Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives: Synthesis, characterization and biological activity of the gold complexes

Haris Bjelosevic; Ilia A. Guzei; Lara C. Spencer; Tina Persson; Frederik H. Kriel; Raymond Hewer; Margo J. Nell; Jiri Gut; Constance E.J. Van Rensburg; Philip J. Rosenthal; Judy Coates; James Darkwa; Sofi K.C. Elmroth

doi:10.1016/j.jorganchem.2012.08.034

Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives: Synthesis, characterization and biological activity of the gold complexes

Haris Bjelosevic
, Ilia A. Guzei
, Lara C. Spencer
, Tina Persson
, Frederik H. Kriel
, Raymond Hewer
, Margo J. Nell
, Jiri Gut
, Constance E.J. Van Rensburg
, Philip J. Rosenthal
, Judy Coates
, James Darkwa
, Sofi K.C. Elmroth

Chemical Sciences

Lund University
University of Wisconsin-Madison
MINTEK
University of Pretoria
University of California at San Francisco

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

32 Citations (Scopus)

Abstract

The synthesis of series of 1,2,1′ substituted bis(diphenylphosphino)- ruthenocenyl (1-4) and ferrocenyl cis-platinum(II) (5-7) and gold(I) (8-12) complexes are described. Crystal structures of 2 and 4, as well as 5, 6 and 10 confirm the molecular geometry of these ligands and their metal complexes. Preliminary investigation of four gold complexes as potential anticancer, antiHIV and antimalaria showed at least one gold compound that has excellent activity towards one of these diseases. The three gold(I) complexes, {1- [1-(dimethylamino)ethyl]-1,2-bis(diphenylphosphino)ruthenocene- κ ²P,P′}bis[chlorogold(I)] (8) (IC ₅₀ = 1.40 μM), {1-[1-(acetoxyethyl)-1′,2-bis(diphenylphosphino)ferrocene- κ ²P,P′]bis[chlorogold(I)] (9) (IC ₅₀ = 0.51 μM), {1-[1-(3-carboxypropanamido)ethyl]-1′,2-bis(diphenylphosphino)- ruthenoceneκ ²P,P′}bis[chlorogold(I)] (12) (IC ₅₀ = 1.784 μM), have the best activities against cancer, HIV and malaria respectively.

Original language	English
Pages (from-to)	52-59
Number of pages	8
Journal	Journal of Organometallic Chemistry
Volume	720
DOIs	https://doi.org/10.1016/j.jorganchem.2012.08.034
Publication status	Published - 1 Dec 2012

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

AntiHIV
Anticancer
Antimalarial agents
Bis(diphenylphosphino)ferrocenyl-
Bis(diphenylphosphino)ruthenocenyl-
Platinum and gold complexes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
Materials Chemistry

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10.1016/j.jorganchem.2012.08.034

Cite this

Bjelosevic, H., Guzei, I. A., Spencer, L. C., Persson, T., Kriel, F. H., Hewer, R., Nell, M. J., Gut, J., Van Rensburg, C. E. J., Rosenthal, P. J., Coates, J., Darkwa, J., & Elmroth, S. K. C. (2012). Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives: Synthesis, characterization and biological activity of the gold complexes. Journal of Organometallic Chemistry, 720, 52-59. https://doi.org/10.1016/j.jorganchem.2012.08.034

@article{124b45da98d34c148732266c0665f2b4,

title = "Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives: Synthesis, characterization and biological activity of the gold complexes",

abstract = "The synthesis of series of 1,2,1′ substituted bis(diphenylphosphino)- ruthenocenyl (1-4) and ferrocenyl cis-platinum(II) (5-7) and gold(I) (8-12) complexes are described. Crystal structures of 2 and 4, as well as 5, 6 and 10 confirm the molecular geometry of these ligands and their metal complexes. Preliminary investigation of four gold complexes as potential anticancer, antiHIV and antimalaria showed at least one gold compound that has excellent activity towards one of these diseases. The three gold(I) complexes, \{1- [1-(dimethylamino)ethyl]-1,2-bis(diphenylphosphino)ruthenocene- κ 2P,P′\}bis[chlorogold(I)] (8) (IC 50 = 1.40 μM), \{1-[1-(acetoxyethyl)-1′,2-bis(diphenylphosphino)ferrocene- κ 2P,P′]bis[chlorogold(I)] (9) (IC 50 = 0.51 μM), \{1-[1-(3-carboxypropanamido)ethyl]-1′,2-bis(diphenylphosphino)- ruthenoceneκ 2P,P′\}bis[chlorogold(I)] (12) (IC 50 = 1.784 μM), have the best activities against cancer, HIV and malaria respectively.",

keywords = "AntiHIV, Anticancer, Antimalarial agents, Bis(diphenylphosphino)ferrocenyl-, Bis(diphenylphosphino)ruthenocenyl-, Platinum and gold complexes",

author = "Haris Bjelosevic and Guzei, \{Ilia A.\} and Spencer, \{Lara C.\} and Tina Persson and Kriel, \{Frederik H.\} and Raymond Hewer and Nell, \{Margo J.\} and Jiri Gut and \{Van Rensburg\}, \{Constance E.J.\} and Rosenthal, \{Philip J.\} and Judy Coates and James Darkwa and Elmroth, \{Sofi K.C.\}",

year = "2012",

month = dec,

day = "1",

doi = "10.1016/j.jorganchem.2012.08.034",

language = "English",

volume = "720",

pages = "52--59",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier B.V.",

}

Bjelosevic, H, Guzei, IA, Spencer, LC, Persson, T, Kriel, FH, Hewer, R, Nell, MJ, Gut, J, Van Rensburg, CEJ, Rosenthal, PJ, Coates, J, Darkwa, J & Elmroth, SKC 2012, 'Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives: Synthesis, characterization and biological activity of the gold complexes', Journal of Organometallic Chemistry, vol. 720, pp. 52-59. https://doi.org/10.1016/j.jorganchem.2012.08.034

Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives: Synthesis, characterization and biological activity of the gold complexes. / Bjelosevic, Haris; Guzei, Ilia A.; Spencer, Lara C. et al.
In: Journal of Organometallic Chemistry, Vol. 720, 01.12.2012, p. 52-59.

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

TY - JOUR

T1 - Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives

T2 - Synthesis, characterization and biological activity of the gold complexes

AU - Bjelosevic, Haris

AU - Guzei, Ilia A.

AU - Spencer, Lara C.

AU - Persson, Tina

AU - Kriel, Frederik H.

AU - Hewer, Raymond

AU - Nell, Margo J.

AU - Gut, Jiri

AU - Van Rensburg, Constance E.J.

AU - Rosenthal, Philip J.

AU - Coates, Judy

AU - Darkwa, James

AU - Elmroth, Sofi K.C.

PY - 2012/12/1

Y1 - 2012/12/1

N2 - The synthesis of series of 1,2,1′ substituted bis(diphenylphosphino)- ruthenocenyl (1-4) and ferrocenyl cis-platinum(II) (5-7) and gold(I) (8-12) complexes are described. Crystal structures of 2 and 4, as well as 5, 6 and 10 confirm the molecular geometry of these ligands and their metal complexes. Preliminary investigation of four gold complexes as potential anticancer, antiHIV and antimalaria showed at least one gold compound that has excellent activity towards one of these diseases. The three gold(I) complexes, {1- [1-(dimethylamino)ethyl]-1,2-bis(diphenylphosphino)ruthenocene- κ 2P,P′}bis[chlorogold(I)] (8) (IC 50 = 1.40 μM), {1-[1-(acetoxyethyl)-1′,2-bis(diphenylphosphino)ferrocene- κ 2P,P′]bis[chlorogold(I)] (9) (IC 50 = 0.51 μM), {1-[1-(3-carboxypropanamido)ethyl]-1′,2-bis(diphenylphosphino)- ruthenoceneκ 2P,P′}bis[chlorogold(I)] (12) (IC 50 = 1.784 μM), have the best activities against cancer, HIV and malaria respectively.

AB - The synthesis of series of 1,2,1′ substituted bis(diphenylphosphino)- ruthenocenyl (1-4) and ferrocenyl cis-platinum(II) (5-7) and gold(I) (8-12) complexes are described. Crystal structures of 2 and 4, as well as 5, 6 and 10 confirm the molecular geometry of these ligands and their metal complexes. Preliminary investigation of four gold complexes as potential anticancer, antiHIV and antimalaria showed at least one gold compound that has excellent activity towards one of these diseases. The three gold(I) complexes, {1- [1-(dimethylamino)ethyl]-1,2-bis(diphenylphosphino)ruthenocene- κ 2P,P′}bis[chlorogold(I)] (8) (IC 50 = 1.40 μM), {1-[1-(acetoxyethyl)-1′,2-bis(diphenylphosphino)ferrocene- κ 2P,P′]bis[chlorogold(I)] (9) (IC 50 = 0.51 μM), {1-[1-(3-carboxypropanamido)ethyl]-1′,2-bis(diphenylphosphino)- ruthenoceneκ 2P,P′}bis[chlorogold(I)] (12) (IC 50 = 1.784 μM), have the best activities against cancer, HIV and malaria respectively.

KW - AntiHIV

KW - Anticancer

KW - Antimalarial agents

KW - Bis(diphenylphosphino)ferrocenyl-

KW - Bis(diphenylphosphino)ruthenocenyl-

KW - Platinum and gold complexes

UR - https://www.scopus.com/pages/publications/84867540119

U2 - 10.1016/j.jorganchem.2012.08.034

DO - 10.1016/j.jorganchem.2012.08.034

M3 - Article

AN - SCOPUS:84867540119

SN - 0022-328X

VL - 720

SP - 52

EP - 59

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

ER -

Platinum(II) and gold(I) complexes based on 1,1′- bis(diphenylphosphino)metallocene derivatives: Synthesis, characterization and biological activity of the gold complexes

Abstract

UN SDGs

Keywords

ASJC Scopus subject areas

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