Novel alkylaminoethyl derivatives of androstane 3-oximes as anticancer candidates: synthesis and evaluation of cytotoxic effects

Ajduković, Jovana J.; Jakimov, Dimitar; Rárová, Lucie; Strnad, Miroslav; Dzichenka, Yaraslau; Usanov, Sergey A.; Škorić, Dušan; Јovanović-Šanta, Suzana; Sakač, Marija N.

doi:10.1039/d1ra07613b

Cited by 10 publications

(7 citation statements)

References 48 publications

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“…Several novel oxime derivatives, such as (17 E )-(pyridin-2-yl)methylidene 3-oximes 1f – 1h were designed and synthesized ( Figure 4 ) [ 42 ]. After the synthesis, the antiproliferative activity of both compounds was assessed in a series of several human cancer cell lines (MCF7, MDA-MB-231, PC3, HeLa, HT29, A549) and a normal human cell line, MRC5.…”

Section: Steroidal Oximes As Antitumor Agentsmentioning

confidence: 99%

“…Most of the compounds summarized here are being evaluated as potential antitumor agents and exert their cytotoxicity against cancer cells mainly by inducing apoptosis; however, the pathways leading to it differ from compounds. For example, the androstane derivatives appear to induce apoptosis [ 34 , 42 , 48 ] by cell cycle arrest at different phases and increased ROS production [ 34 ]. Necroptosis might also be a mechanism involved in the compounds’ cytotoxicity against cancer cells [ 34 ].…”

Section: Mechanisms Of Action Of Steroidal Oximesmentioning

confidence: 99%

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The Structural Diversity and Biological Activity of Steroid Oximes

et al. 2023

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Steroids and their derivatives have been the subject of extensive research among investigators due to their wide range of pharmacological properties, in which steroidal oximes are included. Oximes are a chemical group with the general formula R1R2C=N−OH and they exist as colorless crystals and are poorly soluble in water. Oximes can be easily obtained through the condensation of aldehydes or ketones with various amine derivatives, making them a very interesting chemical group in medicinal chemistry for the design of drugs as potential treatments for several diseases. In this review, we will focus on the different biological activities displayed by steroidal oximes such as anticancer, anti-inflammatory, antibacterial, antifungal and antiviral, among others, as well as their respective mechanisms of action. An overview of the chemistry of oximes will also be reported, and several steroidal oximes that are in clinical trials or already used as drugs are described. An extensive literature search was performed on three main databases—PubMed, Web of Science, and Google Scholar.

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Section: Steroidal Oximes As Antitumor Agentsmentioning

confidence: 99%

Section: Mechanisms Of Action Of Steroidal Oximesmentioning

confidence: 99%

The Structural Diversity and Biological Activity of Steroid Oximes

et al. 2023

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“…The compounds were tested against eight human cancer cell lines. The oxime ether 87 showed very high activities against A-549, HT-29 and MDA-MB-231 (breast cancer cell line), and IC 50 values were 2.0, 3.3 and 4.7 μM, respectively, after 72 h incubation (activity values for reference drug—cisplatin—were 3.2, 4.1 and 2.6 μM, respectively) [ 89 ].…”

Section: The Oxime Ethers With An Anticancer Activitymentioning

confidence: 99%

“…Figure 12. The structures of oxime ethers 80-94 with the anticancer activity.Steroid derivatives, due to their potential anti-cancer properties, have been used to develop new compounds-androst-4-ene oxime ethers with a built-in pyridine ring[89]. The compounds were tested against eight human cancer cell lines.…”

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confidence: 99%

A Review of Biologically Active Oxime Ethers

et al. 2023

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Oxime ethers are a class of compounds containing the >C=N-O-R moiety. The presence of this moiety affects the biological activity of the compounds. In this review, the structures of oxime ethers with specific biological activity have been collected and presented, and bactericidal, fungicidal, antidepressant, anticancer and herbicidal activities, among others, are described. The review includes both those substances that are currently used as drugs (e.g., fluvoxamine, mayzent, ridogrel, oxiconazole), as well as non-drug structures for which various biological activity studies have been conducted. To the best of our knowledge, this is the first review of the biological activity of compounds containing such a moiety. The authors hope that this review will inspire scientists to take a greater interest in this group of compounds, as it constitutes an interesting research area.

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“…[67][68][69] Oximes, vic-dioximes, and their metal complexes have attracted enormous interest from research groups worldwide because they are easily synthesizable by many different methods and their physical and chemical properties are devisable according to their application areas by using different substituents and metal salts. 68,70 These compounds have been employed in many fields of science with many application areas such as catalysis, 71,72 nanoparticles, 73,74 electrochemical sensors, [75][76][77] anti-chemical warfare agents, 76,78 anti-cancer [79][80][81] and anti-bacterial treatments. [82][83][84] Despite the wide usage of oximes in different areas, any notable studies had been working on in the field of energy storage about their properties.…”

Section: Introductionmentioning

confidence: 99%