Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones

Abstract 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′ co...

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Autores principales:	Martin Porubský, Dr. Kristýna Vychodilová, Dr. David Milićević, Dr. Miloš Buděšinský, Jarmila Stanková, Dr. Petr Džubák, Dr. Marián Hajdúch, Prof. Jan Hlaváč
Formato:	article
Lenguaje:	EN
Publicado:	Wiley-VCH 2021
Materias:	amino-BODIPY dyes cytotoxic activity disulfide linkers glutathione hydroxyquinolinones Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/b742bb9e8e714762a46d3291b7ddfd4f
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spelling	oai:doaj.org-article:b742bb9e8e714762a46d3291b7ddfd4f2021-11-27T06:12:47ZCytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones2191-136310.1002/open.202100025https://doaj.org/article/b742bb9e8e714762a46d3291b7ddfd4f2021-11-01T00:00:00Zhttps://doi.org/10.1002/open.202100025https://doaj.org/toc/2191-1363Abstract 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.Martin PorubskýDr. Kristýna VychodilováDr. David MilićevićDr. Miloš BuděšinskýJarmila StankováDr. Petr DžubákDr. Marián HajdúchProf. Jan HlaváčWiley-VCHarticleamino-BODIPY dyescytotoxic activitydisulfide linkersglutathionehydroxyquinolinonesChemistryQD1-999ENChemistryOpen, Vol 10, Iss 11, Pp 1104-1110 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	amino-BODIPY dyes cytotoxic activity disulfide linkers glutathione hydroxyquinolinones Chemistry QD1-999
spellingShingle	amino-BODIPY dyes cytotoxic activity disulfide linkers glutathione hydroxyquinolinones Chemistry QD1-999 Martin Porubský Dr. Kristýna Vychodilová Dr. David Milićević Dr. Miloš Buděšinský Jarmila Stanková Dr. Petr Džubák Dr. Marián Hajdúch Prof. Jan Hlaváč Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones
description	Abstract 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.
format	article
author	Martin Porubský Dr. Kristýna Vychodilová Dr. David Milićević Dr. Miloš Buděšinský Jarmila Stanková Dr. Petr Džubák Dr. Marián Hajdúch Prof. Jan Hlaváč
author_facet	Martin Porubský Dr. Kristýna Vychodilová Dr. David Milićević Dr. Miloš Buděšinský Jarmila Stanková Dr. Petr Džubák Dr. Marián Hajdúch Prof. Jan Hlaváč
author_sort	Martin Porubský
title	Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones
title_short	Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones
title_full	Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones
title_fullStr	Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones
title_full_unstemmed	Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones
title_sort	cytotoxicity of amino‐bodipy modulated via conjugation with 2‐phenyl‐3‐hydroxy‐4(1h)‐quinolinones
publisher	Wiley-VCH
publishDate	2021
url	https://doaj.org/article/b742bb9e8e714762a46d3291b7ddfd4f
work_keys_str_mv	AT martinporubsky cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones AT drkristynavychodilova cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones AT drdavidmilicevic cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones AT drmilosbudesinsky cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones AT jarmilastankova cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones AT drpetrdzubak cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones AT drmarianhajduch cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones AT profjanhlavac cytotoxicityofaminobodipymodulatedviaconjugationwith2phenyl3hydroxy41hquinolinones
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Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones

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