A synthesis of 6-deoxy-6-fluorosucrose suitable for PET applications

Gao, Xuefeng; Gaddam, Vikram; Harmata, Michael

doi:10.1016/j.carres.2014.08.015

Cited by 4 publications

(4 citation statements)

References 8 publications

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“…18 F was produced by the nuclear reaction 18 O(p,n) 18 F using a GE PET Trace cyclotron as described (Rotsch et al, 2015). The precursors (6'-O-Trifluoromethanesulfonyl-2,3,4,6,1',3',4'hepta-O-benzoylsucrose for 6'-[ 18 F]FDS; 1'-O-Trifluoromethanesulfonyl-2,3,4,6,3',4',6'-hepta-O-benzoylsucrose for 1'-[ 18 F]FDS; and 6-O-Trifluoromethanesulfonyl-2,3,4,1',3',4',6'-hepta-Obenzoylsucrose for 6-[ 18 F]FDS ) were prepared as described (Gaddam and Harmata, 2013;Ying et al, 2013;Gao et al, 2014).…”

Section: Radiosynthesis Of [ 18 F]fds Analogsmentioning

confidence: 99%

In vivo transport of three radioactive [18F]-fluorinated deoxysucrose analogs by the maize sucrose transporter ZmSUT1

Trần

Hampton

Brossard

et al. 2017

Plant Physiology and Biochemistry

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Sucrose transporter (SUT) proteins translocate sucrose across cell membranes; however, mechanistic aspects of sucrose binding by SUTs are not well resolved. Specific hydroxyl groups in sucrose participate in hydrogen bonding with SUT proteins. We previously reported that substituting a radioactive fluorine-18 [F] at the C-6' position within the fructosyl moiety of sucrose did not affect sucrose transport by the maize (Zea mays) ZmSUT1 protein. To determine how F substitution of hydroxyl groups at two other positions within sucrose, the C-1' in the fructosyl moiety or the C-6 in the glucosyl moiety, impact sucrose transport, we synthesized 1'-[F]fluoro-1'-deoxysucrose and 6-[F]fluoro-6-deoxysucrose ([F]FDS) analogs. Each [F]FDS derivative was independently introduced into wild-type or sut1 mutant plants, which are defective in sucrose phloem loading. All three (1'-, 6'-, and 6-) [F]FDS derivatives were efficiently and equally translocated, similarly to carbon-14 [C]-labeled sucrose. Hence, individually replacing the hydroxyl groups at these positions within sucrose does not interfere with substrate recognition, binding, or membrane transport processes, and hydroxyl groups at these three positions are not essential for hydrogen bonding between sucrose and ZmSUT1. [F]FDS imaging afforded several advantages compared to [C]-sucrose detection. We calculated that 1'-[F]FDS was transported at approximately a rate of 0.90 ± 0.15 m.h-1 in wild-type leaves, and at 0.68 ± 0.25 m.h-1 in sut1 mutant leaves. Collectively, our data indicated that [F]FDS analogs are valuable tools to probe sucrose-SUT interactions and to monitor sucrose transport in plants.

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Section: Radiosynthesis Of [ 18 F]fds Analogsmentioning

confidence: 99%

In vivo transport of three radioactive [18F]-fluorinated deoxysucrose analogs by the maize sucrose transporter ZmSUT1

Trần

Hampton

Brossard

et al. 2017

Plant Physiology and Biochemistry

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“…The enzymatic approach was recently applied to obtain the first 18 F fluorinated derivative, 1’-[ 18 F]fluoro-1’-deoxysucrose, in 26% yield [ 39 ]. We have recently reported the first purely synthetic approaches for the syntheses of 6’-deoxy-6’-fluorosucrose, 1’-deoxy-1’-fluorosucrose, and 6-deoxy-6-fluorosucrose [ 42 – 44 ]. Here, we report the first radiolabeling of sucrose with 18 F at the 6’ position, and the utility of 6’-deoxy-6’[ 18 F]fluorosucrose ( 18 FS) in studying sucrose phloem transport in maize ( Zea mays ) leaves and specifically with sucrose transporter (SUT) proteins.…”

Section: Introductionmentioning

confidence: 99%

Radiosynthesis of 6’-Deoxy-6’[18F]Fluorosucrose via Automated Synthesis and Its Utility to Study In Vivo Sucrose Transport in Maize (Zea mays) Leaves

et al. 2015

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Sugars produced from photosynthesis in leaves are transported through the phloem tissues within veins and delivered to non-photosynthetic organs, such as roots, stems, flowers, and seeds, to support their growth and/or storage of carbohydrates. However, because the phloem is located internally within the veins, it is difficult to access and to study the dynamics of sugar transport. Radioactive tracers have been extensively used to study vascular transport in plants and have provided great insights into transport dynamics. To better study sucrose partitioning in vivo, a novel radioactive analog of sucrose was synthesized through a completely chemical synthesis route by substituting fluorine-18 (half-life 110 min) at the 6’ position to generate 6’-deoxy-6’[18F]fluorosucrose (18FS). This radiotracer was then used to compare sucrose transport between wild-type maize plants and mutant plants lacking the Sucrose transporter1 (Sut1) gene, which has been shown to function in sucrose phloem loading. Our results demonstrate that 18FS is transported in vivo, with the wild-type plants showing a greater rate of transport down the leaf blade than the sut1 mutant plants. A similar transport pattern was also observed for universally labeled [U-14C]sucrose ([U-14C]suc). Our findings support the proposed sucrose phloem loading function of the Sut1 gene in maize, and additionally demonstrate that the 18FS analog is a valuable, new tool that offers imaging advantages over [U-14C]suc for studying phloem transport in plants.

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“…The synthesis of 6-deoxy-6-fluorosucrose (6-F-sucrose) was reported by Eklund and Robyt ( Eklund and Robyt, 1988 ). Recently, a new route to 6-F-sucrose synthesis has been developed by Gao et al (2014) . Authors also proposed its application in plant imaging using PET ( Gao et al, 2014 ).…”

Section: Questions and Considerations In Future Fdg Experimentsmentioning

confidence: 99%

“…Recently, a new route to 6-F-sucrose synthesis has been developed by Gao et al (2014) . Authors also proposed its application in plant imaging using PET ( Gao et al, 2014 ). Rotsch et al (2015) subsequently demonstrated that 6-F-sucrose translocation closely resembles 14 C-sucrose translocation in maize leaves.…”

Section: Questions and Considerations In Future Fdg Experimentsmentioning

confidence: 99%

Applications of 2-deoxy-2-fluoro-D-glucose (FDG) in Plant Imaging: Past, Present, and Future

Fatangare

Svatoš

2016

Front. Plant Sci.

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The aim of this review article is to explore and establish the current status of 2-deoxy-2-fluoro-D-glucose (FDG) applications in plant imaging. In the present article, we review the previous literature on its experimental merits to formulate a consistent and inclusive picture of FDG applications in plant-imaging research. 2-deoxy-2-fluoro-D-glucose is a [18F]fluorine-labeled glucose analog in which C-2 hydroxyl group has been replaced by a positron-emitting [18F] radioisotope. As FDG is a positron-emitting radiotracer, it could be used in in vivo imaging studies. FDG mimics glucose chemically and structurally. Its uptake and distribution are found to be similar to those of glucose in animal models. FDG is commonly used as a radiotracer for glucose in medical diagnostics and in vivo animal imaging studies but rarely in plant imaging. Tsuji et al. (2002) first reported FDG uptake and distribution in tomato plants. Later, Hattori et al. (2008) described FDG translocation in intact sorghum plants and suggested that it could be used as a tracer for photoassimilate translocation in plants. These findings raised interest among other plant scientists, which has resulted in a recent surge of articles involving the use of FDG as a tracer in plants. There have been seven studies describing FDG-imaging applications in plants. These studies describe FDG applications ranging from monitoring radiotracer translocation to analyzing solute transport, root uptake, photoassimilate tracing, carbon allocation, and glycoside biosynthesis. Fatangare et al. (2015) recently characterized FDG metabolism in plants; such knowledge is crucial to understanding and validating the application of FDG in plant imaging research. Recent FDG studies significantly advance our understanding of FDG translocation and metabolism in plants but also raise new questions. Here, we take a look at all the previous results to form a comprehensive picture of FDG translocation, metabolism, and applications in plants. In conclusion, we summarize current knowledge, discuss possible implications and limitations of previous studies, point to open questions in the field, and comment on the outlook for FDG applications in plant imaging.

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A synthesis of 6-deoxy-6-fluorosucrose suitable for PET applications

Abstract: A new route to 6-deoxy-6-fluorosucrose has been developed. The process proceeds in 8 linear steps in 25% overall yield from sucrose. The steps incorporating fluorine and subsequent deprotection are quite rapid, making the procedure useful in the context of F-labeling for PET applications.

Cited by 4 publications

References 8 publications

In vivo transport of three radioactive [18F]-fluorinated deoxysucrose analogs by the maize sucrose transporter ZmSUT1

In vivo transport of three radioactive [18F]-fluorinated deoxysucrose analogs by the maize sucrose transporter ZmSUT1

Radiosynthesis of 6’-Deoxy-6’[18F]Fluorosucrose via Automated Synthesis and Its Utility to Study In Vivo Sucrose Transport in Maize (Zea mays) Leaves

Applications of 2-deoxy-2-fluoro-D-glucose (FDG) in Plant Imaging: Past, Present, and Future

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