Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2017 Feb 14;12(2):e0172238.
doi: 10.1371/journal.pone.0172238. eCollection 2017.

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

Anna Gliszczyńska  1 , Natalia Niezgoda  1 , Witold Gładkowski  1 , Marta Świtalska  2 , Joanna Wietrzyk  2
Affiliations

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

Anna Gliszczyńska et al. PLoS One. .

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.

PubMed Disclaimer

Conflict of interest statement

The authors have declared that no competing interests exist.

Figures

Fig 1
Fig 1. Prepared acids used in the synthesis of terpene phospholipids.
Fig 2
Fig 2. Synthesis of acid (5).
Reagents (i) CH3C(OEt)3, CH3COOH, 138°C; (ii) KOH, EtOH.
Fig 3
Fig 3. Structures of synthesized isoprenoid phospholipids.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Smith-Warner SA, Spiegelman D, Yaun SS, Adami HO, Beeson WL, van den Brandt PA, et al. Intake of fruits and vegetables and risk of breast cancer: a pooled analysis of cohort studies. J Am Med Assoc. 2001; 285: 769–776. - PubMed
    1. Smith-Warner SA, Giovannucci E. Fruit and vegetable intake and cancer, in: Heber D, Blackburn G (Eds.), Nutritional Oncology, Academic Press, San Diego, CA, 1999, pp. 153–183.
    1. Tatman D, Mo H. Volatile isoprenoid constituents of fruits, vegetables and herbs cumulatively suppress the proliferation of murine B16 melanoma and human HL-60 leukemia cells. Cancer Letters. 2002; 175: 129–139. - PubMed
    1. Mo H, Elson CE. Apoptosis and cell-cycle arrest in human and murine tumor cells are initiated by isoprenoids. J Nutr. 1999; 129: 804–813. - PubMed
    1. He L, Mo H, Hadisusilo S, Qureshi AA, Elson CE. Isoprenoids suppress the growth of murine B16 melanomas in vitro and in vivo. J Nutr. 1997; 127: 668–674. - PubMed

MeSH terms

LinkOut - more resources