A glutathione responsive photosensitizer based on hypocrellin B for photodynamic therapy

Zhe Yu; Tian Liu; Xiuli Zheng; Yanping Wang; Jie Sha; Lin Shan; Tong Mu; Wenjun Zhang; Chun−Sing Lee; Weimin Liu; Pengfei Wang

doi:10.1016/j.saa.2024.125052

A glutathione responsive photosensitizer based on hypocrellin B for photodynamic therapy

Zhe Yu, Tian Liu, Xiuli Zheng, Yanping Wang, Jie Sha, Lin Shan, Tong Mu, Wenjun Zhang, Chun−Sing Lee, Weimin Liu^*, Pengfei Wang^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

5 Citations (Scopus)

Abstract

As a typical natural photosensitizer, hypocrellin B (HB) offers the advantages of high molar extinction coefficient, high phototoxicity, low dark toxicity, and fast metabolism in vivo. However, the lack of tumor specificity hinders its clinical applications. Herein, we designed and synthesized a glutathione (GSH) responsive photosensitizer based on HB. The 7 − nitro − 2,1,3 − benzoxadiazole (NBD) covalently connected to HB not only served as a fluorescence quenching group but also as a GSH activating group. The photosensitizer HB−NBD showed almost no fluorescence and singlet oxygen generation as a result of the photoinduced electron transfer between HB and NBD. The designed photosensitizer HB−NBD can be activated by GSH in solutions and cancer cells, and then obtain recuperative fluorescence and photosensitive activity. © 2024 Elsevier B.V.

Original language	English
Article number	125052
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	325
Online published	29 Aug 2024
DOIs	https://doi.org/10.1016/j.saa.2024.125052
Publication status	Published - 15 Jan 2025

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Research Keywords

Cancer cells
Glutathione
Hypocrellin B
Photocytotoxicity
Photodynamic therapy

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10.1016/j.saa.2024.125052

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title = "A glutathione responsive photosensitizer based on hypocrellin B for photodynamic therapy",

abstract = "As a typical natural photosensitizer, hypocrellin B (HB) offers the advantages of high molar extinction coefficient, high phototoxicity, low dark toxicity, and fast metabolism in vivo. However, the lack of tumor specificity hinders its clinical applications. Herein, we designed and synthesized a glutathione (GSH) responsive photosensitizer based on HB. The 7 − nitro − 2,1,3 − benzoxadiazole (NBD) covalently connected to HB not only served as a fluorescence quenching group but also as a GSH activating group. The photosensitizer HB−NBD showed almost no fluorescence and singlet oxygen generation as a result of the photoinduced electron transfer between HB and NBD. The designed photosensitizer HB−NBD can be activated by GSH in solutions and cancer cells, and then obtain recuperative fluorescence and photosensitive activity. {\textcopyright} 2024 Elsevier B.V.",

keywords = "Cancer cells, Glutathione, Hypocrellin B, Photocytotoxicity, Photodynamic therapy",

author = "Zhe Yu and Tian Liu and Xiuli Zheng and Yanping Wang and Jie Sha and Lin Shan and Tong Mu and Wenjun Zhang and Chun−Sing Lee and Weimin Liu and Pengfei Wang",

year = "2025",

month = jan,

day = "15",

doi = "10.1016/j.saa.2024.125052",

language = "English",

volume = "325",

journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",

issn = "1386-1425",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - A glutathione responsive photosensitizer based on hypocrellin B for photodynamic therapy

AU - Yu, Zhe

AU - Liu, Tian

AU - Zheng, Xiuli

AU - Wang, Yanping

AU - Sha, Jie

AU - Shan, Lin

AU - Mu, Tong

AU - Zhang, Wenjun

AU - Lee, Chun−Sing

AU - Liu, Weimin

AU - Wang, Pengfei

PY - 2025/1/15

Y1 - 2025/1/15

N2 - As a typical natural photosensitizer, hypocrellin B (HB) offers the advantages of high molar extinction coefficient, high phototoxicity, low dark toxicity, and fast metabolism in vivo. However, the lack of tumor specificity hinders its clinical applications. Herein, we designed and synthesized a glutathione (GSH) responsive photosensitizer based on HB. The 7 − nitro − 2,1,3 − benzoxadiazole (NBD) covalently connected to HB not only served as a fluorescence quenching group but also as a GSH activating group. The photosensitizer HB−NBD showed almost no fluorescence and singlet oxygen generation as a result of the photoinduced electron transfer between HB and NBD. The designed photosensitizer HB−NBD can be activated by GSH in solutions and cancer cells, and then obtain recuperative fluorescence and photosensitive activity. © 2024 Elsevier B.V.

AB - As a typical natural photosensitizer, hypocrellin B (HB) offers the advantages of high molar extinction coefficient, high phototoxicity, low dark toxicity, and fast metabolism in vivo. However, the lack of tumor specificity hinders its clinical applications. Herein, we designed and synthesized a glutathione (GSH) responsive photosensitizer based on HB. The 7 − nitro − 2,1,3 − benzoxadiazole (NBD) covalently connected to HB not only served as a fluorescence quenching group but also as a GSH activating group. The photosensitizer HB−NBD showed almost no fluorescence and singlet oxygen generation as a result of the photoinduced electron transfer between HB and NBD. The designed photosensitizer HB−NBD can be activated by GSH in solutions and cancer cells, and then obtain recuperative fluorescence and photosensitive activity. © 2024 Elsevier B.V.

KW - Cancer cells

KW - Glutathione

KW - Hypocrellin B

KW - Photocytotoxicity

KW - Photodynamic therapy

UR - http://www.scopus.com/inward/record.url?scp=85202926080&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85202926080&origin=recordpage

U2 - 10.1016/j.saa.2024.125052

DO - 10.1016/j.saa.2024.125052

M3 - RGC 21 - Publication in refereed journal

SN - 1386-1425

VL - 325

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

M1 - 125052

ER -

A glutathione responsive photosensitizer based on hypocrellin B for photodynamic therapy

Abstract

UN SDGs

Research Keywords

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