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

Suzanne M. Cloonan; John J. Keating; Stephen G. Butler; Andrew J. S. Knox; Anne Marie Jørgensen; Günther H.J. Peters; Dilip Rai; Desmond Corrigan; David G. Lloyd; D Clive Williams; Mary J. Meegan

doi:10.1016/j.ejmech.2009.07.027

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

Suzanne M. Cloonan, John J. Keating, Stephen G. Butler, Andrew J. S. Knox, Anne Marie Jørgensen, Günther H.J. Peters, Dilip Rai, Desmond Corrigan, David G. Lloyd, D Clive Williams, Mary J. Meegan

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

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. (C) 2009 Elsevier Masson SAS. All rights reserved.

Original language	English
Journal	European Journal of Medicinal Chemistry
Volume	44
Issue number	12
Pages (from-to)	4862-4888
Number of pages	27
ISSN	0223-5234
DOIs	https://doi.org/10.1016/j.ejmech.2009.07.027
Publication status	Published - 2009

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Cloonan, S. M., Keating, J. J., Butler, S. G., Knox, A. J. S., Jørgensen, A. M., Peters, G. H. J., Rai, D., Corrigan, D., Lloyd, D. G., Williams, D. C., & Meegan, M. J. (2009). Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents. European Journal of Medicinal Chemistry, 44(12), 4862-4888. https://doi.org/10.1016/j.ejmech.2009.07.027

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title = "Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents",

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. (C) 2009 Elsevier Masson SAS. All rights reserved.",

author = "Cloonan, {Suzanne M.} and Keating, {John J.} and Butler, {Stephen G.} and Knox, {Andrew J. S.} and J{\o}rgensen, {Anne Marie} and Peters, {G{\"u}nther H.J.} and Dilip Rai and Desmond Corrigan and Lloyd, {David G.} and Williams, {D Clive} and Meegan, {Mary J.}",

year = "2009",

doi = "10.1016/j.ejmech.2009.07.027",

language = "English",

volume = "44",

pages = "4862--4888",

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Cloonan, SM, Keating, JJ, Butler, SG, Knox, AJS, Jørgensen, AM, Peters, GHJ, Rai, D, Corrigan, D, Lloyd, DG, Williams, DC & Meegan, MJ 2009, 'Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents', European Journal of Medicinal Chemistry, vol. 44, no. 12, pp. 4862-4888. https://doi.org/10.1016/j.ejmech.2009.07.027

Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents. / Cloonan, Suzanne M.; Keating, John J.; Butler, Stephen G. et al.
In: European Journal of Medicinal Chemistry, Vol. 44, No. 12, 2009, p. 4862-4888.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - Synthesis and serotonin transporter activity of sulphur-substituted alpha-alkyl phenethylamines as a new class of anticancer agents

AU - Cloonan, Suzanne M.

AU - Keating, John J.

AU - Butler, Stephen G.

AU - Knox, Andrew J. S.

AU - Jørgensen, Anne Marie

AU - Peters, Günther H.J.

AU - Rai, Dilip

AU - Corrigan, Desmond

AU - Lloyd, David G.

AU - Williams, D Clive

AU - Meegan, Mary J.

PY - 2009

Y1 - 2009

N2 - 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. (C) 2009 Elsevier Masson SAS. All rights reserved.

AB - 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. (C) 2009 Elsevier Masson SAS. All rights reserved.

U2 - 10.1016/j.ejmech.2009.07.027

DO - 10.1016/j.ejmech.2009.07.027

M3 - Journal article

C2 - 19717215

SN - 0223-5234

VL - 44

SP - 4862

EP - 4888

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 12

ER -

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

Abstract

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