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Molecules 2018, 23(8), 2022; https://doi.org/10.3390/molecules23082022

Synthesis, Characterization, and In Vitro Cancer Cell Growth Inhibition Evaluation of Novel Phosphatidylcholines with Anisic and Veratric Acids

1
Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
2
Department of Experimental Oncology, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Weigla 12, 53-114 Wrocław, Poland
3
Central Laboratory of the Instrumental Analysis, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, Wrocław 50-370, Poland
*
Authors to whom correspondence should be addressed.
Received: 26 June 2018 / Revised: 28 July 2018 / Accepted: 8 August 2018 / Published: 13 August 2018
(This article belongs to the Special Issue Selected Papers on Natural Products for the Future)
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Abstract

Phenolic acids and its methoxy derivatives are known to induce caspase-mediated apoptosis activity and exhibit cytotoxic effect towards various cancer cell lines. However, their low stability and poor bioavailability in the human organism extensively restrict the utility of this group of compounds as anticancer and health-promoting agents. In this report, a series of eight novel phosphatidylcholines (3a-b, 5a-b, 7a-b, 8a-b) containing anisic or veratric acids (1a-b) at sn-1 and/or sn-2 positions were synthesized. The phenoylated phospholipids were obtained in good yields 28–66%. The structures of novel compounds were determined by their spectroscopic data. All synthesized compounds were evaluated for their antiproliferative activity towards six cancer cell lines and normal cell line Balb/3T3. Lipophilization of phenolcarboxylic acids significantly increased their anticancer properties. The asymmetrically substituted phenoylated phosphatidylcholines exhibited higher antiproliferative effect than free acids. Lysophosphatidylcholine (7b) effectively inhibited the proliferation of human leukaemia (MV4-11), breast (MCF-7), and colon (LoVo) cancer cell lines at concentrations of 9.5–20.7 µm and was from 19 to 38-fold more active than corresponding free veratric acid. The conjugation of anisic/veratric acids with the phosphatidylcholine have proved the anticancer potential of these phenolcarboxylic acids and showed that this type of lipophilization is an effective method for the production of active biomolecules. View Full-Text
Keywords: anisic acid; antiproliferative activity; phenolic acids; phosphatidylcholines; structured phospholipids; veratric acid anisic acid; antiproliferative activity; phenolic acids; phosphatidylcholines; structured phospholipids; veratric acid
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Czarnecka, M.; Świtalska, M.; Wietrzyk, J.; Maciejewska, G.; Gliszczyńska, A. Synthesis, Characterization, and In Vitro Cancer Cell Growth Inhibition Evaluation of Novel Phosphatidylcholines with Anisic and Veratric Acids. Molecules 2018, 23, 2022.

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