New palladium(II) and platinum(II) 5,5-diethylbarbiturate complexes with 2-phenylpyridine, 2,2’-bipyridine and 2,2’-dipyridylamine: synthesis, structures, DNA binding, molecular docking, cellular uptake, antioxidant activity and cytotoxicity

Ceyda Icsel, Veysel T. Yilmaz, Yunus Kaya, Hale Samli, William T. A. Harrison, Orhan Buyukgungor

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Abstract

Novel palladium(II) and platinum(II) complexes of 5,5-diethylbarbiturate (barb) with 2-phenylpyridine (Hppy), 2,2′-bipyridine (bpy) and 2,2′-dipyridylamine (dpya) have been prepared and characterized by elemental analysis, IR, UV-Vis, NMR and ESI-MS. Single-crystal diffraction measurements show that complex 1 consists of binuclear [Pd2(μ-barb-κN,O)2(ppy-κN,C)2] moieties, while complexes 3–5 are mononuclear, [M(barb-κN)2(L-κN,N′)] (L = bpy or dpya). 6 has a composition of [Pt(dpya-κN,N′)2][Ag(barb-κN)2]2·4H2O and 2 was assumed to have a structure of [Pt(barb-κN)(Hppy-κN)(ppy-κN,C)]·3H2O. The complexes were found to exhibit significant DNA binding affinity by a non-covalent binding mode, in accordance with molecular docking studies. In addition, complexes 1 and 2 displayed strong binding with supercoiled pUC19 plasmid DNA. Cellular uptake studies were performed to assess the subcellular localization of the selected complexes. A moderate radical scavenging activity of 1 and 2 was confirmed by DPPH and ABTS tests. Complexes 1, 2, and 5 showed selectivity against HT-29 (colon) cell line.
Original languageEnglish
Pages (from-to)6880-6895
Number of pages16
JournalDalton Transactions
Volume44
Issue number15
Early online date2 Mar 2015
DOIs
Publication statusPublished - 21 Apr 2015

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Palladium
Cytotoxicity
Platinum
Antioxidants
DNA
Scavenging
Chemical analysis
Plasmids
Diffraction
Cells
Nuclear magnetic resonance
Single crystals
2-phenylpyridine
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid

Cite this

@article{50049dd9233c43a8a3cf0194a3f87d2a,
title = "New palladium(II) and platinum(II) 5,5-diethylbarbiturate complexes with 2-phenylpyridine, 2,2’-bipyridine and 2,2’-dipyridylamine: synthesis, structures, DNA binding, molecular docking, cellular uptake, antioxidant activity and cytotoxicity",
abstract = "Novel palladium(II) and platinum(II) complexes of 5,5-diethylbarbiturate (barb) with 2-phenylpyridine (Hppy), 2,2′-bipyridine (bpy) and 2,2′-dipyridylamine (dpya) have been prepared and characterized by elemental analysis, IR, UV-Vis, NMR and ESI-MS. Single-crystal diffraction measurements show that complex 1 consists of binuclear [Pd2(μ-barb-κN,O)2(ppy-κN,C)2] moieties, while complexes 3–5 are mononuclear, [M(barb-κN)2(L-κN,N′)] (L = bpy or dpya). 6 has a composition of [Pt(dpya-κN,N′)2][Ag(barb-κN)2]2·4H2O and 2 was assumed to have a structure of [Pt(barb-κN)(Hppy-κN)(ppy-κN,C)]·3H2O. The complexes were found to exhibit significant DNA binding affinity by a non-covalent binding mode, in accordance with molecular docking studies. In addition, complexes 1 and 2 displayed strong binding with supercoiled pUC19 plasmid DNA. Cellular uptake studies were performed to assess the subcellular localization of the selected complexes. A moderate radical scavenging activity of 1 and 2 was confirmed by DPPH and ABTS tests. Complexes 1, 2, and 5 showed selectivity against HT-29 (colon) cell line.",
author = "Ceyda Icsel and Yilmaz, {Veysel T.} and Yunus Kaya and Hale Samli and Harrison, {William T. A.} and Orhan Buyukgungor",
year = "2015",
month = "4",
day = "21",
doi = "10.1039/c5dt00728c",
language = "English",
volume = "44",
pages = "6880--6895",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",
number = "15",

}

TY - JOUR

T1 - New palladium(II) and platinum(II) 5,5-diethylbarbiturate complexes with 2-phenylpyridine, 2,2’-bipyridine and 2,2’-dipyridylamine

T2 - synthesis, structures, DNA binding, molecular docking, cellular uptake, antioxidant activity and cytotoxicity

AU - Icsel, Ceyda

AU - Yilmaz, Veysel T.

AU - Kaya, Yunus

AU - Samli, Hale

AU - Harrison, William T. A.

AU - Buyukgungor, Orhan

PY - 2015/4/21

Y1 - 2015/4/21

N2 - Novel palladium(II) and platinum(II) complexes of 5,5-diethylbarbiturate (barb) with 2-phenylpyridine (Hppy), 2,2′-bipyridine (bpy) and 2,2′-dipyridylamine (dpya) have been prepared and characterized by elemental analysis, IR, UV-Vis, NMR and ESI-MS. Single-crystal diffraction measurements show that complex 1 consists of binuclear [Pd2(μ-barb-κN,O)2(ppy-κN,C)2] moieties, while complexes 3–5 are mononuclear, [M(barb-κN)2(L-κN,N′)] (L = bpy or dpya). 6 has a composition of [Pt(dpya-κN,N′)2][Ag(barb-κN)2]2·4H2O and 2 was assumed to have a structure of [Pt(barb-κN)(Hppy-κN)(ppy-κN,C)]·3H2O. The complexes were found to exhibit significant DNA binding affinity by a non-covalent binding mode, in accordance with molecular docking studies. In addition, complexes 1 and 2 displayed strong binding with supercoiled pUC19 plasmid DNA. Cellular uptake studies were performed to assess the subcellular localization of the selected complexes. A moderate radical scavenging activity of 1 and 2 was confirmed by DPPH and ABTS tests. Complexes 1, 2, and 5 showed selectivity against HT-29 (colon) cell line.

AB - Novel palladium(II) and platinum(II) complexes of 5,5-diethylbarbiturate (barb) with 2-phenylpyridine (Hppy), 2,2′-bipyridine (bpy) and 2,2′-dipyridylamine (dpya) have been prepared and characterized by elemental analysis, IR, UV-Vis, NMR and ESI-MS. Single-crystal diffraction measurements show that complex 1 consists of binuclear [Pd2(μ-barb-κN,O)2(ppy-κN,C)2] moieties, while complexes 3–5 are mononuclear, [M(barb-κN)2(L-κN,N′)] (L = bpy or dpya). 6 has a composition of [Pt(dpya-κN,N′)2][Ag(barb-κN)2]2·4H2O and 2 was assumed to have a structure of [Pt(barb-κN)(Hppy-κN)(ppy-κN,C)]·3H2O. The complexes were found to exhibit significant DNA binding affinity by a non-covalent binding mode, in accordance with molecular docking studies. In addition, complexes 1 and 2 displayed strong binding with supercoiled pUC19 plasmid DNA. Cellular uptake studies were performed to assess the subcellular localization of the selected complexes. A moderate radical scavenging activity of 1 and 2 was confirmed by DPPH and ABTS tests. Complexes 1, 2, and 5 showed selectivity against HT-29 (colon) cell line.

U2 - 10.1039/c5dt00728c

DO - 10.1039/c5dt00728c

M3 - Article

VL - 44

SP - 6880

EP - 6895

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 15

ER -