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. 2022 Oct 29;20(11):682.
doi: 10.3390/md20110682.

Complexing the Marine Sesquiterpene Euplotin C by Means of Cyclodextrin-Based Nanosponges: A Preliminary Investigation

Alessandra Bertoli  1   2 , Anthea LoBue  3 , Luca Quattrini  1 , Stefania Sartini  1 , Beatrice Polini  4 , Sara Carpi  5 , Francesco Paolo Frontini  6 , Graziano Di Giuseppe  2   6 , Graziano Guella  7 , Paola Nieri  1   2 , Concettina La Motta  1   2
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Complexing the Marine Sesquiterpene Euplotin C by Means of Cyclodextrin-Based Nanosponges: A Preliminary Investigation

Alessandra Bertoli et al. Mar Drugs. .

Abstract

Euplotin C is a sesquiterpene of marine origin endowed with significant anti-microbial and anti-tumor properties. Despite the promising functional profile, its progress as a novel drug candidate has failed so far, due to its scarce solubility and poor stability in aqueous media, such as biological fluids. Therefore, overcoming these limits is an intriguing challenge for the scientific community. In this work, we synthesized β-cyclodextrin-based nanosponges and investigated their use as colloidal carriers for stably complex euplotin C. Results obtained proved the ability of the carrier to include the natural compound, showing remarkable values of both loading efficiency and capacity. Moreover, it also allowed us to preserve the chemical structure of the loaded compound, which was recovered unaltered once extracted from the complex. Therefore, the use of β-cyclodextrin-based nanosponges represents a viable option to vehiculate euplotin C, thus opening up its possible use as pharmacologically active compound.

Keywords: ATR-FTIR analysis; ESI-MS analysis; LC-DAD-ESI-MS analysis; NMR analysis; SPE; euplotin C; β-cyclodextrin; β-cyclodextrin-based nanosponges.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of euplotin C and β-cyclodextrin.
Figure 2
Figure 2
Superimposition of the ATR-FTIR spectra of the loaded complex EC-NS (green) and the binary 1:1 mixture of EC and NS (black).
Figure 3
Figure 3
Direct infusion ESI-MS spectrum of EC, showing major ions at 606.9 m/z [2EC + Na+] and at 315.1 m/z [EC + Na+], and ESI-MS/MS spectrum of the EC-sodium adduct at 315.1 m/z.
Figure 4
Figure 4
Direct infusion ESI-MS spectrum of NS and ESI-MS/MS spectrum on the ion at 1157.49 m/z.
Figure 5
Figure 5
Direct infusion ESI-MS spectrum of EC-NS1 extract.
Figure 6
Figure 6
Upper box: LC-PDA-MS chromatograms of EC-NS1 extract and relative MS/MS peak detection at 606.9 m/z and 315.1 m/z for EC compound; lower box: ESI-MS/MS of the ion at 606.9 m/z (top panel) and ESI-MS/MS spectrum of the ion at 315.1 m/z (bottom panel).
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