Synthesis of triphenylphosphonium dibenzothiophene S-oxide derivatives and their effect on cell cycle as photodeoxygenation-based cytotoxic agents.

Abstract:

:Photodeoxygenation of Dibenzothiophene-S-oxide (DBTO) in UV-A light produces atomic oxygen [O(3P)] and the corresponding sulfide, dibenzothiophene (DBT). Recently, DBTO has been derivatized to study the effect of UV-A light-driven photodeoxygenation in lipids, proteins, and nucleic acids. In this study, two DBTO derivatives with triphenylphosphonium groups were synthesized to promote mitochondrial accumulation. The sulfone analogs of these derivatives were also synthesized and used as fluorescent mitochondrial dyes to assess localization in mitochondria of HeLa cells. These derivatives were then used to study the effect of photodeoxygenation on MDA-MB-231 breast cancer cell line using cell viability assays, cell cycle phase determination tests, and RNA-Seq analysis. The DBTO derivatives were found to significantly decrease cell viability only after UV-A irradiation as a result of generating corresponding sulfides that were found to significantly affect gene expression and cell cycle.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Isor A,O'Dea AT,Petroff JT 2nd,Skubic KN,Grady SF,Arnatt CK,McCulla RD

doi

10.1016/j.bioorg.2020.104442

subject

Has Abstract

pub_date

2020-12-01 00:00:00

pages

104442

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(20)31740-5

journal_volume

105

pub_type

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