Stimulus responsive self-assembly of Gemini Amphiphilic Pseudopeptides

Abstract

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Interplay between hydrophilic and hydrophobic interactions in the self-assembly of a gemini amphiphilic pseudopeptide: from nano-spheres to hydrogels

“…5,6 We found that these simple molecules are able to self-assemble into different nanostructures through the cooperative action of polar (H-bonding and dipole-dipole) and non-polar (van der Waals) intermolecular interactions.…”

“…3 Initially inspired by nature and encouraged by previous results, 4 we designed a family of gemini amphiphilic pseudopeptides (GAPs), which are simple C 2 symmetric molecules built from two amino acids connected at their acid ends by a flexible spacer, and bearing two hydrophobic tails at both extremes. 5,6 We found that these simple molecules are able to self-assemble into different nanostructures through the cooperative action of polar (H-bonding and dipole-dipole) and non-polar (van der Waals) intermolecular interactions. 7 Moreover, those GAPs showing specific structural features behaved as stimulus dependent systems, forming amorphous materials in chloroform, fibers in methanol or aqueous methanol at neutral or basic pH, while vesicles when protonated in this medium.…”

“…6 Following the same structural design, we envisioned the preparation of a second generation of GAPs that were more soluble in water, 8 since this is the most interesting medium for studies of biological relevance. Accordingly, we hypothesized that a GAP bearing a nitrogen atom in the middle of the central spacer should be a reasonable structural motif (1 in Scheme 1) for the improvement of the aqueous solubility.…”

“…7 Moreover, those GAPs showing specific structural features behaved as stimulus dependent systems, forming amorphous materials in chloroform, fibers in methanol or aqueous methanol at neutral or basic pH, while vesicles when protonated in this medium. 6 After studying the processes with different techniques, we proposed a structural model for the observed properties, based on the flexibility of the molecules that allows them to fold and unfold upon the action of external chemical forces. 6 Following the same structural design, we envisioned the preparation of a second generation of GAPs that were more soluble in water, 8 since this is the most interesting medium for studies of biological relevance.…”

“…6 After studying the processes with different techniques, we proposed a structural model for the observed properties, based on the flexibility of the molecules that allows them to fold and unfold upon the action of external chemical forces. 6 Following the same structural design, we envisioned the preparation of a second generation of GAPs that were more soluble in water, 8 since this is the most interesting medium for studies of biological relevance. Accordingly, we hypothesized that a GAP bearing a nitrogen atom in the middle of the central spacer should be a reasonable structural motif (1 in Scheme 1) for the improvement of the aqueous solubility.…”