Bis(pyrazolyl) palladium(II), platinum(II) and gold(III) complexes: Syntheses, molecular structures and substitution reactions with l-cysteine

Keter, Frankline K.; Ojwach, Stephen O.; Oyetunji, Olayinka A.; Guzei, Ilia A.; Darkwa, James

doi:10.1016/j.ica.2008.11.030

Cited by 19 publications

(12 citation statements)

References 30 publications

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“…Thus, our choice of bis(pyrazolyl)acetic compounds as ligands to make gold(III) complexes was based on this believe. Unfortunately 11-16 were between 14 and 71 times less active (1.1-5.1 mM) than cisplatin (0.07 mM) when tested against Chinese hamster ovary (CHO) cells (Keter et al 2009b). One similarity drawn from our work (Keter et al 2009b) and that reported by Sakai et al (2000) is that the carboxylic group of the bis(pyrazolyl)acetic ligand reduce the activities of these complexes.…”

Section: Cancersupporting

confidence: 56%

“…Unfortunately 11-16 were between 14 and 71 times less active (1.1-5.1 mM) than cisplatin (0.07 mM) when tested against Chinese hamster ovary (CHO) cells (Keter et al 2009b). One similarity drawn from our work (Keter et al 2009b) and that reported by Sakai et al (2000) is that the carboxylic group of the bis(pyrazolyl)acetic ligand reduce the activities of these complexes. It has been suggested that the bulkiness of the carboxylic moiety and its contribution to the overall reduction of the electron density of the pyrazole may be responsible for the low activity (Ciesielska et al 2006).…”

Section: Cancersupporting

confidence: 56%

“…A series of studies involving quantification of non-bound and bound metal pointed to the inability of 9 and 10 to cross the cell membrane, hence poor activities observed by Onoa et al (1999). Another set of compounds are the bis(pyrazolyl)-palladium(II) (11 and 12), platinum(II) (13 and 14) and gold(III) complexes (15 and 16) reported by us (Keter et al 2009b). The appeal of gold complexes comes from recent indication of their potential as anticancer agents.…”

Section: Cancermentioning

confidence: 96%

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Perspective: the potential of pyrazole-based compounds in medicine

2011

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Pyrazoles are widely used as core motifs for a large number of compounds for various applications such as catalysis, agro-chemicals, building blocks of other compounds and in medicine. The attractiveness of pyrazole and its derivatives is their versatility that allows for synthesis of a series of analogues with different moieties in them, thus affecting the electronics and by extension the properties of the resultant compounds. In medicine pyrazole is found as a pharmacophore in some of the active biological molecules. While pyrazole derivatives have been extensively studied for many applications including anticancer, antimicrobial, anti-inflammatory, antiglycemic, anti-allergy and antiviral, much less has been reported on their metal counterparts in spite of the fact that metals have been shown to impart activity to ligands. Thus this perspective is intended to demonstrate the potential of pyrazole and pyrazolyl metal complexes in the areas of drug discovery and development. Several examples, that include palladium, platinum, copper, gold, zinc, cobalt, nickel, iron, copper, silver and gallium complexes, are used to bolster the above point. For the purposes of this review three areas are discussed, that is pyrazole metal complexes as: (i) anticancer, (ii) antibacterial/parasitic and (iii) antiviral agents.

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Section: Cancersupporting

confidence: 56%

Section: Cancersupporting

confidence: 56%

Section: Cancermentioning

confidence: 96%

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Perspective: the potential of pyrazole-based compounds in medicine

2011

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“…In addition, it is well-known that azoles are valuable reagents in coordination chemistry and that their binding to a transition metal ion affects their properties and activities. Few complexes with pyrazole ligands showing an antitumor activity similar to that of cisplatin have been reported [11][12][13][14][15][16][17][18][19][20], but the effect produced by the substituents on the heterocycle has not been clarified so far. Within this therapeutic context, and in order to clarify this point and to elucidate the influence of mode of binding of this family of ligands in the biological activity of the complexes, we decided to synthesize the new pyrazole derivatives 1a-1c ( Fig.…”

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confidence: 99%

Platinum(II) and palladium(II) complexes with (N,N′) and (C,N,N′)− ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities

Quirante

Ruíz

González

et al. 2011

Journal of Inorganic Biochemistry

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The study of the reactivity of three 1-(2-dimethylaminoethyl)-1H-pyrazole derivatives of general formula [1-(CH 2 ) 2 NMe 2 }-3,5-R 2 -pzol] {where pzol represents pyrazole and R_H (1a), Me (1b) (5c)}. Compounds 4c and 5c arise from the orthometallation of the 3-phenyl ring of ligand 1c. Complex 2a has been further characterized by X-ray crystallography. Ligands and complexes were evaluated for their in vitro antimalarial against Plasmodium falciparum and cytotoxic activities against lung (A549) and breast (MDA MB231 and MCF7) cancer cellular lines. Complexes 2a-2c and 5c exhibited only moderate antimalarial activities against two P. falciparum strains (3D7 and W2). Interestingly, cytotoxicity assays revealed that the platinacycle 4c exhibits a higher toxicity than cisplatin in the three human cell lines and that the complex 2a presents a remarkable cytotoxicity and selectivity in lung (IC 50 = 3 μM) versus breast cancer cell lines (IC 50 N 20 μM). Thus, complexes 2c and 4c appear to be promising leads, creating a novel family of anticancer agents. Electrophoretic DNA migration studies in presence of the synthesized compounds have been performed, in order to get further insights into their mechanism of action.

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“…As a result gold(III) compounds have been thought to have therapeutic effects similar to cisplatin. Research on gold(III) compounds as potential anticancer agents has been reported (Saqqioro et al 2007;Keter et al 2008;Angela et al 2008). There are a few examples of gold(III) compounds that have been reported to show activity against HIV.…”

Section: Gold(iii) Compoundsmentioning

confidence: 99%

HIV therapeutic possibilities of gold compounds

2010

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Highly active antiretroviral therapy (HAART) has resulted in decreased mortality and morbidity from the acquired immune deficiency syndrome caused by the human immunodeficiency virus (HIV). Drug resistance and toxicity of HAART has led to the search for novel inhibitors of HIV infection. Gold-based compounds have shown promising activity against a wide range of clinical conditions and microorganism infections including HIV-1. A typical example is auranofin which resulted in an elevated CD4? T-cell count in an HIV patient being treated for psoriatic arthritis. In addition, reports exist on gold-based inhibitors of reverse transcriptase (RT), protease (PR) and viral entry of host cells. These and other characteristics of goldbased HIV drugs are reviewed here.

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Bis(pyrazolyl) palladium(II), platinum(II) and gold(III) complexes: Syntheses, molecular structures and substitution reactions with l-cysteine

Cited by 19 publications

References 30 publications

Perspective: the potential of pyrazole-based compounds in medicine

Perspective: the potential of pyrazole-based compounds in medicine

Platinum(II) and palladium(II) complexes with (N,N′) and (C,N,N′)− ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities

HIV therapeutic possibilities of gold compounds

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