title: In vitro antifungal activity of organic compounds derived from amino alcohols against onychomycosis.
abstract: Onychomycosis is a fungal infection of the nail caused by high densities of filamentous fungi and yeasts. Treatment for this illness is long-term, and recurrences are frequently detected. This study evaluated in vitro antifungal activities of 12 organic compounds derived from amino alcohols against standard fungal strains, such as Trichophyton rubrum CCT 5507 URM 1666, Trichophyton mentagrophytes ATCC 11481, and Candida albicans ATCC 10231. The antifungal compounds were synthesized from p-hydroxybenzaldehyde (4a-4f) and p-hydroxybenzoic acid (9a-9f). Minimum inhibitory concentrations and minimum fungicidal concentrations were determined according to Clinical and Laboratory Standards Institute protocols M38-A2, M27-A3, and M27-S4. The amine series 4b-4e, mainly 4c and 4e compounds, were effective against filamentous fungi and yeast (MIC from 7.8 to 312μg/mL). On the other hand, the amide series (9a-9f) did not present inhibitory effect against fungi, except amide 9c, which demonstrated activity only against C. albicans. This allowed us to infer that the presence of amine group and intermediate carbon number (8C-11C) in its aliphatic side chain seems to be important for antifungal activity. Although these compounds present cytotoxic activity on macrophages J774, our results suggest that these aromatic compounds might constitute potential as leader molecules in the development of more effective and less toxic analogs that could have considerable implications for future therapies of onychomycosis.
authors.affiliation: Universidade Federal de Juiz de Fora, Faculdade de Farmácia, Núcleo de Pesquisa e Inovação em Ciências da Saúde (NUPICS), Juiz de Fora, MG, Brazil.
authors.forename: César Augusto
authors.initials: CA
authors.lastname: Caneschi
authors.affiliation: Universidade Federal de Juiz de Fora, Instituto de Ciências Exatas, Departamento de Química, Juiz de Fora, MG, Brazil.
authors.forename: Angelina Maria de
authors.initials: AM
authors.lastname: Almeida
authors.affiliation: Universidade Federal de Juiz de Fora, Faculdade de Farmácia, Núcleo de Pesquisa e Inovação em Ciências da Saúde (NUPICS), Juiz de Fora, MG, Brazil.
authors.forename: Francislene Juliana
authors.initials: FJ
authors.lastname: Martins
authors.affiliation: Universidade Federal de Juiz de Fora, Instituto de Ciências Exatas, Departamento de Química, Juiz de Fora, MG, Brazil.
authors.forename: Mireille Le
authors.initials: ML
authors.lastname: Hyaric
authors.affiliation: Fundação Oswaldo Cruz, Instituto Nacional de Infectologia Evandro Chagas, Laboratório de Micologia, Rio de Janeiro, RJ, Brazil.
authors.forename: Manoel Marques Evangelista
authors.initials: MME
authors.lastname: Oliveira
authors.affiliation: Universidade Federal de Juiz de Fora, Instituto de Ciências Biológicas, Departamento de Parasitologia, Microbiologia e Imunologia, Juiz de Fora, MG, Brazil.
authors.forename: Gilson Costa
authors.initials: GC
authors.lastname: Macedo
authors.affiliation: Universidade Federal de Juiz de Fora, Instituto de Ciências Exatas, Departamento de Química, Juiz de Fora, MG, Brazil.
authors.forename: Mauro Vieira de
authors.initials: MV
authors.lastname: Almeida
authors.affiliation: Universidade Federal de Juiz de Fora, Faculdade de Farmácia, Núcleo de Pesquisa e Inovação em Ciências da Saúde (NUPICS), Juiz de Fora, MG, Brazil. Electronic address: nadiacritt@gmail.com.
authors.forename: Nádia Rezende Barbosa
authors.initials: NRB
authors.lastname: Raposo
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D005658:Fungi / Q000145:classification / Q000187:drug effects* / Q000502:physiology; D006801:Humans; D008826:Microbial Sensitivity Tests; D014009:Onychomycosis / Q000188:drug therapy / Q000382:microbiology*
chemical_list: D000605:Amino Alcohols; D000935:Antifungal Agents
keywords: Amides; Amino alcohols; Antifungal activity; Lipophilicity; Onychomycosis