Self-assembly of a tripeptide into a functional coating that resists fouling

Maity, Sibaprasad; Nir, Sivan; Zada, Tal; Reches, Meital

doi:10.1039/c4cc03578j

Cited by 71 publications

(80 citation statements)

References 39 publications

(24 reference statements)

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“…The ability of peptides to self‐assemble, adopting stable secondary conformations, has allowed them to be used in nanotechnology and in materials science as very multifunctional tools . Superhydrophobic coating, tissue engineering, cell culturing, biosensing, and drug delivery are only some of the possible areas of application of peptide‐based supramolecular systems. The driving forces that hold up spontaneous aggregations are pinpointed in hydrogen bonds and hydrophobic and aromatic interactions.…”

Section: Introductionmentioning

confidence: 99%

Structural Characterization of PEGylated Hexaphenylalanine Nanostructures Exhibiting Green Photoluminescence Emission

Diaferia

Sibillano

Altamura

et al. 2017

Chemistry A European J

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Peptides containing aromatic residues are known to exhibit spontaneous phenomena of supramolecular organization into ordered nanostructures (NSs). In this work we studied the structural behavior and optoelectronic properties of new biocompatible materials obtained by the self-assembly of a series of hexaphenylalanines (F6) modified at the N terminus by a PEG chain of different lengths. PEG -F6, PEG -F6, and PEG -F6 peptides were synthesized by coupling sequentially two, three, or four units of amino-carboxy-PEG blocks, each one containing six oxyethylene repetitions. Changes in the length and composition of the PEG chain were found to modulate the structural organization of the phenylalanine-based nanostructures. An increase in the self-aggregation tendency was observed with longer PEG chains, whereas, independently of the PEG length, the peptide NSs display cross-β-like secondary structures with an antiparallel β-strand arrangement. WAXS/GIWAXS diffraction patterns indicate a progressive decrease in fiber order along the series. All the PEG-F6 derivatives present blue photoluminescent (PL) emission at 460 nm, with the adduct with the longest PEG chain (PEG -F6) showing an additional green emission at 530 nm.

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Section: Introductionmentioning

confidence: 99%

Structural Characterization of PEGylated Hexaphenylalanine Nanostructures Exhibiting Green Photoluminescence Emission

Diaferia

Sibillano

Altamura

et al. 2017

Chemistry A European J

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“…The peptide DOPA‐Phe(4F)‐ Phe(4F)‐COOMe was synthesized by solution phase synthesis as reported before.…”

Section: Methodsmentioning

confidence: 99%

“…We have previously shown the self‐assembly of a tripeptide into a coating that prevents biofouling. This peptide combines three properties: an adhesive element in the form of the amino acid DOPA and two fluorinated phenylalanines that allow both the self‐assembly of the peptide into a coating and its antifouling properties …”

Section: Introductionmentioning

confidence: 99%

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

Dolid

Reches

2019

Journal of Peptide Science

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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.

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“…Enormous antifouling materials were developed to alter the physical and/or chemical properties of the surface in order to prevent the accumulation of the organisms on the substrates. To date zwitterionic polymers [2][3][4][5], biodegradable hydrophilic or amphiphlic polymers [6][7][8], bioinspired engineered topographies [9,10], (nano-structured) organic-inorganic hybrid systems [11][12][13], low surface energy elastomers specifically silicone or fluoropolymers [14,15], agricultural and natural products [16,17], and self-assembly of a low molecular weight peptide [18] have been used for preparation of antifouling coatings. Shark skin effect has also been highly valued for fabrication of biomimetic anti-biofouling coatings [19].…”

Section: Introductionmentioning

confidence: 99%