Inclusion of the in-chain sulfur in 3-thiaCTU increases the efficiency of mitochondrial targeting and cell killing by anticancer aryl-urea fatty acids

Rahman, Md Khalilur; Umashankar, Balasubrahmanyam; Choucair, Hassan; Pazderka, Curtis; Bourget, Kirsi; Chen, Yongjuan; Dunstan, Colin R.; Rawling, Tristan; Murray, Michael T.

doi:10.1016/j.ejphar.2022.175470

European Journal of Pharmacology

2023

DOI: 10.1016/j.ejphar.2022.175470

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Inclusion of the in-chain sulfur in 3-thiaCTU increases the efficiency of mitochondrial targeting and cell killing by anticancer aryl-urea fatty acids

Md Khalilur Rahman

Balasubrahmanyam Umashankar

Hassan Choucair

et al.

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2024

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Cited by 2 publications

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Carbon Chain Length in a Novel Anticancer Aryl‐Urea Fatty Acid Modulates Mitochondrial Targeting, Reactive Oxygen Species Production and Cell Killing

Elmaghrabi,

Roseblade,

Rahman

et al. 2024

ChemMedChem

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The cancer cell mitochondrion could be a promising target for the development of new anticancer agents. 16‐([3‐chloro‐5‐(trifluoromethyl)‐phenyl]carbamoylamino)hexadecanoic acid (2) is a novel aryl‐urea fatty acid that targets the mitochondrion in MDA‐MB‐231 breast cancer cells and activates cell death. In the present study, the relationships between alkyl chain length in 2 analogues, mitochondrial disruption and cell killing were evaluated. The chain‐contracted C13‐analogue 7c optimally disrupted the mitochondrial membrane potential (IC50 4.8±0.8 µM). In addition, annexin V‐FITC/7‐AAD assays demonstrated that 7c was most effective cell killing analogue and C11 BODIPY (581/591) assays demonstrated that 7c was also most effective in generating reactive oxygen species in MDA‐MB‐231 cells. Together, carbon chain length is a key factor that determine the capacity of 2 analogues to disrupt the mitochondrial membrane, induce the production of reactive oxygen species and kill breast cancer cells. As an aryl‐urea with enhanced activity and improved drug‐like properties, 7c may be a suitable lead molecule for entry into a program of development of these molecules as anticancer agents.

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Carbon Chain Length in a Novel Anticancer Aryl‐Urea Fatty Acid Modulates Mitochondrial Targeting, Reactive Oxygen Species Production and Cell Killing

Elmaghrabi,

Roseblade,

Rahman

et al. 2024

ChemMedChem

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show abstract

Omega-3 polyunsaturated fatty acid derived lipid mediators: a comprehensive update on their application in anti-cancer drug discovery

Murray

2024

Expert Opinion on Drug Discovery

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Inclusion of the in-chain sulfur in 3-thiaCTU increases the efficiency of mitochondrial targeting and cell killing by anticancer aryl-urea fatty acids

Cited by 2 publications

References 59 publications

Carbon Chain Length in a Novel Anticancer Aryl‐Urea Fatty Acid Modulates Mitochondrial Targeting, Reactive Oxygen Species Production and Cell Killing

Carbon Chain Length in a Novel Anticancer Aryl‐Urea Fatty Acid Modulates Mitochondrial Targeting, Reactive Oxygen Species Production and Cell Killing

Omega-3 polyunsaturated fatty acid derived lipid mediators: a comprehensive update on their application in anti-cancer drug discovery

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