The Bis-urea Motif as a Tool To Functionalize Self-Assembled Nanoribbons

Abstract

Here we present a surfactant molecule (1) containing an ammonium headgroup, in which a bis-ureido group is incorporated in its hydrocarbon chain. Due to strong hydrogen bonding interactions, 1 forms well-defined highly ordered ribbon-like aggregates in water. Moreover, we demonstrate that these ribbons can be functionalized via a modular approach through molecular recognition of other bis-urea containing molecules. The dye disperse orange and biotin were coupled to matching bis-ureido groups and incorporated into the ribbon structure. The anchoring of different functionalities in a modular approach proved to be possible using the molecular recognition capabilities of the bis-ureido moiety, thereby opening possibilities to a wide range of applications.

In vivo bioactivity of DNA‐based coatings: An experimental study in rats

“…In the present study, Bis‐Ureido‐Surfactant (BUS) was used to function as a barrier for the formation of a multicompartment coating. This surfactant molecule functions by the formation of strong hydrogen bonds resulting in well‐defined highly ordered ribbon‐like bilayer aggregates,18 ensuring the presence of DNA at the surface. Apart from acting as a stabilizing unit, bis‐urea units can also be used as an anchor for functional molecules, such as growth factors.…”

“…Multilayered DNA coatings were generated using the LbL deposition technique with BUS18 as the cationic component and DNA as the anionic component. Briefly, the cleaned implants were immersed in an aqueous solution of BUS (5 mg/mL) for 30 min, thereby allowing sufficient time for the adsorption of BUS (the first cationic polyelectrolyte layer) onto the implants.…”

“…In the present study, originally used cationic polyelectrolytes for the generation of DNA‐based coatings were replaced by Bis‐Ureido‐Surfactant (BUS). This surfactant molecule functions by the formation of strong hydrogen bonds resulting in well‐defined highly ordered ribbon‐like bilayer aggregates,18 ensuring the presence of DNA at the surface.…”

A One‐Pot Synthesis of Symmetrical and Unsymmetrical Dipeptide Ureas

“…As shown in Table 4, reacting Ala as aa 1 with Trp (Tryptophan), Phe (Phenylalanine) and Met (Methionine) as aa 2 afforded high yields of the corresponding 1,3-disubstituted urea analogues (Table 4, entries 1, 2 and 3).…”

“…The usefulness of ureas in materials chemistry, [1][2][3] pharmaceutical chemistry, [4][5][6] and biology [7,8] is evident from the publication of many more than a thousand papers reporting their synthesis and applications. These diverse series of compounds have wide series of applications ranging from plasticisers to pharmaceuticals.…”