New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion
Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained c...
| Main Authors: | , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/23/8575 |
| _version_ | 1827642825509961728 |
|---|---|
| author | Julia Laskova Alexander Serdyukov Irina Kosenko Ivan Ananyev Ekaterina Titova Anna Druzina Igor Sivaev Anastasia A. Antonets Alexey A. Nazarov Vladimir I. Bregadze |
| author_facet | Julia Laskova Alexander Serdyukov Irina Kosenko Ivan Ananyev Ekaterina Titova Anna Druzina Igor Sivaev Anastasia A. Antonets Alexey A. Nazarov Vladimir I. Bregadze |
| author_sort | Julia Laskova |
| collection | DOAJ |
| description | Novel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with <i>closo</i>-dodecaborate derivative bearing terminal alkynyl group. Cu<sup>I</sup> catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugates formation. The absorption–emission spectra of the formed conjugates have been presented. The antiproliferative activity and uptake of compounds against several human cell lines were evaluated. |
| first_indexed | 2024-03-09T17:38:25Z |
| format | Article |
| id | doaj.art-1dce95a8dac34072a25ba05a2aa3a906 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T17:38:25Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1dce95a8dac34072a25ba05a2aa3a9062023-11-24T11:44:30ZengMDPI AGMolecules1420-30492022-12-012723857510.3390/molecules27238575New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate AnionJulia Laskova0Alexander Serdyukov1Irina Kosenko2Ivan Ananyev3Ekaterina Titova4Anna Druzina5Igor Sivaev6Anastasia A. Antonets7Alexey A. Nazarov8Vladimir I. Bregadze9A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, RussiaN.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Avenue, 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, RussiaDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, RussiaDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, RussiaA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119334 Moscow, RussiaNovel fluorescent 7-methoxy- and 7-(diethylamino)-coumarins modified with azido-group on the side chain have been synthesized. Their photophysical properties and single crystals structure characteristics have been studied. In order to demonstrate the possibilities of fluorescent labeling, obtained coumarins have been tested with <i>closo</i>-dodecaborate derivative bearing terminal alkynyl group. Cu<sup>I</sup> catalyzed Huisgen 1,3-dipolar cycloaddition reaction has led to fluorescent conjugates formation. The absorption–emission spectra of the formed conjugates have been presented. The antiproliferative activity and uptake of compounds against several human cell lines were evaluated.https://www.mdpi.com/1420-3049/27/23/8575coumarinsazido derivativescloso-dodecaborate“click” reactionfluorescent labelingcellular uptake |
| spellingShingle | Julia Laskova Alexander Serdyukov Irina Kosenko Ivan Ananyev Ekaterina Titova Anna Druzina Igor Sivaev Anastasia A. Antonets Alexey A. Nazarov Vladimir I. Bregadze New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion Molecules coumarins azido derivatives closo-dodecaborate “click” reaction fluorescent labeling cellular uptake |
| title | New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion |
| title_full | New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion |
| title_fullStr | New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion |
| title_full_unstemmed | New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion |
| title_short | New Azido Coumarins as Potential Agents for Fluorescent Labeling and Their “Click” Chemistry Reactions for the Conjugation with <i>closo</i>-Dodecaborate Anion |
| title_sort | new azido coumarins as potential agents for fluorescent labeling and their click chemistry reactions for the conjugation with i closo i dodecaborate anion |
| topic | coumarins azido derivatives closo-dodecaborate “click” reaction fluorescent labeling cellular uptake |
| url | https://www.mdpi.com/1420-3049/27/23/8575 |
| work_keys_str_mv | AT julialaskova newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT alexanderserdyukov newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT irinakosenko newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT ivanananyev newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT ekaterinatitova newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT annadruzina newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT igorsivaev newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT anastasiaaantonets newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT alexeyanazarov newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion AT vladimiribregadze newazidocoumarinsaspotentialagentsforfluorescentlabelingandtheirclickchemistryreactionsfortheconjugationwithiclosoidodecaborateanion |