Portal de investigación
Decyl-riboflavin: membrane-targeted lipophilic photosensitizer for lipid peroxidation and phototoxicity in HeLa cells under blue light irradiation.
Fecha de publicación:
Fecha Ahead of Print:
Autores de IIS La Fe
Participantes ajenos a IIS La Fe
- Ardila Padilla CA
- Uribe Mayor MS
- Urrutia MN
- Rodríguez-Muñiz GM
- Thomas AH
- Dántola ML
- Lhiaubet-Vallet V
- Layana C
- Vignoni M
Grupos
Abstract
Photodynamic therapy (PDT) exploits the controlled generation of reactive species to selectively destroy target cells, offering a minimally invasive alternative to conventional cancer and antimicrobial treatments. A key determinant of PDT efficacy is the ability of the photosensitizer (PS) to localize within lipid membranes, where proximity to polyunsaturated lipids maximizes oxidative damage. Riboflavin (Rf, Vitamin B(2)) is a biocompatible, naturally occurring PS with absorption in the blue light range; however, its inherent hydrophilicity limits membrane interaction. Here, we report the photochemical and biological characterization of 3-decyl-riboflavin (decyl-Rf), a lipophilic Rf derivative designed to direct oxidative damage specifically to the lipid bilayer under blue LED irradiation. Decyl-Rf generates singlet oxygen (Type II) while simultaneously operating through a Type I mechanism. This dual capacity translates into extensive lipid peroxidation and membrane disruption in biomimetic systems, effects essentially absent for hydrophilic Rf. Interaction studies with serum albumin reveal strong ground-state complex formation, which markedly reduces cellular uptake under serum-containing conditions. In HeLa cells, decyl-Rf is efficiently internalized and localizes preferentially in lipid-rich compartments, inducing significant phototoxicity upon blue light irradiation. These results position decyl-Rf as a potent membrane-targeted PS, with its lipid peroxidation capacity suggesting a possible contribution to regulated cell death pathways and provide a mechanistic foundation for lipophilic flavin derivatives as next-generation agents for blue light PDT in oncological and antimicrobial applications.
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Datos de la publicación
- ISSN/ISSNe:
- 0891-5849, 1873-4596
- Tipo:
- Article
- Páginas:
- 381-392
- PubMed:
- 42521042
- Factor de Impacto:
- 1,562 SCImago ℠
- Cuartil:
- Q1 SCImago ℠
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