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Author (up) Carreno, A.; Gacitua, M.; Fuentes, J.A.; Paez-Hernandez, D.; Araneda, C.; Chavez, I.; Soto-Arriaza, M.; Manriquez, J.M.; Polanco, R.; Mora, G.C.; Otero, C.; Swords, W.B.; Arratia-Perez, R. doi  openurl
  Title Theoretical and experimental characterization of a novel pyridine benzimidazole: suitability for fluorescence staining in cells and antimicrobial properties Type Journal Article
  Year 2016 Publication New Journal Of Chemistry Abbreviated Journal New J. Chem.  
  Volume 40 Issue 3 Pages 2362-2375  
  Keywords  
  Abstract 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 H-1, 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.; lambda(ex) = 335 nm; lambda(em) = 510 nm in acetonitrile). Also, the quantum yield (phi = 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.  
  Address [Carreno, Alexander; Paez-Hernandez, Dayan; Arratia-Perez, Ramiro] Univ Andres Bello, Ctr Appl Nanosci CENAP, Doctorado Fisicoquim Mol, Ave Republ 275, Santiago, Chile, Email: acarreno@uc.cl  
  Corporate Author Thesis  
  Publisher Royal Soc Chemistry Place of Publication Editor  
  Language English Summary Language Original Title  
  Series Editor Series Title Abbreviated Series Title  
  Series Volume Series Issue Edition  
  ISSN 1144-0546 ISBN Medium  
  Area Expedition Conference  
  Notes WOS:000372425600059 Approved no  
  Call Number UAI @ eduardo.moreno @ Serial 605  
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