Partial inclusion of bis(1,10-phenanthroline)silver(I) salicylate in β-cyclodextrin: Spectroscopic characterization, in vitro and in silico antimicrobial evaluation

Abstract

Silver complexes containing 1,10-phenanthroline as a coordinated ligand have been of great interest due to their antibacterial and antifungal pharmacological properties. In this paper, we describe the synthesis of a new partial inclusion complex of bis(1,10-phenanthroline)silver(I) salicylate in β-cyclodextrin (β-CD) which was synthesized with a good yield. The compounds were characterized by FTIR, 1 H, 13 C NMR including 1 H− 1 H COSY, TGA/DSC, elemental analysis (CHN), and X-ray powder diffraction. The results suggest the presence of non-covalent interactions such as hydrogen bonds, van der Waals forces, and hydrophobic interactions in the formation of the partial inclusion compound between β-CD and bis(1,10-phenanthroline)silver(I) salicylate [Ag(phen) 2 ] salH. Additionally, an in silico prediction of 1,10-phenanthroline biological activities was carried out and the acquired data suggests several potential targets associated with the antimicrobial activity of this compound and its silver complex. Most predicted targets are related to antimicrobial virulence and resistance that are a serious threat to global public health. The inclusion compound showed a higher inhibiting growth of Candida albicans than the free complex [Ag(phen) 2 ]salH indicating that the formation of the inclusion complex with β-CD increases the bioavailability of the antimicrobial active species [Ag(phen) 2 ] + of the new silver(I) compound.

Assessment of host–guest molecular encapsulation of eugenol using β-cyclodextrin

“…These elongation vibrations were described previously in the literature ( Celebioglu et al, 2018 ; Gao et al, 2020 ). A broad hydroxyl band of pure β-cyclodextrin spectrum ( Figures 3 , 4 ) shows the maximum absorption at 3,384.57 cm −1 , found in the FTIR spectrum of the inclusion complexes which is a good indication of their formation due to the stretching vibrations of the different β-cyclodextrin OH groups ( Yang and Song, 2005 ; Kayaci et al, 2013 ; Celebioglu et al, 2018 ; Briñez-Ortega et al, 2020 ).…”

Biological Activities of Extracts from Ageratum fastigiatum: Phytochemical Study and In Silico Target Fishing Approach

“…The Active-IT system was developed entirely in-house by our research group (NEQUIM) to provide high-quality models to perform large-scale predictions of biological activities. This system is mainly devoted to chemists who work with either organic synthesis or isolation of natural products from Brazilian flora [64][65][67][68]. This system is composed of 4 modules, as depicted graphically in ▶ Fig.…”

“…For each model ensemble, the difference between the Pa and Pi (Pa-Pi) was used to evaluate the potential activity of the modeled compounds. As described in our previous work [64,65,67,68], we used cut-off values of 0.5 and 0.8 for SVM and Naïve Bayes methods, respectively. Biological activities and/or targets with values above these cut-off values are considered potential activities for the analyzed compound.…”

Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results

“…Cyclodextrins are water-soluble cyclic oligo-saccharides with a truncated cone-structure possessed a hydrophobic cavity and hydrophilic outer surface border [1]. Recently, the guesthost cyclodextrin complex formations were examined for many and different ligands like for example: remdesivir [2], water-soluble betulin derivatives [3], thiabendazole [4], ethinyloestradiol [5], bis(1,10-phenanthroline) silver (I) salicylate [6], oncocalyxone A [7], or β-cyclodextrinenhanced Eu 3+ luminescence aggregates with bright red fluorescence of Eu 3+ convenient for environmental detection system [8] and many others [9][10][11][12]. Reactions involving cyclodextrins are still important to the separation [13,14] and food industry [15][16][17] or other kinds of industries [18,19], but mostly to drug delivery systems for various applications in the field of medical biomaterials for example in the technology of polymers to get artificial abdominal wall prosthesis textile with improved biological and antibiotic delivery properties [20].…”