Biological and cytoselective anticancer properties of copper(II)- polypyridyl complexes modulated by auxiliary methylated glycine ligand

Hoi Ling Seng; Wai San Wang; Siew Ming Kong; Han Kiat Alan Ong; Yip Foo Win; Raja Noor Zaliha Raja Raja Noor Zaliha; Makoto Chikira; Weng Kee Leong; Munirah Ahmad; Alan Soo Beng Khoo; Chew Hee Ng

doi:10.1007/s10534-012-9572-4

Biological and cytoselective anticancer properties of copper(II)- polypyridyl complexes modulated by auxiliary methylated glycine ligand

Hoi Ling Seng, Wai San Wang, Siew Ming Kong, Han Kiat Alan Ong, Yip Foo Win, Raja Noor Zaliha Raja Raja Noor Zaliha, Makoto Chikira, Weng Kee Leong, Munirah Ahmad, Alan Soo Beng Khoo, Chew Hee Ng^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

Abstract

A series of ternary copper(II)-1,10-phenanthroline complexes with glycine and methylated glycine derivatives, [Cu(phen)(aa)(H₂O)]NO ₃xH₂O 1-4 (amino acid (aa): glycine (gly), 1; DL-alanine (DL-ala), 2; 2,2-dimethylglycine (C-dmg), 3; sarcosine (sar), 4), were synthesized and characterized by FTIR, elemental analysis, electrospray ionization-mass spectra (ESI-MS), UV-visible spectroscopy and molar conductivity measurement. The determined X-ray crystallographic structures of 2 and 3 show selectively to DNA by intercalation and electrostatic forces, and inhibit topoisomerase I. The effect of the methyl substituents of the coordinated amino acid in the above complexes on these biological properties are presented and discussed. The IC₅₀ values (24 h) of 1-4 for nasopharyngeal cancer cell line HK1 are in the range 2.2-5.2 μM while the corresponding values for normal cell line NP69 are greater than 13.0 lM. All complexes, at 5 μM, induced 41-60 % apoptotic cell death in HK1 cells but no significant cell death in NP69 cells.

Original language	English
Pages (from-to)	1061-1081
Number of pages	21
Journal	BioMetals
Volume	25
Issue number	5
DOIs	https://doi.org/10.1007/s10534-012-9572-4
Publication status	Published - Oct 2012
Externally published	Yes

ASJC Scopus Subject Areas

Biomaterials
General Biochemistry,Genetics and Molecular Biology
General Agricultural and Biological Sciences
Metals and Alloys

Keywords

Anticancer selectivity
Crystal structure
DNA binding
G-quadruplex
Ternary copper(II) complexes
Topoisomerase I

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1007/s10534-012-9572-4

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Seng, H. L., Wang, W. S., Kong, S. M., Alan Ong, H. K., Win, Y. F., Raja Noor Zaliha, R. N. Z. R., Chikira, M., Leong, W. K., Ahmad, M., Khoo, A. S. B., & Ng, C. H. (2012). Biological and cytoselective anticancer properties of copper(II)- polypyridyl complexes modulated by auxiliary methylated glycine ligand. BioMetals, 25(5), 1061-1081. https://doi.org/10.1007/s10534-012-9572-4

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title = "Biological and cytoselective anticancer properties of copper(II)- polypyridyl complexes modulated by auxiliary methylated glycine ligand",

abstract = "A series of ternary copper(II)-1,10-phenanthroline complexes with glycine and methylated glycine derivatives, [Cu(phen)(aa)(H2O)]NO 3xH2O 1-4 (amino acid (aa): glycine (gly), 1; DL-alanine (DL-ala), 2; 2,2-dimethylglycine (C-dmg), 3; sarcosine (sar), 4), were synthesized and characterized by FTIR, elemental analysis, electrospray ionization-mass spectra (ESI-MS), UV-visible spectroscopy and molar conductivity measurement. The determined X-ray crystallographic structures of 2 and 3 show selectively to DNA by intercalation and electrostatic forces, and inhibit topoisomerase I. The effect of the methyl substituents of the coordinated amino acid in the above complexes on these biological properties are presented and discussed. The IC50 values (24 h) of 1-4 for nasopharyngeal cancer cell line HK1 are in the range 2.2-5.2 μM while the corresponding values for normal cell line NP69 are greater than 13.0 lM. All complexes, at 5 μM, induced 41-60 % apoptotic cell death in HK1 cells but no significant cell death in NP69 cells.",

keywords = "Anticancer selectivity, Crystal structure, DNA binding, G-quadruplex, Ternary copper(II) complexes, Topoisomerase I",

author = "Seng, {Hoi Ling} and Wang, {Wai San} and Kong, {Siew Ming} and {Alan Ong}, {Han Kiat} and Win, {Yip Foo} and {Raja Noor Zaliha}, {Raja Noor Zaliha Raja} and Makoto Chikira and Leong, {Weng Kee} and Munirah Ahmad and Khoo, {Alan Soo Beng} and Ng, {Chew Hee}",

year = "2012",

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doi = "10.1007/s10534-012-9572-4",

language = "English",

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T1 - Biological and cytoselective anticancer properties of copper(II)- polypyridyl complexes modulated by auxiliary methylated glycine ligand

AU - Seng, Hoi Ling

AU - Wang, Wai San

AU - Kong, Siew Ming

AU - Alan Ong, Han Kiat

AU - Win, Yip Foo

AU - Raja Noor Zaliha, Raja Noor Zaliha Raja

AU - Chikira, Makoto

AU - Leong, Weng Kee

AU - Ahmad, Munirah

AU - Khoo, Alan Soo Beng

AU - Ng, Chew Hee

PY - 2012/10

Y1 - 2012/10

N2 - A series of ternary copper(II)-1,10-phenanthroline complexes with glycine and methylated glycine derivatives, [Cu(phen)(aa)(H2O)]NO 3xH2O 1-4 (amino acid (aa): glycine (gly), 1; DL-alanine (DL-ala), 2; 2,2-dimethylglycine (C-dmg), 3; sarcosine (sar), 4), were synthesized and characterized by FTIR, elemental analysis, electrospray ionization-mass spectra (ESI-MS), UV-visible spectroscopy and molar conductivity measurement. The determined X-ray crystallographic structures of 2 and 3 show selectively to DNA by intercalation and electrostatic forces, and inhibit topoisomerase I. The effect of the methyl substituents of the coordinated amino acid in the above complexes on these biological properties are presented and discussed. The IC50 values (24 h) of 1-4 for nasopharyngeal cancer cell line HK1 are in the range 2.2-5.2 μM while the corresponding values for normal cell line NP69 are greater than 13.0 lM. All complexes, at 5 μM, induced 41-60 % apoptotic cell death in HK1 cells but no significant cell death in NP69 cells.

AB - A series of ternary copper(II)-1,10-phenanthroline complexes with glycine and methylated glycine derivatives, [Cu(phen)(aa)(H2O)]NO 3xH2O 1-4 (amino acid (aa): glycine (gly), 1; DL-alanine (DL-ala), 2; 2,2-dimethylglycine (C-dmg), 3; sarcosine (sar), 4), were synthesized and characterized by FTIR, elemental analysis, electrospray ionization-mass spectra (ESI-MS), UV-visible spectroscopy and molar conductivity measurement. The determined X-ray crystallographic structures of 2 and 3 show selectively to DNA by intercalation and electrostatic forces, and inhibit topoisomerase I. The effect of the methyl substituents of the coordinated amino acid in the above complexes on these biological properties are presented and discussed. The IC50 values (24 h) of 1-4 for nasopharyngeal cancer cell line HK1 are in the range 2.2-5.2 μM while the corresponding values for normal cell line NP69 are greater than 13.0 lM. All complexes, at 5 μM, induced 41-60 % apoptotic cell death in HK1 cells but no significant cell death in NP69 cells.

KW - Anticancer selectivity

KW - Crystal structure

KW - DNA binding

KW - G-quadruplex

KW - Ternary copper(II) complexes

KW - Topoisomerase I

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Biological and cytoselective anticancer properties of copper(II)- polypyridyl complexes modulated by auxiliary methylated glycine ligand

Abstract

ASJC Scopus Subject Areas

Keywords

UN SDGs

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