Synthesis and characterization of quinoline-based thiosemicarbazones and correlation of cellular iron-binding efficacy to anti-tumor efficacy

Serda, Maciej; Kalinowski, Danuta S.; Mrozek-Wilczkiewicz, Anna; Musioł, Robert; Szurko, Agnieszka; Ratuszna, A.; Pantarat, Namfon; Kovačević, Žaklina; Merlot, Angelica M.; Richardson, Des R.; Polański, Jarosław

doi:10.1016/j.bmcl.2012.07.030

Cited by 63 publications

(38 citation statements)

References 37 publications

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“…TSC are versatile ligands that exhibit wide pharmacological properties for instance, antineoplastic, antibacterial, antiviral, and antifungal activity [33,172]. Their antineoplastic mechanism of action includes the activities for instance; (a) inhibition of cellular iron uptake from transferrin, (b) mobilization of iron from cells, (c) inhibition of RR, and (d) the formation of ROS [173,174]. One of the best studied TSC compounds is Triapine.…”

Section: Xns Ligandsmentioning

confidence: 99%

Iron and Copper Intracellular Chelation as an Anticancer Drug Strategy

et al. 2018

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A very promising direction in the development of anticancer drugs is inhibiting the molecular pathways that keep cancer cells alive and able to metastasize. Copper and iron are two essential metals that play significant roles in the rapid proliferation of cancer cells and several chelators have been studied to suppress the bioavailability of these metals in the cells. This review discusses the major contributions that Cu and Fe play in the progression and spreading of cancer and evaluates select Cu and Fe chelators that demonstrate great promise as anticancer drugs. Efforts to improve the cellular delivery, efficacy, and tumor responsiveness of these chelators are also presented including a transmetallation strategy for dual targeting of Cu and Fe. To elucidate the effectiveness and specificity of Cu and Fe chelators for treating cancer, analytical tools are described for measuring Cu and Fe levels and for tracking the metals in cells, tissue, and the body.

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Section: Xns Ligandsmentioning

confidence: 99%

Iron and Copper Intracellular Chelation as an Anticancer Drug Strategy

et al. 2018

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“…The υ(C=S) in the complexes of 2a(L 1 ) or 2b(L 2 ) shifted to lower frequency thereby indicating the involvement of the thione sulfur in complexes formation. The higher shift of νN-N which was observed on complexation confirmed the coordination of the azomethine nitrogen to the metal ions (Serda et al, 2012). Therefore, this shows that the nitrogen atom of the azomethine group reduces the electron density on the azomethine linkage.…”

Section: Resultsmentioning

confidence: 66%

Preparation and Characterization of Thiosemicarbazones Corrosion Inhibition Effect and the Antimicrobial and Anticancer Effect on their Metal Complexes

Kashar¹,

Abdel‐Motaal²,

Emran³

2017

ESJ

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Benzofurane and naphthofuranethiosemicarbazone ligands 2a (L 1 ) and 2b(L 2 ) and their Cu(II), Co(II), Ni(II), and Pd(II) complexes have been synthesized and characterized by elemental analyses, molar conductance, magnetic susceptibility measurements, IR, NMR, and electronic spectral studies. IR spectra show that the ligands is coordinated to the metal ions in a didentate manner with N,S doner sites. In the presence of tow thiosemicarbazones ligands 2a(L 1 ) and 2b(L 2 ), the corrosion resistance of cast iron in 10.M H 2 SO 4 increases in the order, 2b(L 2 ) >2a(L 1 ). The effect of studied ligands inhibits the corrosion of cast iron extent depending on the structure and high donation of π-electron present inhibitor. Co(II) and Pd (II) complexes possess higher antimicrobial activity than free ligands and other complexes. The [L 1 Pd Cl 2 ]H 2 O complexe shows higher IC50 value of 4.6 µg/ml toward human breast cancer cell lines (MCF-7). For other complexes, European Scientific Journal January 2017 edition vol.13, No.3 ISSN: 1857 -7881 (Print) e -ISSN 1857 250 they are in the range of 2.7-4.3 µg/ml toward the former cells which is related to their metal complexing ability in enzymes.

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“…There have been many reports on the synthesis, structure-activity relationship, and the anticancer effects of these compounds. Several complexes, including thiourea-platinum [18] , -gold [19] , -iron [20] , and -copper [21] , have been synthesized. Thiourea derivatives of classic anticancer drugs such as camptothecin [22] and podophyllum [23] have also been synthesized and tested for the anticancer activities.…”

Section: Discussionmentioning

confidence: 99%