Experimental and computational studies of Schiff bases derived from 4-aminoantipyrine as potential antibacterial and anticancer agents

• Published in: Discover applied sciences Vol. 7; no. 2; pp. 115 - 19
• Main Authors: Zúñiga-Miranda, Johana, González-Pastor, Rebeca, Carrera-Pacheco, Saskya E., Rodríguez-Pólit, Cristina, Barba-Ostria, Carlos, Machado, Antonio, Guamán, Linda P., Alcivar-León, Christian D., Heredia-Moya, Jorge
• Format: Journal Article
• Language: English
• Published: Cham Springer International Publishing 31.01.2025; Springer Nature B.V; Springer
• Subjects: 4-aminopantipyrine; Affinity; Antibacterial; Antibacterial activity; Anticancer; Anticancer properties; Antifungal activity; Antiinfectives and antibacterials; Antimicrobial agents; Antineoplastic drugs; Antitumor activity; Antiviral activity; Applied and Technical Physics; Bacteria; Binding; Biofilms; Biological activity; Cancer; Cell growth; Chemistry/Food Science; Corrosion resistance; Cytotoxicity; DNA topoisomerase; Earth Sciences; Engineering; Environment; Fungicides; Gram-negative bacteria; Gram-positive bacteria; Imines; Investigations; Materials Science; Multidrug resistance; Multidrug-resistant; Organic compounds; Pharmacology; Schiff base; Strains (organisms); Thyroid; Thyroid cancer; Toxicity; Tumor cell lines; Tumor cells; Tumors; Vitamin D; Vitamin D receptors; Schiff base; Multidrug-resistant; Antibacterial; 4-aminopantipyrine; Anticancer
• ISSN: 3004-9261; 2523-3963; 3004-9261; 2523-3971
• DOI: 10.1007/s42452-025-06459-7

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. Article Highlights Six Schiff bases showed antiproliferative activity against tumor cell lines, with compound 3f being the most potent. Compounds 3h and 3b had higher therapeutic index values, with 3h demonstrating selectivity for tumor cells. Compounds 3f and 3h exhibit antibacterial activity against multidrug-resistant bacteria strains, with 3f being the most potent.