Study on Redox Properties and Cytotoxicity of Anthraquinone Derivatives to Understand Antitumor Active Anthracycline Substances

Abstract

This study demonstrates the relation between the redox properties and cytotoxicity of anthraquinone derivatives with a hydroxyl and methoxy group. The redox behavior of the anthraquinone derivatives was initially observed via cyclic voltammetry and their characteristics were investigated using molecular orbital calculations. The cytotoxicity of the anthraquinone derivatives was then evaluated using human leukemia HL-60 and H 2 O 2 resistant HP100 cells, and its correlation with the redox properties of these compounds was investigated. Therefore, it was suggested that the anthraquinone derivatives express cytotoxicity through H 2 O 2 production, and that generation of the oxidized radical form influences their cytotoxicity.

Journey of anthraquinones as anticancer agents – a systematic review of recent literature

“…Cytotoxic studies against HL-60 and HP100 cells (using LDH activity assay) indicated that oxidized radicals played a significant role in inducing cell death. 78 The toxicity towards HL-60 increased with the increase in the concentration of 56. However, the toxicity in relation to HP100 was less than half the toxicity to HL-60, indicating that H 2 O 2 is involved in the process leading to cell death.…”

“…Specifically, the cytotoxicity observed against HL-60 could be ascribed to reactive oxygen species (ROS) originating from electron transfer to oxygen accompanying the formation of reduced or oxidized compound 56 radicals. 78 In another investigation, Roa-Linares et al synthesized 27 terphenyl-1,4-naphthoquinone (NQ), 1,4-anthraquinone (AQ), and heterocycle-fused quinone (HetQ) derivatives to evaluate their cytotoxicity against HeLa and Jurkat tumour cell lines. Compound 57 was found to be the most active against the tested cell lines, and the IC 50 values of 57 observed to be cell lines 0.010 μM, 1.4 μM, and 231.9 μM against HeLa ATCC CRL-1958, Jurkat ATCC TIB-152, and Vero ATCC CCL-81, respectively.…”

Phylobioactive hotspots in plant resources used to treat Chagas disease

“…The 9,10-anthracenedione scaffold is likely to interfere with the parasite redox system as anthraquinones can mediate the production of hydrogen peroxide or ROS via oxygen reduction in situ ( Campos-Martin et al., 2006 ). This is a feasible antichagasic mechanism as anthraquinones have been shown to interfere with redox reactions in cells ( Okumura et al, 2019 ). ROS generation is also the postulated mode of action of the approved antichagasic drug benznidazole ( Pedrosa et al, 2001 ).…”

Crystal structure and Hirshfeld surface analysis of 3,4-dihydro-2H-anthra[1,2-b][1,4]dioxepine-8,13-dione

“…Besides their application as pigments or dyes in textile, photographic, cosmetic and other industries (Wang et al, 2011), anthraquinone derivatives have been used for centuries for medical applications, for example, as laxatives (Oshio et al, 1985), antioxidants (Yen et al, 2000), antimicrobial (Xiang et al, 2008;Yadav et al, 2010) and anitiviral (Alves et al, 2004) agents. Their redox properties and cytotoxicity have been investigated recently (Okumura et al, 2019). Anthraquinone derivatives exhibit various applications in supramolecular and electro-analytical chemistry (Czupryniak et al, 2012).…”