Antibacterial activity of the nitrovinylfuran G1 (Furvina) and its conversion products.
2-Bromo-5-(2-bromo-2-nitrovinyl)furan (G1 or Furvina) is an antimicrobial with a direct reactivity against thiol groups. It is active against Gram-positive and Gram-negative bacteria, yeasts and filamentous fungi. By reacting with thiol groups it causes direct damage to proteins but, as a result, is very short-living and interconverts into an array of reaction products. Our aim was to characterize thiol reactivity of G1 and its conversion products and establish how much of antimicrobial and cytotoxic effects are due to the primary activity of G1 and how much can be attributed to its reaction products. Stability of G1 in growth media as well as its conversion in the presence of thiols was characterized. The structures of G1 decomposition products were determined using NMR and mass-spectroscopy. Concentration- and time-dependent killing curves showed that G1 is bacteriostatic for Escherichia coli at the concentration of 16 μg/ml and bactericidal at 32 μg/ml. However, G1 is inefficient against non-growing E. coli. Addition of cysteine to medium reduces the antimicrobial potency of G1. Nevertheless, the reaction products of G1 and cysteine enabled prolonged antimicrobial action of the drug. Therefore, the activity of 2-bromo-5-(2-bromo-2-nitrovinyl)furan is a sum of its immediate reactivity and the antibacterial effects of the conversion products.
University of Tartu, Institute of Technology, Nooruse 1, Tartu 50411, Estonia.
U Lar
UL
Allas
University of Tartu, Institute of Technology, Nooruse 1, Tartu 50411, Estonia.
Lauri
L
Toom
University of Tartu, Institute of Technology, Nooruse 1, Tartu 50411, Estonia.
Anastasia
A
Selyutina
Institute of Chemistry, University of Tartu, Ravila 14a, Tartu 50411, Estonia.
Uno
U
Mäeorg
Universidad Central "Marta Abreu" de Las Villas, Santa Clara, Cuba.
Ricardo
R
Medina
University of Tartu, Institute of Technology, Nooruse 1, Tartu 50411, Estonia.
Andres
A
Merits
Institute of Chemistry, University of Tartu, Ravila 14a, Tartu 50411, Estonia.
Ago
A
Rinken
University of Tartu, Institute of Technology, Nooruse 1, Tartu 50411, Estonia.|Department of Molecular Biology, Umeå University, Umeå, Sweden.|Laboratory for Molecular Infection Medicine Sweden, Umeå University, Umeå, Sweden.
Vasili
V
Hauryliuk
University of Tartu, Institute of Technology, Nooruse 1, Tartu 50411, Estonia.
Niilo
N
Kaldalu
University of Tartu, Institute of Technology, Nooruse 1, Tartu 50411, Estonia.
Tanel
T
Tenson
D000900:Anti-Bacterial Agents / Q000494:pharmacology* / Q000633:toxicity; D004355:Drug Stability; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D005663:Furans / Q000494:pharmacology* / Q000633:toxicity; D006367:HeLa Cells; D006801:Humans; D008826:Microbial Sensitivity Tests; D014753:Vinyl Compounds / Q000494:pharmacology* / Q000633:toxicity
C577632:2-bromo-5-(2-bromo-2-nitrovinyl)furan; D000900:Anti-Bacterial Agents; D005663:Furans; D014753:Vinyl Compounds