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Theoretical and experimental characterization of a novel pyridine benzimidazole: suitability for fluorescence staining in cells and antimicrobial properties
Ist Teil von
New journal of chemistry, 2016-01, Vol.40 (3), p.2362-2375
Erscheinungsjahr
2016
Quelle
Alma/SFX Local Collection
Beschreibungen/Notizen
Benzimidazoles presenting intramolecular hydrogen bonding interactions have been normally used to better understand the role of H-bonding in biological processes. Here, we present an experimental and theoretical study of a new compound [2,4-di-
tert
-butyl-6-(3
H
-imidazo[4,5-
c
]pyridine-2-yl)phenol]; (
B2
), a benzimidazole derivate, exhibiting an intramolecular hydrogen bond.
B2
was synthesized and characterized by its
1
H, HHCOSY, FT-IR and mass spectra (EI-MS 323 M
+
). The electronic and optical properties of
B2
were studied with theoretical calculations using density functional theory (DFT) and time-dependent DFT (TDDFT).
B2
showed luminescent emission at room temperature in different solvents, with a large Stokes shift (
e.g.
;
λ
ex
= 335 nm;
λ
em
= 510 nm in acetonitrile). Also, the quantum yield (
φ
= 0.21) and theoretical band emission are reported. We found that
B2
exhibited a fluorescence emission at around 500 nm in ethanol and in acetonitrile that could be quenched by aqueous solutions of Hg(NO
3
)
2
in the range of micro molar concentrations. Cyclic voltammetry in acetonitrile showed a strong anodic response due to a quasireversible process, with reduction and oxidation waves at −1.28 and −0.47 V
vs.
SCE. Regarding the biological properties, we assessed the antimicrobial activity of
B2
in
Salmonella enterica
(bacteria),
Cryptococcus
spp. (yeast),
Candida albicans
(yeast),
Candida tropicalis
(yeast) and
Botrytis cinerea
(mold). To this end, we determined the minimal inhibitory concentration (MIC) (for bacteria and yeasts), the growth inhibition halos (for yeasts), and the inhibition of mycelial growth (for the mold). We observed that
B2
exerted an antifungal effect against
Cryptococcus
spp. and
Botrytis cinerea
. In addition, due to its fluorescence properties,
B2
has proven to be a suitable marker to observe bacteria (
Salmonella enterica
and an
Escherichia coli
derivative), yeasts (
Candida albicans
), and even human cells (SKOV-3 and HEK-293) by confocal microscopy.