Density functional theory calculations indicate that van der Waals fullerene dimers and larger oligomers can form interstitial electron traps in which the electrons are even more strongly bound than in isolated fullerene radical anions. The fullerenes behave like "super atoms", and the interstitial electron traps represent one-electron intermolecular σ-bonds. Spectroelectrochemical measurements on a bis-fullerene-substituted peptide provide experimental support. The proposed deep electron traps are relevant for all organic electronics applications in which non-covalently linked fullerenes in van der Waals contact with one another serve as n-type semiconductors.
This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides. The applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted. This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides.
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Medicine and Health Sciences | Social and Behavioral SciencesThe applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted.
Clostridioides (also known as Clostridium) difficile is a Gram-positive anaerobic, spore producing bacterial pathogen that causes severe gastrointestinal infection in humans. The current chemotherapeutic options are inadequate, expensive, and limited, and thus inexpensive drug treatments for C. difficile infection (CDI) with improved efficacy and specificity are urgently needed. To improve the solubility of our cationic amphiphilic 1,1′-binaphthylpeptidomimetics developed earlier that showed promise in an in vivo murine CDI model we have synthesized related compounds with an N-arytriazole or N-naphthyltriazole moiety instead of the 1,1′-biphenyl or 1,1′-binaphthyl moiety. This modification was made to increase the polarity and thus water solubility of the overall peptidomimetics, while maintaining the aromatic character. The dicationic N-naphthyltriazole derivative 40 was identified as a C. difficile-selective antibacterial with MIC values of 8 µg/mL against C. difficile strains ATCC 700057 and 132 (both ribotype 027). This compound displayed increased water solubility and reduced hemolytic activity (32 µg/mL) in an in vitro hemolysis assay and reduced cytotoxicity (CC50 32 µg/mL against HEK293 cells) relative to lead compound 2. Compound 40 exhibited mild efficacy (with 80% survival observed after 24 h compared to the DMSO control of 40%) in an in vivo murine model of C. difficile infection by reducing the severity and slowing the onset of disease.
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