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Rearmed Bifunctional Chelating Ligand for <sup>225</sup>Ac/<sup>155</sup>Tb Precision-Guided Theranostic Radiopharmaceuticals─H<sub>4</sub>noneunpaX

Luke Wharton, Hua Yang, Marı́a de Guadalupe Jaraquemada-Peláez, Helen Merkens, Gokce Engudar, Aidan Ingham, Helena Koniar, Valery Radchenko, P. Kunz, Paul Schaffer, François Bénard, Chris Orvig

2023Journal of Medicinal Chemistry22 citationsDOI

Abstract

Superior bifunctional chelating ligands, which can sequester both α-emitting radionuclides ( 225 Ac, 213 Bi) and their diagnostic companions ( 155 Tb, 111 In), remain a formidable challenge to translating targeted alpha therapy, with complementary diagnostic imaging, to the clinic. H 4 noneupaX, a chelating ligand with an unusual diametrically opposed arrangement of pendant donor groups, has been developed to this end. H 4 noneunpaX preferentially complexes Ln 3+ and An 3+ ions, forming thermodynamically stable (pLa = 17.8, pLu = 21.3) and kinetically inert complexes─single isomeric species by nuclear magnetic resonance and density functional theory. Metal binding versatility demonstrated in radiolabeling [ 111 In]In 3+, [ 155 Tb]Tb 3+, [ 177 Lu]Lu 3+, and [ 225 Ac]Ac 3+ achieved high molar activities under mild conditions. Efficient, scalable synthesis enabled in vivo evaluation of bifunctional H 4 noneunpaX conjugated to two octreotate peptides targeting neuroendocrine tumors. Single photon emission computed tomography/CT and biodistribution studies of 155 Tb-radiotracers in AR42J tumor-bearing mice showed excellent image contrast, good tumor uptake, and high in vivo stability. H 4 noneunpaX shows significant potential for theranostic applications involving 225 Ac/ 155 Tb or 177 Lu/ 155 Tb.

Topics & Concepts

ChemistryBifunctionalBiodistributionChelationIn vivoLigand (biochemistry)Conjugated systemDOTASpect imagingPreclinical imagingRadiochemistryStereochemistryNuclear chemistryIn vitroNuclear medicineInorganic chemistryOrganic chemistryReceptorBiochemistryBiologyMedicineBiotechnologyPolymerCatalysisRadiopharmaceutical Chemistry and ApplicationsMedical Imaging Techniques and ApplicationsLanthanide and Transition Metal Complexes
Rearmed Bifunctional Chelating Ligand for <sup>225</sup>Ac/<sup>155</sup>Tb Precision-Guided Theranostic Radiopharmaceuticals─H<sub>4</sub>noneunpaX | Litcius