[60]Fullerene-peptides: bio-nano conjugates with structural and chemical diversity

Abstract

[60]Fullerene-peptides represent a simple yet chemically diverse example of a bio-nano conjugate. The C moiety provides the following attributes to the conjugate: (a) precise three-dimensional architecture, (b) a large hydrophobic mass and (c) unique electronic properties. Conversely, the peptide component provides: (a) structural diversity depending on the overall length and amino acids composition, (b) charge flexibility and (c) secondary structure and recognition. Recent advances in the synthetic strategy for [60]fullerene-peptide synthesis from both pre-formed peptides and using solid phase peptide synthesis (SPPS) are described. The effects of the hydrophobic C on the secondary structure of the peptide depend on the sequence of the latter, but in general the relative stability of particular structures is greatly enhanced. The ability of the [60]fullerene substituent to dramatically modify both cellular uptake and transdermal transport is discussed as is the effects on cell viability and antimicrobial activity.

An Update on Antimicrobial Peptides (AMPs) and Their Delivery Strategies for Wound Infections

“…Altogether, carbon-based nanosystems show promising results for AMP delivery. Still, concerns of toxicity, induction of granuloma, and potential carcinogenicity in specific models warrant extensive safety studies encompassing a thorough evaluation of their long-term toxicities and pharmacokinetics properties [185,187].…”

“…The fullerene–peptide system could dramatically modify cellular uptake and showed less toxicity to keratinocytes at concentrations below 0.04 mg/mL. They exhibited high efficacy against S. aureus but were inactive against E. coli and C. albicans [ 185 ]. Furthermore, AMP–fullerene systems were developed with high bacteriostatic activity against S. aureus and E. coli , exhibiting low MICs of 8 and 64 μM, respectively [ 186 ].…”

An Update on Antimicrobial Peptides (AMPs) and Their Delivery Strategies for Wound Infections

“…The fullerene-peptide system could dramatically modify cellular uptake and showed less toxicity to keratinocytes at concentrations below 0.04 mg/mL. They exhibited high efficacy against S. aureus, but were inactive against E. coli and C. albicans [156]. Further AMP-fullerene systems were developed with high bacteriostatic activity against S. aureus and E. coli, exhibiting low MICs of 8 and 64 µM, respectively [157].…”

“…Altogether, carbon-based nanosystems show promising results for AMP delivery. Still concerns of toxicity, induction of granuloma, potential carcinogenicity in specific models warrant extensive safety studies encompassing a thorough evaluation of their long-term toxicities and pharmacokinetics properties [156,158].…”

Fullerenes in biology and medicine

“…5 Since then, efficient synthetic methods for fullerene functionalization have been developed. 6, 7 Functionalization with bioactive compounds that exhibit affinity to certain nucleic acids, proteins or cell receptors such as peptides 8-10 or saccharides, 11, 12 functionalization with polar or ionic groups such as hydroxyl, 13, 14 carbonyl 15-17 or quaternary ammonium salts, 18, 19 and encapsulation with macromolecules 20, 21 are the most common approaches to synthesize water-soluble fullerene derivatives for biomedical applications. 22-26 …”