First-in-human study of an 18F-labeled boramino acid: a new class of PET tracers

Lan, Xiaoli; Fan, Kevin; Cai, Weibo

doi:10.1007/s00259-021-05227-0

Cited by 8 publications

(9 citation statements)

References 31 publications

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“…Large neutral amino acid transporter type 1 (LAT-1) mediates the transport of large neutral amino acids (e.g., tyrosine), and its expression levels are elevated in many types of cancer (such as glioma) . In 2015, Liu et al , reported a new class of amino acid mimics named boramino acids, which served as imaging probes for amino acid transporters (AATs) by substituting the carboxylate group (−COO – ) of amino acids with the isosteric trifluoroborate (-BF 3 – ) (Scheme a). Due to the introduction of trifluoroborate, 18 F-labeling of these amino acid derivatives can be efficiently achieved.…”

Section: F/19f Isotope Exchange On B–f Bondmentioning

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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Section: F/19f Isotope Exchange On B–f Bondmentioning

confidence: 99%

Isotope Exchange-Based ¹⁸F-Labeling Methods

Wang

Mou

et al. 2023

Bioconjugate Chem.

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“…In addition to [ 18 F]FBY, a number of amino acids have been tagged by radiofluoride through the exchange reaction on the trifluoroborate moieties [ 75 ]. Examples such as [ 18 F]Ala-BF 3 , [ 18 F]Gln-BF 3 and [ 18 F]Pro-BF 3 showed their values as future BNCT theranostic agents ( Figure 4 ).…”

Section: Facial Radiofluorination Through Exchanging 18 ...mentioning

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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“…As a result, 18 F‐labeled boramino acids, which take advantages of fluorine and boron synergistically has attracted much attention. For instance, 18 F‐trifluoroborate‐derived tyrosine ( 18 F‐FBY) has demonstrated exciting potential in clinical PET imaging [9–10] . Furthermore, both trifluoromethyl and boronic groups have been proved to be valuable functionalities in cold pharmaceuticals, [11–12] as well as in hot radiopharmaceuticals [13–14] (Figure 1a, 1 b).…”

Section: Figurementioning

confidence: 99%

“…Ga and 177 Lu, the collaboration of 18 F and 10 B also harbours superiorities in tumour radiotheranostics. [3][4] Specifically, when 10 B is bombarded by epithermal neutron, its excited isotope 11 B would produce γ-ray during radioactive decay, this laid the foundation of boron neutron capture therapy (BNCT) for treating locally invasive malignant tumours.…”

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confidence: 99%

Synthesis of Secondary Trifluoromethyl Boronic Esters through Visible Light Induced Decarboxylative Alkylation Reactions

Gao

Mao

et al. 2023

Adv Synth Catal

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We demonstrated a practical and general methodology for the synthesis of secondary trifluoromethyl boronic esters through visible light induced decarboxylative alkylation reaction. This reaction was driven by the photochemical activity of electron donor-acceptor (EDA) complex. Except for wide group tolerance, moderate to high yields and simple reaction conditions, the practicality of this protocol was further demonstrated by direct modification of bioactive molecules and further derivations.

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First-in-human study of an 18F-labeled boramino acid: a new class of PET tracers

Cited by 8 publications

References 31 publications

Isotope Exchange-Based ¹⁸F-Labeling Methods

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

Synthesis of Secondary Trifluoromethyl Boronic Esters through Visible Light Induced Decarboxylative Alkylation Reactions

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First-in-human study of an 18F-labeled boramino acid: a new class of PET tracers

Cited by 8 publications

References 31 publications

Isotope Exchange-Based 18F-Labeling Methods

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

Synthesis of Secondary Trifluoromethyl Boronic Esters through Visible Light Induced Decarboxylative Alkylation Reactions

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Isotope Exchange-Based ¹⁸F-Labeling Methods

Isotope Exchange-Based ¹⁸F-Labeling Methods