One-step, rapid, (18)F-(19)F isotopic exchange radiolabeling of difluoro-dioxaborinins: Substituent effect on stability and in vivo applications Journal Article

   

Authors:	An, F.; Nurili, F.; Sayman, H.; Ozer, Z.; Cakiroglu, H.; Aras, O.; Ting, R.
Article Title:	One-step, rapid, (18)F-(19)F isotopic exchange radiolabeling of difluoro-dioxaborinins: Substituent effect on stability and in vivo applications
Abstract:	The β-diketone moiety is commonly present in many anticancer drugs, antibiotics, and natural products. We describe a general method for radiolabeling β-diketone-bearing molecules with fluoride-18. Radiolabeling was carried out via 18F-19F isotopic exchange on nonradioactive difluoro-dioxaborinins, which were generated by minimally modifying the β-diketone as a difluoroborate. Radiochemistry was one-step, rapid (<10 min), and high-yielding (>80%) and proceeded at room temperature to accommodate the half-life of F-18 (t1/2 = 110 min). High molar activities (7.4 Ci/μmol) were achieved with relatively low starting activities (16.4 mCi). It was found that substituents affected both the solvolytic stability and fluorescence properties of difluoro-dioxaborinins. An F-18 radiolabeled difluoro-dioxaborinin probe that was simultaneously fluorescent showed sufficient stability for in vivo positron emission tomography (PET)/fluorescence imaging in mice, rabbits, and patients. These findings will guide the design of probes with specific PET/fluorescence properties; the development of new PET/fluorescence dual-modality reporters; and accurate in vivo tracking of β-diketone molecules.
Journal Title:	Journal of Medicinal Chemistry
Volume:	63
Issue:	21
ISSN:	0022-2623
Publisher:	American Chemical Society
Date Published:	2020-11-12
Start Page:	12693
End Page:	12706
Language:	English
DOI:	10.1021/acs.jmedchem.0c00997
PUBMED:	32787084
PROVIDER:	scopus
PMCID:	PMC8399557
DOI/URL:	https://www.scopus.com/inward/record.uri?eid=2-s2.0-85096151713&doi=10.1021%2facs.jmedchem.0c00997&partnerID=40&md5=ce5961032db50d6d00895b8513bdc0ec
Notes:	Article -- Export Date: 1 December 2020 -- Source: Scopus

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