Synthesis and characterization of 6,6′-bis(2-hydroxyphenyl)-2,2′-bipyridine ligand and its interaction with ct-DNA

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

The tetradentate ligand with four donor atoms OONN was synthesized. Bis(phenoxy)bipyridine ligand was prepared by Suzuki coupling reaction between 6,6′-dibromo-2,2′-bipyridyl and 2-hydroxyphenylboronic acid with presence of palladium (II) acetate. Bis(phenoxy)bipyridine ligand was also synthesized by demethylating of 6,6′-bis(2-methoxyphenyl)-2,2′-bipyridyl ligand through solvent free reaction using pyridine hydrocloride. The formation of both phenoxy and methoxy ligands was confirmed by 1H, 2D cosy and 13C NMR spectroscopy, ESI-MS spectrometry, FTIR spectroscopy. The purity of the ligand was confirmed by melting point. 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 targeted to DNA. In this study, the binding interaction between the synthesized ligand with calf thymus-DNA (ct-DNA) has been investigated by UV/Vis DNA titration study. From the UV/Vis DNA study, it shows that bis(phenoxy)bipyridine ligand bind with ct-DNA via outside binding with binding contant Kb = 1.19 × 103 ± 0.08 M-1.

Original languageEnglish
Title of host publication2015 UKM FST Postgraduate Colloquium: Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2015 Postgraduate Colloquium
PublisherAmerican Institute of Physics Inc.
Volume1678
ISBN (Electronic)9780735413252
DOIs
Publication statusPublished - 25 Sep 2015
Event2015 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2015 - Selangor, Malaysia
Duration: 15 Apr 201516 Apr 2015

Other

Other2015 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2015
CountryMalaysia
CitySelangor
Period15/4/1516/4/15

Fingerprint

calves
deoxyribonucleic acid
ligands
synthesis
interactions
spectroscopy
titration
melting points
palladium
acetates
pyridines
purity
drugs
nuclear magnetic resonance
acids

Keywords

  • Bis(phenoxy)bipyridine
  • ct-DNA
  • intercalating ligand

ASJC Scopus subject areas

  • Physics and Astronomy(all)

Cite this

Selamat, N., Lee, Y. H., Hassan, N. I., & Abd Karim, N. H. (2015). Synthesis and characterization of 6,6′-bis(2-hydroxyphenyl)-2,2′-bipyridine ligand and its interaction with ct-DNA. In 2015 UKM FST Postgraduate Colloquium: Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2015 Postgraduate Colloquium (Vol. 1678). [050017] American Institute of Physics Inc.. https://doi.org/10.1063/1.4931296

Synthesis and characterization of 6,6′-bis(2-hydroxyphenyl)-2,2′-bipyridine ligand and its interaction with ct-DNA. / Selamat, Norhidayah; Lee, Yook Heng; Hassan, Nurul Izzaty; Abd Karim, Nurul Huda.

2015 UKM FST Postgraduate Colloquium: Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2015 Postgraduate Colloquium. Vol. 1678 American Institute of Physics Inc., 2015. 050017.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Selamat, N, Lee, YH, Hassan, NI & Abd Karim, NH 2015, Synthesis and characterization of 6,6′-bis(2-hydroxyphenyl)-2,2′-bipyridine ligand and its interaction with ct-DNA. in 2015 UKM FST Postgraduate Colloquium: Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2015 Postgraduate Colloquium. vol. 1678, 050017, American Institute of Physics Inc., 2015 Postgraduate Colloquium of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology, UKM FST 2015, Selangor, Malaysia, 15/4/15. https://doi.org/10.1063/1.4931296
Selamat N, Lee YH, Hassan NI, Abd Karim NH. Synthesis and characterization of 6,6′-bis(2-hydroxyphenyl)-2,2′-bipyridine ligand and its interaction with ct-DNA. In 2015 UKM FST Postgraduate Colloquium: Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2015 Postgraduate Colloquium. Vol. 1678. American Institute of Physics Inc. 2015. 050017 https://doi.org/10.1063/1.4931296
Selamat, Norhidayah ; Lee, Yook Heng ; Hassan, Nurul Izzaty ; Abd Karim, Nurul Huda. / Synthesis and characterization of 6,6′-bis(2-hydroxyphenyl)-2,2′-bipyridine ligand and its interaction with ct-DNA. 2015 UKM FST Postgraduate Colloquium: Proceedings of the Universiti Kebangsaan Malaysia, Faculty of Science and Technology 2015 Postgraduate Colloquium. Vol. 1678 American Institute of Physics Inc., 2015.
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AB - The tetradentate ligand with four donor atoms OONN was synthesized. Bis(phenoxy)bipyridine ligand was prepared by Suzuki coupling reaction between 6,6′-dibromo-2,2′-bipyridyl and 2-hydroxyphenylboronic acid with presence of palladium (II) acetate. Bis(phenoxy)bipyridine ligand was also synthesized by demethylating of 6,6′-bis(2-methoxyphenyl)-2,2′-bipyridyl ligand through solvent free reaction using pyridine hydrocloride. The formation of both phenoxy and methoxy ligands was confirmed by 1H, 2D cosy and 13C NMR spectroscopy, ESI-MS spectrometry, FTIR spectroscopy. The purity of the ligand was confirmed by melting point. 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 targeted to DNA. In this study, the binding interaction between the synthesized ligand with calf thymus-DNA (ct-DNA) has been investigated by UV/Vis DNA titration study. From the UV/Vis DNA study, it shows that bis(phenoxy)bipyridine ligand bind with ct-DNA via outside binding with binding contant Kb = 1.19 × 103 ± 0.08 M-1.

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