A Supramolecular Approach for Modulated Photoprotection, Lysosomal Delivery, and Photodynamic Activity of a Photosensitizer

Indranil Roy, Sharan Bobbala, Ryan M. Young, Yassine Beldjoudi, Minh T. Nguyen, M. Mustafa Cetin, James A. Cooper, Sean Allen, Ommid Anamimoghadam, Evan A. Scott, Michael R. Wasielewski, J. Fraser Stoddart

Research output: Contribution to journalArticle

Abstract

Prompted by a knowledge of the photoprotective mechanism operating in photosystem supercomplexes and bacterial antenna complexes by pigment binding proteins, we have appealed to a boxlike synthetic receptor (ExBox·4Cl) that binds a photosensitizer, 5,15-diphenylporphyrin (DPP), to provide photoprotection by regulating light energy. The hydrophilic ExBox4+ renders DPP soluble in water and modulates the phototoxicity of DPP by trapping it in its cavity and releasing it when required. While trapping removes access to the DPP triplet state, a pH-dependent release of diprotonated DPP (DPPH2 2+) restores the triplet deactivation pathway, thereby activating its ability to generate reactive oxygen species. We have employed the ExBox4+-bound DPP complex (ExBox4+⊃DPP) for the safe delivery of DPP into the lysosomes of cancer cells, imaging the cells by utilizing the fluorescence of the released DPPH2 2+ and regulating photodynamic therapy to kill cancer cells with high efficiency.

Original languageEnglish
Pages (from-to)12296-12304
Number of pages9
JournalJournal of the American Chemical Society
Volume141
Issue number31
DOIs
Publication statusPublished - Aug 7 2019

Fingerprint

Photosensitizing Agents
Photosensitizers
Cells
Antennas
Photodynamic therapy
Pigments
Fluorescence
Imaging techniques
Oxygen
Water
Artificial Receptors
Phototoxic Dermatitis
5,15-diphenylporphyrin
Photochemotherapy
Lysosomes
Reactive Oxygen Species
Neoplasms
Carrier Proteins
Light

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Roy, I., Bobbala, S., Young, R. M., Beldjoudi, Y., Nguyen, M. T., Cetin, M. M., ... Stoddart, J. F. (2019). A Supramolecular Approach for Modulated Photoprotection, Lysosomal Delivery, and Photodynamic Activity of a Photosensitizer. Journal of the American Chemical Society, 141(31), 12296-12304. https://doi.org/10.1021/jacs.9b03990

A Supramolecular Approach for Modulated Photoprotection, Lysosomal Delivery, and Photodynamic Activity of a Photosensitizer. / Roy, Indranil; Bobbala, Sharan; Young, Ryan M.; Beldjoudi, Yassine; Nguyen, Minh T.; Cetin, M. Mustafa; Cooper, James A.; Allen, Sean; Anamimoghadam, Ommid; Scott, Evan A.; Wasielewski, Michael R.; Stoddart, J. Fraser.

In: Journal of the American Chemical Society, Vol. 141, No. 31, 07.08.2019, p. 12296-12304.

Research output: Contribution to journalArticle

Roy, I, Bobbala, S, Young, RM, Beldjoudi, Y, Nguyen, MT, Cetin, MM, Cooper, JA, Allen, S, Anamimoghadam, O, Scott, EA, Wasielewski, MR & Stoddart, JF 2019, 'A Supramolecular Approach for Modulated Photoprotection, Lysosomal Delivery, and Photodynamic Activity of a Photosensitizer', Journal of the American Chemical Society, vol. 141, no. 31, pp. 12296-12304. https://doi.org/10.1021/jacs.9b03990
Roy, Indranil ; Bobbala, Sharan ; Young, Ryan M. ; Beldjoudi, Yassine ; Nguyen, Minh T. ; Cetin, M. Mustafa ; Cooper, James A. ; Allen, Sean ; Anamimoghadam, Ommid ; Scott, Evan A. ; Wasielewski, Michael R. ; Stoddart, J. Fraser. / A Supramolecular Approach for Modulated Photoprotection, Lysosomal Delivery, and Photodynamic Activity of a Photosensitizer. In: Journal of the American Chemical Society. 2019 ; Vol. 141, No. 31. pp. 12296-12304.
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