Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.

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Cloonan SM, Keating JJ, Butler SG, Knox AJ, Jorgensen AM, Peters GH, Rai D, Corrigan D, Lloyd DG, Williams DC, Meegan MJ

Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents.

Eur J Med Chem. 2009 Dec;44(12):4862-88. doi: 10.1016/j.ejmech.2009.07.027. Epub 2009 Aug 6.

PubMed ID
19717215 [ View in PubMed
]
Abstract

The discovery that some serotonin reuptake transporter (SERT) ligands have the potential to act as pro-apoptotic agents in the treatment of cancer adds greatly to their diverse pharmacological application. 4-Methylthioamphetamine (MTA) is a selective ligand for SERT over other monoamine transporters. In this study, a novel library of structurally diverse 4-MTA analogues were synthesised with or without N-alkyl and/or C-alpha methyl or ethyl groups so that their potential SERT-dependent antiproliferative activity could be assessed. Many of the compounds displayed SERT-binding activity as well as cytotoxic activity. While there was no direct correlation between these two effects, a number of derivatives displayed anti-tumour effects in lymphoma, leukaemia and breast cancer cell lines, showing further potential to be developed as possible chemotherapeutic agents.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
MidomafetamineSodium-dependent dopamine transporterIC 50 (nM)1442N/AN/ADetails
MidomafetamineSodium-dependent noradrenaline transporterIC 50 (nM)405N/AN/ADetails
MidomafetamineSodium-dependent serotonin transporterIC 50 (nM)425N/AN/ADetails