Disubstituted 4-Chloro-3-nitrophenylthiourea Derivatives: Antimicrobial and Cytotoxic Studies

Bielenica, Anna; Sanna, Giuseppina; Madeddu, Silvia; Giliberti, Gabriele; Stefańska, Joanna; Kozioł, Anna E.; Savchenko, Oleksandra; Strzyga-Łach, Paulina; Chrzanowska, Alicja; Kubiak-Tomaszewska, Grażyna; Struga, Marta

doi:10.3390/molecules23102428

Cited by 5 publications

(11 citation statements)

References 43 publications

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“…DMF, an organic solvent that contaminates synthesized complexes, has already been tested on various cells and appears to be nontoxic at the concentrations used in our synthesis (see in the Supplementary Material section ). Considering an influence of starting ligands L1 – L8 on studied cell lines, the derivative L5 , at the concentration 8 µM, caused an approximately 20% decrease in HaCaT cell viability, which indicated its weak cytotoxic impact against normal cells [ 36 ]. In contrast, new complexes are devoid of visible influence on keratinocytes.…”

Section: Resultsmentioning

confidence: 99%

“…In contrast, new complexes are devoid of visible influence on keratinocytes. In preliminary tests published previously, ligands L1 , L3 – L5 and L8 influenced the growth of other cancer cells, such as human leukemia and solid (melanoma, prostate) tumors, as well as normal tissue foreskin fibroblasts [ 36 ]. These results encouraged us to proceed with deeper investigations on the cytotoxicity mechanism of complexes 1 – 8 .…”

Section: Resultsmentioning

confidence: 99%

“…As expected, new copper (II) complexes were much more potent than copper (II) chloride itself (MIC ≥ 128 µg/mL for all strains). Although the complexation of halogen-containing 4-chloro-3-nitrophenylthioureas with copper (II) ion diminished their antibacterial properties [ 36 , 37 ], it incomparably increased their cytotoxicity towards various cancer cell lines, without influencing on normal keratinocytes.…”

Section: Resultsmentioning

confidence: 99%

“…As a part of our research on developing biologically active 1,3-disubstituted thioureas [ 7 , 35 , 36 , 37 ], we have synthesized a series of halogenated copper (II) complexes of (4-chloro-3-nitrophenyl)thiourea and reported their cytotoxic, prooxidant and antimicrobial properties.…”

Section: Introductionmentioning

confidence: 99%

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The Cytotoxic Effect of Copper (II) Complexes with Halogenated 1,3-Disubstituted Arylthioureas on Cancer and Bacterial Cells

Chrzanowska

Drzewiecka-Antonik

Dobrzyńska

et al. 2021

IJMS

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A series of eight copper (II) complexes with 3-(4-chloro-3-nitrophenyl)thiourea were designed and synthesized. The cytotoxic activity of all compounds was assessed in three human cancer cell lines (SW480, SW620, PC3) and human normal keratinocytes (HaCaT). The complexes 1, 3, 5, 7 and 8 were cytotoxic to the studied tumor cells in the low micromolar range, without affecting the normal cells. The complexes 1, 3, 7 and 8 induced lactate dehydrogenase (LDH) release in all cancer cell lines, but not in the HaCaT cells. They provoked early apoptosis in pathological cells, especially in SW480 and PC3 cells. The ability of compounds 1, 3, 7 and 8 to diminish interleukin-6 (IL-6) concentration in a cell was established. For the first time, the influence of the most promising Cu (II) complexes on intensities of detoxifying and reactive oxygen species (ROS) scavenging the enzymes of tumor cells was studied. The cytotoxic effect of all copper (II) conjugates against standard and hospital bacterial strains was also proved.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Cytotoxic Effect of Copper (II) Complexes with Halogenated 1,3-Disubstituted Arylthioureas on Cancer and Bacterial Cells

Chrzanowska

Drzewiecka-Antonik

Dobrzyńska

et al. 2021

IJMS

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“…The thiourea branch represents an important synthon, which is responsible for numerous biological activities, such as antimicrobial, antiviral, antiproliferative, and cytotoxic properties . In addition, the class of (thio)urea derivatives were shown to mediate psychotropic‐like effects in rodents.…”

Section: Introductionmentioning

confidence: 99%

G protein‐coupled receptor binding and pharmacological evaluation of indole‐derived thiourea compounds

Szulczyk

Bielenica

Kędzierska

et al. 2019

Archiv der Pharmazie

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Four 2-(1H-indol-3-yl)ethylthiourea derivatives were prepared by condensation of 2-(1H-indol-3-yl)ethanamine with the corresponding aryl/alkylisothiocyanates in a medium-polarity solvent. Their structures were confirmed by spectral techniques, and the molecular structure of 3 was determined by X-ray crystal analysis. For all derivatives, the binding affinities at the 5-HT 2A and 5-HT 2C receptors, as well as their functional activities at the 5-HT 1A and D 2 receptors, were determined. The arylthioureas 1 and 4 were the most active at the 5-HT 1A receptor, showing, at the same time, significant selectivity over the studied 5-HT 2 and D 2 receptor subtypes.The compounds were tested for their pharmacological activities within the central nervous system in relevant mouse models. The involvement of the serotonergic system in the activity of 1 and 4 was indicated. The antinociceptive action of 4 was linked to its anti-inflammatory activity. K E Y W O R D Sdopamine receptors, inverse agonists, serotonin antagonism, substituent effect

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Proapoptotic effects of halogenated bis‐phenylthiourea derivatives in cancer cells

Strzyga-Łach

Chrzanowska

Kiernozek-Kalińska

et al. 2023

Archiv der Pharmazie

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New halogenated thiourea derivatives were synthesized via the reaction of substituted phenylisothiocyanates with aromatic amines. Their cytotoxic activity was examined in in vitro studies against solid tumors (SW480, SW620, PC3), a hematological malignance (K‐562), and normal keratinocytes (HaCaT). Most of the compounds were more effective against SW480 (1a, 3a, 3b, 5j), K‐562 (2b, 3a, 4a), or PC3 (5d) cells than cisplatin, with favorable selectivity. Their anticancer mechanisms were studied by Annexin V‐fluorescein‐5‐isothiocyanate apoptosis, caspase‐3/caspase‐7 assessment, cell cycle analysis, interleukin‐6 (IL‐6) release inhibition, and reactive oxygen species (ROS) generation assay. Thioureas 1a, 2b, 3a, and 4a were the most potent activators of early apoptosis in K‐562 cells, and substances 1a, 3b, 5j triggered late‐apoptosis or necrosis in SW480 cells. This proapoptotic effect was proved by the significant increase of caspase‐3/caspase‐7 activation. Cell cycle analysis revealed that derivatives 1a, 3a, 5j increased the number of SW480 and K‐562 cells in the sub‐G1 and/or G0/G1 phases, and one evoked cycle arrest at the G2 phase. The most potent thioureas inhibited IL‐6 cytokine secretion from PC3 cells and both colon cancer cell lines. Apoptosis‐inducing compounds also increased ROS production in all tumor cell cultures, which may enhance their anticancer properties.

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Disubstituted 4-Chloro-3-nitrophenylthiourea Derivatives: Antimicrobial and Cytotoxic Studies

Cited by 5 publications

References 43 publications

The Cytotoxic Effect of Copper (II) Complexes with Halogenated 1,3-Disubstituted Arylthioureas on Cancer and Bacterial Cells

The Cytotoxic Effect of Copper (II) Complexes with Halogenated 1,3-Disubstituted Arylthioureas on Cancer and Bacterial Cells

G protein‐coupled receptor binding and pharmacological evaluation of indole‐derived thiourea compounds

Proapoptotic effects of halogenated bis‐phenylthiourea derivatives in cancer cells

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