2014
DOI: 10.1002/cplu.201402031
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Synthesis and Characterization of a Stable Copper(I) Complex for Radiopharmaceutical Applications

Abstract: Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4‐concatenated oxazoles and the mild synthesis of thiazoles from natural amino acids. This report represents the first synthesis of plantazolicin B and includes the first co… Show more

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Cited by 10 publications
(7 citation statements)
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“…This strategy was recently proposed with an open-chain ligand that promoted the formation of a stable complex of Cu + while not achieving S-coordination. 14 In our cyclam derivatives the complex of Cu 2+ was found to be thermodynamically and kinetically efficient with the thiazolyl arms, especially for te2th, but the expected change from N6 to N4S2 coordination upon reduction of Cu 2+ to Cu + was not observed either. This study proved nonetheless that methylthiazolyl pendants lead to quite stable and inert copper complexes even upon metal reduction.…”
Section: Introductionmentioning
confidence: 65%
“…This strategy was recently proposed with an open-chain ligand that promoted the formation of a stable complex of Cu + while not achieving S-coordination. 14 In our cyclam derivatives the complex of Cu 2+ was found to be thermodynamically and kinetically efficient with the thiazolyl arms, especially for te2th, but the expected change from N6 to N4S2 coordination upon reduction of Cu 2+ to Cu + was not observed either. This study proved nonetheless that methylthiazolyl pendants lead to quite stable and inert copper complexes even upon metal reduction.…”
Section: Introductionmentioning
confidence: 65%
“…15 Despite the huge number of BFCs that have been evaluated for [ 64/67 Cu]Cu 2+ complexation, chelating ligands able to simultaneously coordinate both 2+ and 1+ copper oxidation states have received markedly less attention. [16][17][18] Given the borderline character of Cu 2+ according to Pearson's Hard-Soft Acid-Base theory (HSAB), the investigated BFCs for its chelation are mostly confined to polyazamacrocyclic scaffolds with pendant carboxylate arms such as 1,4,7,10-tetraazacyclododecane-1,4,7,10tetraacetic acid (DOTA), 1,4,8,11-tetraazacyclotetradecane-1,4,8,11tetraacetic acid (TETA) and their derivatives (Fig. 1).…”
Section: Introductionmentioning
confidence: 99%
“…The quest for novel BFCs of 64/67 Cu that combine high in vivo stability and kinetic inertness with quantitative and fast radiolabeling in mild conditions and no demetalation upon Cu 2+ /Cu + reduction is still a significant challenge . With regard to the latter decomplexation pathway, only a few attempts have been made to develop BFCs able to securely bind both Cu 2+ and Cu + . ,, In light of this, we have hypothesized that the introduction of soft sulfur donor arms on a cyclen scaffold would stabilize both copper oxidation states, and we have chosen a small library of N-functionalized cyclen derivatives bearing sulfide pendant chains (Figure ). These ligands have recently been considered in our previous works, where the formation of very stable complexes with soft metal ions (Ag + and Cd 2+ ) was observed. …”
Section: Introductionmentioning
confidence: 99%