TY - JOUR
T1 - The Influence of Amino Group Position on Aryl Moiety of SarAr on Metal Complexation and Protein Labelling
AU - Jamier, Vincent
AU - Mume, Eskender
AU - Papamicaël, Cyril
AU - Smith, Suzanne V.
N1 - Publisher Copyright:
© CSIRO 2016.
PY - 2016
Y1 - 2016
N2 - 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 5min 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 30min 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.
AB - 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 5min 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 30min 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.
UR - http://www.scopus.com/inward/record.url?scp=84986182416&partnerID=8YFLogxK
U2 - 10.1071/CH15794
DO - 10.1071/CH15794
M3 - Article
SN - 0004-9425
VL - 69
SP - 1054
EP - 1061
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
IS - 9
ER -