Effect of Rhenium(i) Complexation on Aza-Michael Additions to 5-Amino-1,10-Phenanthroline with [18F]Ethenesulfonyl Fluoride towards PET Optical Tracer Development
Mitchell A. Klenner
A B F , Giancarlo Pascali A C F , Bo Zhang A D , Gianluca Ciancaleoni E , Massimiliano Massi B and Benjamin H. Fraser A
A Human Health, Australian Nuclear Science and Technology Organisation (ANSTO), Lucas Heights, NSW 2229, Australia.
B Department of Chemistry, Curtin University, Bentley, WA 6102, Australia.
C Brain and Mind Centre, University of Sydney, Sydney, NSW 2050, Australia.
D School of Chemistry, Monash University, Melbourne, Vic. 3800, Australia.
E Dipartimento di Chimica e Chimica Industriale Università di Pisa, Pisa 56127, Italy.
F Corresponding authors. Email: mitchk@ansto.gov.au; gianp@ansto.gov.au
Australian Journal of Chemistry 72(4) 288-294 https://doi.org/10.1071/CH18512
Submitted: 17 October 2018 Accepted: 10 December 2018 Published: 14 January 2019
Abstract
Conjugations with the recently developed [18F]ethenesulfonyl fluoride ([18F]ESF) were performed on 5-amino-1,10-phenanthroline, in its free form and coordinated to a rhenium(i) tricarbonyl complex, as a means of radiosynthesizing dual-modal optical and positron emission tomography (PET) tracers. The Michael-donating ability of the aromatic amine was noticeably perturbed on coordination with the rhenium(i) centre, resulting in decreased radiochemical yields from 34 %, in the case of the free ligand, to 1 %. We attribute the decreased nucleophilicity of the amine to metal deactivation from the electron-withdrawing feature of the rhenium(i) tricarbonyl centre, based on spectroscopic and computational evidence, thus highlighting this effect as a crucial parameter in designing late-stage metal coordination methods employing related aza-Michael additions. Photophysical analyses were also performed on the ESF-conjugated rhenium(i) complex, exhibiting a longer decay lifetime from the triplet metal-to-ligand charge transfer excited state when compared with the non-conjugated analogue.
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