4.7 Review

Recent Advances in 18F-Labeled Amino Acids Synthesis and Application

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Multidisciplinary Sciences

[18F]Difluorocarbene for positron emission tomography

Jeroen B. I. Sap et al.

Summary: This study introduces a novel [F-18] difluorocarbene reagent, which resolves the issue of high molar activity in F-18 difluoromethylated molecules by incorporating carbene chemistry, showcasing its versatility and ease of access.

NATURE (2022)

Article Radiology, Nuclear Medicine & Medical Imaging

Metabolic characteristics of [18F]fluoroboronotyrosine (FBY) PET in malignant brain tumors

Ziren Kong et al.

Summary: This study investigated the imaging characteristics of [F-18]fluoroboronotyrosine (FBY) positron emission tomography (PET) in malignant brain tumors. The results showed that elevated FBY uptake can be seen in most malignant brain tumors, and primary glioblastoma (GBM), recurrent glioma, and metastatic brain tumor displayed a significant tumor-to-background ratio.

NUCLEAR MEDICINE AND BIOLOGY (2022)

Article Chemistry, Medicinal

Convenient PET-tracer production via SuFEx 18F-fluorination of nanomolar precursor amounts

Nils Walter et al.

Summary: A protocol for radiolabeling of aryl fluorosulfates using ultrafast isotopic exchange has been developed and optimized. This method allows for efficient labeling of low nanomolar amounts of aryl fluorosulfates without the need for azeotropic drying, base addition, and HPLC purification. The labeled compounds demonstrated sufficient stability in vivo and showed promise as tracers for visualizing specific molecular expressions.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

Article Radiology, Nuclear Medicine & Medical Imaging

18F-Boramino acid PET/CT in healthy volunteers and glioma patients

Zhu Li et al.

Summary: The study found that F-18-FBY is well tolerated by healthy volunteers with rapid clearance and excretion profile. In glioma patients, F-18-FBY uptake increased with tumor grade and showed positive correlations with LAT-1 expression and Ki-67 labeling index. The PET tracer has potential in assessing LAT-1 expression and guiding boron neutron capture therapy in gliomas.

EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING (2021)

Article Chemistry, Multidisciplinary

Sulfur [18F]Fluoride Exchange Click Chemistry Enabled Ultrafast Late-Stage Radiosynthesis

Qinheng Zheng et al.

Summary: Efficient and target-specific fluorination processes remain the main challenge in fluorine-18 PET, but a new ultrafast isotopic exchange method has been developed for the synthesis of novel PET agent aryl [F-18]fluorosulfate. This method enables automated F-18-radiolabeling of diverse aryl fluorosulfates with high yield and molar activity in just 30 seconds at room temperature, without the need for time-consuming HPLC purification steps. Additionally, the imaging application of a designed PARP1-targeting aryl [F-18]fluorosulfate has been successfully demonstrated in vivo.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Radiology, Nuclear Medicine & Medical Imaging

L-type amino acid transporter (LAT) 1 expression in 18F-FET-negative gliomas

Franziska J. Vettermann et al.

Summary: The study found no significant differences in LAT1 expression between F-18-FET-negative and positive gliomas, but higher LAT1 expression in IDH-mutant astrocytomas is associated with a shorter progression-free survival. Further research on mechanisms influencing F-18-FET uptake is necessary.

EJNMMI RESEARCH (2021)

Article Oncology

Evaluation of 3-l- and 3-d-[18F]Fluorophenylalanines as PET Tracers for Tumor Imaging

Felicia Kraemer et al.

Summary: The study evaluated two novel PET tracers, 3-l- and 3-d-[F-18]FPhe, and found that they enable accurate tumor delineation with certain advantages over [F-18]FET, making them promising candidates for further preclinical and clinical evaluations.

CANCERS (2021)

Review Chemistry, Medicinal

Sweetening Pharmaceutical Radiochemistry by 18F-Fluoroglycosylation: Recent Progress and Future Prospects

Sandip S. Shinde et al.

Summary: This paper provides an updated review on the recent progress in F-18-fluoroglycosylation reactions and the preclinical application of F-18-glycoconjugates, including small molecules, peptides, and high-molecular-weight proteins.

PHARMACEUTICALS (2021)

Article Chemistry, Organic

Direct 18F-Labeling of Biomolecules via Spontaneous Site-Specific Nucleophilic Substitution by F- on Phosphonate Prostheses

Chao Wang et al.

Summary: This method achieves high radiochemical yield late-stage direct F-18 labeling of bare biomolecules containing common active groups, with spontaneity and site-selectivity attributed to higher rates of nucleophilic substitution reactions on phosphonates. Rapid access to many medicinally significant F-18-labeled biomolecules is achieved manually or automatically with high radiochemical yields and molar activities.

ORGANIC LETTERS (2021)

Article Oncology

18F-Trifluoromethylated D-Cysteine as a Promising New PET Tracer for Glioma Imaging: Comparative Analysis With MRI and Histopathology in Orthotopic C6 Models

Hui Ma et al.

Summary: This study aimed to explore the potential application of F-18-trifluoromethylated D-cysteine (S-[F-18]CF3-D-CYS) in evaluating glioma using orthotopic C6 glioma models. The results showed that S-[F-18]CF3-D-CYS PET performed well in the diagnosis and evaluation of glioma, suggesting its potential as a valuable tool in the clinical management of gliomas.

FRONTIERS IN ONCOLOGY (2021)

Article Chemistry, Organic

18F-Fluorination: Challenge and Opportunity for Organic Chemists

Riya Halder et al.

Summary: F-18-fluorination is an important and rapidly growing field in organic synthesis that has attracted significant attention from chemists. This manuscript presents a biased perspective on recent advances in the field, with a focus on the author's own chemistry, and discusses challenges for the development of new chemistry with potential impact on imaging. The aim is to provide a useful guide for chemists to develop reliable reaction chemistry suitable for radiofluorination to make a real impact on human health.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Medicinal

Closing the gap between 19F and 18F chemistry

Javier Ajenjo et al.

Summary: Positron emission tomography (PET) is crucial for drug discovery and diagnosis, with F-18 radiotracers playing a significant role. Advances in F-18-radiochemistry have enabled the development of novel processes for F-18-incorporation onto complex molecules. Recently, there has been a resurgence of interest in F-18-radiochemistry, with a focus on using nucleophilic fluoride in place of fluorination reagents derived from molecular fluorine gas.

EJNMMI RADIOPHARMACY AND CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Fluorine-18 labelled Ruppert-Prakash reagent ([18F]Me3SiCF3) for the synthesis of 18F-trifluoromethylated compounds

Anna Pees et al.

Summary: This article describes the first synthesis and application of fluorine-18 labelled Ruppert-Prakash reagent [F-18]Me3SiCF3, which was used to successfully prepare F-18-trifluoromethylated compounds by reacting with benzaldehydes, acetophenones and benzophenones.

CHEMICAL COMMUNICATIONS (2021)

Review Oncology

New aspects of amino acid metabolism in cancer

Lisa Vettore et al.

BRITISH JOURNAL OF CANCER (2020)

Review Radiology, Nuclear Medicine & Medical Imaging

Copper-mediated late-stage radiofluorination: five years of impact on preclinical and clinical PET imaging

Jay S. Wright et al.

CLINICAL AND TRANSLATIONAL IMAGING (2020)

Article Chemistry, Organic

Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling

Robert Szpera et al.

ORGANIC LETTERS (2020)

Review Biochemistry & Molecular Biology

Amino Acid Transporters as Targets for Cancer Therapy: Why, Where, When, and How

Stefan Broer

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2020)

Review Chemistry, Multidisciplinary

Chemistry for Positron Emission Tomography: Recent Advances in 11C-, 18F-, 13N-, and 15O-Labeling Reactions

Xiaoyun Deng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Biotechnology & Applied Microbiology

Tryptophan metabolism as a common therapeutic target in cancer, neurodegeneration and beyond

Michael Platten et al.

NATURE REVIEWS DRUG DISCOVERY (2019)

Article Multidisciplinary Sciences

Direct arene C-H fluorination with 18F- via organic photoredox catalysis

Wei Chen et al.

SCIENCE (2019)

Article Medicine, Research & Experimental

Side Chain Optimization Remarkably Enhances the in Vivo Stability of 18F-Labeled Glutamine for Tumor Imaging

Junyi Chen et al.

MOLECULAR PHARMACEUTICS (2019)

Article Chemistry, Multidisciplinary

Synthesis and Derivatization of 1,1-[18F]Difluorinated Alkenes

Aileen B. Frost et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Oncology

Immune control by amino acid catabolism during tumorigenesis and therapy

Henrique Lemos et al.

NATURE REVIEWS CANCER (2019)

Article Radiology, Nuclear Medicine & Medical Imaging

Preclinical evaluation of an F-18-trifluoroborate methionine derivative for glioma imaging

Xiangyu Yang et al.

EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING (2018)

Review Biochemical Research Methods

Hypervalent aryliodine compounds as precursors for radiofluorination

Victor W. Pike

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS (2018)

Article Biochemical Research Methods

Synthesis, bioconjugation and stability studies of [F-18]ethenesulfonyl fluoride

Bo Zhang et al.

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS (2018)

Article Medicine, Research & Experimental

18F-Alanine Derivative Serves as an ASCT2 Marker for Cancer Imaging

Hui Liu et al.

MOLECULAR PHARMACEUTICS (2018)

Article Radiology, Nuclear Medicine & Medical Imaging

Preclinical study of an 18F-labeled glutamine derivative for cancer imaging

Cong Li et al.

NUCLEAR MEDICINE AND BIOLOGY (2018)

Article Chemistry, Multidisciplinary

Site-Selective, Late-Stage C-H 18F-Fluorination on Unprotected Peptides for Positron Emission Tomography Imaging

Zheliang Yuan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Radiology, Nuclear Medicine & Medical Imaging

Radiosynthesis and biological evaluation of N-(2-[18F]fluoropropionyl)-3,4-dihydroxy-L-phenylalanine as a PET tracer for oncologic imaging

Caihua Tang et al.

NUCLEAR MEDICINE AND BIOLOGY (2017)

Article Medicine, Research & Experimental

Synthesis of 5-[18F]Fluoro-α-methyl Tryptophan: New Trp Based PET Agents

Benjamin C. Giglio et al.

THERANOSTICS (2017)

Article Chemistry, Multidisciplinary

18F-Deoxyfluorination of Phenols via Ru π-Complexes

M. Hassan Beyzavi et al.

ACS CENTRAL SCIENCE (2017)

Review Chemistry, Medicinal

Sulfur-fluorine bond in PET radiochemistry

Giancarlo Pascali et al.

EJNMMI RADIOPHARMACY AND CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Ethenesulfonyl Fluoride: The Most Perfect Michael Acceptor Ever Found?

Quan Chen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Review Chemistry, Multidisciplinary

18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography

Sean Preshlock et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Organic

Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF

Katarina J. Makaravage et al.

ORGANIC LETTERS (2016)

Review Biochemical Research Methods

[18F]6-fluoro-3,4-dihydroxy-L-phenylalanine - recent modern syntheses for an elusive radiotracer

Richard Edwards et al.

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS (2015)

Article Chemistry, Organic

Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

Andrew V. Mossine et al.

ORGANIC LETTERS (2015)

Review Immunology

Cancer immunotherapy by targeting IDO1/TDO and their downstream effectors

Michael Platten et al.

FRONTIERS IN IMMUNOLOGY (2015)

Article Multidisciplinary Sciences

Boramino acid as a marker for amino acid transporters

Zhibo Liu et al.

SCIENCE ADVANCES (2015)

Article Chemistry, Multidisciplinary

A Universal Procedure for the [18F]Trifluoromethylation of Aryl Iodides and Aryl Boronic Acids with Highly Improved Specific Activity

Dion van der Born et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

Article Chemistry, Organic

Copper-Catalyzed [18F]Fluorination of (Mesityl)(aryl)iodonium Salts

Naoko Ichiishi et al.

ORGANIC LETTERS (2014)

Article Chemistry, Multidisciplinary

Late-stage [18F]fluorination: new solutions to old problems

Allen F. Brooks et al.

CHEMICAL SCIENCE (2014)

Article Multidisciplinary Sciences

Glutamine supports pancreatic cancer growth through a KRAS-regulated metabolic pathway

Jaekyoung Son et al.

NATURE (2013)

Review Chemistry, Medicinal

Radiohalogenated nonnatural amino acids as PET and SPECT tumor imaging agents

Jonathan McConathy et al.

MEDICINAL RESEARCH REVIEWS (2012)

Article Chemistry, Inorganic & Nuclear

SiFA-Modified Phenylalanine: A Key Compound for the Efficient Synthesis of 18F-Labelled Peptides

Ljuba Iovkova et al.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2011)

Review Biochemistry & Molecular Biology

Glutamine addiction: a new therapeutic target in cancer

David R. Wise et al.

TRENDS IN BIOCHEMICAL SCIENCES (2010)

Article Chemistry, Inorganic & Nuclear

Automated synthesis of n.c.a. [F-18]FDOPA via nucleophilic aromatic substitution with [F-18]fluoride

B. Shen et al.

APPLIED RADIATION AND ISOTOPES (2009)

Article Chemistry, Multidisciplinary

Arylfluoroborates and alkylfluorosilicates as potential PET imaging agents:: High-yielding aqueous biomolecular 18F-labeling

R Ting et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Biochemistry & Molecular Biology

Human L-type amino acid transporter 1 (LAT1): characterization of function and expression in tumor cell lines

O Yanagida et al.

BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES (2001)