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Design and pharmacophore modeling of biaryl methyl eugenol analogs as breast cancer invasion inhibitors.

Abstract：

:Cell invasion and migration are required for the parent solid tumor cells to metastasize to distant organs. Microtubules form a polarized network, enabling organelle and protein movement throughout the cell. Cytoskeletal elements coordinately regulate cell's motility, adhesion, migration, exocytosis, endocytosis, and division. Thus, microtubule disruption can be a useful target to control cancer cell invasion and metastasis. The phenolic ether methyl eugenol (1), the major component of the essential oil of the leaves of Melaleuca ericifolia Sm. (Myrtaceae), was used as a starting scaffold to design eleven new and three known anti-tubulin agents 2-15 using carbon-carbon coupling reactions. A computer-assisted approach was used to design these new biaryl derivatives using colchicine-binding site of tubulin as the molecular target and colchicine as an active ligand. Several derivatives showed potent inhibitory activity against MDA-MB-231 cell migration at the 1-4microM dose range. The Z isomers, 4 and 15 were more active as invasion inhibitors compared to their structurally related E isomers, 2 and 14. The cytotoxic activities of compounds 2-15 against two breast cancer cell lines MDA-MB-231 and MCF-7 were evaluated. Anti-invasive activity of the semisynthetic derivatives is not due to a direct cytotoxic effect on MDA-MB-231. Analogs 2-15 may promote their anti-invasive activity through the induction of changes in cell morphology. A pharmacophore model was generated involving seven essential features for activity, which was consistent with a previously generated colchicine site inhibitors model.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Abdel Bar FM,Khanfar MA,Elnagar AY,Badria FA,Zaghloul AM,Ahmad KF,Sylvester PW,El Sayed KA

doi

10.1016/j.bmc.2009.12.019

subject

Has Abstract

pub_date

2010-01-15 00:00:00

pages

496-507

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(09)01103-1

journal_volume

18

pub_type

杂志文章

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