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Synthesis and in vitro Bioactivity of Polyunsaturated Fatty Acid Conjugates of Combretastatin A-4

Ojike, Fredrick O., Lavignac, Nathalie, Casely-Hayford, Maxwell A. (2018) Synthesis and in vitro Bioactivity of Polyunsaturated Fatty Acid Conjugates of Combretastatin A-4. Journal of Natural Products, 81 . pp. 2101-2105. ISSN 0163-3864. E-ISSN 1520-6025. (doi:10.1021/acs.jnatprod.7b01062) (KAR id:69154)

Abstract

Combretastatin A-4 (CA-4) (1) is a plant-derived anticancer agent binding to the tubulin colchicine site. Polyunsaturated fatty acids (PUFAs) are readily taken up by cancer cells and have been used to improve cell targeting. In the present study, four CA-4-PUFA conjugates were synthesized by coupling combretastatin A-4 (1) with several polyunsaturated fatty acids. The conjugates (2a–d) were characterized using spectroscopic methods. Their cytotoxicity was evaluated against human breast cancer cells (MCF-7), and the inhibition of tubulin polymerization was determined in vitro. All conjugates influenced tubulin polymerization, with the arachidonic acid conjugate (2c) displaying cytotoxicity similar in potency to the natural product CA-4 (1).

Item Type: Article
DOI/Identification number: 10.1021/acs.jnatprod.7b01062
Subjects: R Medicine
R Medicine > RM Therapeutics. Pharmacology
Divisions: Divisions > Division of Natural Sciences > Medway School of Pharmacy
Depositing User: Maxwell Casely-Hayford
Date Deposited: 19 Sep 2018 15:27 UTC
Last Modified: 18 Dec 2023 10:33 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/69154 (The current URI for this page, for reference purposes)

University of Kent Author Information

Ojike, Fredrick O..

Creator's ORCID:
CReDIT Contributor Roles:

Lavignac, Nathalie.

Creator's ORCID: https://orcid.org/0000-0002-9259-7603
CReDIT Contributor Roles:

Casely-Hayford, Maxwell A..

Creator's ORCID: https://orcid.org/0000-0003-4054-4371
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