Synthesis of Fluorine-Containing Analogues of 1-Lysoglycerophospholipids via Horner–Wadsworth–Emmons Reaction

Nakao, Michiyasu; Tanaka, K.; Kitaike, Syuji; Sano, Shigeki

doi:10.1055/s-0036-1588826

Cited by 4 publications

(2 citation statements)

References 5 publications

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“…Differently, 5-methylpicolinonitrile was brominated and reacted with ethylene glycol to afford 36. Formation of the Tz ring and conversion to the fluorine analogue gave 38 [45]. Nosylation of the same alcohol intermediate yielded 38a.…”

Section: Synthesis Of the Bispyridyl Tzsmentioning

confidence: 99%

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Development of 18F-Labeled Bispyridyl Tetrazines for In Vivo Pretargeted PET Imaging

et al. 2022

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Pretargeted PET imaging is an emerging and fast-developing method to monitor immuno-oncology strategies. Currently, tetrazine ligation is considered the most promising bioorthogonal reaction for pretargeting in vivo. Recently, we have developed a method to 18F-label ultrareactive tetrazines by copper-mediated fluorinations. However, bispyridyl tetrazines—one of the most promising structures for in vivo pretargeted applications—were inaccessible using this strategy. We believed that our successful efforts to 18F-label H-tetrazines using low basic labeling conditions could also be used to label bispyridyl tetrazines via aliphatic nucleophilic substitution. Here, we report the first direct 18F-labeling of bispyridyl tetrazines, their optimization for in vivo use, as well as their successful application in pretargeted PET imaging. This strategy resulted in the design of [18F]45, which could be labeled in a satisfactorily radiochemical yield (RCY = 16%), molar activity (Am = 57 GBq/µmol), and high radiochemical purity (RCP > 98%). The [18F]45 displayed a target-to-background ratio comparable to previously successfully applied tracers for pretargeted imaging. This study showed that bispyridyl tetrazines can be developed into pretargeted imaging agents. These structures allow an easy chemical modification of 18F-labeled tetrazines, paving the road toward highly functionalized pretargeting tools. Moreover, bispyridyl tetrazines led to near-instant drug release of iTCO-tetrazine-based ‘click-to-release’ reactions. Consequently, 18F-labeled bispyridyl tetrazines bear the possibility to quantify such release in vivo in the future.

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Section: Synthesis Of the Bispyridyl Tzsmentioning

confidence: 99%

“…Rf = 0. (45) To a solution of 44 (0.006 g, 0.83 mmol) in 5 mL of CH 2 Cl 2 was added 2 mL of TFA. The mixture was stirred at room temperature for 4 h. The solvent was then removed under reduced pressure.…”

Section: -(((2-fluoroethyl)amino)methyl)benzonitrile (23)mentioning

confidence: 99%

Development of 18F-Labeled Bispyridyl Tetrazines for In Vivo Pretargeted PET Imaging

et al. 2022

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Concentration-dependence of specific rotation of optically active glycerol analogues and structurally related compounds: The significance of intermolecular hydrogen bonding

Nakao,

Nakamura,

Yamada

et al. 2024

Results in Chemistry

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Selective Transesterification of 2,2,2-Trifluoroethyl Phosphates: Synthesis of Mixed Unsymmetrical Phosphates

et al. 2019

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A selective transesterification starting with tris(2,2,2trifluoroethyl) phosphate has been developed. This method involves a three-step substitution for 2,2,2-trifluoroethoxy groups and enables the facile synthesis of mixed unsymmetric phosphate triesters from three different alcohols. The substitution of the trifluoroethoxy group at the phosphorus proceeds selectively in the presence of DBU or lithium alkoxides. This method can be applied for the preparation of phospholipids.

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Synthesis of Fluorine-Containing Analogues of 1-Lysoglycerophospholipids via Horner–Wadsworth–Emmons Reaction

Cited by 4 publications

References 5 publications

Development of 18F-Labeled Bispyridyl Tetrazines for In Vivo Pretargeted PET Imaging

Development of 18F-Labeled Bispyridyl Tetrazines for In Vivo Pretargeted PET Imaging

Concentration-dependence of specific rotation of optically active glycerol analogues and structurally related compounds: The significance of intermolecular hydrogen bonding

Selective Transesterification of 2,2,2-Trifluoroethyl Phosphates: Synthesis of Mixed Unsymmetrical Phosphates

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