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Click-Chemistry Reactions in Radiopharmaceutical Chemistry: Fast & Easy Introduction of Radiolabels into Biomolecules for In Vivo Imaging

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Abstract:

Today the term “click chemistry” is often used equivalent with the copper-catalyzed 1,3-dipolar Huisgen cycloaddition. Originally, the concept was introduced in 2001 to describe reactions fulfilling a set of criteria that are most useful for chemical syntheses in drug research. In radiopharmaceutical chemistry where short lived radioisotopes are introduced into various different substance classes for in vivo imaging of biochemical processes, the expanding field of radioactive bioconjugation has become predominant. Labeled biomolecules such as peptides, proteins and oligonucleotides generated via bioconjugation of chelators for radiometal introduction as well as novel valuable secondary precursors for 18F labeling have enriched the growing field of molecular imaging substantially. When introducing radioactive nuclides with a very short half-life into biomolecules, some of the typical criteria defined by click-chemistry are more crucial than others. Time is always the most important issue, whereas avoiding the formation of by-products that have to be removed without chromatography is of minor importance. The short-lived radionuclide 11C for example has a physical half-life of only 20 min so that the labeling procedure cannot exceed 40-60 minutes (2-3 half-lifes). In this contribution, we outline reactions and molecules which meet the requirements of click chemistry reactions and are suitable for radiosyntheses of short lived SPECT (99mTc: t1/2 = 6 h, 111In: t1/2 = 2.81 d) and PET (11C: t1/2 = 20.3 min to 64Cu: t1/2 = 12.7 h) radiotracers for in vivo imaging of biological processes and review the contributions in the field of radiochemical “click-reactions” - 1,3-dipolar Huisgen cycloadditions and beyond.

Keywords: Click chemistry; bioconjugation; in vivo imaging; radionuclides

Document Type: Research Article

DOI: http://dx.doi.org/10.2174/092986710790820615

Affiliations: Lady Davis Institute for Medical Research, Jewish General Hospital, 3755, Chemin de la Cote-Ste-Catherine, Montreal, H3T 1E2, Quebec, Canada.

Publication date: April 1, 2010

More about this publication?
  • Current Medicinal Chemistry covers all the latest and outstanding developments in medicinal chemistry and rational drug design. Each issue contains a series of timely in-depth reviews written by leaders in the field covering a range of the current topics in medicinal chemistry. Current Medicinal Chemistry is an essential journal for every medicinal chemist who wishes to be kept informed and up-to-date with the latest and most important developments.
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