Macrocyclic copper(II) complexes containing diazacyclam-based ligand : spectral, structural and docking studies
Abstract
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.
Citation
Mardani , Z , Moeini , K , Darroudi , M , Carpenter-Warren , C , Slawin , A M Z & Woollins , J D 2019 , ' Macrocyclic copper(II) complexes containing diazacyclam-based ligand : spectral, structural and docking studies ' , Journal of Coordination Chemistry , vol. 72 , no. 18 , pp. 3030-3045 . https://doi.org/10.1080/00958972.2019.1684477
Publication
Journal of Coordination Chemistry
Status
Peer reviewed
ISSN
0095-8972Type
Journal article
Rights
Copyright © 2019 Informa UK Limited, trading as Taylor & Francis Group. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1080/00958972.2019.1684477
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