Macrobicyclic Cage Amine Ligands for Copper Radiopharmaceuticals: A Single Bivalent Cage Amine Containing Two Lys(3)-bombesin Targeting Peptides
Author
Ma, MT; Cooper, MS; Paul, RL; Shaw, KP; Karas, JA; Scanlon, D; White, JM; Blower, PJ; Donnelly, PSDate
2011-07-18Source Title
INORGANIC CHEMISTRYPublisher
AMER CHEMICAL SOCUniversity of Melbourne Author/s
SCANLON, DENIS; White, Jonathan; Donnelly, Paul; MA, MICHELLE; Karas, JohnAffiliation
ChemistryMetadata
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Journal ArticleCitations
Ma, M. T., Cooper, M. S., Paul, R. L., Shaw, K. P., Karas, J. A., Scanlon, D., White, J. M., Blower, P. J. & Donnelly, P. S. (2011). Macrobicyclic Cage Amine Ligands for Copper Radiopharmaceuticals: A Single Bivalent Cage Amine Containing Two Lys(3)-bombesin Targeting Peptides. INORGANIC CHEMISTRY, 50 (14), pp.6701-6710. https://doi.org/10.1021/ic200681s.Access Status
This item is currently not available from this repositoryARC Grant code
ARC/LE0775481Description
C1 - Journal Articles Refereed
Abstract
The synthesis of new cage amine macrobicyclic ligands with pendent carboxylate functional groups designed for application in copper radiopharmaceuticals is described. Reaction of [Cu((NH(2))(2)sar)](2+) (sar = 3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane) with either succinic or glutaric anhydride results in selective acylation of the primary amine atoms of [Cu((NH(2))(2)sar)](2+) to give derivatives with either one or two aliphatic carboxylate functional groups separated from the cage amine framework by either a four- or five-atom linker. The Cu(II) serves to protect the secondary amine nitrogen atoms from acylation, and can be removed to give the free ligands. The newly appended carboxylate functional groups can be used as sites of attachment for cancer-targeting peptides such as Lys(3)-bombesin. The synthesis of the first dimeric sarcophagine-peptide conjugate, possessing two Lys(3)-bombesin peptides tethered to a single cage amine, is presented. This species has been radiolabeled with copper-64 at ambient temperature and there is minimal dissociation of Cu(II) from the conjugate even after two days of incubation in human serum.
Keywords
Bioinorganic Chemistry; Transition Metal Chemistry; Inorganic Chemistry not elsewhere classified; Proteins and Peptides; Organic Chemical Synthesis; Expanding Knowledge in the Chemical SciencesExport Reference in RIS Format
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