Recent Advances in Synthetic Methods for Radioiodination.

Organic compounds bearing radioisotopes of iodine are widely used for biological research, diagnostic imaging and radiotherapy. Early reported synthetic methods for the incorporation of radioiodine have generally involved high temperature reactions or strongly oxidizing conditions. To overcome these limitations and to cope with the demand for novel radioiodinated probes, there has been a surge in the development of new synthetic methodology for radioiodination. This synopsis describes the key transformations developed recently.

[1]  T. Cailly,et al.  Improvements of C–H Radio-Iodination of N-Acylsulfonamides toward Implementation in Clinics , 2019, Synthesis.

[2]  A. Sutherland.  Radiohalogenation of Organic Compounds: Practical Considerations and Challenges for Molecular Imaging , 2019, Synthesis.

[3]  L. Carroll,et al.  Iodination of terminal alkynes using KI/CuSO4 – A facile method with potential for radio-iodination , 2019, Tetrahedron letters.

[4]  S. Pimlott,et al.  Mechanism of Cu-Catalyzed Aryl Boronic Acid Halodeboronation Using Electrophilic Halogen: Development of a Base-Catalyzed Iododeboronation for Radiolabeling Applications. , 2019, Organic letters.

[5]  F. Pecorari,et al.  Prosthetic groups for radioiodination and astatination of peptides and proteins: A comparative study of five potential bioorthogonal labeling strategies. , 2019, Bioorganic & medicinal chemistry.

[6]  P. Barbey,et al.  Palladium-Mediated Site-Selective C-H Radio-iodination. , 2018, Organic Letters.

[7]  T. Cailly,et al.  Boron reagents for divergent radiochemistry. , 2018, Chemical Society reviews.

[8]  S. H. Park,et al.  Efficient and Site-Specific 125I-Radioiodination of Bioactive Molecules Using Oxidative Condensation Reaction , 2018, ACS omega.

[9]  R. Mach,et al.  Rapid Cu-Catalyzed [211At]Astatination and [125I]Iodination of Boronic Esters at Room Temperature. , 2018, Organic letters.

[10]  P. Riss,et al.  An acylation‐Finkelstein approach to radioiodination of bioactives: The role of amide group anchimeric assistance , 2018 .

[11]  Hai Yan,et al.  Synthesis and evaluation of radiolabeled AGI-5198 analogues as candidate radiotracers for imaging mutant IDH1 expression in tumors. , 2018, Bioorganic & medicinal chemistry letters.

[12]  J. Maher,et al.  A Dual Reporter Iodinated Labeling Reagent for Cancer Positron Emission Tomography Imaging and Fluorescence-Guided Surgery , 2018, Journal of medicinal chemistry.

[13]  K. Sano,et al.  Synthesis of radioiodinated probes targeted toward matrix metalloproteinase-12. , 2018, Bioorganic & medicinal chemistry letters.

[14]  S. Pimlott,et al.  Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes , 2017, Chemistry.

[15]  R. Mach,et al.  Consensus nomenclature rules for radiopharmaceutical chemistry - Setting the record straight. , 2017, Nuclear medicine and biology.

[16]  M. Brechbiel,et al.  Bifunctional aryliodonium salts for highly efficient radioiodination and astatination of antibodies. , 2017, Bioorganic & medicinal chemistry.

[17]  S. Pimlott,et al.  A one-pot radioiodination of aryl amines via stable diazonium salts: preparation of 125I-imaging agents. , 2017, Chemical communications.

[18]  W. Banks,et al.  Development of rhenacarborane complexes as central nervous system (CNS) drug delivery agents , 2017 .

[19]  M. C. Feiters,et al.  Design of Radioiodinated Pharmaceuticals: Structural Features Affecting Metabolic Stability towards in Vivo Deiodination , 2017, European journal of organic chemistry.

[20]  Xiaoyuan Chen,et al.  A Highly Efficient Copper-Mediated Radioiodination Approach Using Aryl Boronic Acids. , 2016, Chemistry.

[21]  Sean M. Preshlock,et al.  Radiosynthesis of SPECT tracers via a copper mediated 123I iodination of (hetero)aryl boron reagents. , 2016, Chemical communications.

[22]  M. Brechbiel,et al.  Unexpected Behavior of the Heaviest Halogen Astatine in the Nucleophilic Substitution of Aryliodonium Salts. , 2016, Chemistry.

[23]  S. Corvaisier,et al.  Synthesis and evaluation of novel serotonin 4 receptor radiotracers for single photon emission computed tomography. , 2016, European journal of medicinal chemistry.

[24]  S. H. Park,et al.  Highly efficient method for 125I-radiolabeling of biomolecules using inverse-electron-demand Diels-Alder reaction. , 2016, Bioorganic & medicinal chemistry.

[25]  A. Faivre-Chauvet,et al.  Ionic liquid supported organotin reagents to prepare molecular imaging and therapy agents. , 2016, Organic & biomolecular chemistry.

[26]  S. Pimlott,et al.  Silver(I)-Catalyzed Iodination of Arenes: Tuning the Lewis Acidity of N-Iodosuccinimide Activation. , 2016, The Journal of organic chemistry.

[27]  S. H. Park,et al.  Critical analysis of radioiodination techniques for micro and macro organic molecules , 2016, Journal of Radioanalytical and Nuclear Chemistry.

[28]  J. Valliant,et al.  (125)I-Tetrazines and Inverse-Electron-Demand Diels-Alder Chemistry: A Convenient Radioiodination Strategy for Biomolecule Labeling, Screening, and Biodistribution Studies. , 2016, Bioconjugate chemistry.

[29]  Lin Zhu,et al.  PET/SPECT imaging agents for neurodegenerative diseases. , 2014, Chemical Society reviews.

[30]  A. Brownell,et al.  Development of [(123)I]IPEB and [(123)I]IMPEB as SPECT Radioligands for Metabotropic Glutamate Receptor Subtype 5. , 2014, ACS medicinal chemistry letters.

[31]  A. Ouadi,et al.  Synthesis of new 123I-labeled free fatty acids analogues and first evaluation as potential tracers for SPECT imaging to elucidate fatty acid flux in mouse , 2013 .

[32]  S. Pimlott,et al.  Nickel-mediated radioiodination of aryl and heteroaryl bromides: rapid synthesis of tracers for SPECT imaging. , 2013, Angewandte Chemie.

[33]  M. Lythgoe,et al.  A one-pot three-component radiochemical reaction for rapid assembly of 125I-labeled molecular probes. , 2013, Journal of the American Chemical Society.

[34]  G. Kabalka,et al.  Syntheses and characterization of polymer-supported organotrifluoroborates: applications in radioiodination reactions. , 2010, Chemical communications.

[35]  G. Kabalka,et al.  Triolborates: water-soluble complexes of arylboronic acids as precursors to iodoarenes , 2010 .

[36]  J. Valliant,et al.  A convenient method for the preparation of fluorous tin derivatives for the fluorous labeling strategy. , 2008, The Journal of organic chemistry.

[37]  J. Maublant,et al.  Evaluation of radiolabeled (hetero)aromatic analogues of N-(2-diethylaminoethyl)-4-iodobenzamide for imaging and targeted radionuclide therapy of melanoma. , 2008, Journal of medicinal chemistry.

[38]  J. Papon,et al.  Synthesis, radiosynthesis, and biological evaluation of new proteasome inhibitors in a tumor targeting approach. , 2008, Journal of medicinal chemistry.

[39]  G. Kabalka.  Isotope incorporation via organoboranes , 2007 .

[40]  J. Valliant,et al.  A new strategy for preparing molecular imaging and therapy agents using fluorine-rich (fluorous) soluble supports. , 2006, Journal of the American Chemical Society.

[41]  G. Kabalka,et al.  A facile synthesis of radioiodinated alkynyl iodides using potassium alkynyltrifluoroborates , 2005 .

[42]  D. Wilbur,et al.  Radiohalogens for imaging and therapy. , 2005, Chemical Society reviews.

[43]  G. Kabalka,et al.  [123I]Iodocognex, a potent spect agent to map acetylcholinesterase via a boronic acid precursor , 2001 .

[44]  A. Khalaj,et al.  A new and simple synthesis of N‐succinimidyl‐4‐[127/125I]iodobenzoate involving a microwave ‐ accelerated iodination step , 2001 .

[45]  Robert B. Innis,et al.  Evaluation of the monoamine uptake site ligand [131I]methyl 3β-(4-Iodophenyl)-tropane-2β-carboxylate ([123I]β-CIT) in non-human primates: Pharmacokinetics, biodistribution and SPECT brain imaging coregistered with MRI , 1993 .

[46]  M. Zalutsky,et al.  No-carrier-added synthesis of meta-[131I]iodobenzylguanidine. , 1993, Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine.

[47]  M. Goodman,et al.  Synthesis and evaluation of radioiodinated 2-(2(RS)-aminopropyl)-5- iodothiophenes as brain imaging agents. , 1992, Journal of medicinal chemistry.

[48]  R. Varma,et al.  The synthesis of radiolabeled compounds via organometallic intermediates , 1990 .

[49]  P. C. Srivastava,et al.  Potential cerebral perfusion agents: synthesis and evaluation of a radioiodinated vinylalkylbarbituric acid analogue. , 1983, Journal of medicinal chemistry.

[50]  R. Counsell,et al.  Radioiodination techniques for small organic molecules , 1982 .

[51]  D. Wieland,et al.  Solid-phase exchange radioiodination of aryl iodides. Facilitation by ammonium sulfate , 1982 .

[52]  Andrew V. Sutherland,et al.  Molecular tracers for the PET and SPECT imaging of disease. , 2011, Chemical Society reviews.

[53]  K. M. Jones.  Radio-Iodination Methods for the Production of SPECT Imaging Agents , 2010 .

[54]  F. de Vos,et al.  Radiosynthesis, in vitro and in vivo evaluation of 123I-labeled anandamide analogues for mapping brain FAAH. , 2009, Bioorganic & medicinal chemistry.