Steroid-fullerene adducts from Diels–Alder reactions: characterization and the effect on the activity of Ca2+-ATPase

Li, Liansheng; Hu, Yiming; Wu, Yunying; Yue, Jiachang; Yang, Fan

doi:10.1039/b007498p

Cited by 25 publications

(20 citation statements)

References 28 publications

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“…[15][16][17] In particular, the roles of sterols in diverse biological systems have been widely studied, and it has been determined that hydroxyl groups have a strong impact in the interaction with the receptor. [24] 4-Membered rings have also been obtained by [2+2] cycloaddition involving steroids [25] and cyclopropanation (Bingel's reaction) yields steroid-methanofullerenes. [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.…”

Section: Introductionmentioning

confidence: 99%

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%

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

et al. 2018

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“…On the other hand, the effect of steroid-fullerene adducts prepared through Diels-Alder reactions were evaluated on sarcoplasmic reticulum (SR) Ca 2+ -ATPase and survival of human lung adenocarcinoma cancer A549 cells. [39] The synthesis of steroidal derivatives of fullerenes in which cholesterol, or a cholesterol derivative, is attached through an ester, amide, or ether bond to one of a variety of linkers connected to fullerene through a pyrrolidine ring has very recently been described. [40] The steroid moiety can confer useful solubility in components of biological fluids and/or pharmacologically acceptable carriers and can also affect the biodistribution of the fullerenes, which makes these derivatives useful in imaging, diagnosis, and the treatment or management of disease.…”

Section: Introductionmentioning

confidence: 99%

Functional Chimeras: New Bingel–Hirsch‐Type Steroid–Fullerene Hybrids

et al. 2009

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Cyclopropanations between C60 and readily available malonates bearing different steroid moieties (4–6) by the Bingel–Hirsch protocol has allowed the synthesis of a new series of hybrid functionalized chimeras (7–9). Whereas cycloadducts 7 and 8 showed the expected chemical structures, the presence of the diene moiety in the ergosterol unit of malonate 6 resulted in the production of the corresponding cycloadduct with an additional oxygen molecule. A thorough spectroscopical study (1H and 13C NMR, COSY, DEPT, HMQC, and HMBC) allowed the structure of monocycloadduct 9 to be unambiguously unraveled as that of an endoperoxide, as a result of the sensitizing effect of the C60 unit, which efficiently promotes the addition of excited singlet oxygen to the diene moiety of the steroid. Cyclic voltammetry of hybrids 7–9, as well as their electronic spectra, support the exclusive formation of the corresponding monoadducts. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…We highlighted that the optimal balance is reached with the couples amine polar head/ester linker or carboxylic acid polar head/amide linker, the possible formation of inter-molecular H-bonds greatly enhancing the film cohesion and/or rigidity. We believe that these informations will be useful when aiming at elaborating new supramolecular assemblies of C 60 multiadducts at surfaces and interfaces with specific functionalisation for biological applications [50,51].…”

Section: Resultsmentioning

confidence: 99%

Spreading behaviour of a series of amphiphilic [3 : 3] [60]fullerene hexakisadducts: a systematic study

Hartnagel

Hirsch

Felder‐Flesch

et al. 2008

Journal of Experimental Nanoscience

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The spreading behaviour at the air-water interface of a series of [60]fullerene [3 : 3] hexakisadducts has been studied as a function of the hydrophobichydrophilic balance of the amphiphiles. More precisely, by changing both the nature and the size of the polar headgroup, by varying the nature of the chemical linker and/or spacer, by modifying the nature and/or the length of the spacer, it has been possible to perform a systematic study. The latter was carried out not only according to the pH of the aqueous subphase but also to its temperature highlighted various behaviours which in particular allowed to us to conclude that the optimal chemical design for this type of amphiphilic molecules is reached with the couples amine polar head/ester linker (Hexa-4) or carboxylic acid polar head/ amide linker (Hexa-5).

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Steroid-fullerene adducts from Diels–Alder reactions: characterization and the effect on the activity of Ca2+-ATPase

Cited by 25 publications

References 28 publications

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

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

Functional Chimeras: New Bingel–Hirsch‐Type Steroid–Fullerene Hybrids

Spreading behaviour of a series of amphiphilic [3 : 3] [60]fullerene hexakisadducts: a systematic study

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