Malaysian Journal of Analytical Sciences Vol 20 No 1 (2016): 111 - 120

 

 

 

SYNTHESIS AND CHARACTERIZATION OF 6,6’-BIS(2-HYDROXYPHENYL)-2,2’-BIPYRIDYL LIGAND AND ITS PLATINUM COMPLEX FOR THE INTERACTION WITH CT-DNA

 

(Sintesis dan Pencirian Ligan 6,6’-Bis(2-Hidroksifenil)-2,2’-Bipiridil dan Kompleks Platinum untuk Kajian Interaksi dengan CT-DNA)

 

Norhidayah Selamat, Lee Yook Heng, Nurul Izzaty Hassan, Nurul Huda Abd Karim*

 

School of Chemical Sciences and Food Technology,

Faculty of Sciences and Technology,

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia

 

*Corresponding author: nurulhuda@ukm.edu.my

 

 

Abstract

A tetradentate ligand with four donor atoms OONN and its platinum metal complex were synthesized. Bis(phenoxy)bipyridine ligand was prepared by Suzuki coupling reaction between 6,6’-dibromo-2,2’-bipyridyl and 2-hydroxyphenylboronic acid with the presence of palladium (II) acetate. The formation of platinum complex was done by introducing the ligand with platinum (II) chloride in benzonitrile. Both ligand and complex structures were confirmed by ¹H, 2D cosy and ¹³C NMR spectroscopy, ESI-MS spectrometry and FTIR spectroscopy. Binding studies of small molecules with DNA are useful to understand the reaction mechanism and to provide guidance for the application and design of new and more efficient drugs or sensors targeted on DNA. In this study, the binding interaction between the synthesized ligand and complex with calf thymus DNA (CT-DNA) has been investigated using UV-Visible and emission DNA titration. From the UV-Visible DNA study, it showed that platinum (II) bipyridine complex had higher affinity towards CT-DNA with binding constant K_b=(3.1 ± 0.02 x 10⁵) ± 0.02 M^-1 compared to that of bis(phenoxy) bipyridine ligand with binding constant (K_b ) = (1.19 ± 0.08) × 10³ M^-1. These findings will be valuable for the potential use of platinum (II) bipyridine complex as a phosphorescent probe in optical sensor DNA.

 

Keyword: bis(phenoxy)bipyridine, intercalating ligand, calf thymus-DNA, DNA interaction

 

Abstrak

Ligan tetradentat dengan empat atom penderma OONN dan kompleks platinumnya telah disintesis. Ligan bis(fenoksi)bipiridin disediakan melalui tindak balas pengkupelan Suzuki antara 6,6’-dibromo-2,2’-bipiridil dan asid 2-hidroksifenilboronik dengan kehadiran palladium(II) asetat. Pembentukan kompleks platinum dilakukan dengan menambahkan platinum(II) klorida terhadap ligan di dalam benzonitril. Kedua-dua struktur ligan dan kompleks dibuktikan dengan spekroskopi ¹H, 2D dan ¹³C RMN, spektrometri ESI-MS dan spektroskopi FTIR. Kajian pengikatan terhadap molekul kecil dengan DNA sangat berguna untuk memahami mekanisme tindak balas dan untuk panduan bagi aplikasi dan reka bentuk dadah yang baharu dan berkesan atau sensor target kepada DNA. Dalam kajian ini, interaksi ikatan antara ligan dan kompleks terhadap DNA timus anak lembu (CT-DNA) dilakukan dengan kajian titratan ultra lembayung boleh Nampak dan titratan pendaflour. Kaedah tersebut membuktikan bahawa kompleks platinum (II) bipiridin mempunyai ikatan yang lebih kuat terhadap CT-DNA berbanding dengan ligan iaitu sebanyak K_b=(3.1 ± 0.02 x 10⁵) ± 0.02 M^-1 berbanding K_b=(1.19 ± 0.08) x 10³ M^-1. Penemuan ini sangat bernilai dan berpotensi dalam menjadikan kompleks platinum (II) bipiridin sebagai prob fosforesen dalam sensor DNA optik.

 

Kata kunci: bis(fenoksi)bipiridin, ligan berinterkalasi, DNA timus, interaksi DNA

 

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