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Title: Copper (II) complexes of substituted salicylaldehyde dibenzyl semicarbazones: Synthesis, cytotoxicity and interaction with quadruplex DNA
Authors: Siti Munira bte Haidad Ali
Yan, Yaw Kai
Lee, Peter Peng Foo
Khong, Kenny Zhi Xiang
Mahasin Alam Sk
Lim, Kok Hwa
Klejevskaja, Beata
Vilar, Ramon
Keywords: Copper(II)
Quadruplex DNA
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
ISSN: 1477-9226 (print)
1477-9234 (online)
Other Identifiers: 10.1039/C3DT52297K
Appears in Collections:Journal Articles

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