Isotopologues of potassium 2,2,2-trifluoroethoxide for applications in positron emission tomography and beyond

The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroetho...

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Published inNature communications Vol. 15; no. 1; pp. 5798 - 10
Main Authors Zhao, Qunchao, Telu, Sanjay, Jana, Susovan, Morse, Cheryl L., Pike, Victor W.
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 10.07.2024
Nature Publishing Group
Nature Portfolio
Subjects
140/131
140/58
639/638/403/933
639/638/549/933
692/4017
Aliphatic compounds
Carbon Radioisotopes - chemistry
Drug development
Drug discovery
Drugs
Fluorine
Fluorine Radioisotopes - chemistry
Formaldehyde
Humanities and Social Sciences
Humans
Isotopic labeling
Medical imaging
multidisciplinary
Polymers
Positron emission
Positron emission tomography
Positron-Emission Tomography - methods
Potassium
Potassium - chemistry
Radioactive tracers
Radiopharmaceuticals - chemical synthesis
Radiopharmaceuticals - chemistry
Science
Science (multidisciplinary)
Stable isotopes
Substrates
Tomography
Tracers
Transition metals
Trifluoromethane
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Abstract The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF 3 CH 2 OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 ( t 1/2  = 20.4 min) or fluorine-18 ( t 1/2  = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11 C- or 18 F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development. The 2,2,2-trifluoroethoxy group features in drugs and potential tracers for biomedical imaging with positron emission tomography. Herein, the authors report the conversion of fluoroform into potassium 2,2,2-trifluoroethoxide isotopologues and their applications in late stage 2,2,2-trifluoroethoxylations of aromatic and aliphatic substrates for positron emission tomography and stable isotope labeling.
AbstractList The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF CH OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 (t  = 20.4 min) or fluorine-18 (t  = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added C- or F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development.
Abstract The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF3CH2OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 (t 1/2 = 20.4 min) or fluorine-18 (t 1/2 = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11C- or 18F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development.
The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF3CH2OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 (t1/2 = 20.4 min) or fluorine-18 (t1/2 = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11C- or 18F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development.The 2,2,2-trifluoroethoxy group features in drugs and potential tracers for biomedical imaging with positron emission tomography. Herein, the authors report the conversion of fluoroform into potassium 2,2,2-trifluoroethoxide isotopologues and their applications in late stage 2,2,2-trifluoroethoxylations of aromatic and aliphatic substrates for positron emission tomography and stable isotope labeling.
The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF 3 CH 2 OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 ( t 1/2  = 20.4 min) or fluorine-18 ( t 1/2  = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11 C- or 18 F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development.
The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF 3 CH 2 OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 ( t 1/2  = 20.4 min) or fluorine-18 ( t 1/2  = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11 C- or 18 F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development. The 2,2,2-trifluoroethoxy group features in drugs and potential tracers for biomedical imaging with positron emission tomography. Herein, the authors report the conversion of fluoroform into potassium 2,2,2-trifluoroethoxide isotopologues and their applications in late stage 2,2,2-trifluoroethoxylations of aromatic and aliphatic substrates for positron emission tomography and stable isotope labeling.
The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF3CH2OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 (t1/2 = 20.4 min) or fluorine-18 (t1/2 = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11C- or 18F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development.The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we describe a rapid and transition metal-free conversion of fluoroform with paraformaldehyde into highly reactive potassium 2,2,2-trifluoroethoxide (CF3CH2OK) and demonstrate robust applications of this synthon in one-pot, two-stage 2,2,2-trifluoroethoxylations of both aromatic and aliphatic precursors. Moreover, we show that these transformations translate easily to fluoroform that has been labeled with either carbon-11 (t1/2 = 20.4 min) or fluorine-18 (t1/2 = 109.8 min), so allowing the appendage of complex molecules with a no-carrier-added 11C- or 18F- 2,2,2-trifluoroethoxy group. This provides scope to create candidate PET tracers with radioactive and metabolically stable 2,2,2-trifluoroethoxy moieties. We also exemplify syntheses of isotopologues of potassium 2,2,2-trifluoroethoxide and show their utility for stable isotopic labeling which can be of further benefit for drug discovery and development.
ArticleNumber 5798
Author Jana, Susovan
Zhao, Qunchao
Pike, Victor W.
Morse, Cheryl L.
Telu, Sanjay
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Snippet The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET). Herein, we...
Abstract The 2,2,2-trifluoroethoxy group increasingly features in drugs and potential tracers for biomedical imaging with positron emission tomography (PET)....
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SubjectTerms 140/131
140/58
639/638/403/933
639/638/549/933
692/4017
Aliphatic compounds
Carbon Radioisotopes - chemistry
Drug development
Drug discovery
Drugs
Fluorine
Fluorine Radioisotopes - chemistry
Formaldehyde
Humanities and Social Sciences
Humans
Isotopic labeling
Medical imaging
multidisciplinary
Polymers
Positron emission
Positron emission tomography
Positron-Emission Tomography - methods
Potassium
Potassium - chemistry
Radioactive tracers
Radiopharmaceuticals - chemical synthesis
Radiopharmaceuticals - chemistry
Science
Science (multidisciplinary)
Stable isotopes
Substrates
Tomography
Tracers
Transition metals
Trifluoromethane
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Title Isotopologues of potassium 2,2,2-trifluoroethoxide for applications in positron emission tomography and beyond
URI https://link.springer.com/article/10.1038/s41467-024-49975-7
https://www.ncbi.nlm.nih.gov/pubmed/38987549
https://www.proquest.com/docview/3078200207
https://www.proquest.com/docview/3078716485
https://pubmed.ncbi.nlm.nih.gov/PMC11237122
https://doaj.org/article/30644c5756d942b890538d65ccd30767
Volume 15
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