A Theoretical Study of the Binding of [Re6Se8(OH)2(H2O)4] Rhenium Clusters to DNA Purine Base Guanine

Alvarado-Soto, Leonor; Ramírez-Tagle, Rodrigo

doi:10.3390/ma8073938

Cited by 7 publications

(5 citation statements)

References 31 publications

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“…All structural and electronic properties were obtained using the Amsterdam Density Functional (ADF) code (Te Velde et al, 2001 ). All molecular structures were fully optimized by an analytical energy gradient method as implemented by Verluis and Ziegler using the hybrid B3LYP functional and the standard Slater-type-orbital (STO) basis set with triple-z quality double plus polarization functions (TZ2P) for all the atoms (Stephens et al, 1994 ; Ramírez-Tagle et al, 2010 ; Cohen et al, 2012 ; Alvarado-Soto and Ramirez-Tagle, 2015 ; Bjorgaard et al, 2015 ). Frequency analyses were performed after geometry optimization to corroborate the minimum and to compare with experimental infrared spectra.…”

Section: Experimental Computational Methods and Biological Essaysmentioning

confidence: 99%

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

et al. 2018

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It has been reported that the structure of the Schiff bases is fundamental for their function in biomedical applications. Pyridine Schiff bases are characterized by the presence of a pyridine and a phenolic ring, connected by an azomethine group. In this case, the nitrogen present in the pyridine is responsible for antifungal effects, where the phenolic ring may be also participating in this bioactivity. In this study, we synthesized two new pyridine Schiff Bases: (E)-2-[(3-Amino-pyridin-4-ylimino)-methyl]-4,6-difluoro-phenol (F1) and (E)- 2-[(3-Amino-pyridin-4-ylimino)-methyl]-6-fluoro-phenol (F2), which only differ in the fluorine substitutions in the phenolic ring. We fully characterized both F1 and F2 by FTIR, UV-vis, 1H; 13C; 19F-NMR, DEPT, HHCOSY, TOCSY, and cyclic voltammetry, as well as by computational studies (DFT), and NBO analysis. In addition, we assessed the antifungal activity of both F1 (two fluorine substitution at positions 4 and 6 in the phenolic ring) and F2 (one fluorine substitution at position 6 in the phenolic ring) against yeasts. We found that only F1 exerted a clear antifungal activity, showing that, for these kind of Schiff bases, the phenolic ring substitutions can modulate biological properties. In addition, we included F1 and F2 into in epichlorohydrin-β-cyclodextrin polymer (βCD), where the Schiff bases remained inside the βCD as determined by the ki, TGA, DSC, and SBET. We found that the inclusion in βCD improved the solubility in aqueous media and the antifungal activity of both F1 and F2, revealing antimicrobial effects normally hidden by the presence of common solvents (e.g., DMSO) with some cellular inhibitory activity. The study of structural prerequisites for antimicrobial activity, and the inclusion in polymers to improve solubility, is important for the design of new drugs.

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Section: Experimental Computational Methods and Biological Essaysmentioning

confidence: 99%

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

et al. 2018

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“…Synthesis of the metal clusters with simple heterocyclic ligands [9,[31][32][33][34] are also of interest, as such compounds that can lead to additional properties, which include supramolecular, porous crystalline structures [35][36][37] or versatile redox properties [27]. Moreover, the study of octahedral complexes with simple heterocycles that are related to biological molecules such as nucleotides and amino-acids may uncover the potential of these compound as, for example, anticancer agents [38].…”

Section: Introductionmentioning

confidence: 99%

Octahedral chalcogenide rhenium cluster complexes with imidazole

et al. 2019

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Reactions of [{Re6Q8}Br6] 4−/3− (Q = S, Se) with molten imidazole lead to the formation of two new neutral cluster complexes [{Re6Q8}(imzH)4(imz)2] (imzH = imidazole). The interaction of [{Re6Q8}(imzH)4(imz)2] with hydrohalic acids resulted in cationic complexes [{Re6Q8}(imzH)6]X2 (X = Cl, Br). All compounds were characterised by X-ray single-crystal and powder diffraction analyses, elemental analysis, energy dispersive X-ray and IR spectroscopies. The luminescence of the neutral compounds [{Re6Q8}(imzH)4(imz)2] was also studied.

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“…All structural and electronic properties were obtained using the Amsterdam Density Functional (ADF) code (Te Velde et al, 2001 ). All molecular structures were fully optimized by an analytical energy gradient method as implemented by Verluis and Ziegler (Echeverria et al, 2009 ; Ramírez-Tagle et al, 2010 ; Alvarado-Soto and Ramirez-Tagle, 2015 ; Bjorgaard et al, 2015 ), using the hybrid B3LYP functional and the standard Slater-type-orbital (STO) basis set with triple-ζ quality double plus polarization functions (TZ2P) for all the atoms (Rabanal-Leon et al, 2014 ; Zhang et al, 2016 ). Frequency analyses were performed after the geometry optimization to corroborate the minimum and to compare with experimental infrared spectra.…”

Section: Methodsmentioning

confidence: 99%

New Properties of a Bioinspired Pyridine Benzimidazole Compound as a Novel Differential Staining Agent for Endoplasmic Reticulum and Golgi Apparatus in Fluorescence Live Cell Imaging

et al. 2018

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In this study, we explored new properties of the bioinspired pyridine benzimidazole compound B2 (2,4-di-tert-butyl-6-(3H-imidazo[4,5-c]pyridine-2-yl)phenol) regarding its potential use as a differential biomarker. For that, we performed 1D 1HNMR (TOCSY), UV-Vis absorption spectra in different organic solvents, voltammetry profile (including a scan-rate study), and TD-DFT calculations that including NBO analyses, to provide valuable information about B2 structure and luminescence. In our study, we found that the B2 structure is highly stable, where the presence of an intramolecular hydrogen bond (IHB) seems to have a crucial role in the stability of luminescence, and its emission can be assigned as fluorescence. In fact, we found that the relatively large Stokes Shift observed for B2 (around 175 nm) may be attributed to the stability of the B2 geometry and the strength of its IHB. On the other hand, we determined that B2 is biocompatible by cytotoxicity experiments in HeLa cells, an epithelial cell line. Furthermore, in cellular assays we found that B2 could be internalized by passive diffusion in absence of artificial permeabilization at short incubation times (15 min to 30 min). Fluorescence microscopy studies confirmed that B2 accumulates in the endoplasmic reticulum (ER) and Golgi apparatus, two organelles involved in the secretory pathway. Finally, we determined that B2 exhibited no noticeable blinking or bleaching after 1 h of continuous exposure. Thus, B2 provides a biocompatible, rapid, simple, and efficient way to fluorescently label particular organelles, producing similar results to that obtained with other well-established but more complex methods.

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A Theoretical Study of the Binding of [Re6Se8(OH)2(H2O)4] Rhenium Clusters to DNA Purine Base Guanine

Cited by 7 publications

References 31 publications

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

Two New Fluorinated Phenol Derivatives Pyridine Schiff Bases: Synthesis, Spectral, Theoretical Characterization, Inclusion in Epichlorohydrin-β-Cyclodextrin Polymer, and Antifungal Effect

Octahedral chalcogenide rhenium cluster complexes with imidazole

New Properties of a Bioinspired Pyridine Benzimidazole Compound as a Novel Differential Staining Agent for Endoplasmic Reticulum and Golgi Apparatus in Fluorescence Live Cell Imaging

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