Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents
Abstract Schiff bases are organic compounds recognized for their biological activities, including antiviral, antibacterial, antifungal, and anticancer properties, making them promising candidates in medicinal chemistry. In this studio, a series of Schiff bases 3a–h derived from 4-aminoantipyrine and...
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| Format: | Article |
| Language: | English |
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Springer
2025-01-01
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| Series: | Discover Applied Sciences |
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| Online Access: | https://doi.org/10.1007/s42452-025-06459-7 |
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| author | Johana Zúñiga-Miranda Rebeca González-Pastor Saskya E. Carrera-Pacheco Cristina Rodríguez-Pólit Carlos Barba-Ostria Antonio Machado Linda P. Guamán Christian D. Alcivar-León Jorge Heredia-Moya |
| author_facet | Johana Zúñiga-Miranda Rebeca González-Pastor Saskya E. Carrera-Pacheco Cristina Rodríguez-Pólit Carlos Barba-Ostria Antonio Machado Linda P. Guamán Christian D. Alcivar-León Jorge Heredia-Moya |
| author_sort | Johana Zúñiga-Miranda |
| collection | DOAJ |
| description | Abstract Schiff bases are organic compounds recognized for their biological activities, including antiviral, antibacterial, antifungal, and anticancer properties, making them promising candidates in medicinal chemistry. In this studio, a series of Schiff bases 3a–h derived from 4-aminoantipyrine and substituted cinnamaldehydes were evaluated in vitro against liver (HepG2) and thyroid (THJ29T) cancer cells, Gram-positive and Gram-negative multidrug-resistant bacteria, and biofilm-forming pathogens. Six compounds demonstrated anticancer activity, though some exhibited toxicity to non-tumor cells. Compounds 3b, 3f, and 3h showed notable anticancer potential, while 3f and 3h also exhibited strong antibacterial effects, with 3f being the most effective against multidrug-resistant bacteria strains. These Schiff bases also inhibit biofilm formation, suggesting their potential for treating biofilm-related infections. In-silico analyses of their ADME properties, global reactivity descriptors, and binding affinities corroborated these findings. The Schiff base 3f has a strong binding affinity for DNA gyrase and vitamin D receptor, suggesting potential mechanisms for its antibacterial and anticancer activities. |
| format | Article |
| id | doaj-art-a00625bd2bac48c2a490ecc365b8889b |
| institution | Kabale University |
| issn | 3004-9261 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Springer |
| record_format | Article |
| series | Discover Applied Sciences |
| spelling | doaj-art-a00625bd2bac48c2a490ecc365b8889b2025-02-02T12:36:42ZengSpringerDiscover Applied Sciences3004-92612025-01-017211910.1007/s42452-025-06459-7Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agentsJohana Zúñiga-Miranda0Rebeca González-Pastor1Saskya E. Carrera-Pacheco2Cristina Rodríguez-Pólit3Carlos Barba-Ostria4Antonio Machado5Linda P. Guamán6Christian D. Alcivar-León7Jorge Heredia-Moya8Universidad UTE, Facultad de Ciencias de La Salud Eugenio Espejo, Centro de Investigación Biomédica (CENBIO)Universidad UTE, Facultad de Ciencias de La Salud Eugenio Espejo, Centro de Investigación Biomédica (CENBIO)Universidad UTE, Facultad de Ciencias de La Salud Eugenio Espejo, Centro de Investigación Biomédica (CENBIO)Universidad UTE, Facultad de Ciencias de La Salud Eugenio Espejo, Centro de Investigación Biomédica (CENBIO)Universidad San Francisco de Quito (USFQ), Colegio de Ciencias de La Salud Quito, Escuela de MedicinaUniversidad San Francisco de Quito (USFQ), Colegio de Ciencias Biológicas y Ambientales (COCIBA), Instituto de Microbiología, Laboratorio de BacteriologíaUniversidad UTE, Facultad de Ciencias de La Salud Eugenio Espejo, Centro de Investigación Biomédica (CENBIO)Universidad Central del Ecuador, Facultad de Ciencias QuímicasUniversidad UTE, Facultad de Ciencias de La Salud Eugenio Espejo, Centro de Investigación Biomédica (CENBIO)Abstract Schiff bases are organic compounds recognized for their biological activities, including antiviral, antibacterial, antifungal, and anticancer properties, making them promising candidates in medicinal chemistry. In this studio, a series of Schiff bases 3a–h derived from 4-aminoantipyrine and substituted cinnamaldehydes were evaluated in vitro against liver (HepG2) and thyroid (THJ29T) cancer cells, Gram-positive and Gram-negative multidrug-resistant bacteria, and biofilm-forming pathogens. Six compounds demonstrated anticancer activity, though some exhibited toxicity to non-tumor cells. Compounds 3b, 3f, and 3h showed notable anticancer potential, while 3f and 3h also exhibited strong antibacterial effects, with 3f being the most effective against multidrug-resistant bacteria strains. These Schiff bases also inhibit biofilm formation, suggesting their potential for treating biofilm-related infections. In-silico analyses of their ADME properties, global reactivity descriptors, and binding affinities corroborated these findings. The Schiff base 3f has a strong binding affinity for DNA gyrase and vitamin D receptor, suggesting potential mechanisms for its antibacterial and anticancer activities.https://doi.org/10.1007/s42452-025-06459-7Schiff base4-aminopantipyrineAntibacterialAnticancerMultidrug-resistant |
| spellingShingle | Johana Zúñiga-Miranda Rebeca González-Pastor Saskya E. Carrera-Pacheco Cristina Rodríguez-Pólit Carlos Barba-Ostria Antonio Machado Linda P. Guamán Christian D. Alcivar-León Jorge Heredia-Moya Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents Discover Applied Sciences Schiff base 4-aminopantipyrine Antibacterial Anticancer Multidrug-resistant |
| title | Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents |
| title_full | Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents |
| title_fullStr | Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents |
| title_full_unstemmed | Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents |
| title_short | Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents |
| title_sort | experimental and computational studies of schiff bases derived from 4 aminoantipyrine as potential antibacterial and anticancer agents |
| topic | Schiff base 4-aminopantipyrine Antibacterial Anticancer Multidrug-resistant |
| url | https://doi.org/10.1007/s42452-025-06459-7 |
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