Anticancer Activities of bis(pyrazol-1-ylthiocarbonyl)disulfides against HeLa cells

Keter, Frankline K.; Nell, Margo; Guzei, Ilia A.; Omondi, Bernard; Darkwa, James

doi:10.3184/030823409x450453

Cited by 15 publications

(8 citation statements)

References 22 publications

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“…All commercially available chemicals were used as received. Pyrazol-1-yldithiocarbamate ( L1 ), 3,5-dimethylpyrazol-1-yldithiocarbamate ( L2 ), and indazol-1-yldithiocarbamate ( L3 ) were synthesized according to literature methods. , Gold starting materials [Au 2 Cl 2 (dppe)], [Au 2 Cl 2 (dppp)], and [Au 2 Cl 2 (dpph)] {dppe = 1,2-bis(diphenyl-phosphino)ethane; dppp = 1,3-bis(diphenylphosphino)propane; and dpph = 1,6-bis(diphenyl-phosphino)hexane} were synthesized according to the literature procedures . Infrared (IR) spectra were recorded as KBr pellets on a Bruker Tensor27 spectrophotometer.…”

Section: Methodsmentioning

confidence: 99%

Phosphinogold(I) Dithiocarbamate Complexes: Effect of the Nature of Phosphine Ligand on Anticancer Properties

et al. 2014

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The reactions of potassium salts of the dithiocarbamates L {where L = pyrazolyldithiocarbamate (L1), 3,5-dimethylpyrazolyldithiocarbamate (L2), or indazolyldithiocarbamate (L3)} with the gold precursors [AuCl(PPh3)], [Au2Cl2(dppe)], [Au2Cl2(dppp)], or [Au2Cl2(dpph)] lead to the new gold(I) complexes [AuL(PPh3)] (1–3), [Au2L2(dppe)] (4–6), [(Au2L2)(dppp)] (7–9), and [Au2(L)2(dpph)] (10–12) {where dppe = 1,2-bis(diphenylphosphino)ethane, dppp = 1,3-bis(diphenylphosphino)propane, and dpph = 1,6-bis(diphenylphosphino)hexane}. These gold compounds were characterized by a combination of NMR and infrared spectroscopy, microanalysis, and mass spectrometry; and in selected cases by single-crystal X-ray crystallography. Compounds 4–6, which have dppe ligands, are unstable in solution for prolonged periods, with 4 readily transforming to the Au18 cluster [Au18S8(dppe)6]Cl2 (4a) in dichloromethane. Compounds 1–3 and 7–12 are all active against human cervical epithelioid carcinoma (HeLa) cells, but the most active compounds are 10 and 11, with IC50 values of 0.51 μM and 0.14 μM, respectively. Compounds 10 and 11 are more selective toward HeLa cells than they are toward normal cells, with selectivities of 25.0 and 70.5, respectively. Further tests, utilizing the 60-cell-line Developmental Therapeutics Program at the National Cancer Institute (U.S.A.), showed 10 and 11 to be active against nine other types of cancers.

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Section: Methodsmentioning

confidence: 99%

Phosphinogold(I) Dithiocarbamate Complexes: Effect of the Nature of Phosphine Ligand on Anticancer Properties

et al. 2014

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“…[ 21 ] The derivatives of phenyl hydrazine 5f,g , pyrazole, and indazole 5h–j were successfully prepared with potassium hydroxide as a base and either aqueous ethanol or tetrahydrofuran as solvents. [ 22,23 ] Potential by‐products are S , S ′‐dialkyl derivatives stemming from overalkylation of the dithiocarbazate moiety. [ 17 ] In fact, applying reaction conditions a‐d on benzenesulfonyl hydrazide ( 9k ) did not yield the desired dithiocarbazate 5k , but the dialkylation product 10a was the main product (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

From dithiocarbamates to branched dithiocarbazates: Compounds with potent antischistosomal activity

Gallinger

Obermann

Lange-Grünweller

et al. 2022

Archiv der Pharmazie

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Schistosomiasis or bilharzia is caused by blood flukes of the genus Schistosoma and represents a considerable health and economic burden in tropical and subtropical regions. The treatment of this infectious disease relies on one single drug: praziquantel (PZQ). Therefore, new and potent antischistosomal compounds need to be developed. In our previous work, starting with the drug disulfiram, we developed dithiocarbamates with in vitro antischistosomal activities in the low micromolar range. Based on these results, we report in this study on the synthesis and biological testing of the structurally related dithiocarbazates against Schistosoma mansoni, one of the major species of schistosomes. In total, three series of dithiocarbazate derivatives were examined, and we found that the antischistosomal activity of N-unbranched dithiocarbazates increased by further N-substitution.Comparable tetra-substituted dithiocarbazates were rarely described in the literature, thus a synthesis route was established. Due to the elaborate synthesis, the branched dithiocarbazates (containing an N-aminopiperazine) were simplified, but the resulting branched dithiocarbamates (containing a 4-aminopiperidine) were considerably less active. Taken together, dithiocarbazate-containing compounds with an in vitro antischistosomal activity of 5 µM were obtained.

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“…Since the discovery that 3-methylpyrazole and 4-ethylpyrazole have potential medicinal value, there has been a rapid growth in synthesizing new derivatives of pyrazole as anticancer (Manfredini et al 1992;Komeda et al 2000;Gamage et al 2002;MoukhaChafiq et al 2002;Rostom et al 2003;Duivenvoorden et al 2005;Park et al 2005;Keter et al 2009a), antibacterial (Jungheim 1989;Aiello et al 2000;Genin et al 2000a;Kucukguzel et al 2000;El-Gaby et al 2000;Farghaly et al 2001;Moukha-Chafiq et al 2002;Haque et al 2002;Kaymakcıoglu and Rollas 2002;Panda et al 2002;Adnan and Abdel-Aziem 2004;Tanitame et al 2004;Akbas and Berber 2005;Bekhit et al 2005;Bildirici et al 2007;Abunada et al 2008;Radi et al 2010), antiparasitic (Garg et al 1973;Rathelot et al 2002), antiviral (Comber et al 1991;Manfredini et al 1992;Storer et al 1999;Johansson et al 2002;Rostom et al 2003;Sweeney et al 2008), analgesics (Menozzi et al 1997;Pinto et al 1999) antiglycemic agents (Bauer et al 1968;Kees et al 1996;Bebernitz et al 2001) and even as anti-inflammatory agents …”

Section: N N Hmentioning

confidence: 99%

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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Anticancer Activities of bis(pyrazol-1-ylthiocarbonyl)disulfides against HeLa cells

Cited by 15 publications

References 22 publications

Phosphinogold(I) Dithiocarbamate Complexes: Effect of the Nature of Phosphine Ligand on Anticancer Properties

Phosphinogold(I) Dithiocarbamate Complexes: Effect of the Nature of Phosphine Ligand on Anticancer Properties

From dithiocarbamates to branched dithiocarbazates: Compounds with potent antischistosomal activity

Perspective: the potential of pyrazole-based compounds in medicine

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