title: Synthesis of the novel (±)-2-methoxy-6-icosynoic acid--a fatty acid that induces death of neuroblastoma cells.
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.
authors: Department of Chemistry, University of Puerto Rico, Rio Piedras campus, PO Box 23346, San Juan, PR 00931-3346.
authors: Elsie A
authors: EA
authors: Orellano
authors: Michelle M
authors: MM
authors: Cartagena
authors: Karolyna
authors: K
authors: Rosado
authors: Néstor M
authors: NM
authors: Carballeira
mesh_terms: D017209:Apoptosis / Q000187:drug effects; D045744:Cell Line, Tumor; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D006367:HeLa Cells; D006801:Humans; D008823:Micelles; D009447:Neuroblastoma / Q000378:metabolism / Q000473:pathology; D013237:Stereoisomerism
chemical_list: C585819:2-methoxy-6-icosynoic acid; D005227:Fatty Acids; D005231:Fatty Acids, Unsaturated; D008823:Micelles
keywords: Cancer; Methoxylated fatty acids; Micelles; Neuroblastoma; Synthesis
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