Synthesis of Mono and Bis[60]fullerene‐Based Dicationic Peptoids

Jennepalli, Sreenu; Hammer, Katherine A.; Riley, Thomas V.; Pyne, Stephen G.; Keller, P. A.

doi:10.1002/ejoc.201403046

Cited by 12 publications

(7 citation statements)

References 40 publications

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“…As part of an ongoing antibacterial drug research project a series of mono substituted and disubstituted peptide fullerene derivatives (Figure 2) were synthesised. 9 These were prepared from the acid 23 and diacid 25, respectively. Although these derivatives did not show any substantial anti-bacterial activity, their synthesis has progressed the development of the important field of fullerenyl amino acids and peptide derivatives, in particular, their synthesis and isolation as peptide salts (156-160) and the high incorporation of basic amino acids with side chains.…”

Section: Biological Applicationsmentioning

confidence: 99%

“…This diacid 25 has been used to synthesise potential biologically useful fullerene amino acid derivatives. 9 BF 3 $Et 2 O and NaCNBH 3 mediated reductive ring-opening of the dihydrofullerenoproline derivative 8b 26 yields ethyl N-benzhydrylfullerenyl[60]glycinate 27, which was N-deprotected to give ethyl fullerenylglycinate 10 28, a true fullerenyl a-amino ester, which was fully characterized as its more stable N-acetyl derivative 29. Therefore, the original structure 26 could be considered as a protected version of 28.…”

Section: Assocmentioning

confidence: 99%

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

2014

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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. Disciplines Medicine and Health Sciences | Social and Behavioral SciencesThe applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted.

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Section: Biological Applicationsmentioning

confidence: 99%

Section: Assocmentioning

confidence: 99%

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

2014

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“…The first [60]fullerene peptide was prepared by the reaction of a N-terminal free pentapeptide (Ala-Aib-Ala-Aib-Ala-OMe) with a methanofullerene through a linker based on a benzoic acid moiety ( Figure 3) 23 . Following this report, a wide range of alternative linkage groups have been reported as being equally effective in facilitating the attachment of a preformed peptide [24][25][26][27][28][29][30] . Much of this work has been subject to recent reviews [17][18][19][20] , and a selection of the [60]fullerene derivatives used are also shown in Figure 3.…”

Section: Using a Preformed Peptidementioning

confidence: 91%

“…However, it was shown that the antimicrobial activity was most probably inherently due to the C 60 rather than the specific sequence, since the fullero-peptide H-Gly-Orn-Gly-Fgu-Gly-Orn-Gly-NH2 showed equal or better activity 34 . The presence of C 60 itself is clearly not totally a prerequisite for antimicrobial activity since, in a study of a series of [60]fullerene peptide derivatives, tested using the broth microdilution method against Staphylococcus aureus NCTC 6571 and Escherichia coli NCTC 10418, all the fullerenyl-based compounds were inactive, even at higher concentrations, with MIC greater than 100-340 (mg/mL) 28 .…”

Section: Toxicity and Antimicrobial Activitymentioning

confidence: 99%

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

Barron

2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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[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.

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“…Fulleropeptides synthesized by Prato's research group [ 17 ] showed a good bacteriostatic activity against Gram-positive bacterium S. aureus making it interesting for potential antimicrobial chemotherapeutics. Recently, Keller et al [ 18 ] reported the synthesis of fullerenedihydropyrrole cationic peptides, which did not show antibacterial activity. Neuroprotective and antioxidant properties are based on the fact that fullerene derivatives possess an extended π-bond system, with high electron and free-radical species affinities.…”

Section: Introductionmentioning

confidence: 99%

Fulleropeptide esters as potential self-assembled antioxidants

Bjelaković¹,

Kop²,

Đorđević³

et al. 2015

Beilstein J. Nanotechnol.

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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.

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Synthesis of Mono and Bis[60]fullerene‐Based Dicationic Peptoids

Cited by 12 publications

References 40 publications

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

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

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

Fulleropeptide esters as potential self-assembled antioxidants

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