Design, synthesis, and characterization of fullerene–peptide–steroid covalent hybrids

Bjelaković, Mira S.; Kop, Tatjana J.; Vlajić, Marina; Đorđević, Jelena; Milić, Dragana

doi:10.1016/j.tet.2014.09.070

Cited by 19 publications

(36 citation statements)

References 42 publications

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“…ral products. [17,18,20,21] Gathering these two entities has allowed these conjugates to be more soluble than pristine [60]fullerene in aqueous medium as well as in organic solvents. [13,14] It has also been shown that certain structural modifications induced the change of biological response, giving compounds with a wide scope of biological activity.…”

Section: Introductionmentioning

confidence: 99%

“…[17,18,20,21] Gathering these two entities has allowed these conjugates to be more soluble than pristine [60]fullerene in aqueous medium as well as in organic solvents. Thus, some studies have been published reporting on the antioxidant activity of fulleropyrrolidines endowed with an steroid unit, [20,21,27] the effect of steroid-fullerene adducts on sarcoplasmic reticulum (SR) Ca 2+ -ATPase and survival of human lung adenocarcinoma cancer A549 cells. [23] The synthetic methods for preparing hybrid steroid-fullerenes are based on the electrophilic character of C 60 , the most common reactions reported for the modifications of fullerenes being the cycloadditions.…”

Section: Introductionmentioning

confidence: 99%

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Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

et al. 2018

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New hybrid fullerene–steroid derivatives were prepared by using the Bingel–Hirsch protocol, by treatment of [60]fullerene with malonates bearing the appropriate steroid moieties obtained, in turn, from the functionalization of epiandrosterone, an important naturally occurring steroid hormone. Monocycloadduct C60‐steroid conjugates were obtained by functionalization of ring A or ring D of the steroid moiety. We have also described the multistep preparation of a [60]fullerene hybrid dumbbell endowed with two fullerene units connected through an epiandrosterone molecule by a cyclopropanation reaction. The new compounds have been spectroscopically characterized and their redox potentials, determined by cyclic voltammetry, reveal three reversible reduction waves for monocycloadducts (8, 9 and 11, 12), whereas dumbbell‐type derivative 10 exhibits the best electron‐accepting abilities of the Bingel‐type fullerene–steroid series. Theoretical calculations at semiempirical (AM1) and single point B3LYP‐D3/6‐31G+(d,p) levels have predicted the most stable conformations for the hybrid compounds and allow explaining the observed regioselectivity in the cyclopropanation reaction with dimalonate 7 during the synthesis of the dumbbell derivative.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

et al. 2018

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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%

“…The self-assembling properties and morphology of [60]fullerene peptides of different chain lengths, in comparison with the native amino acid, have been studied using scanning electron microscopy (SEM) 29 . Figure 11(a) shows a comparison of the self-organized structures of the tert-butyl ester of the parent [60]fullerene amino acid, Fp-GABA-O t Bu (c.f.…”

Section: Structural Effectsmentioning

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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“…Additionally, morphological characterization 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 , Fig.…”

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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Design, synthesis, and characterization of fullerene–peptide–steroid covalent hybrids

Cited by 19 publications

References 42 publications

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

Steroid–Fullerene Hybrids from Epiandrosterone: Synthesis, Characterization and Theoretical Study

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

Fulleropeptide esters as potential self-assembled antioxidants

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