Fulleropeptide esters as potential self-assembled antioxidants

Abstract

SummaryThe potential use of amphiphilic fullerene derivatives as a bionanomaterial was investigated by cyclic voltammetry (CV), scanning electron microscopy (SEM), and the ferrous ion oxidation–xylenol orange (FOX) method. Despite the disrupted delocalization of the π-electronic system over the C60 sphere, its antioxidant capacity remained high for all twelve derivatives. The compounds expressed up to two-fold and 5–12-fold better peroxide quenching capacity as compared to pristine C60 and standard antioxidant vitamin C, respectively. During precipitation and slow evaporation of the solvent, all compounds underwent spontaneous self-assembly giving ordered structures. The size and morphology of the resulting particles depend primarily on the sample concentration, and somewhat on the side chain structure.

Aggregation Behavior and Antioxidant Properties of Amphiphilic Fullerene C60 Derivatives Cofunctionalized with Cationic and Nonionic Hydrophilic Groups

“…To date, evaluations of the radical scavenging capabilities of water soluble C 60 derivatives are restricted to fullerenols, 34,36−43 carboxylated fullerenes, 30−35 and fulleropeptides. 70 These studies suffered from the ill-defined molecular structures of the C 60 derivatives, which made it difficult to establish the structure−property relationship. On the other hand, some water soluble C 60 derivatives with defined structures have been synthesized, and their aggregation behavior in water has been investigated.…”

“…To date, evaluations of the radical scavenging capabilities of water soluble C 60 derivatives are restricted to fullerenols, ,− carboxylated fullerenes, − and fulleropeptides . These studies suffered from the ill-defined molecular structures of the C 60 derivatives, which made it difficult to establish the structure–property relationship.…”

Self-assembly of amphiphilic amino acid derivatives for biomedical applications

“…For instance, heating the hydrogels led to a reversible gel-sol transition, and Fig. 1 Various nanostructures obtained from the self-assembly of different amphiphilic amino acid derivatives: (a) spherical micelles, 38 (b) microfibers, 39 (c) spherical vesicles, 44 (d) nanoparticles, 45 (e) nanofibers (hydrogel), 58 (f) nanotubes, 59 (g) nanorods, 65 (h) flower-liked structures, 65 (i) spiral-liked structures, 65 (j) artichoke-liked structures, 65 (k) hollow spherical vesicles, 66 (l) rosette nanotubes. 73 Reproduced with permission.…”

“…Reproduced with permission. 65 Copyright 2015, Beilstein Institute for the Advancement of Chemical Sciences (Open access). Reproduced with permission.…”

Self-Assembling Peptides and Carbon Nanomaterials Join Forces for Innovative Biomedical Applications

“…Peptides can indeed be very convenient to enhance fullerenes’ solubility in water and direct their supramolecular behavior, whilst maintaining their electronic properties and resulting antioxidant activity, as demonstrated through covalent conjugation [ 151 , 152 ]. Alternatively, a non-covalent approach can be envisaged, for instance by embedding fullerenes within the hydrogel matrix formed by self-assembling peptides; the resulting hybrid material could be envisaged for photodynamic antibacterial therapy, because of the fullerenes’ well-established electronic properties with the additional benefit of the injectable matrix formed due to the presence of the peptide [ 115 ].…”