Malaysian
Journal of Analytical Sciences Vol 21 No 3 (2017): 544 - 551
DOI:
https://doi.org/10.17576/mjas-2017-2103-04
INTERACTION
OF N,N’-BIS[4-[1-(2-HYDROXYETHOXY)] SALICYLIDENE]-PHENYLDIAMINE-NICKEL(II) AND
COPPER(II) COMPLEXES WITH G-QUADRUPLEX DNA
(Interaksi
Antara Kompleks N, N'-Bis [4- [1- (2-Hidroksietoksi)] Saliksalidin]
-Fenildiamina-Nikel(II) dan Kuprum(II) Bersama DNA G-Kuadrupleks)
Roshatiara
Shamsuddin, Muhammad Ameerullah Sahudin, Nur Hasyareeda Hassan, Nurul Huda Abd
Karim*
School
of Chemical Sciences and Food Technology, Faculty of Science and Technology,
Universiti
Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia
*Corresponding author: nurulhuda@ukm.edu.my
Received: 29
December 2016; Accepted: 28 March 2017
Abstract
Binding studies of metal complexes with
DNA has attracted many interests due to their importance in cancer therapy and
molecular biology. In this study, N,N’-bis[4-[1-(2-hydroxyethoxy)]salicylidene]-phenyldiamine
and its metal Ni(II) and Cu(II) complexes have been synthesized and
characterized. The complexes were structurally characterized using standard
spectroscopic 1D 1H, 2D COSY, HMQC and 13C NMR
spectroscopy, FTIR spectroscopy and ESI-MS spectrometry. The binding
interaction between synthesized metal complexes and G-quadruplex DNA has been investigated
using UV/Vis DNA titration study. Ni(II) and Cu(II) complexes bind strongly to
G-quadruplex DNA (Kb = (5.42 ± 2.48) x 106 M-1 and (1.42 ± 2.48) x 106
M-1 respectively) via end stacking mode. Both complexes show
selectivity for G-quadruplex DNA over CT- DNA by 2.15- and 1.82-fold,
respectively.
Keywords: metal complexes, DNA binding, G-quadruplex DNA
Abstrak
Kajian mengenai pengikatan kompleks logam bersama DNA
telah menarik perhatian penyelidik disebabkan kepentingannya dalam perubatan
terapi kanser dan molekular biologi. Dalam kajian ini, N, N'-bis [4-[1-(2-hidroksietoksi)]
saliksalidin]-fenildiamina bersama logam Ni(II) dan Cu(II) kompleks telah
berjaya disintesis dan dicirikan. Struktur kompleks telah dicirikan menggunakan
spektroskopi piawai 1D 1H, 2D COSY, HMQC dan spektroskopi 13C
NMR, spektroskopi FTIR dan spektrometri ESI-MS. Pengikatan antara kompleks
logam yang disintesis bersama DNA G-kuadrupleks telah dikaji dengan menggunakan
kajian titratan DNA UV/Vis. Ni(II) dan Cu(II) kompleks memberikan nilai
ikatan yang tinggi kepada DNA G-kuadrupleks ((5.42
± 2.48) x 106
M-1 dan (1.42 ±
2.48) x 106 M-1) melalui mod penyusunan akhir. Ni(II) dan
Cu(II) kompleks menunjukkan pemilihan pengikatan terhadap G-kuadrupleks DNA
berbanding CT- DNA dengan 2.15 dan 1.82 kali ganda setiap satu.
Kata kunci: kompleks logam, pengikatan DNA, DNA G-kuadrupleks
References
1. Thomas,
P. G., Huw, E. L. W., Katarzyna, I. G., Stephen, R., Neil, J. O., Malcolm, F.
G. S., John, E. M. and Mark S. S. (2009). Selectivity of small molecule ligands
for parallel and anti-parallel DNA G-quadruplex structures. Organic and Biomolecular Chemistry, 7:
4194 – 4200.
2. Xu-Jian,
L., Qi-Pin, Q., Yu-Lan, L., Yan-Cheng, L. and Hong L. (2014). Synthesis, antitumor
activity and G-Quadruplex DNA/ct-DNA binding property of cationic platinum(II)
complex of 2-(4-nitro)-imidazo-[5,6-f][1,10]-phenanthroline. Indian
Journal of Chemistry, 53: 787 – 792.
3. Hasani,
L., Hakimian, F. and Safaei, E. (2014). Spectroscopic investigation on the
interaction of copper porphyrazines and phthalocyanine with human
telomeric G-Quadruplex DNA. Biophysical Chemistry, 187: 7 – 13.
4. Nurul,
H. A. K., Oscar, M., Arun, S., Alenxander, J. T., Sushobhan, G., Marina, K. K.
and Vilar, R. (2014). Salphen metal complexes as tunable G-quadruplex binders
and optical probes. RSC Advances, 4:
3355 – 3363.
5. Nancy,
H. C., Nurul, H. A. K., Gary, N. P., Mekala, G., Vanessa, P., Alan, K. T.,
Ramon, V. and Stephen, N. (2012). Molecular basis of structure−activity
relationships between salphen metal complexes and human telomeric DNA quadruplexes.
Journal of Medical Chemistry, 55: 209
− 222.
6. Sofia,
G., Inês, R., Filipa, M., Isabel, C. S., Elisabetta, G., Beata, K., Jorge,
G-C., Mauro, R., Ramon, V. and António P. (2016). Anthracene-terpyridine metal
complexes as new G-quadruplex DNA binders. Journal
of Inorganic Biochemistry, 160: 275 – 286.
7. Ang, D.
L., Harper, B. W., Cubo, L., Mendoza, O., Vilar, R., & Aldrich-Wright, J. (2016).
Quadruplex DNA-stabilising dinuclear platinum (ii) terpyridine complexes with
flexible linkers. Chemistry–A European
Journal, 22(7), 2317 – 2325.
8. Taetz,
S., Murdter, T. E., Zappc, J., Boettcher, S., Baldes, C., Kleideiter, E.,
Piotrowska, K., Schaefer, U. F., Klotz, U., Lehr and C.-M. (2008). Decomposition
of the telomere-targeting agent BRACO19 in physiological media results in products
with decreased inhibitory potential. International Journal of Pharmaceutics,
357: 6 – 14.
9.
Julie,
E. R., Stephen, N. and Ramon, V. (2007). Stabilisation of human telomeric
quadruplex DNA and inhibition of telomerase by a platinum phenanthroline
complex. Chemical Communications, 42:
4366 – 4368.
10.
Siti,
N. H, Yaakob, R. and Haslina, A. (2016). Synthesis, characterization and DNA
binding activity of a potential DNA intercalator. Malaysian Journal of Analytical Sciences, 20(4): 760 – 769.
11.
Fun,
H. K., Kia, R., Mirkhani, V. and Zargoshi, H. (2008). {5, 5-Dihydroxy-2,
2-[o-phenylenebis (nitrilomethylidyne)] diphenolato} nickel (II) dihydrate. Acta Crystallographica Section E: Structure
Reports Online, 64(9): 1181 – 1182.
12.
Verity
S. S., Kogularamanan S., Arun S., Andrew J. P. W., David J. M. and Ramon V.
(2015). Syntheses of polypyridyl metal complexes and studies of their interaction
with quadruplex DNA. Dalton Transactions
(RSC Publishing), 44: 3686 – 3700
13.
Nurul
Huda Abd Karim (2012). Studies towards elucidating the binding modes between
metal-salphen complexes and G-quadruplex DNA. Thesis Doctor of Philosophy,
Imperial College London.
14.
Roshatiara, S. and Nurul Huda, A. K. (2016). Synthesis and characterization of
N,N’-bis[4-[1-(2-hydroxyethoxy)]salicylidene]-phenyldiamine-nickel(II)]
complex. AIP Publishing, 1784:
030007
15.
Subbaraj,
P., Ramu, A., Raman, N. and Dharmaraja, J. (2015). Synthesis, characterization,
DNA interaction and pharmacological studies of substituted benzophenone derived
Schiff base metal(II) complexes. Journal
of Saudi Chemical Society, 19: 207 – 216.
16.
Krishnamoorthy,
P., Sathyadevi, P., Alan, H. C., Rachel, R. B. and Dharmaraj, N. (2011).
Evaluation of DNA binding, DNA cleavage, protein binding and in vitro cytotoxic
activities of bivalent transition metal hydrazone complexes. European Journal of Medicinal Chemistry,
46: 3376 – 3387.
17.
Selamat,
N., Heng, L. Y., Hassan, N. I. and Karim, N. H. A. (2016). Synthesis and
Characterization of 6, 6’-bis (2-hydroxyphenyl)-2, 2’-bipyridyl ligand and its
platinum complex for the interaction with CT-DNA. Malaysian Journal of Analytical Sciences, 20(1): 111 – 120.
18.
Bordbar,
M., Khodaie, F., Tabatabaee, M., Yeganeh-Faal, A., Mehri lighvan, Z. and
Mohammad-Ganji, S. (2016). Interaction studies of DNA binding with new Cu(II)
complex by spectrophotometric, spectrofluorometric, voltammetric and circular
dichroism techniques. Bulgarian Chemical
Communication, 48(3): 422 – 429.