Open AccessCytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1 H )‐Quinolinones
Author(s) -
Porubský Martin,
Vychodilová Kristýna,
Milićević David,
Buděšinský Miloš,
Stanková Jarmila,
Džubák Petr,
Hajdúch Marián,
Hlaváč Jan
Publication year - 2021
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.202100025
Subject(s) - bodipy , linker , chemistry , cytotoxicity , glutathione , cytotoxic t cell , cysteine , amino acid , conjugate , maleimide , fluorescence , derivative (finance) , cleavage (geology) , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , in vitro , enzyme , biology , mathematical analysis , paleontology , physics , mathematics , quantum mechanics , fracture (geology) , computer science , economics , financial economics , operating system
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.