TY - JOUR
T1 - Theoretical and experimental characterization of a novel pyridine benzimidazole
T2 - Suitability for fluorescence staining in cells and antimicrobial properties
AU - Carreño, Alexander
AU - Gacitúa, Manuel
AU - Fuentes, Juan A.
AU - Páez-Hernández, Dayán
AU - Araneda, Carmen
AU - Chávez, Ivonne
AU - Soto-Arriaza, Marco
AU - Manríquez, Juan M.
AU - Polanco, Rubén
AU - Mora, Guido C.
AU - Otero, Carolina
AU - Swords, Wesley B.
AU - Arratia-Pérez, Ramiro
N1 - Funding Information:
This work has been funded by Project RC120001 of the Iniciativa Cient?fica Milenio (ICM) del Ministerio de Economia, Fomento y Turismo del Gobierno de Chile; FONDECYT 11140294, 1150629, 11121506; Guido A. Mora thanks N?cleo UNAB Grant DI-22-12/N. We are grateful to Dr Maria A. Del Valle (PUC) and Dr LuisVelasquez (CIMIS) for instrumentals facilities; Dr Marcelo Preite (PUC) and Monique Riviere-Baudet (U. Paul Sabatier, France) for valuable NMR and Mass spectra discussions; Dr Gerald. J. Meyer (Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, United States) for photophysical measurement; BSc Miriam Barros (Confocal microscopy, UNAB) and BA Alfonso Inzunza G. for his help with the English translation.
Publisher Copyright:
© The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016.
PY - 2016
Y1 - 2016
N2 - 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-(3H-imidazo[4,5-c]pyridine-2-yl)phenol]; (B2), a benzimidazole derivate, exhibiting an intramolecular hydrogen bond. B2 was synthesized and characterized by its 1H, 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.; λex = 335 nm; λem = 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(NO3)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.
AB - 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-(3H-imidazo[4,5-c]pyridine-2-yl)phenol]; (B2), a benzimidazole derivate, exhibiting an intramolecular hydrogen bond. B2 was synthesized and characterized by its 1H, 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.; λex = 335 nm; λem = 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(NO3)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.
UR - http://www.scopus.com/inward/record.url?scp=84960510875&partnerID=8YFLogxK
U2 - 10.1039/c5nj02772a
DO - 10.1039/c5nj02772a
M3 - Article
AN - SCOPUS:84960510875
SN - 1144-0546
VL - 40
SP - 2362
EP - 2375
JO - New Journal of Chemistry
JF - New Journal of Chemistry
IS - 3
ER -