TY - JOUR
T1 - Macrocyclic copper(II) complexes containing diazacyclam-based ligand
T2 - spectral, structural and docking studies
AU - Mardani, Zahra
AU - Moeini, Keyvan
AU - Darroudi, Majid
AU - Carpenter-Warren, Cameron
AU - Slawin, Alexandra M. Z.
AU - Woollins, J. Derek
PY - 2019/11/6
Y1 - 2019/11/6
N2 - The macrocyclic copper complex, [Cu(ACE)(NO3)2] (ACE = 1,3,6,10,12,15-hexaazatricyclo[13.3.1.16,10]eicosane), was synthesized by template condensation from a mixture of N1-(2-aminoethyl)-1,3-diaminopropane,
formaldehyde and copper(II) nitrate. Replacement of the nitrate with
thiocyanato and azido ligands gives [Cu(ACE)NSC]NSC (2) and the 1D-coordination polymer, [Cu(ACE)(μ-N3)]n[N3]n (3), respectively. Complex 1, [Cu(ACE)(NO3)]NO3, is an intermediate product in which one of the nitrate ions is separated from its parent molecule. The formation of 1 allowed us to conclude that the mechanism of ion exchange in the parent molecule is similar to SN1. These complexes have been characterized by FT-IR spectroscopy and X-ray crystallography. In the crystal structures of 1 and 2, the copper(II) ion has a distorted square pyramidal geometry in which the N4-donor ACE ligand lies on the equatorial plane and other ligand occupies the axial position. The copper(II) ion in 3
has an octahedral geometry, coordinating to one ACE ligand in the
equatorial plane and two N-donor bridging azido groups in the axial
positions. In all structures, owing to the Jahn-Teller effect, the
coordinated bond length of the axial position is longer than the
equatorial ones. The ability of the ACE ligand and its complexes 1 and 2,
along with their analogues, to interact with 10 selected
biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR,
TS, Top II and B-DNA) was investigated by docking calculations and
compared with that of doxorubicin.
AB - The macrocyclic copper complex, [Cu(ACE)(NO3)2] (ACE = 1,3,6,10,12,15-hexaazatricyclo[13.3.1.16,10]eicosane), was synthesized by template condensation from a mixture of N1-(2-aminoethyl)-1,3-diaminopropane,
formaldehyde and copper(II) nitrate. Replacement of the nitrate with
thiocyanato and azido ligands gives [Cu(ACE)NSC]NSC (2) and the 1D-coordination polymer, [Cu(ACE)(μ-N3)]n[N3]n (3), respectively. Complex 1, [Cu(ACE)(NO3)]NO3, is an intermediate product in which one of the nitrate ions is separated from its parent molecule. The formation of 1 allowed us to conclude that the mechanism of ion exchange in the parent molecule is similar to SN1. These complexes have been characterized by FT-IR spectroscopy and X-ray crystallography. In the crystal structures of 1 and 2, the copper(II) ion has a distorted square pyramidal geometry in which the N4-donor ACE ligand lies on the equatorial plane and other ligand occupies the axial position. The copper(II) ion in 3
has an octahedral geometry, coordinating to one ACE ligand in the
equatorial plane and two N-donor bridging azido groups in the axial
positions. In all structures, owing to the Jahn-Teller effect, the
coordinated bond length of the axial position is longer than the
equatorial ones. The ability of the ACE ligand and its complexes 1 and 2,
along with their analogues, to interact with 10 selected
biomacromolecules (BRAF kinase, CatB, DNA gyrase, HDAC7, rHA, RNR, TrxR,
TS, Top II and B-DNA) was investigated by docking calculations and
compared with that of doxorubicin.
KW - Macrocycle
KW - Diazacyclam
KW - Copper complex
KW - Template synthesis
KW - Docking study
U2 - 10.1080/00958972.2019.1684477
DO - 10.1080/00958972.2019.1684477
M3 - Article
SN - 0095-8972
VL - 72
SP - 3030
EP - 3045
JO - Journal of Coordination Chemistry
JF - Journal of Coordination Chemistry
IS - 18
ER -