Rapid Identification of Unknown Impurities in 3-Bromo-5-(trifluoromethyl)aniline by LC-SPE/NMR

Harča, Miroslava; Habinovec, Iva; Meštrović, Ernest; Biljan, Ivana; Novak, Predrag

doi:10.5562/cca3042

Cited by 3 publications

(4 citation statements)

References 26 publications

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“…Modern and sophisticated hyphenated techniques such as LC-NMR, LC-MS and others have frequently been used to analyze complex mixtures without initial separation of the constituents that have enabled rapid screening of pharmaceutical and biological samples [25][26][27][28][29][30][31][32][33]. Initial sensitivity limitations of LC-NMR have in the past two decades been largely alleviated by technological developments that include cryo-platforms, capillary NMR with micro-coil probes and coupling of solid phase extraction system (SPE) into an LC-SPE-NMR set up [30,[34][35][36][37][38]. The latter methodology has been widely used for analyzing natural products, metabolites and drug impurities but has less frequently been applied for monitoring chemical reactions and structural identification of the reaction products [39][40][41][42][43].…”

Section: Resultsmentioning

confidence: 99%

Rapid Structure Determination of Bioactive 4″-Tetrahydrofurfuryl Macrozone Reaction Mixture Components by LC-SPE/Cryo NMR and MS

et al. 2021

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LC-SPE/cryo NMR and MS methodologies have been developed and employed for a rapid structure determination of 4″-tetrahydrofurfuryl macrozone reaction mixture components. Macrozones, novel conjugates of azithromycin, and thiosemicarbazones have shown very good in vitro antibacterial activities against susceptible and some resistant bacterial strains and are promising agents for further development. The post-column multiple trapping of the chromatographically separated reaction mixture components on the SPE cartridges increased the sensitivity and together with cryogenically cooled NMR probe made it possible to identify and structurally characterize main 4″-tetrahydrofurfuryl macrozone reaction mixture compounds including those present at very low concentration level. This approach has several advantages over a classical off-line procedure, efficiency and low solvent consumption being the two most important ones. All identified components were process-related. It has been demonstrated that two different kinds of compounds with respect to structure were identified, i.e., macrolide-related and thiosemicarbazone-related ones. This methodology can serve as a platform for reliable and effective macrolides reaction components structure profiling, serving as both isolation and identification tools.

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Section: Resultsmentioning

confidence: 99%

Rapid Structure Determination of Bioactive 4″-Tetrahydrofurfuryl Macrozone Reaction Mixture Components by LC-SPE/Cryo NMR and MS

et al. 2021

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“…This approach allows for a comprehensive assessment of NP content. In the future, much more complete assessments will be performed for Safety by Design, which is implemented in industry to address all possible challenges from the beginning [36].…”

Section: Separation Methods Of Antimicrobial Nps In Coatingsmentioning

confidence: 99%

“…In the realm of nanomaterial analysis, researchers have leveraged various analytical techniques to evaluate the purity and characteristics of polymer nanoparticles. Harča et al [36] employed nuclear magnetic resonance ( 1 H NMR) spectroscopy to assess the purity of these nanoparticles, shedding light on the presence of monomer residues and oligomers. Concurrently, gel permeation was utilized to determine the molecular weight.…”

Section: Microscopical Investigation Of Antimicrobial Nps In Coatingsmentioning

confidence: 99%

Characterization of Nanoparticles in Antimicrobial Coatings for Medical Applications—A Review

Rezić,

Meštrović

2023

Coatings

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This review discusses relevant topics concerning the understanding of the characterization of antimicrobial coatings due to powerful antimicrobial nanoparticles in their composition. These coatings are utilized in the surface modification of yarns and materials designed for use in medical and dental applications. Various physical and chemical methods are employed to create these coatings, ensuring the development of efficient, homogeneous, and uniform layers on diverse surfaces and materials. The primary objective is to confer antimicrobial and/or antiviral properties upon these materials. For these coatings to be effective, they must incorporate active compounds that can combat a wide array of microorganisms, including those that have developed resistance to antibiotics. Examples of such active compounds include metallic nanoparticles such as silver, copper, and gold, as well as nanoparticles of metal oxides such as zinc, titanium, and aluminum. Upon the application of these coatings to medical materials, extensive testing and characterization procedures are undertaken, which will be thoroughly detailed in this review. It is crucial to emphasize that the absence of proper characterization and testing of nanoparticles in antimicrobial coatings could lead to the absence of standards, norms, or procedures necessary to safeguard human health and the environment. Despite their widespread application in the medical field, concerns have been raised regarding the potential toxicity of nanoparticles to living organisms. Consequently, this paper provides a comprehensive overview of the current state-of-the-art methodologies for characterizing nanoparticles in antimicrobial coatings, specifically focusing on materials with varying roughness and structures. Additionally, it outlines the issues associated with the potential accumulation of antimicrobial nanoparticles within the human body.

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“…Recent technological developments such as cryo-platforms, capillary NMR with microcoil probes and the introduction of solid phase extraction (SPE) into an LC-SPE-NMR system have made it possible to detect compounds present at a very low concentration level [ 16 , 17 , 18 ]. Fully hyphenated LC-SPE-NMR or hyphenated LC-SPE in combination with cryo NMR, e.g., LC-SPE/cryo NMR, today represent widely accepted tools for dereplication and discovery of complex natural product mixtures, metabolites and bioactive and drug substances.…”

Section: Introductionmentioning

confidence: 99%

Screening of Novel Antimicrobial Diastereomers of Azithromycin–Thiosemicarbazone Conjugates: A Combined LC-SPE/Cryo NMR, MS/MS and Molecular Modeling Approach

et al. 2022

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A well-known class of antibacterials, 14- and 15-membered macrolides are widely prescribed to treat upper and lower respiratory tract infections. Azithromycin is a 15-membered macrolide antibiotic possessing a broad spectrum of antibacterial potency and favorable pharmacokinetics. Bacterial resistance to marketed antibiotics is growing rapidly and represents one of the major global hazards to human health. Today, there is a high need for discovery of new anti-infective agents to combat resistance. Recently discovered conjugates of azithromycin and thiosemicarbazones, the macrozones, represent one such class that exhibits promising activities against resistant pathogens. In this paper, we employed an approach which combined LC-SPE/cryo NMR, MS/MS and molecular modeling for rapid separation, identification and characterization of bioactive macrozones and their diastereomers. Multitrapping of the chromatographic peaks on SPE cartridges enabled sufficient sample quantities for structure elucidation and biological testing. Furthermore, two-dimensional NOESY NMR data and molecular dynamics simulations revealed stereogenic centers with inversion of chirality. Differences in biological activities among diastereomers were detected. These results should be considered in the process of designing new macrolide compounds with bioactivity. We have shown that this methodology can be used for a fast screening and identification of the macrolide reaction components, including stereoisomers, which can serve as a source of new antibacterials.

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Rapid Identification of Unknown Impurities in 3-Bromo-5-(trifluoromethyl)aniline by LC-SPE/NMR

Cited by 3 publications

References 26 publications

Rapid Structure Determination of Bioactive 4″-Tetrahydrofurfuryl Macrozone Reaction Mixture Components by LC-SPE/Cryo NMR and MS

Rapid Structure Determination of Bioactive 4″-Tetrahydrofurfuryl Macrozone Reaction Mixture Components by LC-SPE/Cryo NMR and MS

Characterization of Nanoparticles in Antimicrobial Coatings for Medical Applications—A Review

Screening of Novel Antimicrobial Diastereomers of Azithromycin–Thiosemicarbazone Conjugates: A Combined LC-SPE/Cryo NMR, MS/MS and Molecular Modeling Approach

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