Characterization of the fragmentation mechanisms in electrospray ionization tandem mass spectrometry of chloroquinoline derivatives with larvicidal activity against Aedes aegypti
Fuente:
Wiley Open Access
Salvato in:
| Autori principali: | , , , , , , , , , , |
|---|---|
| Natura: | Artículo Open Access |
| Pubblicazione: |
Wiley
2024
|
| Soggetti: | |
| Accesso online: | |
| Tags: |
Aggiungi Tag
Nessun Tag, puoi essere il primo ad aggiungerne!!
|
| _version_ | 1867006507957092352 |
|---|---|
| author | Rodrigo Moreira da Silva Jéssica Guastalli Barbieri Valter Eduardo Murie Maíra Rosato Silveira Silvério Rafael Augusto Soldi Lorena Carneiro Albernaz Laila Salmen Espindola Paulo Cézar Vieira Giuliano Cesar Clososki Ricardo Vessecchi Norberto Peporine Lopes |
| author_facet | Rodrigo Moreira da Silva Jéssica Guastalli Barbieri Valter Eduardo Murie Maíra Rosato Silveira Silvério Rafael Augusto Soldi Lorena Carneiro Albernaz Laila Salmen Espindola Paulo Cézar Vieira Giuliano Cesar Clososki Ricardo Vessecchi Norberto Peporine Lopes Rodrigo Moreira da Silva Jéssica Guastalli Barbieri Valter Eduardo Murie Maíra Rosato Silveira Silvério Rafael Augusto Soldi Lorena Carneiro Albernaz Laila Salmen Espindola Paulo Cézar Vieira Giuliano Cesar Clososki Ricardo Vessecchi Norberto Peporine Lopes |
| collection | Wiley Open Access |
| contents | Characterization of the fragmentation mechanisms in electrospray ionization tandem mass spectrometry of chloroquinoline derivatives with larvicidal activity against Aedes aegypti Rodrigo Moreira da Silva Jéssica Guastalli Barbieri Valter Eduardo Murie Maíra Rosato Silveira Silvério Rafael Augusto Soldi Lorena Carneiro Albernaz Laila Salmen Espindola Paulo Cézar Vieira Giuliano Cesar Clososki Ricardo Vessecchi Norberto Peporine Lopes Rapid Communications in Mass Spectrometry Rationale 4,7‐Dichloroquinoline (DCQ) represents a group of synthetic molecules inspired by natural products with important roles in biological and biomedical areas. This work aimed to characterize DCQ and its derivatives by high‐resolution electrospray ionization (ESI) mass spectrometry and tandem mass spectrometry (ESI‐MS/MS), supported by theoretical calculations. Biological assays were carried out with DCQ and its derivatives to determine LC 50 values against Aedes aegypti larvae. Methods Five DCQ derivatives were synthesized by using previously described protocols. ESI‐MS/MS analyses were carried out with a quadrupole/time‐of‐flight and ion‐trap instrument. The proposed gas‐phase protonation sites and fragmentation were supported by density functional theory calculations. The larvicidal tests were performed with the Ae. aegypti Rockefeller strain, and the LC 50 values were determined by employing five test concentrations. Larval mortality was determined after treatment for 48 h. Results DCQ bromides or aldehydes (C‐3 or C‐8 positions), as well as the trimethylsilyl derivative (C‐3 position), were prepared. Detailed ESI‐MS/MS data revealed heteroatom elimination through an exception to the even‐electron rule, to originate open‐shell species. Computational studies were used to define the protonation sites and fragmentation pathways. High activity of DCQ and its derivatives against Ae. aegypti larvae was demonstrated. Conclusion Our results provided a well‐founded characterization of the fragmentation reactions of DCQ and its derivatives, which can be useful for complementary studies of the development of a larvicidal product against Ae. aegypti . 10.1002/rcm.9739 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| doi_str_mv | 10.1002/rcm.9739 |
| format | Artículo Open Access |
| id | wiley_oa_10_1002_rcm_9739 |
| institution | Wiley Open Access |
| license_str_mv | http://onlinelibrary.wiley.com/termsAndConditions#vor |
| publishDate | 2024 |
| publisher | Wiley |
| record_format | wiley_oa |
| spellingShingle | Characterization of the fragmentation mechanisms in electrospray ionization tandem mass spectrometry of chloroquinoline derivatives with larvicidal activity against Aedes aegypti Rodrigo Moreira da Silva Jéssica Guastalli Barbieri Valter Eduardo Murie Maíra Rosato Silveira Silvério Rafael Augusto Soldi Lorena Carneiro Albernaz Laila Salmen Espindola Paulo Cézar Vieira Giuliano Cesar Clososki Ricardo Vessecchi Norberto Peporine Lopes Rapid Communications in Mass Spectrometry Characterization of the fragmentation mechanisms in electrospray ionization tandem mass spectrometry of chloroquinoline derivatives with larvicidal activity against Aedes aegypti Rodrigo Moreira da Silva Jéssica Guastalli Barbieri Valter Eduardo Murie Maíra Rosato Silveira Silvério Rafael Augusto Soldi Lorena Carneiro Albernaz Laila Salmen Espindola Paulo Cézar Vieira Giuliano Cesar Clososki Ricardo Vessecchi Norberto Peporine Lopes Rapid Communications in Mass Spectrometry Rationale 4,7‐Dichloroquinoline (DCQ) represents a group of synthetic molecules inspired by natural products with important roles in biological and biomedical areas. This work aimed to characterize DCQ and its derivatives by high‐resolution electrospray ionization (ESI) mass spectrometry and tandem mass spectrometry (ESI‐MS/MS), supported by theoretical calculations. Biological assays were carried out with DCQ and its derivatives to determine LC 50 values against Aedes aegypti larvae. Methods Five DCQ derivatives were synthesized by using previously described protocols. ESI‐MS/MS analyses were carried out with a quadrupole/time‐of‐flight and ion‐trap instrument. The proposed gas‐phase protonation sites and fragmentation were supported by density functional theory calculations. The larvicidal tests were performed with the Ae. aegypti Rockefeller strain, and the LC 50 values were determined by employing five test concentrations. Larval mortality was determined after treatment for 48 h. Results DCQ bromides or aldehydes (C‐3 or C‐8 positions), as well as the trimethylsilyl derivative (C‐3 position), were prepared. Detailed ESI‐MS/MS data revealed heteroatom elimination through an exception to the even‐electron rule, to originate open‐shell species. Computational studies were used to define the protonation sites and fragmentation pathways. High activity of DCQ and its derivatives against Ae. aegypti larvae was demonstrated. Conclusion Our results provided a well‐founded characterization of the fragmentation reactions of DCQ and its derivatives, which can be useful for complementary studies of the development of a larvicidal product against Ae. aegypti . 10.1002/rcm.9739 http://onlinelibrary.wiley.com/termsAndConditions#vor |
| title | Characterization of the fragmentation mechanisms in electrospray ionization tandem mass spectrometry of chloroquinoline derivatives with larvicidal activity against Aedes aegypti |
| topic | Rapid Communications in Mass Spectrometry |
| url | https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/rcm.9739 |