Synthesis of the Novel (±)-2-methoxy-6-icosynoic Acid--a Fatty Acid That Induces Death of Neuroblastoma Cells

Overview

Journal Chem Phys Lipids

Specialty Biochemistry

Date 2013 May 8

PMID 23648411

Citations 3

Authors

Elsie A Orellano

Michelle M Cartagena

Karolyna Rosado

Nestor M Carballeira

Affiliations

Soon will be listed here.

Abstract

The first total synthesis for the novel fatty acid (±)-2-methoxy-6-icosynoic acid was accomplished in seven steps and in a 14% overall yield starting from 2-(4-bromobutoxy)-tetrahydro-2H-pyran. The title compound displayed an EC50=23±1 μM against the human SH-SY5Y neuroblastoma cell line and an EC50=26±1 μM against the human adenocarcinoma cervix cell line (HeLa) after 48 h of exposure. The corresponding non-methoxylated analog 6-icosynoic acid did not display cytotoxicity (EC50>500 μM) toward the studied cell lines as well as the 2-methoxyicosanoic acid (EC50>300 μM). The critical micelle concentration (CMC=20-30 μM) for the (±)-2-methoxy-6-icosynoic acid was also determined. It was found that α-methoxylation decreases the CMC of a fatty acid.

Citing Articles

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Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria.

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Synthesis of marine α-methoxylated fatty acid analogs that effectively inhibit the topoisomerase IB from Leishmania donovani with a mechanism different from that of camptothecin.

Carballeira N, Montano N, Alvarez-Velilla R, Prada C, Reguera R, Balana-Fouce R Mar Drugs. 2013; 11(10):3661-75.

PMID: 24084785 PMC: 3826128. DOI: 10.3390/md11103661.

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