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Article

Synthesis of [18F]F-γ-T-3, a Redox-Silent γ-Tocotrienol (γ-T-3) Vitamin E Analogue for Image-Based In Vivo Studies of Vitamin E Biodistribution and Dynamics

1
The Centre for Molecular Imaging and Translational Research Laboratory, The Peter MacCallum Cancer Centre, 305 Grattan Street, Melbourne, VIC 3000, Australia
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, El Sultan Hussein St. Azarita, Alexandria 21521, Egypt
3
Department of Oncology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB T6G 2E1, Canada
4
Katz Group Centre for Pharmacy and Health Research, Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, AB T6G 2E1, Canada
*
Author to whom correspondence should be addressed.
Academic Editor: Anne Roivainen
Received: 30 October 2020 / Revised: 20 November 2020 / Accepted: 30 November 2020 / Published: 3 December 2020
(This article belongs to the Special Issue Natural Products: Therapeutic Properties and Beyond)
Vitamin E, a natural antioxidant, is of interest to scientists, health care pundits and faddists; its nutritional and biomedical attributes may be validated, anecdotal or fantasy. Vitamin E is a mixture of tocopherols (TPs) and tocotrienols (T-3s), each class having four substitutional isomers (α-, β-, γ-, δ-). Vitamin E analogues attain only low concentrations in most tissues, necessitating exacting invasive techniques for analytical research. Quantitative positron emission tomography (PET) with an F-18-labeled molecular probe would expedite access to Vitamin E’s biodistributions and pharmacokinetics via non-invasive temporal imaging. (R)-6-(3-[18F]Fluoropropoxy)-2,7,8-trimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-chromane ([18F]F-γ-T-3) was prepared for this purpose. [18F]F-γ-T-3 was synthesized from γ-T-3 in two steps: (i) 1,3-di-O-tosylpropane was introduced at C6-O to form TsO-γ-T-3, and (ii) reaction of this tosylate with [18F]fluoride in DMF/K222. Non-radioactive F-γ-T-3 was synthesized by reaction of γ-T-3 with 3-fluoropropyl methanesulfonate. [18F]F-γ-T-3 biodistribution in a murine tumor model was imaged using a small-animal PET scanner. F-γ-T-3 was prepared in 61% chemical yield. [18F]F-γ-T-3 was synthesized in acceptable radiochemical yield (RCY 12%) with high radiochemical purity (>99% RCP) in 45 min. Preliminary F-18 PET images in mice showed upper abdominal accumulation with evidence of renal clearance, only low concentrations in the thorax (lung/heart) and head, and rapid clearance from blood. [18F]F-γ-T-3 shows promise as an F-18 PET tracer for detailed in vivo studies of Vitamin E. The labeling procedure provides acceptable RCY, high RCP and pertinence to all eight Vitamin E analogues. View Full-Text
Keywords: nutraceuticals; antioxidants; Vitamin E; Vitamin E analogues; tocopherol (TP); tocotrienol (T-3); γ-T-3; F-γ-T-3; radiofluorination; [18F]F-γ-T-3; F-18 positron emission tomography (F-18 PET) nutraceuticals; antioxidants; Vitamin E; Vitamin E analogues; tocopherol (TP); tocotrienol (T-3); γ-T-3; F-γ-T-3; radiofluorination; [18F]F-γ-T-3; F-18 positron emission tomography (F-18 PET)
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MDPI and ACS Style

Roselt, P.; Cullinane, C.; Noonan, W.; Elsaidi, H.; Eu, P.; Wiebe, L.I. Synthesis of [18F]F-γ-T-3, a Redox-Silent γ-Tocotrienol (γ-T-3) Vitamin E Analogue for Image-Based In Vivo Studies of Vitamin E Biodistribution and Dynamics. Molecules 2020, 25, 5700. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25235700

AMA Style

Roselt P, Cullinane C, Noonan W, Elsaidi H, Eu P, Wiebe LI. Synthesis of [18F]F-γ-T-3, a Redox-Silent γ-Tocotrienol (γ-T-3) Vitamin E Analogue for Image-Based In Vivo Studies of Vitamin E Biodistribution and Dynamics. Molecules. 2020; 25(23):5700. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25235700

Chicago/Turabian Style

Roselt, Peter, Carleen Cullinane, Wayne Noonan, Hassan Elsaidi, Peter Eu, and Leonard I. Wiebe. 2020. "Synthesis of [18F]F-γ-T-3, a Redox-Silent γ-Tocotrienol (γ-T-3) Vitamin E Analogue for Image-Based In Vivo Studies of Vitamin E Biodistribution and Dynamics" Molecules 25, no. 23: 5700. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25235700

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