Balanced Intersystem Crossing in Iodinated Silicon-Fluoresceins Allows New Class of Red Shifted Theranostic Agents.


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Cetin S., Elmazoglu Z., Karaman O., Gunduz H., Günbaş E. G. , Kolemen S.

ACS medicinal chemistry letters, vol.12, pp.752-757, 2021 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 12
  • Publication Date: 2021
  • Doi Number: 10.1021/acsmedchemlett.1c00018
  • Journal Name: ACS medicinal chemistry letters
  • Journal Indexes: Science Citation Index Expanded, Scopus, BIOSIS, Chemical Abstracts Core, EMBASE
  • Page Numbers: pp.752-757
  • Keywords: Photodynamic therapy, cancer, theranostic, silicon-fluorescein, fluorescence imaging, SINGLET OXYGEN GENERATION, SUBSTITUTED XANTHENE DYES, PHOTODYNAMIC THERAPY, BODIPY DYES, CANCER, PHOTOSENSITIZERS, PROBES

Abstract

© 2021 The Authors. Published by American Chemical Society.Iodination of the silicon-fluorescein core revealed a new class of highly cytotoxic, red-shifted and water-soluble photosensitizer (SF-I) which is also fairly emissive to serve as a theranostic agent. Singlet oxygen generation capacity of SF-I was evaluated chemically, and up to 45% singlet oxygen quantum yield was reported in aqueous solutions. SF-I was further tested in triple negative breast (MDA MB-231) and colon (HCT-116) cancer cell lines, which are known to have limited chemotherapy options as well as very poor prognosis. SF-I induced efficient singlet oxygen generation and consequent photocytotoxicity in both cell lines upon light irradiation with a negligible dark toxicity while allowing cell imaging at the same time. SF-I marks the first ever example of a silicon xanthene-based photosensitizer and holds a lot of promise as a small-molecule-based theranostic scaffold.