0545174 - ÚOCHB 2022 RIV DE eng J - Journal Article
Porubský, M. - Vychodilová, K. - Milićević, D. - Buděšínský, Miloš - Stanková, J. - Džubák, P. - Hajdúch, M. - Hlaváč, J.
Cytotoxicity of Amino-BODIPY Modulated via Conjugation with 2-Phenyl-3-Hydroxy-4(1H)-Quinolinones.
ChemistryOpen. Roč. 10, č. 11 (2021), s. 1104-1110. ISSN 2191-1363. E-ISSN 2191-1363
Research Infrastructure: CZ-OPENSCREEN III - 90130; EATRIS-CZ III - 90133
Institutional support: RVO:61388963
Keywords : amino-BODIPY dyes * cytotoxic activity * disulfide linkers * glutathione * hydroxyquinolinones
OECD category: Organic chemistry
Impact factor: 2.630, year: 2021
Method of publishing: Open access
https://doi.org/10.1002/open.202100025

The combination of cytotoxic amino-BODIPY dye and 2-phenyl-3-hydroxy-4(1H)-quinolinone (3-HQ) derivatives into one molecule gave rise to selective activity against lymphoblastic or myeloid leukemia and the simultaneous disappearance of the cytotoxicity against normal cells. Both species′ conjugation can be realized via a disulfide linker cleavable in the presence of glutathione characteristic for cancer cells. The cleavage liberating the free amino-BODIPY dye and 3-HQ derivative can be monitored by ratiometric fluorescence or by the OFF-ON effect of the amino-BODIPY dye. A similar cytotoxic activity is observed when the amino-BODIPY dye and 3-HQ derivative are connected through a non-cleavable maleimide linker. The work reports the synthesis of several conjugates, the study of their cleavage inside cells, and cytotoxic screening.
Permanent Link: http://hdl.handle.net/11104/0321921