Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-Nucleophiles
Azanone (HNO) is an elusive electrophilic reactive nitrogen species of growing pharmacological and biological significance. Here, we present a comparative kinetic study of HNO reactivity toward selected cyclic <i>C</i>-nucleophiles under aqueous conditions at pH 7.4. We applied the compe...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-11-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/23/12982 |
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| author | Angelika Artelska Monika Rola Michał Rostkowski Marlena Pięta Jakub Pięta Radosław Michalski Adam Bartłomiej Sikora |
| author_facet | Angelika Artelska Monika Rola Michał Rostkowski Marlena Pięta Jakub Pięta Radosław Michalski Adam Bartłomiej Sikora |
| author_sort | Angelika Artelska |
| collection | DOAJ |
| description | Azanone (HNO) is an elusive electrophilic reactive nitrogen species of growing pharmacological and biological significance. Here, we present a comparative kinetic study of HNO reactivity toward selected cyclic <i>C</i>-nucleophiles under aqueous conditions at pH 7.4. We applied the competition kinetics method, which is based on the use of a fluorescein-derived boronate probe FlBA and two parallel HNO reactions: with the studied scavenger or with O<sub>2</sub> (<i>k</i> = 1.8 × 10<sup>4</sup> M<sup>−1</sup>s<sup>−1</sup>). We determined the second-order rate constants of HNO reactions with 13 structurally diverse <i>C</i>-nucleophiles (<i>k</i> = 33–20,000 M<sup>−1</sup>s<sup>−1</sup>). The results show that the reactivity of HNO toward <i>C</i>-nucleophiles depends strongly on the structure of the scavenger. The data are supported with quantum mechanical calculations. A comprehensive discussion of the HNO reaction with <i>C</i>-nucleophiles is provided. |
| first_indexed | 2024-03-10T04:52:47Z |
| format | Article |
| id | doaj.art-e4389525b19e47be97aa58aaf2e277f1 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T04:52:47Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-e4389525b19e47be97aa58aaf2e277f12023-11-23T02:31:15ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-11-0122231298210.3390/ijms222312982Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-NucleophilesAngelika Artelska0Monika Rola1Michał Rostkowski2Marlena Pięta3Jakub Pięta4Radosław Michalski5Adam Bartłomiej Sikora6Institute of Applied Radiation Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of Applied Radiation Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of Applied Radiation Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of Applied Radiation Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of Applied Radiation Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of Applied Radiation Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandInstitute of Applied Radiation Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, PolandAzanone (HNO) is an elusive electrophilic reactive nitrogen species of growing pharmacological and biological significance. Here, we present a comparative kinetic study of HNO reactivity toward selected cyclic <i>C</i>-nucleophiles under aqueous conditions at pH 7.4. We applied the competition kinetics method, which is based on the use of a fluorescein-derived boronate probe FlBA and two parallel HNO reactions: with the studied scavenger or with O<sub>2</sub> (<i>k</i> = 1.8 × 10<sup>4</sup> M<sup>−1</sup>s<sup>−1</sup>). We determined the second-order rate constants of HNO reactions with 13 structurally diverse <i>C</i>-nucleophiles (<i>k</i> = 33–20,000 M<sup>−1</sup>s<sup>−1</sup>). The results show that the reactivity of HNO toward <i>C</i>-nucleophiles depends strongly on the structure of the scavenger. The data are supported with quantum mechanical calculations. A comprehensive discussion of the HNO reaction with <i>C</i>-nucleophiles is provided.https://www.mdpi.com/1422-0067/22/23/12982azanone<i>C</i>-nucleophilesAngeli’s saltboronate probeperoxynitrite |
| spellingShingle | Angelika Artelska Monika Rola Michał Rostkowski Marlena Pięta Jakub Pięta Radosław Michalski Adam Bartłomiej Sikora Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-Nucleophiles International Journal of Molecular Sciences azanone <i>C</i>-nucleophiles Angeli’s salt boronate probe peroxynitrite |
| title | Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-Nucleophiles |
| title_full | Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-Nucleophiles |
| title_fullStr | Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-Nucleophiles |
| title_full_unstemmed | Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-Nucleophiles |
| title_short | Kinetic Study on the Reactivity of Azanone (HNO) toward Cyclic <i>C</i>-Nucleophiles |
| title_sort | kinetic study on the reactivity of azanone hno toward cyclic i c i nucleophiles |
| topic | azanone <i>C</i>-nucleophiles Angeli’s salt boronate probe peroxynitrite |
| url | https://www.mdpi.com/1422-0067/22/23/12982 |
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