Experimental and computational study on dimers of 5-halo-1H-indole-2-carboxylic acids and their microbiological activity

Balcerek, Martyna; Szmigiel-Bakalarz, Ksenia; Lewańska, Monika; Günther, Daniel; Malik, Magdalena; Morzyk-Ociepa, Barbara

doi:10.1016/j.molstruc.2022.134492

Cited by 5 publications

(5 citation statements)

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“…An FTIR spectrometer was employed for the characterization of the functional group. As shown in Figure B, a wide and scattered peak ranging from 3200 to 2500 cm –1 was observed with typical peaks 2965 and 2550 cm –1 , indicating that the −COOH groups from DPA formed a dimer due to O atoms with a relatively strong ability to attract electrons. , Furthermore, HRTEM was used to characterize the morphology of the DPA@Ag/Cu NCs. As shown in Figure C, DPA@Ag/Cu NCs were monodispersed and exhibited a highly uniform spherical structure with a size range of 1.0–4.5 nm and an average diameter of 2.5 nm (Figure D).…”

Section: Resultsmentioning

confidence: 99%

d-Penicillamine@Ag/Cu Nanocluster-Based Fluorescent Nanoneuron for Logic Screening Phosphonate-Type Organophosphate Pesticides and Steganographically Encrypting Information

Fan

Dong

et al. 2023

Anal. Chem.

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Organophosphate pesticides are used in agriculture due to their high effectiveness and low persistence in eradicating insects and pests. However, conventional detection methods encounter the limitation of undesired detection specificity. Thus, screening phosphonate-type organophosphate pesticides (OOPs) from their analogues, phosphorothioate organophosphate pesticides (SOPs), remains a challenge. Here, we reported a D-penicillamine@Ag/Cu nanocluster (DPA@Ag/Cu NCs)based fluorescence assay to screen OOPs from 21 kinds of organophosphate pesticides, which can be used for logic sensing and information encryption. Acetylthiocholine chloride was enzymatically split by acetylcholinesterase (AChE) to produce thiocholine, which reduced the fluorescence of DPA@Ag/Cu NCs due to the transmission of electrons from DPA@Ag/Cu NCs donor to the thiol group acceptor. Impressively, OOPs acted as an AChE inhibitor and retained the high fluorescence of DPA@Ag/Cu NCs due to the stronger positive electricity of the phosphorus atom. Conversely, SOPs possessed weak toxicity to AChE, which led to low fluorescence intensity. By setting 21 kinds of organophosphate pesticides as the inputs and the fluorescence of the resulting products as the outputs, DPA@Ag/Cu NCs could serve as a fluorescent nanoneuron to construct Boolean logic tree and complex logic circuit for molecular computing. As a proof of concept, by converting the selective response patterns of DPA@Ag/Cu NCs into binary strings, molecular cryptosteganography for encoding, storing, and concealing information was successfully achieved. This study is expected to advance the progress and practical application of nanoclusters in the area of logic detection and information security while also enhancing the relationship between molecular sensors and the world of information.

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Section: Resultsmentioning

confidence: 99%

d-Penicillamine@Ag/Cu Nanocluster-Based Fluorescent Nanoneuron for Logic Screening Phosphonate-Type Organophosphate Pesticides and Steganographically Encrypting Information

Fan

Dong

et al. 2023

Anal. Chem.

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“…We identified this compound as 6-methoxy-1H-Indole-2-carboxylic acid using 1D-and 2D-NMR and LC-PDA-MS spectral studies. This compound contains the indole carboxylic acid moiety, which had been previously reported for its antifungal and antimicrobial activities [63] from various microorganisms and algae [23]. Furthermore, 4-[(1E)-3-methylbuta-1,3-dienyl]-1H-indole-3-carbaldehyde (indiacene A) and -[(1E,3E)-4-chloro-3-methylbuta-1,3-dienyl]-1H-indole-3-carbaldehyde (indiacene B)-prenyl indoles harboring the same moiety were extracted and purified from the culture broth of the Myxobacterium Sandaracinus amylolyticus [25].…”

Section: Discussionmentioning

confidence: 99%

Identification, Characterization, and Production Optimization of 6-Methoxy-1H-Indole-2-Carboxylic Acid Antifungal Metabolite Produced by Bacillus toyonensis Isolate OQ071612

El-Sayed,

Abdelaziz,

Ali

et al. 2023

Microorganisms

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Fungal infections currently pose a real threat to human lives. In the current study, soil bacterial isolates were screened for the production of antifungal compounds to combat human fungal pathogens. Notably, the bacterial F1 isolate exhibited antimycotic action towards the Candida albicans ATCC 10231 and Aspergillus niger clinical isolates. By employing phenotypic and molecular techniques, we identified the F1 isolate as the Bacillus toyonensis isolate OQ071612. The purified extract showed stability within a pH range of 6–7 and at temperatures of up to 50 °C. It demonstrated potential antifungal activity in the presence of various surfactants, detergents, and enzymes. The purified extract was identified as 6-methoxy-1H-Indole-2-carboxylic acid using advanced spectroscopic techniques. To optimize the antifungal metabolite production, we utilized response surface methodology (RSM) with a face-centered central composite design, considering nutritional and environmental variables. The optimal conditions were as follows: starch (5 g/L), peptone (5 g/L), agitation rate of 150 rpm, pH 6, and 40 °C temperature. A confirmatory experiment validated the accuracy of the optimization process, resulting in an approximately 3.49-fold increase in production. This is the first documented report on the production and characterization of 6-methoxy-1H-Indole-2-carboxylic acid (MICA) antifungal metabolite from Bacillus toyonensis.

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“…In the spectrum of polymorph 2, a very strong band appears at 1259 cm −1 , and can be assigned to this mode. Interestingly, in the spectra of halogen derivatives of I2CA, which form analogous cyclic dimers through O-H• • • O interactions, the ν(C=O) and ν(C-O) stretching vibrations were similarly assigned in the ranges 1659-1653 cm −1 and 1291-1254 cm −1 , respectively [18]. On the other hand, for polymorph 1, which revealed a different pattern of intermolecular hydrogen bonds, the ν(C=O) and ν(C-O) stretching vibrations were observed at 1695 and 1206 cm −1 , respectively [16,20].…”

Section: Mir Spectra Of Mi2ca Polymorphmentioning

confidence: 98%

“…In the case of I2CA, crystallographic analysis revealed that two chains of I2CA molecules formed a flat ribbon held together by intermolecular hydrogen bonds O-H• • • O and N-H• • • O [17]. Recent studies of three halogen derivatives, XI2CA, where X = F, Cl, and Br have shown the presence of cyclic dimeric structures with linear double O-H• • • O hydrogen bonds in the solid state [18].…”

Section: Introductionmentioning

confidence: 99%

Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-ray Diffraction, Infrared Spectroscopy, and DFT Calculations

Polak,

Bąkowicz,

Morzyk-Ociepa

2024

Molecules

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This study presents a new 5-methoxy-1H-indole-2-carboxylic acid (MI2CA) polymorph investigated by single-crystal X-ray diffraction, infrared spectroscopy, and density functional theory (ωB97X-D) calculations employing two basis sets (6-31++G(d,p) and aug-cc-pVTZ). The compound crystallizes in the monoclinic system, space group P21/c (a = 4.0305(2) Å, b = 13.0346(6) Å, c = 17.2042(9) Å, β = 91.871(5)°, Z = 4). In the crystalline structure, the formation of cyclic dimers via double hydrogen bonds O−H⋯O between MI2CA molecules was observed. Interactions between the NH groups of the indole rings and the adjacent methoxy groups, as well as C–H⋯O contacts, significantly influence the spatial arrangement of molecules. The results from DFT calculations, including dimeric and trimeric structures, agree well with the experimental structural and spectroscopic data. Analysis of the infrared spectra confirms the conclusions drawn from X-ray diffraction studies and reveals differences between the IR spectra of the newly obtained polymorph and that reported earlier in the literature. This comprehensive study sheds some light on the MI2CA polymorphism and is important for a potential pharmacological applications of this compound.

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Experimental and computational study on dimers of 5-halo-1H-indole-2-carboxylic acids and their microbiological activity

Cited by 5 publications

References 50 publications

d-Penicillamine@Ag/Cu Nanocluster-Based Fluorescent Nanoneuron for Logic Screening Phosphonate-Type Organophosphate Pesticides and Steganographically Encrypting Information

d-Penicillamine@Ag/Cu Nanocluster-Based Fluorescent Nanoneuron for Logic Screening Phosphonate-Type Organophosphate Pesticides and Steganographically Encrypting Information

Identification, Characterization, and Production Optimization of 6-Methoxy-1H-Indole-2-Carboxylic Acid Antifungal Metabolite Produced by Bacillus toyonensis Isolate OQ071612

Discovery of a New Polymorph of 5-Methoxy-1H-Indole-2-Carboxylic Acid: Characterization by X-ray Diffraction, Infrared Spectroscopy, and DFT Calculations

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