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Synthesis of hexa aza cages, SarAr-NCS and AmBaSar and a study of their metal complexation, conjugation to nanomaterials and proteins for application in radioimaging and therapy.

Authors
  • Mume, Eskender1
  • Asad, Ali
  • Di Bartolo, Nadine M
  • Kong, Linggen
  • Smith, Christopher
  • Sargeson, Alan M
  • Price, Roger
  • Smith, Suzanne V
  • 1 Centre for Antimatter-Matter Studies (CAMS), Australian Nuclear Science and Technology Organisation (ANSTO), Menai, NSW 2234, Australia. suzanne @bnl.gov. , (Australia)
Type
Published Article
Journal
Dalton Transactions
Publisher
The Royal Society of Chemistry
Publication Date
Oct 28, 2013
Volume
42
Issue
40
Pages
14402–14410
Identifiers
DOI: 10.1039/c3dt51199e
PMID: 23851350
Source
Medline
License
Unknown

Abstract

A novel hexa aza cage, N(1)-(4-isothiocyanatobenzyl)-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane-1,8-diamine (SarAr-NCS) was synthesized in good yield and characterized by (1)H NMR and electrospray mass spectrometry. A new method for the synthesis of the related N(1)-(4-carboxybenzyl)-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane-1,8-diamine (AmBaSar) using the p-carboxybenzaldehyde is reported. The complexation of Cu(2+), Co(2+) and Zn(2+) by the two ligands over a range of pHs was found to be similar to the parent derivative SarAr. SarAr-NCS was conjugated to both silica particles (≈90 nm diam.) and the model B72.3 murine antibody. The SarAr-NCSN-silica particles were radiolabeled with Cu(2+) doped (64)Cu and the number of ligands conjugated was calculated to be an average of 7020 ligands per particle. Conjugation of SarAr-NCS to the B72.3 antibody was optimized over a range of conditions. The SarAr-NCSN-B72.3 conjugate was stored in buffer and as a lyophilized powder at 4 °C over 38 days. Its radiolabeling efficiency, stability and immunoreactivity were maintained. The development of a high yielding synthesis of SarAr-NCS should provide an entry point for a wide range of Cu and Zn radiometal PET imaging agents and potentially radiotherapeutic agents with (67)Cu.

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