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 language | English (US) |
|---|---|
| Pages (from-to) | 12296-12304 |
| Number of pages | 9 |
| Journal | Journal of the American Chemical Society |
| Volume | 141 |
| Issue number | 31 |
| DOIs | |
| State | Published - Aug 7 2019 |
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ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
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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 journal › Article
TY - JOUR
T1 - A Supramolecular Approach for Modulated Photoprotection, Lysosomal Delivery, and Photodynamic Activity of a Photosensitizer
AU - Roy, Indranil
AU - Bobbala, Sharan
AU - Young, Ryan M.
AU - Beldjoudi, Yassine
AU - Nguyen, Minh T.
AU - Cetin, M. Mustafa
AU - Cooper, James A.
AU - Allen, Sean
AU - Anamimoghadam, Ommid
AU - Scott, Evan A.
AU - Wasielewski, Michael R.
AU - Stoddart, J. Fraser
PY - 2019/8/7
Y1 - 2019/8/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85071066994&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85071066994&partnerID=8YFLogxK
U2 - 10.1021/jacs.9b03990
DO - 10.1021/jacs.9b03990
M3 - Article
C2 - 31256588
AN - SCOPUS:85071066994
VL - 141
SP - 12296
EP - 12304
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 31
ER -