The Influence of Amino Group Position on Aryl Moiety of SarAr on Metal Complexation and Protein Labelling
Vincent Jamier A B , Eskender Mume A C , Cyril Papamicaël B and Suzanne. V. Smith A C D
+ Author Affiliations
- Author Affiliations
A Center of Excellence in Antimatter Matter Studies (CAMS), Australian Nuclear Science and Technology Organisation (ANSTO), Locked Bag 2001, Kirrawee DC NSW 2232, Australia.
B UMR CNRS COBRA 6014, 1 Rue Tesnière 76130 Mont-Saint-Aignan, France.
C CAMS, Australian National University, Canberra, ACT 0200, Australia.
D Corresponding author. Email: Suzanneoznq@gmail.com
Australian Journal of Chemistry 69(9) 1054-1061 https://doi.org/10.1071/CH15794
Submitted: 6 October 2015 Accepted: 17 March 2016 Published: 10 May 2016
Abstract
New hexaazamacrobicyclic cage bi-functional chelators (BFCs), 1-N-(3-aminobenzyl)-3,6,10,13,16,19-hexaazabicyclo[6.6.6]eicosane-1,8-diamine (m-SarAr) and 1-N-(2-aminobenzyl)-3,6,10,13,16,19-hexaazabicyclo[6.6.6]eicosane-1,8-diamine (o-SarAr), were synthesised. Their complexation with selected transitions metal ions i.e. CuII, CoII, and CdII was investigated over a range of pH at micromolar concentrations. CuII was complexed by m-SarAr and o-SarAr rapidly within 5 min in pH range of 5–9 at ambient temperature. In contrast, the complexation of CoII and CdII by these ligands was slower. The conjugation efficiencies of p-SarAr, m-SarAr, and o-SarAr to bovine serum albumin (BSA) were compared under various reactions. Conditions were optimised to a molar ratio of BSA/N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC)/BFC of 1 : 250 : 50 in pH 5 buffer for 30 min at ambient temperature. Under these conditions, the average number of p-SarAr, m-SarAr, or o-SarAr attached to BSA were determined to be 2.21 ± 0.16, 4.90 × 10–1 ± 2.48 × 10–2, and 2.67 × 10–2 ± 2.67 × 10–3, respectively. This fundamental study clearly demonstrates that the position of the amine on the phenyl ring has a significant effect on the metal complexation and conjugation reactions with BSA.
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