Isoprenoid-phospholipid conjugates as potential therapeutic agents: Synthesis, characterization and antiproliferative studies

Anna Gliszczyńska; Natalia Niezgoda; Witold Gładkowski; Marta Świtalska; Joanna Wietrzyk

doi:10.1371/journal.pone.0172238

Isoprenoid-phospholipid conjugates as potential therapeutic agents: Synthesis, characterization and antiproliferative studies

PLoS One. 2017 Feb 14;12(2):e0172238. doi: 10.1371/journal.pone.0172238. eCollection 2017.

Authors

Anna Gliszczyńska¹, Natalia Niezgoda¹, Witold Gładkowski¹, Marta Świtalska², Joanna Wietrzyk²

Affiliations

¹ Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland.
² Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Department of Experimental Oncology, Wrocław, Poland.

Abstract

The aim of this research was to extend application field of isoprenoid compounds by their introduction into phospholipid structure as the transport vehicle. The series of novel isoprenoid phospholipids were synthesized in high yields (24-97%), their structures were fully characterized and its anticancer activity was investigated in vitro towards several cell lines of different origin. Most of synthesized compounds showed a significantly higher antiproliferative effect on tested cell lines than free terpene acids. The most active phosphatidylcholine analogue, containing 2,3-dihydro-3-vinylfarnesoic acids instead of fatty acids in both sn-1 and sn-2 position, inhibits the proliferation of colon cancer cells at 13.6 μM.

MeSH terms

A549 Cells
Animals
Antineoplastic Agents* / chemical synthesis
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
BALB 3T3 Cells
Cell Proliferation / drug effects*
Colonic Neoplasms / drug therapy*
Colonic Neoplasms / metabolism
Colonic Neoplasms / pathology
Dose-Response Relationship, Drug
Hep G2 Cells
Humans
MCF-7 Cells
Mice
Phospholipids* / chemical synthesis
Phospholipids* / chemistry
Phospholipids* / pharmacology
Terpenes* / chemical synthesis
Terpenes* / chemistry
Terpenes* / pharmacology

Substances

Antineoplastic Agents
Phospholipids
Terpenes

Grants and funding

This project was financed by National Science Center of Poland no. 2013/09/D/NZ9/02457. Publication was supported by Wroclaw Centre of Biotechnology, programme The Leading National Research Centre (KNOW) for years 2014-2018 (http://know.wroc.pl).