Synthesis, characterization and antitumor activity of 2-methyl-9-substituted acridines

Kumar, Rajesh; Sharma, Ankita; Sharma, Shikha; Silakari, Om; Singh, Mandeep; Kaur, Manmeet

doi:10.1016/j.arabjc.2012.12.035

Cited by 24 publications

(7 citation statements)

References 30 publications

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“…The results show that compound 23 displayed a higher level of in vitro cytotoxic activity against A‐549 and MCF‐7 cancer cell lines, with IC 50 values of 187.5 and 212.5 μg/mL, respectively. The cancer cell cytotoxicity of acridine derivatives against A‐549 cell lines was found to be greater than that against MCF‐7 cell lines (Kumar et al, 2017).…”

Section: Anticancer Efficacy Of 9‐aminoacridine Derivativesmentioning

confidence: 99%

“…Acridine derivatives with substitutes at this position are characterized by marked antibacterial (Chen et al, 2019; Hamzi et al, 2013; Kudryavtseva, Bogatyrev, Sysoev, & Klimova, 2019; Sing, Kumar, Prasad, Sharma, & Silakari, 2011), antiviral (Lyakhov, Suveyzdis, Litvinova, Rybalko, & Dyadyun, 2000), anticancer (Cholewinski, Dzierzbicka, & Kolodziejczyk, 2011; de Mela Rego, de Sena, Moura, Jacob, et al, 2017; Demeunynck, Charmantray, & Martelli, 2001; Ismail et al, 2018; Kumar et al, 2017; Prajapati et al, 2017), antiprotozoal, antioxidant, antimalarial, antihelmintic, insectidal, fungicidal, and many other interesting biochemical and physical properties (Agili, 2018; Habeeb Unnisa Begum Nagma Fathima, Tasleem, 2018; Rupar, Dobričić, Aleksić, Brborić, & Čudina, 2018) (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

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A new look at 9‐substituted acridines with various biological activities

Kožurková

Sabolová

Kristián

2020

J of Applied Toxicology

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Heterocycles have long been the focus of intensive study in attempts to develop novel therapeutic compounds, and acridine, a polynuclear nitrogen molecule containing a heterocycle, has attracted a considerable amount of scientific attention. Acridine derivatives have been studied in detail and have been found to possess multitarget properties, which inhibit topoisomerase enzymes that regulate topological changes in DNA and interfere with the essential biological function of DNA. This article describes some recent advancements in the field of new 9-substituted acridine heterocyclic agents and describes both the structure and the structure-activity relationship of the most promising molecules. The article will also present the IC 50 values of the novel derivatives against various human cancer cell lines. The mini review also investigates the topoisomerase inhibition and antibacterial and antimalarial activity of these polycyclic aromatic derivatives.

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Section: Anticancer Efficacy Of 9‐aminoacridine Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A new look at 9‐substituted acridines with various biological activities

Kožurková

Sabolová

Kristián

2020

J of Applied Toxicology

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“…Acridine derivatives have been explored as potential therapeutic agents for the treatment of cancer due to their Novel tetrahydroacridine and cyclopentaquinoline derivatives with fluorobenzoic acid moiety induce cell cycle arrest and apoptosis in lung cancer cells by activation of DNA damage signaling non-covalent interaction with DNA by intercalative binding. 3,4 Moreover, acridines are able to decrease the activity of enzymes such as topoisomerase I and II that are involved in replication and transcription as well as recombination and chromosome segregation. 5,6 The biological activity of acridines is mainly a result of their planarity of aromatic structures, which are able to interact within the DNA structure by intercalation.…”

Section: Introductionmentioning

confidence: 99%

Novel tetrahydroacridine and cyclopentaquinoline derivatives with fluorobenzoic acid moiety induce cell cycle arrest and apoptosis in lung cancer cells by activation of DNA damage signaling

et al. 2017

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Lung cancer is still the leading cause of cancer-related death worldwide, indicating a necessity to develop more effective therapy. Acridine derivatives are potential anticancer agents due to their ability to intercalate DNA as well as inhibit enzymes involved in replication and transcription. Recently, we have evaluated anticancer activity of 32 novel acridine-based compounds. We found that the most effective were tetrahydroacridine and cyclopentaquinoline derivatives with fluorobenzoic acid containing eight and nine carbon atoms in the aliphatic chain. The aim of this study was to determine the molecular mechanisms of compounds-induced cell cycle arrest and apoptosis in human lung adenocarcinoma cells. All compounds activated Ataxia telangiectasia mutated kinase and phosphorylated histone H2A.X at Ser139 indicating DNA damage. Treatment of cells with the compounds increased phosphorylation and accumulation of p53 that regulate cell cycle as well as apoptosis. All compounds induced G0/1 cell cycle arrest by phosphorylation of cyclin-dependent kinase 2 at Tyr15 resulting in attenuation of the kinase activity. In addition, cyclopentaquinoline derivatives induced expression of cyclin-dependent kinase 2 inhibitor, p21; however, tetrahydroacridine derivatives had no significant effect on p21. Moreover, all compounds decreased the mitochondrial membrane potential accompanied by increased expression of Bax and down-regulation of Bcl-2, suggesting activation of the mitochondrial pathway. All compounds also significantly attenuated the migration rates of lung cancer cells. Collectively, our findings suggest a central role of activation of DNA damage signaling in response to new acridine derivatives treatment to induce cell cycle arrest and apoptosis in cancer cells and provide support for their further development as potential drug candidates.

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“…During the recent years, acridine‐based compounds attract major interest because of their distinct properties and applications in the field of biology and industry [1,2]. The key features of the acridine derivatives are their ability for DNA binding [3], RNA binding [4], and human topoisomerase inhibitor activities [5] Moreover, acridine derivatives play a significant role as bioactive compounds such as antiherpes [6], antibacterial [7], antifungal [8], antiviral [9], anticancer [10], anti‐HIV [11], antitumor [12], Alzheimer's diseases [13], and antiproliferative [14] agents. In addition to the above potential properties, acridine moieties are found to have wide applications in organic light emitting diodes (OLEDs) [15], thermal activated delayed fluorescence (TADF) [16], chemiluminescence [17], radiotherapy (RT) [18], dyes‐sensitized photovoltaics [19], and organic semiconductors [20].…”

Section: Introductionmentioning

confidence: 99%

“…During the recent years, acridine-based compounds attract major interest because of their distinct properties and applications in the field of biology and industry [1,2]. The key features of the acridine derivatives are their ability for DNA binding [3], RNA binding [4], and human topoisomerase inhibitor activities [5] Moreover, acridine derivatives play a significant role as bioactive compounds such as antiherpes [6], antibacterial [7], antifungal [8], antiviral [9], anticancer [10], anti-HIV [11], antitumor [12], Alzheimer's diseases [13], and antiproliferative [14] agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new 1H‐spiro[acridine‐9,3′‐indoline]‐1,2′(2H,10H)‐dione derivatives using aqueous ethanol as a reaction medium

Vinoth

Lalitha

2022

Journal of Heterocyclic Chem

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One‐pot three component synthesis of novel spiro[acridine‐9,3′‐indoline]‐1,2′(2H,10H)‐dione derivatives has been performed through the condensation of isatin, dimedone, and aniline under greener conditions. The remarkable features of this synthesis are use of ethanol:water mixture as a greener solvent and isolation of products by simple washing with water. The structures of the synthesized compounds have been well elucidated by various spectroscopic techniques.

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Synthesis, characterization and antitumor activity of 2-methyl-9-substituted acridines

Cited by 24 publications

References 30 publications

A new look at 9‐substituted acridines with various biological activities

A new look at 9‐substituted acridines with various biological activities

Novel tetrahydroacridine and cyclopentaquinoline derivatives with fluorobenzoic acid moiety induce cell cycle arrest and apoptosis in lung cancer cells by activation of DNA damage signaling

Synthesis of new 1H‐spiro[acridine‐9,3′‐indoline]‐1,2′(2H,10H)‐dione derivatives using aqueous ethanol as a reaction medium

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