Please use this identifier to cite or link to this item: http://hdl.handle.net/10497/16607
Title: 
Copper (II) complexes of substituted salicylaldehyde dibenzyl semicarbazones: Synthesis, cytotoxicity and interaction with quadruplex DNA
Authors: 
Keywords: 
Copper(II)
Semicarbazones
Quadruplex DNA
Cytotoxicity
Molecular docking
Issue Date: 
2009
Citation: 
Siti Munira Haidad Ali, Yan, Y. K., Lee, P. P. F., Khong, K. Z. X., Sk, M. A., Lim, K. H., ... & Vilar, R. (2014). Copper (II) complexes of substituted salicylaldehyde dibenzyl semicarbazones: synthesis, cytotoxicity and interaction with quadruplex DNA. Dalton Transactions, 43(3), 1449-1459.
Abstract: 
A series of substituted salicylaldehyde dibenzyl semicarbazones [RC6H3(OH)CH=NNHCON(
CH2Ph)2] and their copper(II) complexes were synthesized and characterized. The
chloridocopper(II) complexes of the 4-OH and 5-OH substituted ligands (complexes 9 and 7)
show modest affinity and good selectivity (over duplex DNA) for the quadruplex formed
from the 22AG human telomeric (HTelo) DNA sequence. Substitution of the chlorido
ligands of these two complexes with pyridine yielded derivatives (7-py and 9-py) with
increased affinity for HTelo. These derivatives also show good selectivity for HTelo over
calf-thymus DNA (170- and 211-fold, respectively). The X-ray crystal structures of 9 and 9-
py were determined. Molecular docking studies based on these structures show that the
complexes stack on the 5′-end of the HTelo quadruplex, with the hydroxyl group forming a
hydrogen bond with a guanine residue. Complexes 7, 9, 7-py and 9-py display significant
cytotoxicity against MOLT-4 human leukaemia cells. Interestingly, they have low to
negligible cytotoxicity against the non-cancerous IMR-90 human fibroblasts.
Description: 
This is the final draft, after peer-review, of a manuscript published in Dalton Transactions. The published version is available online at http://dx.doi.org/10.1039/C3DT52297K
URI: 
ISSN: 
1477-9226 (print)
1477-9234 (online)
Other Identifiers: 
10.1039/C3DT52297K
Appears in Collections:Journal Articles

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