An Approach to Nanobioparticles – Synthesis and Characterization of Fulleropeptides

Abstract

Two sets of new peptides incorporating fulleropyrrolidine units – Fp‐GABAn‐Glym‐OtBu – have been designed, synthesized and completely characterized. In the first series the chain contained only GABA (γ‐aminobutyric) residues, whereas in the second one glycine moieties were also inserted as well as GABA. Most of the target compounds were prepared by DCC/DMAP‐assisted coupling of previously synthesized GABA‐containing fulleropyrrolidinic acid and corresponding C‐protected small peptides, although for two fulleropeptides [3+2] cycloadditions of azomethine ylides to C60 were employed. All new compounds were characterized by standard spectroscopic methods. Complete assignments of peptide spin systems were achieved by extensive NMR analysis (1H, 13C, H,H‐COSY, HSQC, HMBC and TOCSY).

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

“…The fulleropyrrolidine peptides containing only GABA (γ-aminobutyric) residues, having zero or one glycine moiety have been reported (Figure 6). 43 The authors claim that these may be used as nanobioparticles. However, no results related to these properties were reported.…”

Morphological characterization of fullerene–androsterone conjugates

“…The covalent linkage of C 60 to moieties, such as porphyrins [3], anionic polymethine cyanine [4], and other bioactive molecules such as amino acids [5], peptides [6–7], nucleotides, sugars and steroids [8–9], have allowed the solubilization of these hybrid derivatives in aqueous media, thus enhancing certain biological activities. For the potential use of C 60 derivatives as drug delivery systems, the size of the particles is important.…”

Fulleropeptide esters as potential self-assembled antioxidants

“…The functionalized fullerenes are able to self-assemble into a plethora of supramolecular structures, such as spheres, nanotubes, vesicles, rods, nanowires, and nanofibers [9][10][11]. Also, formation of diverse morphologies of self-assembled fullerene derivatives under different external conditions has also been the subject of interest of Nakanishi's research group [24] and Fp-peptides 2-12 [27]. [12,13].…”

“…Additionally, morphological characteriza-tion of self-organized structures of fullerene-steroid [26] and fullerene-peptide-steroid hybrids [25] in solution and in the solid state was studied by SEM. In our previous work [27], we described the synthesis and provided a thorough spectral characterization of a series of fulleropeptide tert-butyl esters (2-12, Figure 1) consisting of two aliphatic amino acids, γ-aminobutyric acid (GABA) and glycine (Gly), using fulleropyrrolidinic ester 1 as a starting compound. In continuation of our interest in the chemistry of fullerene-peptide hybrids, we assumed that their further characterization could contribute to a better understanding of the synergy of the molecular subunits, as well as to potential applications in the field of new bionanomaterials.…”