Triphenylphosphonium (TPP)-Conjugated Quinolone Analogs Displayed Significantly Enhanced Fungicidal Activity Superior to Its Parent Molecule.
In: Journal of Fungi, Jg. 9 (2023-06-01), Heft 6, S. 685-695
Online
academicJournal
Zugriff:
Although 1-hydroxy-4-quinolone derivatives, such as 2-heptyl-4-hydroxyquinoline-N-oxide (HQNO), aurachin C, and floxacrine, have been reported as effective cytochrome bc 1 complex inhibitors, the bioactivity of these products is not ideal, presumably due to their low bioavailability in tissues, particularly their poor solubility and low mitochondrial accumulation. In order to overcome the drawbacks of these compounds and develop their use as agricultural fungicides acting by cytochrome bc 1 inhibition, in this study, three novel mitochondria-targeting quinolone analogs (mitoQNOs) were designed and synthesized by conjugating triphenylphosphonium (TPP) with quinolone. They exhibited greatly enhanced fungicidal activity compared to the parent molecule, especially mitoQNO 11 , which showed high antifungal activity against Phytophthora capsici and Sclerotinia sclerotiorum with EC 50 values of 7.42 and 4.43 μmol/L, respectively. In addition, mitoQNO 11 could inhibit the activity of the cytochrome bc 1 complex of P. capsici in a dose-dependent manner and effectively depress its respiration and ATP production. The greatly decreased mitochondrial membrane potential and massively generated reactive oxygen species (ROS) strongly suggested that the inhibition of complex III led to the leakage of free electrons, which resulted in the damage of the pathogen cell structure. The results of this study indicated that TPP-conjugated QNOs might be used as agricultural fungicides by conjugating them with TPP. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Fungi is the property of MDPI and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Titel: |
Triphenylphosphonium (TPP)-Conjugated Quinolone Analogs Displayed Significantly Enhanced Fungicidal Activity Superior to Its Parent Molecule.
|
---|---|
Autor/in / Beteiligte Person: | Wang, Jiayao ; Liu, Xuelian ; Yin, Fahong ; Xu, Yanjun ; Fu, Bin ; Li, Jiaqi ; Qin, Zhaohai |
Link: | |
Zeitschrift: | Journal of Fungi, Jg. 9 (2023-06-01), Heft 6, S. 685-695 |
Veröffentlichung: | 2023 |
Medientyp: | academicJournal |
ISSN: | 2309-608X (print) |
DOI: | 10.3390/jof9060685 |
Schlagwort: |
|
Sonstiges: |
|