In vitro production of reactive oxygen species (ROS) by sampangine

Oxoisoaporphines and Aporphines: Versatile Molecules with Anticancer Effects

“…Sampangine is structurally close to the marine alkaloid ascidemin (Figure 4). The structure is composed of four aromatic rings that include two N heteroatoms in the A and B ring, and quinone group (C=O) in the C ring [32,100].…”

“…Nasiri et al demonstrated that sampangine produces ROS in vitro without the involvement of cellular components in a heme-independent manner. They evaluated the ROS production using DTT (dithiotheitol) as a mild reducing agent and observed that radical production occurs directly on the iminoquinone toxicophore of sampangine [32]. The planar geometry of sampangine suggests the potential DNA interaction through intercalation between adjacent base pairs.…”

“…For sampangine and derivates of this family, their anticancer mechanism is not achieved by a direct interaction with DNA or telomerase, but is mainly through ROS production [32]. ROS are highly reactive molecules that are partially reduced oxygen derivates, which have a single unpaired electron acting as a second messenger in different cellular processes, both in normal and cancer cells [33].…”

“…In the case of sampangines compounds, their mechanisms of action are related with induced cell death via apoptosis through ROS modulation [31,32] interfering with immortality and avoiding cell death hallmarks of cancer cells. Nevertheless, more research could be developed to fully understand the effects of oxoisoporphines and aporphines with hallmarks of cancer cell, as a part of the rationale design of cancer therapies based on this molecule.…”

Synthesis and Biological Screening of New Lawson Derivatives as Selective Substrate‐Based Inhibitors of Cytochrome bo3 Ubiquinol Oxidase from Escherichia coli

“…[2] The naphthalenebased 1,4-diketone compounds are interacting with a broad spectrum of biological targets through two different mechanisms, by either forming covalent bonds due to their electro-philic properties or reducing oxygen. [3,4] Derivatization of the 1,4-naphthoquinones scaffold into novel inhibitors opens potential avenues to increase the possibility of interaction with biological molecules, in particular also to gain target specificity [5][6][7] Consequently, the inhibitory properties of 1,4naphthoquinones and their derivatives have been elucidated in multiple studies presenting, for example, antimalarial, [8][9][10] anticancer, [11][12][13] antibacterial, [14,15] antiseptic or cytotoxic [16,17] activities. The respiratory chain of E. coli performs redox chemistry by exclusively using quinols as electron carriers.…”