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pH-Sensitive and Lysosome Targetable Photosensitizers Based on BODIPYs

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Abstract

Photodynamic therapy (PDT) is an effective and U.S. Food and Drug Administration (FDA) approved treatment for cancer and other diseases. Photosensitizer is one of the three key components that harvest the energy of light at a certain wavelength. Compared to the conventional fluorophores used as photosensitizers, boron dipyrromethene (BODIPY) derivatives have grown fast in recent years due to their low dark toxicity, versatile tunable sites, and easiness of being paired with other treatments. In this paper, two pH-sensitive BODIPY-based photosensitizers (BDC and BDBrC) were synthesized by adding carbazole moieties onto the BODIPY cores (BD and BDBr) through condensation reactions. BDBrC has two Br atoms at the BODIPY core that promote singlet oxygen generation and further red-shift the absorption maximum peak. Both compounds showed sensitivity toward pH change and generated more singlet oxygen under acidic conditions. The cellular uptake and cell imaging experiments showed that BDBrC can selectively target the lysosome organelle. The further dark cell viability and light cytotoxicity indicate the light triggered PDT treatment can be accomplished with BDBrC.

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Acknowledgements

We wish to acknowledge the support from the Department of Chemistry and Environmental Science at New Jersey Institute of Technology (NJIT).

Funding

New Jersey Health Foundation, PC 57-20.

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Authors and Affiliations

  1. Department of Chemistry and Environmental Science, College of Science and Liberal Arts, New Jersey Institute of Technology, 323 Martin Luther King Jr. Blvd, University Heights, Newark, NJ, 07102, USA

    Xiangshan Liu, Shupei Yu & Yuanwei Zhang

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  1. Xiangshan Liu
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  2. Shupei Yu
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  3. Yuanwei Zhang
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X.L. and Y.S., investigation, methodology, and writing original draft, Y.Z., supervision, project administration, and review & editing.

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Correspondence to Yuanwei Zhang.

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Liu, X., Yu, S. & Zhang, Y. pH-Sensitive and Lysosome Targetable Photosensitizers Based on BODIPYs. J Fluoresc (2024). https://doi.org/10.1007/s10895-023-03562-z

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