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Open AccessArticle

In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa

1
Centro de Investigacións Científicas Avanzadas (CICA) e Departamento de Química, Facultade de Ciencias, AE CICA-INIBIC, Universidade da Coruña, 15071 A Coruña, Spain
2
Servicio de Microbioloxía, Instituto de Investigación Biomédica, AE CICA-INIBIC Complexo Hospitalario Universitario A Coruña, 15006 A Coruña, Spain
*
Authors to whom correspondence should be addressed.
Same contribution to this work.
Mar. Drugs 2020, 18(6), 326; https://doi.org/10.3390/md18060326
Received: 1 June 2020 / Revised: 16 June 2020 / Accepted: 17 June 2020 / Published: 23 June 2020
(This article belongs to the Special Issue Structure–Activity Relationship of Marine Bioactive Compounds)
The pyrrole-imidazoles, a group of alkaloids commonly found in marine sponges belonging to the genus Agelas, display a wide range of biological activities. Herein, we report the first chemical study of the secondary metabolites of the sponge A. dilatata from the coastal area of the Yucatan Peninsula (Mexico). In this study, we isolated eight known alkaloids from an organic extract of the sponge. We used NMR and MS analysis and comparison with existing databases to characterize the alkaloids: ageliferin (1), bromoageliferin (2), dibromoageliferin (3), sceptrin (4), nakamuric acid (5), 4-bromo-1H-pyrrole-2-carboxylic acid (6), 4,5-dibromopyrrole-2-carboxylic acid (7) and 3,7-dimethylisoguanine (8). We also evaluated, for the first time, the activity of these alkaloids against the most problematic multidrug-resistant (MDR) pathogens, i.e., the Gram-negative bacteria Pseudomonas aeruginosa, Klebsiella pneumoniae and Acinetobacter baumannii. Bromoageliferin (2) displayed significant activity against P. aeruginosa. Comparison of the antibacterial activity of ageliferins 13 (of similar structure) against P. aeruginosa revealed some relationship between structure and activity. Furthermore, in in vitro assays, 2 inhibited growth and biofilm production in clinical strains of P. aeruginosa. Moreover, 2 increased the survival time in an in vivo Galleria mellonella model of infection. The findings confirm bromoageliferin (2) as a potential lead for designing new antibacterial drugs. View Full-Text
Keywords: Agelas dilatata; Yucatan Peninsula; pyrrole-imidazole alkaloids; Pseudomonas aeruginosa; structure-activity relationships; antibacterial; biofilm inhibition; Galleria mellonella Agelas dilatata; Yucatan Peninsula; pyrrole-imidazole alkaloids; Pseudomonas aeruginosa; structure-activity relationships; antibacterial; biofilm inhibition; Galleria mellonella
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Pech-Puch, D.; Pérez-Povedano, M.; Martinez-Guitian, M.; Lasarte-Monterrubio, C.; Vázquez-Ucha, J.C.; Bou, G.; Rodríguez, J.; Beceiro, A.; Jimenez, C. In Vitro and In Vivo Assessment of the Efficacy of Bromoageliferin, an Alkaloid Isolated from the Sponge Agelas dilatata, against Pseudomonas aeruginosa. Mar. Drugs 2020, 18, 326.

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