Turning an Antioxidant into a Prooxidant : Light-induced Mitochondrial Apoptosis in Mammalian Cells by an Ergothioneine-based Neutral Small Molecule /

By: Contributor(s): Material type: TextTextLanguage: en Publication details: Bangalore : Indian Institute of Science, 2025Description: viii, 201 p. : col. ill. ; e-Thesis 18.98 MbSubject(s): DDC classification:
  • 616.01816 PUN
Online resources: Dissertation note: PhD ; 2025 ; Inorganic and Physical Chemistry (IPC) Summary: Mitochondria-targeted compounds gained significant interest due to their applications in fundamental research, diagnostics, and therapeutics. In this work, we present a detailed investigation of the ergothioneine-based mitochondria-targeted neutral molecule, which is an antioxidant in the dark and turns prooxidant in light inside mammalian cells. This molecule was designed using a fragment-based approach for simultaneous mitochondrial imaging and targeted antioxidant activity. However, it forms a charge-separated state within 10 picoseconds under visible light, leading to triplet-state formation upon charge recombination. Mitochondrial biomolecules first reduce this redox-active triplet state to its one-electron reduced form, which reduces molecular oxygen via one-electron transfer to form superoxide radicals selectively inside mitochondria. This leads to mitochondrial lipid peroxidation, increased mitochondrial membrane permeability transition pore formation, mitochondrial depolarization, and eventually, apoptotic cell death.
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PhD ; 2025 ; Inorganic and Physical Chemistry (IPC)

Mitochondria-targeted compounds gained significant interest due to their applications in fundamental research, diagnostics, and therapeutics. In this work, we present a detailed investigation of the ergothioneine-based mitochondria-targeted neutral molecule, which is an antioxidant in the dark and turns prooxidant in light inside mammalian cells. This molecule was designed using a fragment-based approach for simultaneous mitochondrial imaging and targeted antioxidant activity. However, it forms a charge-separated state within 10 picoseconds under visible light, leading to triplet-state formation upon charge recombination. Mitochondrial biomolecules first reduce this redox-active triplet state to its one-electron reduced form, which reduces molecular oxygen via one-electron transfer to form superoxide radicals selectively inside mitochondria. This leads to mitochondrial lipid peroxidation, increased mitochondrial membrane permeability transition pore formation, mitochondrial depolarization, and eventually, apoptotic cell death.

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