Carboranyl-1,8-naphthalimide intercalators induce lysosomal membrane permeabilization and ferroptosis in cancer cell lines

The synthesis of carborane-1,8-naphthalimide conjugates and evaluation of their DNA-binding ability and anticancer activity were performed. A series of 4-carboranyl-3-nitro-1,8-naphthalimide derivatives, mitonafide and pinafide analogs, were synthesised via amidation and reductive amination reaction...

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Published in:Journal of enzyme inhibition and medicinal chemistry 2023-12, Vol.38 (1), p.2171028
Main Authors: Rykowski, Sebastian, Gurda-Woźna, Dorota, Fedoruk-Wyszomirska, Agnieszka, Orlicka-Płocka, Marta, Kowalczyk, Aleksandra, Stączek, Paweł, Denel-Bobrowska, Marta, Biniek-Antosiak, Katarzyna, Rypniewski, Wojciech, Wyszko, Eliza, Olejniczak, Agnieszka B.
Format: Article
Language:English
Subjects:
1,8-naphthalimides
anticancer activity
Antineoplastic Agents - chemistry
Antitumor activity
Biology
Calf thymus
Cancer
Carborane
Cell cycle
Cell Line
Cell Line, Tumor
Chemistry
Circular dichroism
Cytotoxicity
Deoxyribonucleic acid
DNA
DNA - chemistry
DNA topoisomerase (ATP-hydrolysing)
Ferroptosis
Glutathione
Intercalating Agents
intercalation
Lipid peroxidation
Lysosomes - metabolism
Membrane potential
Naphthalimides
Neoplasms
Pharmaceutical sciences
Reactive oxygen species
Research Paper
Spectroscopy
Thermal denaturation
Thymus gland
Tumor cell lines
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cited_by cdi_FETCH-LOGICAL-c562t-7d126b089df6b52b5de02133740fa3f457c288488573ab2e570891c6a6d9d9983
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container_title Journal of enzyme inhibition and medicinal chemistry
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creator Rykowski, Sebastian
Gurda-Woźna, Dorota
Fedoruk-Wyszomirska, Agnieszka
Orlicka-Płocka, Marta
Kowalczyk, Aleksandra
Stączek, Paweł
Denel-Bobrowska, Marta
Biniek-Antosiak, Katarzyna
Rypniewski, Wojciech
Wyszko, Eliza
Olejniczak, Agnieszka B.
description The synthesis of carborane-1,8-naphthalimide conjugates and evaluation of their DNA-binding ability and anticancer activity were performed. A series of 4-carboranyl-3-nitro-1,8-naphthalimide derivatives, mitonafide and pinafide analogs, were synthesised via amidation and reductive amination reactions, and their calf thymus DNA (ct-DNA)-binding properties were investigated using circular dichroism, UV-vis spectroscopy, and thermal denaturation. Results showed that conjugates 34-37 interacted very strongly with ct-DNA (ΔT m = 10.00-13.00 °C), indicating their ability to intercalate with DNA, but did not inhibit the activity of topoisomerase II. The conjugates inhibited the cell growth of the HepG2 cancer cell line in vitro. The same compounds caused the G2M phase arrest. Cell lines treated with these conjugates showed an increase in reactive oxygen species, glutathione, and Fe 2+ levels, lipid peroxidation, and mitochondrial membrane potential relative to controls, indicating the involvement of ferroptosis. Furthermore, these conjugates caused lysosomal membrane permeabilization in HepG2 cells but not in MRC-5 cells.
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A series of 4-carboranyl-3-nitro-1,8-naphthalimide derivatives, mitonafide and pinafide analogs, were synthesised via amidation and reductive amination reactions, and their calf thymus DNA (ct-DNA)-binding properties were investigated using circular dichroism, UV-vis spectroscopy, and thermal denaturation. Results showed that conjugates 34-37 interacted very strongly with ct-DNA (ΔT m = 10.00-13.00 °C), indicating their ability to intercalate with DNA, but did not inhibit the activity of topoisomerase II. The conjugates inhibited the cell growth of the HepG2 cancer cell line in vitro. The same compounds caused the G2M phase arrest. Cell lines treated with these conjugates showed an increase in reactive oxygen species, glutathione, and Fe 2+ levels, lipid peroxidation, and mitochondrial membrane potential relative to controls, indicating the involvement of ferroptosis. 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subjects 1,8-naphthalimides
anticancer activity
Antineoplastic Agents - chemistry
Antitumor activity
Biology
Calf thymus
Cancer
Carborane
Cell cycle
Cell Line
Cell Line, Tumor
Chemistry
Circular dichroism
Cytotoxicity
Deoxyribonucleic acid
DNA
DNA - chemistry
DNA topoisomerase (ATP-hydrolysing)
Ferroptosis
Glutathione
Intercalating Agents
intercalation
Lipid peroxidation
Lysosomes - metabolism
Membrane potential
Naphthalimides
Neoplasms
Pharmaceutical sciences
Reactive oxygen species
Research Paper
Spectroscopy
Thermal denaturation
Thymus gland
Tumor cell lines
title Carboranyl-1,8-naphthalimide intercalators induce lysosomal membrane permeabilization and ferroptosis in cancer cell lines
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