Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones
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...
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| Published in | ChemistryOpen (Weinheim) Vol. 10; no. 11; pp. 1104 - 1110 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
John Wiley & Sons, Inc
01.11.2021
John Wiley and Sons Inc Wiley-VCH |
| Subjects | |
| Online Access | Get full text |
| ISSN | 2191-1363 2191-1363 |
| DOI | 10.1002/open.202100025 |
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| 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.
Amino‐BODIPY conjugates with various 2‐phenyl‐3‐hydroxyquinolinones (3‐HQs) connected via cleavable disulfide linker and non‐cleavable maleimide linker were prepared and tested on cytotoxic activity and fluorescent ratiometric “OFF‐ON” monitoring of cleavage inside the cells was demonstrated. Disulfide conjugates exhibited improved cytotoxicity compared to the free 3‐HQs whereas non‐cleavable maleimide conjugates stayed inactive proving that disulfide linker is responsible for cleavage inside the cells and therefore resulting in cytotoxicity of disulfide Amino‐BODIPY‐3HQ conjugates. |
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| AbstractList | 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.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. 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. 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. Amino‐BODIPY conjugates with various 2‐phenyl‐3‐hydroxyquinolinones (3‐HQs) connected via cleavable disulfide linker and non‐cleavable maleimide linker were prepared and tested on cytotoxic activity and fluorescent ratiometric “OFF‐ON” monitoring of cleavage inside the cells was demonstrated. Disulfide conjugates exhibited improved cytotoxicity compared to the free 3‐HQs whereas non‐cleavable maleimide conjugates stayed inactive proving that disulfide linker is responsible for cleavage inside the cells and therefore resulting in cytotoxicity of disulfide Amino‐BODIPY‐3HQ conjugates. 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. Amino‐BODIPY conjugates with various 2‐phenyl‐3‐hydroxyquinolinones (3‐HQs) connected via cleavable disulfide linker and non‐cleavable maleimide linker were prepared and tested on cytotoxic activity and fluorescent ratiometric “OFF‐ON” monitoring of cleavage inside the cells was demonstrated. Disulfide conjugates exhibited improved cytotoxicity compared to the free 3‐HQs whereas non‐cleavable maleimide conjugates stayed inactive proving that disulfide linker is responsible for cleavage inside the cells and therefore resulting in cytotoxicity of disulfide Amino‐BODIPY‐3HQ conjugates. 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. 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. |
| Author | Milićević, David Hajdúch, Marián Buděšinský, Miloš Porubský, Martin Vychodilová, Kristýna Stanková, Jarmila Hlaváč, Jan Džubák, Petr |
| AuthorAffiliation | 3 Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám. 542/2 160 00 Prague Czech Republic 1 Department of Organic Chemistry Faculty of Science Palacký University Tř. 17. Listopadu 12 771 46 Olomouc Czech Republic 2 Institute of Molecular and Translational Medicine Faculty of Medicine and Dentistry Palacký University Hněvotínská 5 779 00 Olomouc Czech Republic |
| AuthorAffiliation_xml | – name: 3 Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám. 542/2 160 00 Prague Czech Republic – name: 1 Department of Organic Chemistry Faculty of Science Palacký University Tř. 17. Listopadu 12 771 46 Olomouc Czech Republic – name: 2 Institute of Molecular and Translational Medicine Faculty of Medicine and Dentistry Palacký University Hněvotínská 5 779 00 Olomouc Czech Republic |
| Author_xml | – sequence: 1 givenname: Martin surname: Porubský fullname: Porubský, Martin organization: Palacký University – sequence: 2 givenname: Kristýna surname: Vychodilová fullname: Vychodilová, Kristýna organization: Palacký University – sequence: 3 givenname: David surname: Milićević fullname: Milićević, David organization: Palacký University – sequence: 4 givenname: Miloš surname: Buděšinský fullname: Buděšinský, Miloš organization: Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences – sequence: 5 givenname: Jarmila surname: Stanková fullname: Stanková, Jarmila organization: Palacký University – sequence: 6 givenname: Petr surname: Džubák fullname: Džubák, Petr organization: Palacký University – sequence: 7 givenname: Marián surname: Hajdúch fullname: Hajdúch, Marián organization: Palacký University – sequence: 8 givenname: Jan surname: Hlaváč fullname: Hlaváč, Jan email: jan.hlavac@upol.cz organization: Palacký University |
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| Keywords | disulfide linkers cytotoxic activity amino-BODIPY dyes hydroxyquinolinones glutathione |
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| Snippet | 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... 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... 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... 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... |
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| SubjectTerms | amino-BODIPY dyes Cancer Cleavage Conjugation cytotoxic activity Cytotoxicity disulfide linkers Disulfides Dyes Fibroblasts Fluorescence Fluorescent Dyes Glutathione hydroxyquinolinones Leukemia Microscopy Quinolones - toxicity Toxicity |
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| Title | Cytotoxicity of Amino‐BODIPY Modulated via Conjugation with 2‐Phenyl‐3‐Hydroxy‐4(1H)‐Quinolinones |
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