Synthesis, characterisation, and biological activity of the ruthenium complexes of the N4-tetradentate (N4-TL), 1,6-Di(29-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2)

Aleksandra Bjelosevic; Jennette Sakoff; Jayne Gilbert; Yingjie Zhang; Christopher Gordon; Janice R. Aldrich-Wright

doi:10.1071/CH19528

Synthesis, characterisation, and biological activity of the ruthenium complexes of the N₄-tetradentate (N4-TL), 1,6-Di(29-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2)

Aleksandra Bjelosevic
, Jennette Sakoff
, Jayne Gilbert
, Yingjie Zhang
, Christopher Gordon
, Janice R. Aldrich-Wright

School of Science

Calvary Mater Newcastle Hospital
Australian Nuclear Science and Technology Organisation

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

2 Citations (Scopus)

Abstract

A series of complexes of the type rac-[Ru(N4-TL)(PL)]2+ (where N4-TL"‰="‰1,6-di(2"²-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2, N4-TL-2) and PL"‰="‰1,10-phenanthroline (phen, Ru-2), dipyrido[3,2-d:2"²,3"²-f]quinoxaline (dpq, Ru-3), 7,8-dimethyl-dipyrido[3,2-a:2"²,3"²-c]phenazine (dppzMe2, Ru-4), 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBz, Ru-5), 2-(p-tolyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzMe, Ru-6), and 2-(4-nitrophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzNO2, Ru-7), were synthesised. All structures were confirmed using NMR, electrospray ionisation mass spectrometry (ESI-MS), high-performance liquid chromatography (HPLC), and UV analysis and for four complexes X-ray crystallography. The in"‰vitro cytotoxicity assays revealed that Ru-6 was 5, 10, and 40-fold more potent than oxaliplatin, cisplatin, and carboplatin, respectively.

Original language	English
Pages (from-to)	956-968
Number of pages	13
Journal	Australian Journal of Chemistry
Volume	73
Issue number	10
DOIs	https://doi.org/10.1071/CH19528
Publication status	Published - Oct 2020

Bibliographical note

Publisher Copyright:
© CSIRO 2020.

Keywords

ligands (biochemistry)
metal complexes
ruthenium compounds
synthesis

Access to Document

10.1071/CH19528

Cite this

@article{059b963fa9494ae7a638861e4c2f3982,

title = "Synthesis, characterisation, and biological activity of the ruthenium complexes of the N4-tetradentate (N4-TL), 1,6-Di(29-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2)",

abstract = "A series of complexes of the type rac-[Ru(N4-TL)(PL)]2+ (where N4-TL{"}‰={"}‰1,6-di(2{"}²-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2, N4-TL-2) and PL{"}‰={"}‰1,10-phenanthroline (phen, Ru-2), dipyrido[3,2-d:2{"}²,3{"}²-f]quinoxaline (dpq, Ru-3), 7,8-dimethyl-dipyrido[3,2-a:2{"}²,3{"}²-c]phenazine (dppzMe2, Ru-4), 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBz, Ru-5), 2-(p-tolyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzMe, Ru-6), and 2-(4-nitrophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzNO2, Ru-7), were synthesised. All structures were confirmed using NMR, electrospray ionisation mass spectrometry (ESI-MS), high-performance liquid chromatography (HPLC), and UV analysis and for four complexes X-ray crystallography. The in{"}‰vitro cytotoxicity assays revealed that Ru-6 was 5, 10, and 40-fold more potent than oxaliplatin, cisplatin, and carboplatin, respectively.",

keywords = "ligands (biochemistry), metal complexes, ruthenium compounds, synthesis",

author = "Aleksandra Bjelosevic and Jennette Sakoff and Jayne Gilbert and Yingjie Zhang and Christopher Gordon and Aldrich-Wright, \{Janice R.\}",

note = "Publisher Copyright: {\textcopyright} CSIRO 2020.",

year = "2020",

month = oct,

doi = "10.1071/CH19528",

language = "English",

volume = "73",

pages = "956--968",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO",

number = "10",

}

Synthesis, characterisation, and biological activity of the ruthenium complexes of the N₄-tetradentate (N4-TL), 1,6-Di(29-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2). / Bjelosevic, Aleksandra; Sakoff, Jennette; Gilbert, Jayne et al.
In: Australian Journal of Chemistry, Vol. 73, No. 10, 10.2020, p. 956-968.

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

TY - JOUR

T1 - Synthesis, characterisation, and biological activity of the ruthenium complexes of the N4-tetradentate (N4-TL), 1,6-Di(29-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2)

AU - Bjelosevic, Aleksandra

AU - Sakoff, Jennette

AU - Gilbert, Jayne

AU - Zhang, Yingjie

AU - Gordon, Christopher

AU - Aldrich-Wright, Janice R.

PY - 2020/10

Y1 - 2020/10

N2 - A series of complexes of the type rac-[Ru(N4-TL)(PL)]2+ (where N4-TL"‰="‰1,6-di(2"²-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2, N4-TL-2) and PL"‰="‰1,10-phenanthroline (phen, Ru-2), dipyrido[3,2-d:2"²,3"²-f]quinoxaline (dpq, Ru-3), 7,8-dimethyl-dipyrido[3,2-a:2"²,3"²-c]phenazine (dppzMe2, Ru-4), 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBz, Ru-5), 2-(p-tolyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzMe, Ru-6), and 2-(4-nitrophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzNO2, Ru-7), were synthesised. All structures were confirmed using NMR, electrospray ionisation mass spectrometry (ESI-MS), high-performance liquid chromatography (HPLC), and UV analysis and for four complexes X-ray crystallography. The in"‰vitro cytotoxicity assays revealed that Ru-6 was 5, 10, and 40-fold more potent than oxaliplatin, cisplatin, and carboplatin, respectively.

AB - A series of complexes of the type rac-[Ru(N4-TL)(PL)]2+ (where N4-TL"‰="‰1,6-di(2"²-pyridyl)-2,5-dimethyl-2,5-diazahexane (picenMe2, N4-TL-2) and PL"‰="‰1,10-phenanthroline (phen, Ru-2), dipyrido[3,2-d:2"²,3"²-f]quinoxaline (dpq, Ru-3), 7,8-dimethyl-dipyrido[3,2-a:2"²,3"²-c]phenazine (dppzMe2, Ru-4), 2-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBz, Ru-5), 2-(p-tolyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzMe, Ru-6), and 2-(4-nitrophenyl)-1H-imidazo[4,5-f][1,10]phenanthroline (phenpyrBzNO2, Ru-7), were synthesised. All structures were confirmed using NMR, electrospray ionisation mass spectrometry (ESI-MS), high-performance liquid chromatography (HPLC), and UV analysis and for four complexes X-ray crystallography. The in"‰vitro cytotoxicity assays revealed that Ru-6 was 5, 10, and 40-fold more potent than oxaliplatin, cisplatin, and carboplatin, respectively.

KW - ligands (biochemistry)

KW - metal complexes

KW - ruthenium compounds

KW - synthesis

UR - http://hdl.handle.net/1959.7/uws:56309

U2 - 10.1071/CH19528

DO - 10.1071/CH19528

M3 - Article

SN - 0004-9425

VL - 73

SP - 956

EP - 968

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 10

ER -