《Synthesis, distribution analysis and mechanism studies of N-acyl glucosamine-bearing oleanolic saponins》 was published in Bioorganic Chemistry in 2020. These research results belong to Juang, Yu-Pu; Lin, You-Yu; Chan, She-Hung; Chang, Chun-Kai; Shie, Jiun-Jie; Hsieh, Yves S. Y.; Guh, Jih-Hwa; Liang, Pi-Hui. Reference of Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine The article mentions the following:
A series of N-acyl glucosamine-bearing triterpenoid saponins has been synthesized with cytotoxic activities evaluated against HL-60, PC-3, HCT-116, and CT-26 tumor cells. Saponins incorporated an oleanolic acid (OA) triterpenoidal core exhibited the highest cytotoxic activity. To study the influence of the lengths of acyl-carbon chain on N-position of glucosamine, cells were treated with 28-propargylamides and then reacted with an azido-fluorogenic probe under CuAAC click reactions to visualize the intact distributions of these compounds by confocal microscopy and flow cytometry; it was found that cytotoxic-active compounds (30-32) located in the cytosol and inactive compounds bearing longer carbon chains (33-35) were impenetrable across cell membranes. Our study demonstrated the defined lipophilic acyl-carbon chain length can precisely regulate the cytotoxic activity of saponins, which is useful for the future development of cytotoxic agents. Furthermore, using quant. proteomics and immuno-labeling, the mechanism of cytotoxicity induced by the synthetic saponin after membrane penetration could be a result of activation of death receptor pathway and inhibition of PI3K/Akt/mTOR pathway. The experimental part of the paper was very detailed, including the reaction process of Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8Reference of Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine)
Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine(cas: 510758-28-8) can stabilizes Cu(I) towards disproportionation and oxidation thus enhancing its catalytic effect in the azide-acetylene cycloaddition.Reference of Tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)aminePolytriazolylamines were synthesized by the copper(I)-catalyzed ligation of azides and alkynes.
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics