The author of 《Chiral recognition of homochiral poly (amidoamine) dendrimers substituted with R- and S-glycidol by keratinocyte (HaCaT) and squamous carcinoma (SCC-15) cells in vitro》 were Malinga-Drozd, Malgorzata; Uram, Lukasz; Wrobel, Konrad; Wolowiec, Stanislaw. And the article was published in Polymers (Basel, Switzerland) in 2021. Reference of (R)-Oxiran-2-ylmethanol The author mentioned the following in the article:
The generation 2 and 3 poly(amidoamine) dendrimers (PAMAM G2 and G3) were converted into N-(2,3-dihydroxy)propyl derivatives by the addition of enantiomerically pure S- and R-glycidol. The homochiral dendrimers bind to HaCaT and SCC-15 cell membranes with an R/S glycidol enantioselectivity ratio of 1.5:1, as was quant. determined by fluorescence microscopy and visualized by confocal microscopy. Fully substituted G2 and G3 dendrimers were equipped with 32 and 64 N-(2,3-dihydroxy)propyl residues and showed effectively radial symmetry for homochiral derivatives in 13C NMR spectrum in contrary to analogs obtained by reaction with rac-glycidol. The sub-stoichiometric derivatives of G2 and G3 were also obtained in order to characterize them spectroscopically. The homochiral dendrimers were labeled with two different fluorescent labels, fluorescein, and rhodamine B, using their isothiocyanates to react with G2 and G3 followed by the addition of S- and R-glycidol. Obtained fluorescent derivatives were deficiently filled with N-(2,3-dihydroxy)propyl substituents due to steric hindrance imposed by the attached label. Nevertheless, these derivatives were used to determine their ability to bind to the cell membrane of human keratinocytes (HaCaT) and squamous carcinoma cells (SCC-15). Confocal microscopy images obtained from cells treated with variously labeled conjugates and fluorescence anal. with fluorescence reader allowed us to conclude that R-glycidol derivatives were bound and entered the cells preferentially, with higher accumulation in cancer cells. The G3 polyamidoamine (PAMAM)-based dendrimers were taken up more efficiently than G2 derivatives Moreover, S- and R-glycidol furnished dendrimers were highly biocompatible with no toxicity up to 300 Μ M concentrations, in contrast to the amine-terminated PAMAM analogs. The experimental process involved the reaction of (R)-Oxiran-2-ylmethanol(cas: 57044-25-4Reference of (R)-Oxiran-2-ylmethanol)
(R)-Oxiran-2-ylmethanol(cas: 57044-25-4) is a chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product.Reference of (R)-Oxiran-2-ylmethanol
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