Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis and Radiosynthesis of a Novel PET Fluorobenzyl Piperazine for Melanoma Tumour Imaging; [18F]MEL054

Stephen R. Taylor A C , Maxine P. Roberts A F , Naomi A. Wyatt A , Tien Q. Pham A , Daniela Stark A D , Thomas Bourdier A E , Peter Roselt B , Andrew Katsifis A E and Ivan Greguric A

A LifeSciences Division, Australian Nuclear Science and Technology Organisation, Locked Bag 2001, Kirrawee DC, NSW 2232, Australia.

B Centre for Molecular Imaging, The Peter MacCallum Cancer Centre, 12 St Andrew’s Place, East Melbourne, Vic. 3002, Australia.

C Current address: Department of Nuclear Medicine, Level 3, Ned Hanlon Building, Royal Brisbane and Women’s Hospital, Metro North Health Service District, Herston, Qld 4029, Australia.

D Current address: Cyclopet Pty Ltd Macquarie University Hospital, 3 Technology Place, Macquarie University, Lower Northern Sydney, NSW 2341, Australia.

E Current address: Department of PET & Nuclear Medicine, Building 63, Level A7, Royal Prince Alfred Hospital, Missenden Road, Camperdown, NSW 2050, Australia.

F Corresponding author. Email: maxine.roberts@ansto.gov.au

Australian Journal of Chemistry 66(4) 491-499 http://dx.doi.org/10.1071/CH12489
Submitted: 29 October 2012  Accepted: 12 December 2012   Published: 18 February 2013

Abstract

2-{2-[4-(4-[18F]-Fluorobenzyl)piperazin-1-yl]-2-oxoethyl}isoindolin-1-one ([18F]MEL054), is a new potent indolinone-based melanin binder designed to target melanotic tumours. [18F]MEL054 was prepared by an automated two-step radiosynthesis, comprising of the preparation of 4-[18F]fluorobenzaldehyde from 4-formyl-N,N,N-trimethylanilinium triflate, followed by reductive alkylation with 2-(2-oxo-2-piperazin-1-ylethyl)isoindolin-1-one. 4-[18F]Fluorobenzaldehyde was prepared on a GE TRACERlab FXFN module in 68 ± 8 % radiochemical yield (RCY, non-decay corrected), purified by a Sep-Pak Plus C18 cartridge and eluted into the reactor of an in-house modified Nuclear Interface [18F]FDG synthesis module for the subsequent reductive alkylation reaction. HPLC purification produced [18F]MEL054 in a collected RCY of 34 ± 9 % (non-decay corrected), the total preparation time (including Sep-Pak Plus C18 and HPLC purification) did not exceed 105 min. The radiochemical purity of [18F]MEL054 was greater than 99 % with a specific radioactivity of 71–119 GBq μmol–1 and [18F]MEL054 remained stable in saline solution (>98 %) after 3 h.

Graphical Abstract Image


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