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Combining eugenol and dihydroeugenol with a piperazine moiety to create new antimicrobial agents that are effective against resistant species.
Lapa, Igor Rodrigues; Dos Santos Siqueira, Fallon; Cordeiro, Cleydson Finotti; de Campos, Marli Matiko Anraku; Bonfilio, Rudy; de Figueiredo Diniz, Lívia; Pereira, Gabriella Martiniano; Hawkes, Jamie Anthony; Franco, Lucas Lopardi; Carvalho, Diogo Teixeira.
Affiliation
  • Lapa IR; Faculdade de Ciências Farmacêuticas, Departamento de Alimentos e Medicamentos, Universidade Federal de Alfenas, MG, 37130-001, Brazil.
  • Dos Santos Siqueira F; Departamento de Análises Clínicas e Toxicológicas, Universidade Federal de Santa Maria, RS, 9710590, Brazil.
  • Cordeiro CF; Faculdade de Ciências Farmacêuticas, Departamento de Alimentos e Medicamentos, Universidade Federal de Alfenas, MG, 37130-001, Brazil.
  • de Campos MMA; Departamento de Análises Clínicas e Toxicológicas, Universidade Federal de Santa Maria, RS, 9710590, Brazil.
  • Bonfilio R; Faculdade de Ciências Farmacêuticas, Departamento de Alimentos e Medicamentos, Universidade Federal de Alfenas, MG, 37130-001, Brazil.
  • de Figueiredo Diniz L; Instituto de Ciências Biomédicas, Departamento de Patologia e Parasitologia, Universidade Federal de Alfenas, MG, 37130-001, Brazil.
  • Pereira GM; Instituto de Ciências Biomédicas, Departamento de Patologia e Parasitologia, Universidade Federal de Alfenas, MG, 37130-001, Brazil.
  • Hawkes JA; Faculdade de Ciências Farmacêuticas, Departamento de Alimentos e Medicamentos, Universidade Federal de Alfenas, MG, 37130-001, Brazil.
  • Franco LL; Faculdade de Ciências Farmacêuticas, Departamento de Alimentos e Medicamentos, Universidade Federal de Alfenas, MG, 37130-001, Brazil.
  • Carvalho DT; Faculdade de Ciências Farmacêuticas, Departamento de Alimentos e Medicamentos, Universidade Federal de Alfenas, MG, 37130-001, Brazil. Electronic address: diogo.carvalho@unifal-mg.edu.br.
Microb Pathog ; 184: 106369, 2023 Nov.
Article in En | MEDLINE | ID: mdl-37778705
Historically, the piperazine moiety has been demonstrated to possess pharmacophoric properties, and has subsequently been incorporated in many drugs that have antitumor, antimalarial, antiviral, antibacterial and antifungal properties. Derivatives of eugenol and dihydroeugenol have also been reported as being bioactive compounds. This study reports the synthesis of a range of eugenol/dihydroeugenol - piperazine derivatives which have been tested as antimicrobial compounds against Gram positive, Gram negative and rapid-growing mycobacteria (RGM). The rationale employed in the design of the structural pattern of these new derivatives, provides useful insights into the structure-activity relationships (SAR) of the series. Antimicrobial activity tests were extremely encouraging, with the majority of the synthesised compounds being more active than eugenol and dihydroeugenol starting materials. The antimicrobial potential was most notable against the Gram-negative species K. pneumoniae and P. aeruginosa, but there was also significant performance against the Gram-positive strains S. epidermidis and S. aureus and the Rapidly Growing Mycobacteria (RGM) strains tested. Tests using the synthesised compounds against multidrug-resistance clinical (MDR) isolates also showed high activity. The biofilm inhibition tests using M. fortuitum showed that all evaluated derivatives were able to inhibit biofilm formation even at low concentrations. In terms of structural-activity relationships; the results generated by this study demonstrate that the compounds with bulky substituents on the piperazine subunit were much more active than those with less bulky groups, or no groups. Importantly, the derivatives with a sulfonamide side chain were the most potent compounds. A further observation was that those compounds with a para-substituted benzenesulfonamide ring stand out, regardless of whether this substituent is a donor or an electron-withdrawing group.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Eugenol / Anti-Infective Agents Language: En Journal: Microb Pathog Journal subject: DOENCAS TRANSMISSIVEIS / MICROBIOLOGIA Year: 2023 Document type: Article Affiliation country: Brazil Country of publication: United kingdom

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Eugenol / Anti-Infective Agents Language: En Journal: Microb Pathog Journal subject: DOENCAS TRANSMISSIVEIS / MICROBIOLOGIA Year: 2023 Document type: Article Affiliation country: Brazil Country of publication: United kingdom