediated H2Se release in cellular environments. Importantly, mechanistic investigations and density functional theory (DFT) calculations illustrate the plausible pathways of Cys-activated H2Se release from arylselenoamides in detail, which may help understand the mechanistic issues of the H2S release from pharmacologically important arylthioamides. We anticipate that the well-defined chemistries of Cys-activated H2Se donor motifs will be useful for studying Se biology and for development of new H2Se donors and bioconjugate techniques.
Metabolite profiling reveals a role for intercellular dihydrocamalexic acid in the response of mature Arabidopsis thaliana to Pseudomonas syringae
Kempthorne, Christine J.,Nielsen, Alexander J.,Wilson, Daniel C.,McNulty, James,Cameron, Robin K.,Liscombe, David K.
, (2021/04/12)
The leaf intercellular space is a site of plant-microbe interactions where pathogenic bacteria such as Pseudomonas syringae grow. In Arabidopsis thaliana, the biosynthesis of tryptophan-derived indolic metabolites is induced by P. syringae infection. Using high-resolution mass spectrometry-based profiling and biosynthetic mutants, we investigated the role of indolic compounds and other small molecules in the response of mature Arabidopsis to P. syringae. We observed dihydrocamalexic acid (DHCA), the precursor to the defense-related compound camalexin, accumulating in intercellular washing fluids (IWFs) without further conversion to camalexin. The indolic biosynthesis mutant cyp71a12/cyp71a13 was more susceptible to P. syringae compared to mature wild-type plants displaying age-related resistance (ARR). DHCA and structural analogs inhibit P. syringae growth (MIC ~ 500 μg/mL), but not at concentrations found in IWFs, and DHCA did not inhibit biofilm formation in vitro. However, infiltration of exogenous DHCA enhanced resistance in mature cyp71a12/cyp71a13. These results provide evidence that DHCA derived from CYP71A12 and CYP71A13 activity accumulates in the intercellular space and contributes to the resistance of mature Arabidopsis to P. syringae without directly inhibiting bacterial growth.
Synthesis method of thiazoline heterocyclic compound and application of thiazoline heterocyclic compound in biomolecular modification
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, (2020/01/12)
The invention discloses a synthesis method of a thiazoline heterocyclic compound and application of the thiazoline heterocyclic compound in biomolecular modification, and relates to the technical field of organic synthesis. The synthesis method comprises the following steps: mixing a thioalkene ether compound and a compound containing a 1, 2-mercaptoethylamine skeleton structure in a solvent, andadding a weak base to react for 60-240 minutes at the reaction temperature of 20-60 DEG C to obtain the dihydrothiazole heterocyclic compound. The synthesis method of the thiazolidine heterocyclic compound is mild and efficient, can quickly react in water at room temperature, and overcomes the defects of violent reaction conditions, long reaction time and the like in the traditional synthetic method; by means of the synthesis method, biomolecules such as polypeptide and protein containing the nitrogen-terminal cysteine residues can be efficiently and accurately modified, and application of detection and treatment methods and the like is further developed.
