Synthesis of Radioiodinated Compounds. Classical Approaches and Achievements of Recent Years

Abstract

This review demonstrates the progress in the synthesis of radioiodinated compounds over the past decade. The possibilities and limitations of radiopharmaceuticals with different iodine isotopes, as well as the synthesis of low and high molecular weight compounds containing radioiodine, are discussed. An analysis of synthesis strategies, substrate frameworks, isolation methods, and metabolic stability, and the possibility of industrial production of radioiodinated organic derivatives which can find applications in the synthesis of drugs and diagnostics are presented.

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“…Obtaining a pure 131 I‐ 5p is crucial for the biodistribution study, as the presence of free iodine species in the administered form can cause accumulation of radioiodine thyroid gland, stomach, and salivary glands [ 37 ] resulting in false radioactivity uptake values. Thus, purification of 131 I‐ 5p was achieved using preparative TLC with the aid of chloroform: methanol as a developing mixture (4.8:0.2 vol/vol).…”

“…[36] Direct electrophilic aromatic substitution is one of the commonly used radioiodination methods provided that a suitable compound is chosen. [36,37] Electophilic radioiodination is achieved by generation of an electophilic iodonium species in situ with the aid of oxidizing agents such as Nchloroamides. [36,37] In radiochemistry, the efficiency of a radiolabelling reaction is often expressed in terms of percent radiochemical yield (%RCY ± SD) which is the percentage of isolated radiolabelled product compared to the starting radioactivity.…”

“…[36,37] Electophilic radioiodination is achieved by generation of an electophilic iodonium species in situ with the aid of oxidizing agents such as Nchloroamides. [36,37] In radiochemistry, the efficiency of a radiolabelling reaction is often expressed in terms of percent radiochemical yield (%RCY ± SD) which is the percentage of isolated radiolabelled product compared to the starting radioactivity. [36] In this context, radioiodination of 5p was planned using 131 I via electrophilic substitution under the oxidative conditions of chloramine-T (CAT).…”

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“…31 Due to their relatively long half-lives, radioiodinated pharmaceuticals can be produced and shipped to clinics not equipped for radiopharmaceutical production. 35 The application of radioiodine for theranostic applications also benefits from a well-established and expanding toolbox for the iodination of larger proteins and small molecules. 36 However, despite their long history in clinical nuclear medicine, many common iodinated radiopharmaceuticals suffer significant drawbacks with regard to complex production (volatile radioiodine), in vivo stability issues, complex and undesirable decay pathways and energies, or biologically incompatible half-lives.…”

“…125 I (EC, Auger e -, t 1/2 = 59.4 days) is commonly used as an Auger emitter for brachytherapy and as a radiolabel for preclinical radiological assays . Due to their relatively long half-lives, radioiodinated pharmaceuticals can be produced and shipped to clinics not equipped for radiopharmaceutical production . The application of radioiodine for theranostic applications also benefits from a well-established and expanding toolbox for the iodination of larger proteins and small molecules .…”