Fluorodeoxysorbitol

Fluorodeoxysorbitol

Structural formula of [18F]-fluorodeoxysorbitol
Identifiers
IUPAC name (2R,3R,4S,5S)-5-Fluorohexane-1,2,3,4,6-pentol
CAS Number	34339-80-5 [18F]: 1582302-46-2
PubChem CID	21126041
ChemSpider	19993475
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](CO)F)O)O)O)O
InChI InChI=1S/C6H13FO5/c7-3(1-8)5(11)6(12)4(10)2-9/h3-6,8-12H,1-2H2/t3-,4+,5+,6+/m0/s1 Key:FHMVCKHFSUAUMP-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

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.