A lysosome-localized thionaphthalimide as a potential heavy-atom-free photosensitizer for selective photodynamic therapy

Van Nghia Nguyen, Gain Baek, Sujie Qi, Seonye Heo, Yubin Yim, Juyoung Yoon

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

A novel sulfur-substituted naphthalimide (LSNI-S) was synthesized and investigated as a promising lysosome-targeting photosensitizer for photodynamic cancer therapy. The introduction of a dual-functional morpholine group to the 4-position of the naphthalimide backbone combined with the substitution of oxygen atoms by sulfur atoms could facilitate intersystem crossing from the excited singlet state to the reactive triplet state, leading to an excellent singlet oxygen generation efficiency of LSNI-S in organic solvents (ΦΔ ≈ 0.84 in air-saturated acetonitrile). Interestingly, LSNI-S could produce reactive oxygen species via both type-I and type-II mechanisms under physiological conditions. In particular, cell studies demonstrated that LSNI-S selectively localizes in lysosomes of cancer cells and exhibits excellent photodynamic therapy efficacy.

Original languageEnglish
Article number108265
JournalDyes and Pigments
Volume177
DOIs
StatePublished - Jun 2020

Keywords

  • Heavy-atom-free photosensitizer
  • Intersystem crossing
  • Photodynamic therapy
  • Reactive oxygen species
  • Sulfur-substituted naphthalimide

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