Cytotoxic activity of acridin-3,6-diyl dithiourea hydrochlorides in human leukemia line HL-60 and resistant subline HL-60/ADR

Vantová, Zuzana; Paulíková, Helena; Sabolová, Danica; Kožurková, Mária; M, Suchanova; Janovec, Ladislav; Kristián, Pavol; Imrich, Ján

doi:10.1016/j.ijbiomac.2009.04.018

Cited by 20 publications

(12 citation statements)

References 36 publications

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“…EPR measurements showed that superoxide radical anion and singlet oxygen were produced after irradiation (UV-A, >300 nm) of AcrDIM and AcrDTU derivatives (Grolmusová et al, 2013;Čižeková et al, 2014). Investigation of a DNA binding of AcrDIMs and AcrDTUs by UV-VIS and fluorescence spectrophotometric titrations, circular dichroism spectroscopy, and denaturation transition temperature measurements confirmed their affinity toward DNA (Vantová et al, 2009, Janovec et al, 2011. We suppose that ROS generated after illumination of AcrDIMs or AcrDTUs could damage the DNA.…”

Section: Introductionmentioning

confidence: 69%

“…In the dark, only three derivatives had cytotoxic effects, while the cytotoxicity of other eleven compounds has been observed after irradiation. In a search for new anticancer drugs, our team synthesized and studied new derivatives from a proflavine family (Kožurková et al, 2008;Vantová et al, 2009;Janovec et al, 2011;Paulíková et al, 2012). Photocytotoxicity of two groups of derivatives, 3,6-bis((1-alkyl-5-oxo-imidazolidin-2-yliden) imino)acridine hydrochlorides (AcrDIMs) and 1',1"-(acridin-3,6)-3',3"-diyldithiourea hydrochlorides (AcrDTUs), was studied by Čižeková et al (2014) and Grolmusová et al (2015).…”

Section: Introductionmentioning

confidence: 99%

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Photocleavage of pDNA by bis-imidazolidino and bis-thioureido proflavines

Cisárikováa

Abaffy

Imrich

et al. 2015

Acta Chimica Slovaca

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New photosensitizers are needed for photodynamic antimicrobial and anticancer chemotherapy. Two new groups of proflavine derivatives have been recently prepared and their action on the cancer cells has been investigated by our research team. In this paper, we studied an effect of UV-A irradiation of two groups of proflavines: 3,6-bis((1-alkyl-5-oxo-imidazolidin-2-yliden)imino)acridine hydrochlorides (AcrDIMs) and 1’,1”-(acridin-3,6-diyl)-3’,3”-dialkyldithiourea hydrochlorides (AcrDTUs) on a plasmid DNA (pDNA). These compounds induced a photocleavage of pDNA characteristic by generation of free radicals, single strand DNA breaks and formation of an open circular form of pDNA.

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Section: Introductionmentioning

confidence: 69%

Section: Introductionmentioning

confidence: 99%

Photocleavage of pDNA by bis-imidazolidino and bis-thioureido proflavines

Cisárikováa

Abaffy

Imrich

et al. 2015

Acta Chimica Slovaca

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“…In spite of that, cytotoxicity of some acridines may not be connected with their interaction with nuclear DNA but they could induce an ER stress or oxidative stress in cells. Such types of acridines were prepared in our laboratory [33][34][35]. It was proven that 3,6-bis((1-n-alkyl-5-oxo-imidazolidin-2-yliden) imino)acridine hydrochlorides were localized in mitochondria [36].…”

Section: Discussionmentioning

confidence: 99%

Intracellular distribution of 3,6-bis(3-alkylguanidino)acridines determines their cytotoxicity

L¹,

Paulíková²,

Bačová³

et al. 2015

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Cytotoxicity of two derivatives of 3,6-bis(3-alkylguanidino)acridines (GNDAs; pentyl-and hexyl-GNDA) was determined against three cell lines: a murine immortalized fibroblast cell line NIH-3T3, a human ovarian carcinoma cell line A2780, and a human neuroblastoma cell line SH-SY5Y. We found out that these GNDAs were cytotoxic against A2780 and NIH-3T3 cells but they showed only a marginal cytotoxicity against neuroblastoma cells SH-SY5Y. To explain differences in cytotoxicity, intracellular distribution of GNDAs was monitored. GNDAs were accumulated in A2780 and NIH-3T3 cells in the nuclei (fluorescence microscopy). In contrast to these cell lines, in SH-SY5Y cells, GNDAs were localized outside of the nuclei, at the plasma membrane and surroundings, extending also to the cytosol. This distribution of GNDAs was confirmed by an ImageStream Flow Cytometer. Acetylcholinesterase (AChE) activity in the SH-SY5Y cells decreased upon incubation with GNDAs. Kinetic studies showed that GNDAs were able to inhibit AChE by the same mode as tacrine (9-amino-1,2,3,4-tetrahydroacridine), a known inhibitor of AChE. A low cytotocity of GNDAs against SH-SY5Y cells could be caused by their affinity to AChE (the enzyme is localized mainly at the plasma membrane). The interaction of GNDAs with AChE may affect their intracellular distribution and consequently the cytotoxicity.

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“…As was mentioned above, some comprehensive reviews and papers of acridine derivatives have reported anticancer and intercalating properties due to the planar structure of the acridine skeleton (Antonini et al, 2003;Brana et al, 2001;Cholewinski et al, 2011;Demeunynck, 2004;Galvez-Peralta et al, 2009;Ihmels & Otto, 2005;Kumar et al, 2009;Moloney et al, 2001;Murza et al, 2003;Neidle & Abraham, 1984;Pereira et al, 2005;Ryan et al, 2013;Tsankov et al, 1998). The interesting qualities of acridine ureas and thioureas have inspired Kožurkova and her team ( Janovec et al, 2007;Kožurkova et al, 2008Kožurkova et al, , 2011Sabolova et al, 2006;Vantova et al, 2009) to examine further potential uses of these new bioactive derivatives.…”

Section: Synthesis Of Thioureasmentioning

confidence: 99%

“…The reaction was carried out with 3,6-diisothiocyanatoacridine and an excess of appropriate amines in methanol. The low solubility of these derivatives led Vantova et al (2009) to synthesize the corresponding hydrochlorides 11a-e to allow biological testing ( Fig. 9); these compounds were prepared through the conversion of dithiourea products with equimolar amounts of HCl in methanol.…”

Section: Synthesis Of Thioureasmentioning

confidence: 99%

A review on acridinylthioureas and its derivatives: biological and cytotoxic activity

2017

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Acridines possess two characteristics that have led many researchers to consider the agents interesting targets for future development as potential farmacophores: the planar acridine skeleton, which is able to intercalate into DNA, and the intense fluorescence of the agents. This review offers a study of the multifunctional character of acridines and the synthesis of novel acridine derivatives, with particular focus being placed on isothiocyanates and their congeners, e.g. thioureas, isothioureas, quaternary ammonium salts and platinum/gold conjugates. The review provides an overview of the structure, spectral properties, DNA binding and biological activity of acridinylthiourea congeners. These acridinylthiourea derivatives display significant cytotoxic activities against different types of cancer cell lines at micromolar concentrations. Copyright © 2017 John Wiley & Sons, Ltd.

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Cytotoxic activity of acridin-3,6-diyl dithiourea hydrochlorides in human leukemia line HL-60 and resistant subline HL-60/ADR

Cited by 20 publications

References 36 publications

Photocleavage of pDNA by bis-imidazolidino and bis-thioureido proflavines

Photocleavage of pDNA by bis-imidazolidino and bis-thioureido proflavines

Intracellular distribution of 3,6-bis(3-alkylguanidino)acridines determines their cytotoxicity

A review on acridinylthioureas and its derivatives: biological and cytotoxic activity

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