Steroid dimers—In vitro cytotoxic and antimicrobial activities

Krstić, Natalija M.; Matić, Ivana Z.; Juranić, Zorica D.; Novaković, Irena; Sladić, Dušan

doi:10.1016/j.jsbmb.2014.06.005

Cited by 24 publications

(28 citation statements)

References 38 publications

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“…quotient method [22]. The cytotoxicity assay procedure has been described elsewhere [3,23]. Stock solutions of compounds were prepared in DMSO at a concentration of 10 mM.…”

Section: Single Crystal X-ray Crystallographymentioning

confidence: 99%

“…The final concentration of DMSO did not cause any toxicity to the cells. Survival of cells was determined by MTT assay after 72 h of continuous action, according to the method of Mosmann [24], which was modified by Ohno and Abe [25] and described in detail in our previous studies [3][4][5]23].…”

Section: Single Crystal X-ray Crystallographymentioning

confidence: 99%

“…and 5a for 24 h and 48 h. After incubation, the cells were collected, washed and fixed in 70% ethanol, according to the standard procedure [23,26,27]. Cell cycle phase distributions were determined using a FACSCalibur flow cytometer (BD Biosciences, Franklin Lakes, NJ, USA).…”

Section: Cell Cycle Analysismentioning

confidence: 99%

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Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro

Živković

Matić

Rodić

et al. 2017

The Journal of Steroid Biochemistry and Molecular Biology

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The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (E)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC values from 8.5μM to 14.9μM), eight on HeLa cells (IC values ranging from 8.9μM to 15.1μM) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC values from 12.7μM to 25.6μM) than cisplatin (21.5μM) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.

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“…quotient method [22]. The cytotoxicity assay procedure has been described elsewhere [3,23]. Stock solutions of compounds were prepared in DMSO at a concentration of 10 mM.…”

Section: Single Crystal X-ray Crystallographymentioning

confidence: 99%

Section: Single Crystal X-ray Crystallographymentioning

confidence: 99%

See 1 more Smart Citation

Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro

Živković

Matić

Rodić

et al. 2017

The Journal of Steroid Biochemistry and Molecular Biology

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“…cephalostatin I, ritterazines A, and crellastatin A) and show potent antiproliferative activities against human cancer cell lines [9,10]. Inspired by the structural novelty and promising bioactivities of steroidal dimers, a large number of new steroidal dimers have been synthesized and assessed for their biological potential [11][12][13]. However, their detailed mechanisms of action are less studied.…”

Section: Introductionmentioning

confidence: 99%

Steroidal Dimer by001 Inhibits Proliferation and Migration of Esophageal Cancer Cells via Multiple Mechanisms

Wang¹,

Zhou²,

Shi³

et al. 2017

Preprint

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Following our previous success in identifying new steroid-based anticancer agents, we herein disclosed the structural requirements for retaining high potency against cancer cells and associated modes of action. The structurally novel steroidal dimer by001 inhibited growth of different esophageal cancer cells and colony formation at low micromolar levels, elevated cellular ROS levels and caused mitochondrial dysfunction. Mechanistic studies showed that by001 induced cell death through the mitochondria and death receptor-mediated apoptotic pathways and autophagy induction, as well as inhibited migration.

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“…The biological activity of some dimeric steroid esters showed considerable prolongation of hormonal effects compared to the respective monomer [8]. Other derivatives were found to show appreciable cytotoxicity [9].…”

Section: Introductionmentioning

confidence: 99%