The effect of end‐group substitution on surface self‐assembly of peptides

Abstract

Biofouling, the undesirable accumulation of organisms onto surfaces, affects many areas including health, water, and energy. We previously designed a tripeptide that self‐assembles into a coating that prevents biofouling. The peptide comprises three amino acids: DOPA, which allows its adhesion to the surface, and two fluorinated phenylalanine residues that direct its self‐assembly into a coating and acquire it with antifouling properties. This short peptide has an ester group at its C‐terminus. To examine the importance of this end group for the self‐assembly and antifouling properties of the peptide, we synthesized and characterized tripeptides with different end groups (ester, amide, or carboxylic group). Our results indicate that different groups at the C‐terminus of the peptide can lead to a change in the peptide assembly on the surface and its adsorption process. However, this change only affects the antifouling properties of the coating toward Gram‐positive bacteria (Staphylococcus epidermidis), whereas Gram‐negative bacteria (Escherichia coli) are not affected.

Continuous flow fabrication of Fmoc-cysteine based nanobowl infused core–shell like microstructures for pH switchable on-demand anti-cancer drug delivery

“…Such a difference in the assembly behaviour of the amino acid mimetic with a mere modification in the N-terminal residue is quite exciting and has been previously observed in the case of other peptides and amino acids, where the self-assembly behaviour was decisively altered by varying the end groups. 51,52 Furthermore, it was observed that the particles exhibited concentration dependent assembly behaviour and NBs were obtained at higher amino acid concentrations. Interestingly, we also observed that the formation of NBs can be tuned by varying microfluidics flow parameters.…”

Fluorinated peptide biomaterials

“…To address both of these criteria, fluoropeptide scaffolds comprised of dihydroxyphenylalanine (DOPA) residues have been designed to promote tissue adhesion of the antibacterial biomaterial. [27,139] Dolid et al demonstrated how antifouling activity of DOPA-based fluoropeptide coatings depend on C-terminal modifications. [27] Here, amide modifications were found to change the C F to promote host cell attachment and spreading (>35% viable cell coverage).…”

“…[27,139] Dolid et al demonstrated how antifouling activity of DOPA-based fluoropeptide coatings depend on C-terminal modifications. [27] Here, amide modifications were found to change the C F to promote host cell attachment and spreading (>35% viable cell coverage). [139] Antibacterial resin dental composites have been Streptococcus mutans to 95%, while retaining similar biocompatibility and mechanical strength as commercial dental resins (Figure 9).…”

“…demonstrated how antifouling activity of DOPA‐based fluoropeptide coatings depend on C‐terminal modifications. [ 27 ] Here, amide modifications were found to change the CF bond configuration and alter the surface energy of the titanium implant to which its applied, consequently improving biofouling resistance toward a variety of Gram‐positive and ‐negative pathogens. Moreover, Yuran et al .…”

“…These cooperative processes pattern molecules into thermodynamically favorable, higher-ordered structural states either driven by microenvironmental cues or triggered upon presentation of a chemical interface or biologic stimulus. [24][25][26][27] The resulting three-dimensional hierarchical structures possess unique electro-and bio-chemical properties that often only emerge upon formation of the supramolecular functional state. Examples of such assemblies can be found across all forms of natural life, from microorganisms to mammals.…”