Antibacterial activity of the nitrovinylfuran G1 (Furvina) and its conversion products
Allas, Ülar ; Toom, Lauri ; Selyutina, Anastasia ; Mäeorg, Uno ; Medina, Ricardo ; Merits, Andres ; Rinken, Ago ; Hauryliuk, Vasili LU
; Kaldalu, Niilo
and Tenson, Tanel
(2016)
In Scientific Reports
6.
- Abstract
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... (More)
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 nongrowing 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.
(Less)
- author
- Allas, Ülar
; Toom, Lauri
; Selyutina, Anastasia
; Mäeorg, Uno
; Medina, Ricardo
; Merits, Andres
; Rinken, Ago
; Hauryliuk, Vasili
LU
; Kaldalu, Niilo
and Tenson, Tanel
- publishing date
- 2016-11-10
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Scientific Reports
- volume
- 6
- article number
- 36844
- publisher
- Nature Publishing Group
- external identifiers
-
- scopus:84995422371
- pmid:27830730
- ISSN
- 2045-2322
- DOI
- 10.1038/srep36844
- language
- English
- LU publication?
- no
- additional info
- Copyright: Copyright 2016 Elsevier B.V., All rights reserved.
- id
- 3eb88da8-6ccb-4e7b-9364-ff8a23f23578
- date added to LUP
- 2021-09-24 20:40:07
- date last changed
- 2024-06-15 17:35:15
@article{3eb88da8-6ccb-4e7b-9364-ff8a23f23578,
abstract = {{<p>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 nongrowing 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.</p>}},
author = {{Allas, Ülar and Toom, Lauri and Selyutina, Anastasia and Mäeorg, Uno and Medina, Ricardo and Merits, Andres and Rinken, Ago and Hauryliuk, Vasili and Kaldalu, Niilo and Tenson, Tanel}},
issn = {{2045-2322}},
language = {{eng}},
month = {{11}},
publisher = {{Nature Publishing Group}},
series = {{Scientific Reports}},
title = {{Antibacterial activity of the nitrovinylfuran G1 (Furvina) and its conversion products}},
url = {{http://dx.doi.org/10.1038/srep36844}},
doi = {{10.1038/srep36844}},
volume = {{6}},
year = {{2016}},
}