Synthesis, crystal structures, DNA binding and cytotoxicity of two novel platinum(II) complexes containing 2-(hydroxymethyl)pyridine and pyridine-2-carboxylate ligands

Ceyda Icsel; Veysel T. Yilmaz; Aysegul Golcu; Engin Ulukaya; Orhan Buyukgungor

doi:10.1016/j.bmcl.2013.01.119

Synthesis, crystal structures, DNA binding and cytotoxicity of two novel platinum(II) complexes containing 2-(hydroxymethyl)pyridine and pyridine-2-carboxylate ligands

Ceyda Icsel, Veysel T. Yilmaz^*, Aysegul Golcu, Engin Ulukaya, Orhan Buyukgungor

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

Two new platinum(II) complexes, trans-[Pt(2-mpy)₂] ·4H₂O (1) and [PtCl(2-pyc)(2-hmpy)]·H₂O (2), where 2-hmpy = 2-(hydroxymethyl)pyridine, 2-mpy = deprotonated 2-hmpy and 2-pyc = pyridine-2-carboxylate, have been synthesized and characterized by elemental analysis, IR, NMR, and X-ray crystallography. The DNA binding affinities of these complexes for Fish Sperm DNA (FS-DNA) were investigated using fluorescence, viscosity, thermal denaturation and gel electrophoresis measurements. Fluorescence analysis indicates that complex 1 binds to DNA by a single intercalative mechanism, while complex 2 exhibits two types of interactions such as intercalation and covalent binding. Gel electrophoresis assay demonstrates ability of the complexes to cleavage the supercoiled pBR322 plasmid DNA. The in vitro cytotoxicities of both complexes were preliminarily evaluated and the cytotoxicity of complex 1 against the human lung cancer cells (H1299) is similar to oxaliplatin, but higher than transplatin and carboplatin.

Original language	English
Pages (from-to)	2117-2122
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	7
DOIs	https://doi.org/10.1016/j.bmcl.2013.01.119
Publication status	Published - 1 Apr 2013
Externally published	Yes

Funding

We thank Uludag University for the financial support given to the project.

Funders	Funder number
Uludag University

Keywords

2-(Hydroxymethyl)pyridine
Cytotoxic activity
DNA binding
Pt(II) complexes
Pyridine-2-carboxylate

UN SDGs

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

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10.1016/j.bmcl.2013.01.119

Cite this

@article{8deb2e1d552c41838dccca39229145cd,

title = "Synthesis, crystal structures, DNA binding and cytotoxicity of two novel platinum(II) complexes containing 2-(hydroxymethyl)pyridine and pyridine-2-carboxylate ligands",

abstract = "Two new platinum(II) complexes, trans-[Pt(2-mpy)2] ·4H2O (1) and [PtCl(2-pyc)(2-hmpy)]·H2O (2), where 2-hmpy = 2-(hydroxymethyl)pyridine, 2-mpy = deprotonated 2-hmpy and 2-pyc = pyridine-2-carboxylate, have been synthesized and characterized by elemental analysis, IR, NMR, and X-ray crystallography. The DNA binding affinities of these complexes for Fish Sperm DNA (FS-DNA) were investigated using fluorescence, viscosity, thermal denaturation and gel electrophoresis measurements. Fluorescence analysis indicates that complex 1 binds to DNA by a single intercalative mechanism, while complex 2 exhibits two types of interactions such as intercalation and covalent binding. Gel electrophoresis assay demonstrates ability of the complexes to cleavage the supercoiled pBR322 plasmid DNA. The in vitro cytotoxicities of both complexes were preliminarily evaluated and the cytotoxicity of complex 1 against the human lung cancer cells (H1299) is similar to oxaliplatin, but higher than transplatin and carboplatin.",

keywords = "2-(Hydroxymethyl)pyridine, Cytotoxic activity, DNA binding, Pt(II) complexes, Pyridine-2-carboxylate",

author = "Ceyda Icsel and Yilmaz, \{Veysel T.\} and Aysegul Golcu and Engin Ulukaya and Orhan Buyukgungor",

year = "2013",

month = apr,

day = "1",

doi = "10.1016/j.bmcl.2013.01.119",

language = "English",

volume = "23",

pages = "2117--2122",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

number = "7",

}

Synthesis, crystal structures, DNA binding and cytotoxicity of two novel platinum(II) complexes containing 2-(hydroxymethyl)pyridine and pyridine-2-carboxylate ligands. / Icsel, Ceyda; Yilmaz, Veysel T.; Golcu, Aysegul et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 23, No. 7, 01.04.2013, p. 2117-2122.

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

TY - JOUR

T1 - Synthesis, crystal structures, DNA binding and cytotoxicity of two novel platinum(II) complexes containing 2-(hydroxymethyl)pyridine and pyridine-2-carboxylate ligands

AU - Icsel, Ceyda

AU - Yilmaz, Veysel T.

AU - Golcu, Aysegul

AU - Ulukaya, Engin

AU - Buyukgungor, Orhan

PY - 2013/4/1

Y1 - 2013/4/1

N2 - Two new platinum(II) complexes, trans-[Pt(2-mpy)2] ·4H2O (1) and [PtCl(2-pyc)(2-hmpy)]·H2O (2), where 2-hmpy = 2-(hydroxymethyl)pyridine, 2-mpy = deprotonated 2-hmpy and 2-pyc = pyridine-2-carboxylate, have been synthesized and characterized by elemental analysis, IR, NMR, and X-ray crystallography. The DNA binding affinities of these complexes for Fish Sperm DNA (FS-DNA) were investigated using fluorescence, viscosity, thermal denaturation and gel electrophoresis measurements. Fluorescence analysis indicates that complex 1 binds to DNA by a single intercalative mechanism, while complex 2 exhibits two types of interactions such as intercalation and covalent binding. Gel electrophoresis assay demonstrates ability of the complexes to cleavage the supercoiled pBR322 plasmid DNA. The in vitro cytotoxicities of both complexes were preliminarily evaluated and the cytotoxicity of complex 1 against the human lung cancer cells (H1299) is similar to oxaliplatin, but higher than transplatin and carboplatin.

AB - Two new platinum(II) complexes, trans-[Pt(2-mpy)2] ·4H2O (1) and [PtCl(2-pyc)(2-hmpy)]·H2O (2), where 2-hmpy = 2-(hydroxymethyl)pyridine, 2-mpy = deprotonated 2-hmpy and 2-pyc = pyridine-2-carboxylate, have been synthesized and characterized by elemental analysis, IR, NMR, and X-ray crystallography. The DNA binding affinities of these complexes for Fish Sperm DNA (FS-DNA) were investigated using fluorescence, viscosity, thermal denaturation and gel electrophoresis measurements. Fluorescence analysis indicates that complex 1 binds to DNA by a single intercalative mechanism, while complex 2 exhibits two types of interactions such as intercalation and covalent binding. Gel electrophoresis assay demonstrates ability of the complexes to cleavage the supercoiled pBR322 plasmid DNA. The in vitro cytotoxicities of both complexes were preliminarily evaluated and the cytotoxicity of complex 1 against the human lung cancer cells (H1299) is similar to oxaliplatin, but higher than transplatin and carboplatin.

KW - 2-(Hydroxymethyl)pyridine

KW - Cytotoxic activity

KW - DNA binding

KW - Pt(II) complexes

KW - Pyridine-2-carboxylate

UR - https://www.scopus.com/pages/publications/84875220138

U2 - 10.1016/j.bmcl.2013.01.119

DO - 10.1016/j.bmcl.2013.01.119

M3 - Article

C2 - 23434229

AN - SCOPUS:84875220138

SN - 0960-894X

VL - 23

SP - 2117

EP - 2122

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 7

ER -

Synthesis, crystal structures, DNA binding and cytotoxicity of two novel platinum(II) complexes containing 2-(hydroxymethyl)pyridine and pyridine-2-carboxylate ligands

Abstract

Funding

Keywords

UN SDGs

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