New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.

Marc Stierhof; Kine Østnes Hansen; Mukesh Sharma; Klaus Feussner; Karolina Subko; Fernando Fernández Díaz-Rullo; Johan Isaksson; Ignacio Pérez-Victoria; David Clarke; Espen Hansen; Marcel Jaspars; Jioji N. Tabudravu

doi:10.1016/j.tet.2016.09.016

New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.

Marc Stierhof, Kine Østnes Hansen, Mukesh Sharma, Klaus Feussner, Karolina Subko, Fernando Fernández Díaz-Rullo, Johan Isaksson, Ignacio Pérez-Victoria, David Clarke, Espen Hansen, Marcel Jaspars, Jioji N. Tabudravu^*

^*Corresponding author for this work

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Abstract

Four new callipeltin A derivatives (N–Q) have been isolated from the Solomon Island marine sponge Asteropus sp. Their structures were established by spectroscopic techniques followed by acid hydrolysis and derivatisation of the free amino acids, and subsequent LCMS analysis of the derivatives. The compounds were evaluated for their activity against cancer cell lines A2058 (melanoma), HT-29 (colorectal adenocarcinoma) and MCF-7 (breast adenocarcinoma) and non-malignant MRC-5 fibroblast cells. While the acyclic callipeltins P and Q were inactive the cyclic callipeltins N and O showed significant cytotoxicity against all exposed cell lines with IC₅₀ values as low as 0.16 μM confirming the role of cyclic configuration in biological activity.

Original language	English
Pages (from-to)	6929-6934
Number of pages	6
Journal	Tetrahedron
Volume	72
Issue number	44
Early online date	13 Sept 2016
DOIs	https://doi.org/10.1016/j.tet.2016.09.016
Publication status	Published - 3 Nov 2016

Bibliographical note

Acknowledgements

J.T., E.H., I.P.V., and M.J. acknowledge the financial support of the EU seventh Framework Programme Project ‘PharmaSea’ (Grant no. KBBE 2012-2016) (Contract no. 312184) and acknowledge the support of the RSC for use of the MarinLit Data Base. K.F. and M.C. acknowledge the support of the NCDDG (Grant no. U19 CA67786) awarded to Professor C. M. Ireland, University of Utah, USA. J.T. and M.S. thank Dr. Somayah Elsayed Sameer of the University of Aberdeen for advice on amino acid hydrolysis and derivatisation.

Keywords

Antiproliferative activity
Asteropus
Callipeltin
Derivatisation
LCMS
NMR

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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abstract = "Four new callipeltin A derivatives (N–Q) have been isolated from the Solomon Island marine sponge Asteropus sp. Their structures were established by spectroscopic techniques followed by acid hydrolysis and derivatisation of the free amino acids, and subsequent LCMS analysis of the derivatives. The compounds were evaluated for their activity against cancer cell lines A2058 (melanoma), HT-29 (colorectal adenocarcinoma) and MCF-7 (breast adenocarcinoma) and non-malignant MRC-5 fibroblast cells. While the acyclic callipeltins P and Q were inactive the cyclic callipeltins N and O showed significant cytotoxicity against all exposed cell lines with IC50 values as low as 0.16 μM confirming the role of cyclic configuration in biological activity.",

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note = "Acknowledgements J.T., E.H., I.P.V., and M.J. acknowledge the financial support of the EU seventh Framework Programme Project {\textquoteleft}PharmaSea{\textquoteright} (Grant no. KBBE 2012-2016) (Contract no. 312184) and acknowledge the support of the RSC for use of the MarinLit Data Base. K.F. and M.C. acknowledge the support of the NCDDG (Grant no. U19 CA67786) awarded to Professor C. M. Ireland, University of Utah, USA. J.T. and M.S. thank Dr. Somayah Elsayed Sameer of the University of Aberdeen for advice on amino acid hydrolysis and derivatisation.",

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N1 - Acknowledgements J.T., E.H., I.P.V., and M.J. acknowledge the financial support of the EU seventh Framework Programme Project ‘PharmaSea’ (Grant no. KBBE 2012-2016) (Contract no. 312184) and acknowledge the support of the RSC for use of the MarinLit Data Base. K.F. and M.C. acknowledge the support of the NCDDG (Grant no. U19 CA67786) awarded to Professor C. M. Ireland, University of Utah, USA. J.T. and M.S. thank Dr. Somayah Elsayed Sameer of the University of Aberdeen for advice on amino acid hydrolysis and derivatisation.

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AB - Four new callipeltin A derivatives (N–Q) have been isolated from the Solomon Island marine sponge Asteropus sp. Their structures were established by spectroscopic techniques followed by acid hydrolysis and derivatisation of the free amino acids, and subsequent LCMS analysis of the derivatives. The compounds were evaluated for their activity against cancer cell lines A2058 (melanoma), HT-29 (colorectal adenocarcinoma) and MCF-7 (breast adenocarcinoma) and non-malignant MRC-5 fibroblast cells. While the acyclic callipeltins P and Q were inactive the cyclic callipeltins N and O showed significant cytotoxicity against all exposed cell lines with IC50 values as low as 0.16 μM confirming the role of cyclic configuration in biological activity.

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New cytotoxic callipeltins from the Solomon Island marine sponge Asteropus sp.

Abstract

Bibliographical note

Keywords

UN SDGs

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