Red-shifted and pH-responsive imidazole-based azo dyes with potent antimicrobial activity

Daniela Dantas; Ana I. Ribeiro; Filipe Carvalho; Eva Gil-Martins; Renata Silva; Fernando Remião; Andrea Zille; Fátima Cerqueira; Eugénia Pinto; Alice M. Dias

doi:10.1039/D3CC00372H

Red-shifted and pH-responsive imidazole-based azo dyes with potent antimicrobial activity†

Daniela Dantas,^a Ana I. Ribeiro,

^ab Filipe Carvalho,^a Eva Gil-Martins,^c Renata Silva,^c Fernando Remião,^c Andrea Zille,

^b Fátima Cerqueira,^defg Eugénia Pinto^gh and Alice M. Dias

*^a

Author affiliations

* Corresponding authors

^a Centre of Chemistry, Department of Chemistry, University of Minho, Campus of Gualtar, Braga 4710-057, Portugal
E-mail: ad@quimica.uminho.pt

^b Centre for Textile Science and Technology (2C2T), University of Minho, Campus of Azurém, Guimarães 4800-058, Portugal

^c UCIBIO-REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal

^d Molecular Oncology and Viral Pathology Group, Research Center of IPO Porto (CI-IPOP)/RISE@CI-IPOP (Health Research Network), Portuguese Oncology Institute of Porto (IPO Porto)/Porto Comprehensive Cancer Center (Porto.CCC), Porto 4200-072, Portugal

^e Faculty of Health Sciences, Fernando Pessoa University, Porto 4200-150, Portugal

^f FP-I3ID, FP-BHS, Universidade Fernando Pessoa, Porto 4249-004, Portugal

^g CIIMAR/CIMAR, Interdisciplinary Centre of Marine and Environmental Research, Terminal de Cruzeiros do Porto de Leixões, Matosinhos 4450-208, Portugal

^h Laboratory of Microbiology, Biological Sciences Department, Faculty of Pharmacy of University of Porto, Porto 4050-313, Portugal

Abstract

A novel route is described to obtain 2—aminoimidazole azo dyes with a unique substituent pattern in the heteroaryl unit that provides halochromic properties, exhibiting vibrant colours that change from magenta to deep blue. Potent antimicrobial properties against infectious yeasts were demonstrated. No cytotoxicity was detected for concentrations lower than 16 μg mL⁻¹.

Chemical Communications

Red-shifted and pH-responsive imidazole-based azo dyes with potent antimicrobial activity†

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Red-shifted and pH-responsive imidazole-based azo dyes with potent antimicrobial activity

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