Quinoline and ferrocene conjugates: Synthesis, computational study and biological evaluations

Maračić, Silvija; Lapić, Jasmina; Djaković, Senka; Opačak-Bernardi, Teuta; Glavaš‐Obrovac, Ljubica; Vrček, Valerije; Raić‐Malić, Silvana

doi:10.1002/aoc.4628

Cited by 20 publications

(27 citation statements)

References 53 publications

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“…Taking into account the well‐known biological activity of ferrocene derivatives and ferrocenyl‐appended heterometallics and in continuation of our research on ferrocene‐based hybrids and organometallic complexes with anticancer activity, [ 31–33 ] herein we report the synthesis and characterization of aniline, benzothiazole and dipyridylamine (dpa) ferrocenes and their Zn(II) and Cu(II) complexes. In addition, we investigated the redox property and coordination of Cu(II) and Zn(II) ions, as well as cytotoxic activity of N ‐heterocyclic ferrocene derivatives and their Zn(II) and Cu(II) complexes.…”

Section: Introductionmentioning

confidence: 99%

Ferrocene conjugates linked by 1,2,3‐triazole and their Zn(II) and Cu(II) complexes: Synthesis, characterization and biological activity

Jakopec

Juraj

Brozović

et al. 2022

Applied Organom Chemis

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Ferrocene derivatives with mono‐ (8a–c) and bis‐1,2,3‐triazolyl (9 and 10a–13c) chelating groups were synthesized by regioselective copper(I)‐catalysed 1,3‐dipolar cycloaddition of terminal alkynes with ferrocene azides. Metal complexes of the ligands were prepared with Cu(II) and Zn(II) salts. Crystal structures of ligands 9 and 11a were determined, as well as the structures of complexes [Cu(8a)2](CF3SO3)2 (8aCu) and [Cu(8c)2(CH3OH)2](BF4)2 (8cCu). In addition to NMR and UV–Vis spectroscopy, the metal complexes were characterized by cyclic voltammetry. The cytotoxic effect of ferrocene conjugates and their Zn(II) and Cu(II) complexes was explored, and cell cycle analysis was performed. The complex [Cu(8c)2](CF3SO3)2 showed the most prominent and selective cytotoxicity on cervical carcinoma (HeLa), ovarian cancer (MES‐OV), non‐small cell lung cancer (A549) and breast carcinoma (MDA‐MB‐231) cells. This complex increased cell population in the S and G2/M phase of the cell cycle, which was accompanied by an increase of the cells present in the sub‐G0/G1 fraction.

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Section: Introductionmentioning

confidence: 99%

Ferrocene conjugates linked by 1,2,3‐triazole and their Zn(II) and Cu(II) complexes: Synthesis, characterization and biological activity

Jakopec

Juraj

Brozović

et al. 2022

Applied Organom Chemis

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“…Based on the above-mentioned data and in continuation of our research on 1,2,3triazolyl-appended heterocycles [26,[33][34][35] and their amidino derivatives [8,36,37] as anticancer and antipathogenic agents, herein, we report the synthesis and antiproliferative evaluations of novel indole, quinoline and coumarin-based aromatic amidines 1-11 and amidoximes 12-22. Since nucleic acids are a major target for a large number of anticancer drugs, one of our aims was to investigate the binding of small molecules to DNA and RNA [29].…”

Section: Chemistrymentioning

confidence: 99%

Amidine- and Amidoxime-Substituted Heterocycles: Synthesis, Antiproliferative Evaluations and DNA Binding

et al. 2021

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The novel 1,2,3-triazolyl-appended N- and O-heterocycles containing amidine 4–11 and amidoxime 12–22 moiety were prepared and evaluated for their antiproliferative activities in vitro. Among the series of amidine-substituted heterocycles, aromatic diamidine 5 and coumarine amidine 11 had the most potent growth-inhibitory effect on cervical carcinoma (HeLa), hepatocellular carcinoma (HepG2) and colorectal adenocarcinoma (SW620), with IC50 values in the nM range. Although compound 5 was toxic to non-tumor HFF cells, compound 11 showed certain selectivity. From the amidoxime series, quinoline amidoximes 18 and 20 showed antiproliferative effects on lung adenocarcinoma (A549), HeLa and SW620 cells emphasizing compound 20 that exhibited no cytostatic effect on normal HFF fibroblasts. Results of CD titrations and thermal melting experiments indicated that compounds 5 and 10 most likely bind inside the minor groove of AT-DNA and intercalate into AU-RNA. Compounds 6, 9 and 11 bind to AT-DNA with mixed binding mode, most probably minor groove binding accompanied with aggregate binding along the DNA backbone.

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“…With this motivation, Silvija Maračić and co-workers unlock the synthesis of quinoline triazole fused ferrocene derivatives and Raji cancer cells with a neglected cytotoxic effect towards normal cells (MDCK1) (Scheme 9). [64] Vinod. D Jadhav and Challa Gangu Naidu et al brought forward the synthesis of quinoline-triazine hybrid pharmacophores 46 a-g and 48 a-f involving [ Further mechanism study and functionalization of these quinoline-triazine hybrids may helpful in anticancer drug development (Scheme 10).…”

Section: 1 Quinoline-123-triazole Hybridsmentioning

confidence: 99%

Navigating the Synthesis of Quinoline Hybrid Molecules as Promising Anticancer Agents

Panda

Chakroborty

2020

ChemistrySelect

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The emergence of drug resistance and low specificity with side effects are the significant challenges in pharmaceutical sectors for control of cancer nowadays. Notwithstanding, this is an imperative prerequisite to develop novel anticancer agents through mainstream medicinal chemistry approaches. The intriguing quinoline and its derivatives have demonstrated as significant building blocks for the locating of new promising anticancer agents. Consequently, quinoline moiety with the addition of suitable congeners would offer a strategy for the development of potential drug candidates. This present review article summarizes the recent advances (2018‐2020) of quinoline hybrids and their anticancer activity. The mechanism action and plausible structure‐activity relationship have discussed.

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Quinoline and ferrocene conjugates: Synthesis, computational study and biological evaluations

Cited by 20 publications

References 53 publications

Ferrocene conjugates linked by 1,2,3‐triazole and their Zn(II) and Cu(II) complexes: Synthesis, characterization and biological activity

Ferrocene conjugates linked by 1,2,3‐triazole and their Zn(II) and Cu(II) complexes: Synthesis, characterization and biological activity

Amidine- and Amidoxime-Substituted Heterocycles: Synthesis, Antiproliferative Evaluations and DNA Binding

Navigating the Synthesis of Quinoline Hybrid Molecules as Promising Anticancer Agents

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