Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton

Samadaei, Mahzeiar; Pinter, Matthias; Senfter, Daniel; Madlener, Sibylle; Rohr-Udilova, Nataliya; Iwan, Dominika; Kamińska, Karolina; Wojaczyńska, Elżbieta; Wojaczyński, Jacek; Kochel, Andrzej

doi:10.3390/molecules25102355

Cited by 11 publications

(8 citation statements)

References 29 publications

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“…The general approach to the evaluation of biological activity of investigated compounds followed the one described in our previous study on sulfonamides based on 2-azanorbornane skeleton [ 33 ]. All compounds were dissolved in dimethyl sulfoxide (DMSO).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives

et al. 2021

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N-Heterocycles are considered as desirable scaffolds for the development of novel lead compounds for anticancer drug research. Among them, phosphorus-containing amino-derivatives play a crucial role. A series of imines and products of their further reactions with P-nucleophiles were obtained starting from vicinal bisamines. Reaction of ethylenediamine and α-carbonyl esters yielded in novel unexpected products, which structures were confirmed by crystallographic measurements. The cytotoxic activity evaluation was done on a variety of cell lines including HUH7, AKH12, DAOY, UW228-2, D283, D425, and U251. Human umbilical vein endothelial cells (HUVECs) were used as control. Two of the tested compounds, bearing TADDOL-derived, and trifluoromethyl substituents showed a significant effect on cell viability, though comparable to nonmalignant cells.

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Section: Resultsmentioning

confidence: 99%

Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives

et al. 2021

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“…According to the obtained results, the test substances are cytotoxic at high concentrations and long-term exposure but they are not genotoxic in human peripheral lymphocytes [23]. Samadaei et al (2020) reported the cytotoxic activity of chiral sulfonamides based on the 2-azabicycloalkane skeleton [24].…”

Section: (A) (B) (C) (D) (E) (F) (G) (H) (ı) (J) (K) (L) (M) (N) (O) (P) (R) (S)mentioning

confidence: 99%

Allium cepa Kök Ucu Hücrelerinde Sülfonamid-Aldehit Türevinin Sitotoksik ve Genotoksik Etkileri

Eroğlu¹,

Gümüş²,

Gümüş³

et al. 2021

Düzce Üniversitesi Bilim Ve Teknoloji Dergisi

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The continuous production and release into the environment of chemicals has revealed the need to determine their cytotoxicity and genotoxicity. Sulfonamide-aldehyde (SA) derivatives, whose biological activity properties vary in a wide spectrum, are frequently used in agriculture, medicine, pharmacy and many other fields. These compounds have an important cycle in the ecological system due to their use and diversity. In the present study, the potential cytotoxic and genotoxic effects of sulfonamide-aldehyde derivative were investigated using Allium test system with the concentrations of 6.25, 12.5, 25, 50, and 100 µM. In A. cepa cells, the increasing concentrations of SA caused cytotoxic effects by inducing nuclear lesions and inhibition of mitotic index. In addition, the increasing concentrations of SA caused genotoxic effects by inducing micronucleus and chromosome aberrations, which the most common ones are C-mitosis, sticky metaphase, and anaphase bridge. The results indicate that the concentration of 25 µM is EC50 in micronucleus, nuclear lesions, and chromosome aberrations; and 50 µM is EC50 in mitotic index (p < 0.05).

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“…The cytotoxic activity of the chiral sulfonamides was evaluated by human hepatocellular carcinoma, glioblastoma, and medulloblastoma cell lines. The compounds were shown to notably reduce cell viability as compared to nonmalignant cells [25]. The cytotoxicity of sulfonamide-based azaheterocyclic schiff base derivatives was performed on human keratinocyte and MCF-7 cell lines.…”

Section: Cytotoxic and Genotoxic Effectsmentioning

confidence: 99%

Cytotoxic and Genotoxic Effects of Some Azo Dyes in Allium cepa Root Tip Cells

Gümüş

Eroğlu

Gümüş

et al. 2020

Türk Doğa Ve Fen Dergisi

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Azo dyes (AD-1, AD-2) were synthesized from the reaction diazonium salts of the aromatic amines salt with the enaminone derivative. The chemical structure of the synthesized novel azo dye (AD-2) was characterized by elemental analysis and other spectral techniques (FTIR, 1 H NMR and 13 C NMR). Azo dyes are used frequently in the industry and pose a great danger especially for water resources. In this respect, azo dyes threaten many products indirectly in agricultural applications. In this study, the cytotoxic and genotoxic effects of potential azo dyes (AD-1, AD-2) that can be used in industrial applications were determined using Allium test system in five different concentrations (6.25, 12.5, 25, 50 and 100 µM). As a result of the cytogenetic analyzes, it was determined that both azo dyes significantly reduced the number of divisions of A. cepa cells and caused chromosomal abnormalities in dividing cells. As a result, in this research, it is emphasized that the azo dyes (AD-1, AD-2), which are potentially used in the industry, cause genotoxic and cytotoxic effects in the living structures.

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Synthesis and Cytotoxic Activity of Chiral Sulfonamides Based on the 2-Azabicycloalkane Skeleton

Cited by 11 publications

References 29 publications

Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives

Cytotoxic Activity of Piperazin-2-One-Based Structures: Cyclic Imines, Lactams, Aminophosphonates, and Their Derivatives

Allium cepa Kök Ucu Hücrelerinde Sülfonamid-Aldehit Türevinin Sitotoksik ve Genotoksik Etkileri

Cytotoxic and Genotoxic Effects of Some Azo Dyes in Allium cepa Root Tip Cells

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