Tumor microenvironment-activated nanosystems with selenophenol substituted BODIPYs as photosensitizers for photodynamic therapy

Wei Gao; Ming Li; Ge Xu; Rongchen Wang; Ben Shi; Tianli Zhu; Jie Gao; Xianfeng Gu; Ping Shi; Chunchang Zhao

doi:10.1016/j.bmcl.2019.126854

Tumor microenvironment-activated nanosystems with selenophenol substituted BODIPYs as photosensitizers for photodynamic therapy

Bioorg Med Chem Lett. 2020 Jan 15;30(2):126854. doi: 10.1016/j.bmcl.2019.126854. Epub 2019 Dec 3.

Authors

Wei Gao¹, Ming Li², Ge Xu¹, Rongchen Wang¹, Ben Shi¹, Tianli Zhu¹, Jie Gao³, Xianfeng Gu⁴, Ping Shi⁵, Chunchang Zhao⁶

Affiliations

¹ Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, PR China.
² State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, PR China.
³ Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, PR China.
⁴ Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, PR China. Electronic address: xfgu@fudan.edu.cn.
⁵ State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, PR China. Electronic address: ship@ecust.edu.cn.
⁶ Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, PR China. Electronic address: zhaocchang@ecust.edu.cn.

PMID: 31859157
DOI: 10.1016/j.bmcl.2019.126854

Abstract

NIR-light-absorbing photosensitizers with the capability of selective localization and activation in tumor regions are of great importance for practical photodynamic therapy (PDT). Here, selenophenol substituted BODIPYs were designed and synthesized as new photosensitizers for PDT. One of these obtained BODIPYs, IBSeOV, possesses an intense and low energy absorption with a high singlet oxygen quantum yield (Φ_Δ = 60%). Considering manganese dioxide (MnO₂) nanosheets as versatile nanocarriers in cancer theranostics, nanosystem IBSeOV/MnO₂ was then fabricated to furnish tumor environment selective activation. Such designed nanoplatform allowed for GSH-controllable ¹O₂ production and exhibited low cytotoxicity in dark but good photocytotoxicity to cancer cells. The in vivo antitumor outcome suggested the high treatment efficiency of IBSeOV/MnO₂ for tumor therapy.

Keywords: BODIPY; MnO(2) nanosheets; Photodynamic therapy; Photosensitizer.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / pharmacology
Benzene Derivatives / therapeutic use*
Humans
Nanostructures
Organoselenium Compounds / pharmacology
Organoselenium Compounds / therapeutic use*
Photochemotherapy / methods*
Photosensitizing Agents / pharmacology
Photosensitizing Agents / therapeutic use*
Tumor Microenvironment

Substances

Benzene Derivatives
Organoselenium Compounds
Photosensitizing Agents
benzeneselenol