Chirality inversion, supramolecular hydrogelation and lectin binding of two thiolactose amphiphiles constructed on a di-lauroyl- l -tartaric acid scaffold

KOVENSKY, JOSÉ; WOLOSIUK, ALEJANDRO; DI CHENNA, PABLO HÉCTOR; KOVENSKY, JOSÉ; CANO, MARÍA EMILIA; DI CHENNA, PABLO HÉCTOR; WOLOSIUK, ALEJANDRO; CANO, MARÍA EMILIA; UHRIG, MARÍA LAURA; LESUR, DAVID; UHRIG, MARÍA LAURA; LESUR, DAVID

NEW JOURNAL OF CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE; Año: 2017 vol. 41 p. 14754 - 14765

1144-0546

Herein we report the synthesis, characterization and self-assembly properties of two new thiolactose based amphiphilesconstructed on a di-lauroyl-L-tartaric acid scaffold that only differ in the length of the spacer by an ethylenglycol unit.Upon dissolution in hot water the amphiphiles give rise to diferent colloidal systems at 25 °C: the one with the shorter linker forms a supramolecular thermoreversible hydrogel at a concentration of 0.1 w/v% while the other renders a colloidal system at high dilution (0.005 w/v%). Dynamic Light Scattering, Electron Microscopy (TEM, SEM and E-SEM),fluorescence CMC determination, SAXS and Circular Dichroism experiments were used to characterize bothssystems. The experiments indicate that only the amphiphile carrying the shorter linker is able to form a crossed-linked network of micellar fibers and thus, a stable hydrogel is observed. The difference of an ethylenglycol unit on the spacer also causes the adoption of a different molecular assembly evidenced by the inversion of the self-assembled chiral arrangement. Additionally, the amphiphiles were evaluated for their ability to bind to the PNA lectin using a turbidimetric method.Agglutination was observed in both cases, a process that was disrupted upon the addition of an excessof the disaccharide lactose.