Fluorodeoxysorbitol

Fluorodeoxysorbitol
	Structural formula of Fluorodeoxysorbitol
Identifiers
	IUPAC name (2R,3R,4S,5R)-6-fluorohexane-1,2,3,4,5-pentol;
PubChem CID	90046347;
Chemical and physical data
Formula	C6H13FO5
Molar mass	184.163 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C([C@H]([C@H]([C@@H]([C@H](CF)O)O)O)O)O;
	InChI InChI=1S/C6H13FO5/c7-1-3(9)5(11)6(12)4(10)2-8/h3-6,8-12H,1-2H2/t3-,4+,5+,6+/m0/s1; Key:ASKYZMAYXZUXQF-SLPGGIOYSA-N;

[18F] Fluorodeoxysorbitol (commonly called ¹⁸F-FDS) is a radiolabeled analog of the sugar alcohol sorbitol, in which a fluorine-18 (¹⁸F) radionuclide replaces the hydrogen at the 2-position. It is used as a radiotracer in positron emission tomography (PET) for imaging certain microbial infections and renal function.^[1]^[2]^[3]

Synthesis

Chemically, ¹⁸F-FDS is 2-deoxy-2-[¹⁸F]-fluoro-D-sorbitol: a sorbitol analog modified by substitution of the 2-position hydrogen with radioactive fluorine-18. This modification preserves the structure sufficiently to be recognized and taken up by certain microbes that naturally metabolize sorbitol.^[4]^[5]

One of the key advantages of fluorodeoxysorbitol is its relatively easy synthesis. It can be produced via a simple one-step reduction from [¹⁸F]-fluorodeoxyglucose, which is widely available in radiochemistry facilities. This provides easier production at facilities with PET-imaging capability.^[6]

References

^ Rua, Marta; Simón, Jon Ander; Collantes, María; Ecay, Margarita; Leiva, José; Carmona-Torre, Francisco; Ramos, Rocío; Pareja, Félix; Pulagam, Krishna R.; Llop, Jordi; Del Pozo, José Luis; Peñuelas, Iván (2023). "Infection-specific PET imaging with 18F-fluorodeoxysorbitol and 2-[18F]F-ρ-aminobenzoic acid: An extended diagnostic tool for bacterial and fungal diseases". Frontiers in Microbiology. 14 1094929. doi:10.3389/fmicb.2023.1094929. ISSN 1664-302X. PMC 9905739. PMID 36760503.
^ Li, Junling; Zheng, Huaiyu; Olson, Jenna; Warawa, Jonathan M.; Ng, Chin K. (December 2024). "Differentiation Between Responders and Non-Responders to Antibiotic Treatment in Mice Using 18F-Fluorodeoxysorbitol/PET". Molecular Imaging and Biology. 26 (6): 934–942. doi:10.1007/s11307-024-01957-3. ISSN 1536-1632. PMID 39407054.
^ Kim, Dong-Yeon; Pyo, Ayoung; Ji, Sehyeon; You, Sung-Hwan; Kim, Seong Eun; Lim, Daejin; Kim, Heejung; Lee, Kyung-Hwa; Oh, Se-Jeong; Jung, Ye-rim; Kim, Uh Jin; Jeon, Subin; Kwon, Seong Young; Kang, Sae-Ryung; Lee, Hyang Burm (2022-04-08). "In vivo imaging of invasive aspergillosis with 18F-fluorodeoxysorbitol positron emission tomography". Nature Communications. 13 (1): 1926. doi:10.1038/s41467-022-29553-5. ISSN 2041-1723. PMC 8993802. PMID 35395822.
^ Werner, Rudolf A.; Chen, Xinyu; Lapa, Constantin; Koshino, Kazuhiro; Rowe, Steven P.; Pomper, Martin G.; Javadi, Mehrbod S.; Higuchi, Takahiro (2019-08-01). "The next era of renal radionuclide imaging: novel PET radiotracers". European Journal of Nuclear Medicine and Molecular Imaging. 46 (9): 1773–1786. doi:10.1007/s00259-019-04359-8. ISSN 1619-7089. PMC 6647203. PMID 31144061.
^ Rua, Marta; Simón, Jon Ander; Collantes, María; Ecay, Margarita; Leiva, José; Carmona-Torre, Francisco; Ramos, Rocío; Pareja, Félix; Pulagam, Krishna R.; Llop, Jordi; Del Pozo, José Luis; Peñuelas, Iván (2023-01-25). "Infection-specific PET imaging with 18F-fluorodeoxysorbitol and 2-[18F]F-ρ-aminobenzoic acid: An extended diagnostic tool for bacterial and fungal diseases". Frontiers in Microbiology. 14 1094929. doi:10.3389/fmicb.2023.1094929. ISSN 1664-302X. PMC 9905739. PMID 36760503.
^ Werner, Rudolf A.; Ordonez, Alvaro A.; Sanchez-Bautista, Julian; Marcus, Charles; Lapa, Constantin; Rowe, Steven P.; Pomper, Martin G.; Leal, Jeffrey P.; Lodge, Martin A.; Javadi, Mehrbod S.; Jain, Sanjay K.; Higuchi, Takahiro (May 2019). "Novel Functional Renal PET Imaging With 18F-FDS in Human Subjects". Clinical Nuclear Medicine. 44 (5): 410–411. doi:10.1097/RLU.0000000000002494. ISSN 1536-0229. PMC 6449191. PMID 30762825.

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[1] Rua, Marta; Simón, Jon Ander; Collantes, María; Ecay, Margarita; Leiva, José; Carmona-Torre, Francisco; Ramos, Rocío; Pareja, Félix; Pulagam, Krishna R.; Llop, Jordi; Del Pozo, José Luis; Peñuelas, Iván (2023). "Infection-specific PET imaging with 18F-fluorodeoxysorbitol and 2-[18F]F-ρ-aminobenzoic acid: An extended diagnostic tool for bacterial and fungal diseases". Frontiers in Microbiology. 14 1094929. doi:10.3389/fmicb.2023.1094929. ISSN 1664-302X. PMC 9905739. PMID 36760503.

[2] Li, Junling; Zheng, Huaiyu; Olson, Jenna; Warawa, Jonathan M.; Ng, Chin K. (December 2024). "Differentiation Between Responders and Non-Responders to Antibiotic Treatment in Mice Using 18F-Fluorodeoxysorbitol/PET". Molecular Imaging and Biology. 26 (6): 934–942. doi:10.1007/s11307-024-01957-3. ISSN 1536-1632. PMID 39407054.

[3] Kim, Dong-Yeon; Pyo, Ayoung; Ji, Sehyeon; You, Sung-Hwan; Kim, Seong Eun; Lim, Daejin; Kim, Heejung; Lee, Kyung-Hwa; Oh, Se-Jeong; Jung, Ye-rim; Kim, Uh Jin; Jeon, Subin; Kwon, Seong Young; Kang, Sae-Ryung; Lee, Hyang Burm (2022-04-08). "In vivo imaging of invasive aspergillosis with 18F-fluorodeoxysorbitol positron emission tomography". Nature Communications. 13 (1): 1926. doi:10.1038/s41467-022-29553-5. ISSN 2041-1723. PMC 8993802. PMID 35395822.

[4] Werner, Rudolf A.; Chen, Xinyu; Lapa, Constantin; Koshino, Kazuhiro; Rowe, Steven P.; Pomper, Martin G.; Javadi, Mehrbod S.; Higuchi, Takahiro (2019-08-01). "The next era of renal radionuclide imaging: novel PET radiotracers". European Journal of Nuclear Medicine and Molecular Imaging. 46 (9): 1773–1786. doi:10.1007/s00259-019-04359-8. ISSN 1619-7089. PMC 6647203. PMID 31144061.

[5] Rua, Marta; Simón, Jon Ander; Collantes, María; Ecay, Margarita; Leiva, José; Carmona-Torre, Francisco; Ramos, Rocío; Pareja, Félix; Pulagam, Krishna R.; Llop, Jordi; Del Pozo, José Luis; Peñuelas, Iván (2023-01-25). "Infection-specific PET imaging with 18F-fluorodeoxysorbitol and 2-[18F]F-ρ-aminobenzoic acid: An extended diagnostic tool for bacterial and fungal diseases". Frontiers in Microbiology. 14 1094929. doi:10.3389/fmicb.2023.1094929. ISSN 1664-302X. PMC 9905739. PMID 36760503.

[6] Werner, Rudolf A.; Ordonez, Alvaro A.; Sanchez-Bautista, Julian; Marcus, Charles; Lapa, Constantin; Rowe, Steven P.; Pomper, Martin G.; Leal, Jeffrey P.; Lodge, Martin A.; Javadi, Mehrbod S.; Jain, Sanjay K.; Higuchi, Takahiro (May 2019). "Novel Functional Renal PET Imaging With 18F-FDS in Human Subjects". Clinical Nuclear Medicine. 44 (5): 410–411. doi:10.1097/RLU.0000000000002494. ISSN 1536-0229. PMC 6449191. PMID 30762825.

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