2014
DOI: 10.1021/ic402825t
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Cu-Free 1,3-Dipolar Cycloaddition Click Reactions To Form Isoxazole Linkers in Chelating Ligands for fac-[MI(CO)3]+ Centers (M = Re, 99mTc)

Abstract: Isoxazole ring formation was examined as a potential Cu-free alternative click reaction to CuI-catalyzed alkyne/azide cycloaddition. The isoxazole reaction was explored at macroscopic and radiotracer concentrations with the fac-[MI(CO)3]+ (M = Re, 99mTc) core for use as a noncoordinating linker strategy between covalently linked molecules. Two click assembly methods (click, then chelate and chelate, then click) were examined to determine the feasibility of isoxazole ring formation with either alkyne-functional… Show more

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Cited by 5 publications
(6 citation statements)
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“…Additionally, the use of Cu­(I) ions as catalysts hindered their utility in clinical nuclear medicine due to strict current good manufacturing practices . Therefore, other biorthogonal reactions that do not require copper catalysts, have been proposed. However, the lack of ideal selectivity, slow reaction kinetics, moderate to mild stability under aqueous conditions and reversible substitution in vivo are potential drawbacks of these reactions. Most recently, biocompatible copper-free stain-promoted alkyne-azide cycloaddition (SPAAC) has attracted lot of interest due to the rapid rate of the reaction and excellent biorthogonal properties, which makes it an excellent candidate for radiolabeling of heat-sensitive targeting molecules. , Several 18F-labeled dibenzocyclooctyne (ADIBO) prosthetic groups have been reported in the literature for in vitro labeling as well as in vivo pre-targeting of peptides for tumor imaging. , Therefore, we adopted the chelate-then-click strategy with the SPAAC click reaction.…”
Section: Discussionmentioning
confidence: 99%
“…Additionally, the use of Cu­(I) ions as catalysts hindered their utility in clinical nuclear medicine due to strict current good manufacturing practices . Therefore, other biorthogonal reactions that do not require copper catalysts, have been proposed. However, the lack of ideal selectivity, slow reaction kinetics, moderate to mild stability under aqueous conditions and reversible substitution in vivo are potential drawbacks of these reactions. Most recently, biocompatible copper-free stain-promoted alkyne-azide cycloaddition (SPAAC) has attracted lot of interest due to the rapid rate of the reaction and excellent biorthogonal properties, which makes it an excellent candidate for radiolabeling of heat-sensitive targeting molecules. , Several 18F-labeled dibenzocyclooctyne (ADIBO) prosthetic groups have been reported in the literature for in vitro labeling as well as in vivo pre-targeting of peptides for tumor imaging. , Therefore, we adopted the chelate-then-click strategy with the SPAAC click reaction.…”
Section: Discussionmentioning
confidence: 99%
“…91 In addition, Bottorff et al have developed a synthetic strategy to generate isoxazole ligands via click chemistry (Figure 8B). 101 Yet in the end, it is undeniable that the “click-to-chelate” methodology represents the gold standard in this area. Indeed, this approach not only provides a cardinal example of the modularity and flexibility provided by click chemistry but also stands as one of the most useful and innovative developments in 99m Tc chemistry of the past decade.…”
Section: Creating Coordination Scaffoldsmentioning
confidence: 99%
“…Bailey et al, for example, used the CuAAC reaction in the synthesis H 4 azapa: a carboxypyridine-based chelator for 111 In 3+ and 177 Lu 3+ (Figure A) . In addition, Bottorff et al have developed a synthetic strategy to generate isoxazole ligands via click chemistry (Figure B) . Yet in the end, it is undeniable that the “click-to-chelate” methodology represents the gold standard in this area.…”
Section: Creating Coordination Scaffoldsmentioning
confidence: 99%
“…Therefore, alternative click reactions which do not require a metal catalyst are being investigated for generating targeted radiopharmaceuticals and other applications. 813 Among these reactions, isoxazole formation, 14 thioether formation, 15,16 and hydrazone generation have been successfully utilized in proof-of-concept studies with the fac -[M I (CO) 3 ] + core. 17 …”
Section: Introductionmentioning
confidence: 99%
“…Therefore, alternative click reactions which do not require a metal catalyst are being investigated for generating targeted radiopharmaceuticals and other applications. 8−13 Among these reactions, isoxazole formation, 14 thioether formation, 15,16 and hydrazone generation have been successfully utilized in proof-of-concept studies with the fac-[M I (CO) 3 ] + core. 17 In addition to click reactions, amine-reactive functionalities have also been used in facile approaches for labeling biomolecules with Re and 99m Tc complexes in prelabeling or preconjugate strategies, which are analogous to the chelate, then click strategy.…”
Section: ■ Introductionmentioning
confidence: 99%