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.

 




Previous                    Content                    Next