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Synthesis and Characterization of Novel Radiolabelled Substrates for Imaging of GLUT5 Expression in Human Breast Cancer Using Positron Emission Tomography Open Access


Other title
Breast Cancer
Positron Emission Tomography
Hexose Transport
Type of item
Degree grantor
University of Alberta
Author or creator
Trayner, Brendan J
Supervisor and department
Cheeseman, Chris I (Physiology)
Examining committee member and department
Luyt, Len (External - Oncology/Chemistry, University of Western Ontario)
Murray, David (Oncology)
Mercer, John (Oncology)
McEwan, Sandy (Oncology)
Department of Physiology

Date accepted
Graduation date
Doctor of Philosophy
Degree level
Overactive glucose transport and metabolism has been widely recognized as one of the fundamental hallmarks of cancer and its progression. The facilitative glucose transporter GLUT1 is widely overexpressed in many tumor types compared to their untransformed counterparts. Due to this, the glucose analogue, 2-deoxy-2-[18F]fluoro-D-glucose (FDG) has been used widely for the imaging of malignant neoplastic tissue through a non-invasive technique, positron emission tomography (PET). PET scans have been very successful in the imaging of many breast cancers expressing high levels of GLUT1, but unfortunately, many breast tumors do not express GLUT1 at high levels, if at all. Clinically, this lack of GLUT1 expression in tumors has led to false-negatives in patients’ PET scans. Interestingly, in 1996 it was first identified that the fructose transporting facilitative hexose transporter GLUT5 is highly expressed in transformed breast tissue compared to the untransformed surrounding tissue. This finding has led to the suggestion that radiolabeled substrates for GLUT5 may be effective in imaging GLUT1 negative, GLUT5 positive tumors. We have rationally designed and synthesized several compounds based around previously performed structural studies and analyzed their behaviour both in vitro and in vivo. The C-6 labelled fructose analogue 6-deoxy-6-[18F]fluoro-D-fructose (6-FDF) has shown favourable in vitro and in vivo characteristics for the imaging of GLUT5 expressing breast tumors. Additionally, its dosimetry and excretory profile suggest the viability of the compound for a clinical trial. Other substrates based on the C2 symmetric fructose mimic 2,5-anhydro-D-mannitol (2,5-AM) have also been examined for their behaviour in vitro and in vivo. Further work will be spent on further characterizing additional fructose and 2,5-AM analogues that will shed more light on the structural requirements of GLUT5 and perhaps lead to other tracers that will show utility in the imaging of GLUT5 expressing breast cancer with PET.
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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