Research progress of 18F labeled small molecule positron emission tomography (PET) imaging agents

Zhang, Mingliang; Zhang, Hang; Xu, Haiwei

doi:10.1016/j.ejmech.2020.112629

Cited by 20 publications

(20 citation statements)

References 172 publications

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“…The 18 F isotope has a halflifetime (t 1/2 ) of 110 min, so this tracer has a big advantage as compared to other radionuclides like 11 C which has only a half-life of 20 min. Recently, many 18 F labeled imaging agents have been developed and regularly used for the detection of various diseases (Zhang et al 2020). Last year in 2021, pylarify (piflufolastat 18 F) 12, a drug for PET has been approved by FDA to recognize prostate-specific membrane antigen (PSMA) (Fig.…”

Section: Brief Outlook Of Fluoro Compoundsmentioning

confidence: 99%

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

et al. 2023

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During the last twenty years, organic fluorination chemistry established itself as an important tool to get a biologically active compound. This belief can be supported by the fact that every year, we are getting fluorinated drugs in the market in extremely significant numbers. Last year, also ten fluorinated drugs have been approved by FDA and during the COVID-19 pandemic, fluorinated drugs played a very crucial role to control the disease and saved many lives. In this review, we surveyed all ten fluorinated drugs approved by FDA in 2021 and all fluorinated drugs which were directly-indirectly used during the COVID-19 period, and emphasis has been given particularly to their synthesis, medicinal chemistry, and development process. Out of ten approved drugs, one drug pylarify, a radioactive diagnostic agent for cancer was approved for use in positron emission tomography imaging. Also, very briefly outlined the significance of fluorinated drugs through their physical, and chemical properties and their effect on drug development.

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Section: Brief Outlook Of Fluoro Compoundsmentioning

confidence: 99%

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

et al. 2023

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“…The introduction of one or more F atoms or F-containing groups into drug molecules is a common strategy to improve their stability and bioavailability. − 18 F, a radioisotope of 19 F, has favorable nuclide properties for PET, i.e., a moderate half-life (about 110 min), a high β + decay ratio (97%), and a relatively low maximum positron energy (634 keV) . Due to the excellent properties of fluorinated drugs and the universal use of medical cyclotrons in medical institutions, , the development of simple, mild, and efficient 18 F-labeling methods has become an important goal of radiopharmaceutical chemistry research. , …”

Section: Introductionmentioning

confidence: 99%

“…Nucleophilic fluorination reactions with [ 18 F]F – (usually made from [ 18 O]H 2 O via 18 O(p,n) 18 F) as the high A m 18 F source are more specific and frequently used compared to electrophilic fluorination reactions. ,,, The theoretical maximum A m up to 6.3 × 10 4 GBq/μmol and maximum A m of 43 000 GBq/μmol in practice and the high selectivity of the nucleophilic fluorinating reagents fulfills the high A m requirement by some receptors imaging . Common nucleophilic substitution reactions require the preparation of a certain leaving group on the precursor that allows S N 1, S N 2, or S N Ar fluorination under nucleophilic attack of [ 18 F]F – . , Besides, azeotropic drying of [ 18 F]F – and the addition of phase-transfer catalysts are always demanded to improve the nucleophilicity and solubility of [ 18 F]F – in aprotic solvents. − …”

Section: Introductionmentioning

confidence: 99%

Isotope Exchange-Based ¹⁸F-Labeling Methods

Wang

Mou

et al. 2023

Bioconjugate Chem.

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18 F-Labeling methods for the preparation of 18 F-labeled molecular probes can be classified into electrophilic fluorination, nucleophilic fluorination, metal-F coordination, and 18 F/ 19 F isotope exchange. Isotope exchange-based 18 F-labeling methods demonstrate mild conditions featuring water resistance and facile high-performance liquid chromatography-free purification in direct 18 F-labeling of substrates. This paper systematically reviews isotope exchange-based 18 F-labeling methods sorted by the adjacent atom bonding with F, i.e., carbon and noncarbon atoms (Si, B, P, S, Ga, Fe, etc.). The respective isotope exchange mechanism, radiolabeling condition, radiochemical yield, molar activity, and stability of the 18 F-product are mainly discussed for each isotope exchange-based 18 F-labeling method as well as the cuttingedge application of the corresponding 18 F-labeled molecular probes.

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“…However, fluoro substituents can act as pharmacophore isosteres, such as CF 3 ,to mimic the C=O oxygen group [ 4 ]. On the other hand, fluorine compounds can act as diagnostic agents for positron emission tomography (PET) applications [ 6 , 7 , 8 ]. Its unstable isotope, the radioactive 18 F atom, serves as the tool to extract the pharmacokinetic information.…”

Section: Introductionmentioning

confidence: 99%

Recent Development of Radiofluorination of Boron Agents for Boron Neutron Capture Therapy of Tumor: Creation of 18F-Labeled C-F and B-F Linkages

Deng

2023

Pharmaceuticals

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Boron neutron capture therapy (BNCT) is a binary therapeutic technique employing a boron agent to be delivered to the tumor site followed by the irradiation of neutrons. Biofunctional molecules/nanoparticles labeled with F-18 can provide an initial pharmacokinetic profile of patients to guide the subsequent treatment planning procedure of BNCT. Borono phenylalanine (BPA), recognized by the l-type amino acid transporter, can cross the blood-brain barrier and be accumulated in gliomas. The radiofluoro BNCT agents are reviewed by considering (1) less cytotoxicity, (2) diagnosing and therapeutic purposes, (3) aqueous solubility and extraction route, as well as (4), the trifluoroborate effect. A trifluoroborate-containing amino acid such as fluoroboronotyrosine (FBY) represents an example with both functionalities of imaging and therapeutics. Comparing with the insignificant cytotoxicity of clinical BPA with IC50 > 500 μM, FBY also shows minute toxicity with IC50 > 500 μM. [18F]FBY is a potential diagnostic agent for its tumor to normal accumulation (T/N) ratio, which ranges from 2.3 to 24.5 from positron emission tomography, whereas the T/N ratio of FBPA is greater than 2.5. Additionally, in serving as a BNCT therapeutic agent, the boron concentration of FBY accumulated in gliomas remains uncertain. The solubility of 3-BPA is better than that of BPA, as evidenced by the cerebral dose of 3.4%ID/g vs. 2.2%ID/g, respectively. While the extraction route of d-BPA differs from that of BPA, an impressive T/N ratio of 6.9 vs. 1.5 is noted. [18F]FBPA, the most common clinical boron agent, facilitates the application of BPA in clinical BNCT. In addition to [18F]FBY, [18F] trifluoroborated nucleoside analog obtained through 1,3-dipolar cycloaddition shows marked tumoral uptake of 1.5%ID/g. Other examples using electrophilic and nucleophilic fluorination on the boron compounds are also reviewed, including diboronopinacolone phenylalanine and nonsteroidal anti-inflammatory agents.

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Research progress of 18F labeled small molecule positron emission tomography (PET) imaging agents

Cited by 20 publications

References 172 publications

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

Isotope Exchange-Based ¹⁸F-Labeling Methods

Recent Development of Radiofluorination of Boron Agents for Boron Neutron Capture Therapy of Tumor: Creation of 18F-Labeled C-F and B-F Linkages

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Research progress of 18F labeled small molecule positron emission tomography (PET) imaging agents

Cited by 20 publications

References 172 publications

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

Fluorine-a small magic bullet atom in the drug development: perspective to FDA approved and COVID-19 recommended drugs

Isotope Exchange-Based 18F-Labeling Methods

Recent Development of Radiofluorination of Boron Agents for Boron Neutron Capture Therapy of Tumor: Creation of 18F-Labeled C-F and B-F Linkages

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Isotope Exchange-Based ¹⁸F-Labeling Methods