Piperazine based antimicrobial polymers: a review

Jalageri, Manohara Dhulappa; Nagaraja, Akshatha; Puttaiahgowda, Yashoda Malgar

doi:10.1039/d1ra00341k

Cited by 35 publications

(17 citation statements)

References 93 publications

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“…Piperazine is a common functional group in medicinal chemistry, prevalent in the structures of diverse small-molecule pharmaceuticals as well as in multiple psychoactive substances . Consequently, many studies involving liquid chromatography and tandem mass spectrometry have been carried out to identify signature MS/MS transitions for the detection and quantitation of these compounds. ,, Among these studies, frequently reported fragmentations involve cleavage at the bond connecting the piperazine with the rest of the molecule, formation of tetrahydropyrazinium product ions, loss of neutral piperazine or formation of piperazine radical cations .…”

Section: Resultsmentioning

confidence: 99%

“…Piperazine. Piperazine is a common functional group in medicinal chemistry, prevalent in the structures of diverse small-molecule pharmaceuticals 41 as well as in multiple psychoactive substances. 42 Consequently, many studies involving liquid chromatography and tandem mass spectrometry have been carried out to identify signature MS/MS transitions for the detection and quantitation of these compounds.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Fragmentation of Polyfunctional Compounds Recorded Using Automated High-Throughput Desorption Electrospray Ionization

Morato

Kaerner

et al. 2021

J. Am. Soc. Mass Spectrom.

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Using desorption electrospray ionization (DESI) as part of an automated high-throughput system, tandem mass spectra of the compounds in a pharmaceutical library were recorded in the positive mode under standardized conditions. Quality control filtering yielded an MS/MS library of 16 662 spectra. Fragmentation of subsets of the compounds in the library chosen to contain a single instance of a particular functional group (amide, piperazine, sulfonamide) was predicted by experts, and the results were compared with the experimental data. Expert performance was good to excellent for all the cases evaluated. Substituents on the functional groups were found to exert important secondary control over the fragmentation, with the main effect observed being product ion stabilization by aromatic substitution, which was consistent across the different groups evaluated. These substituent effects are generally explicable in terms of standard physical organic chemistry considerations of product ion stability as controlling fragmentation. A somewhat unexpected feature was the incidence of homolytic cleavages, driven by the stability of substituted amine radical cations. The findings of this study are intended to lay the groundwork for machine learning approaches to performing MS/ MS spectrum → structure and structure → MS/MS spectrum operations on the same experimental data set. The effort involved and the success achieved in computer-aided interpretation, now underway, will be compared with the expert performance as described here.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Fragmentation of Polyfunctional Compounds Recorded Using Automated High-Throughput Desorption Electrospray Ionization

Morato

Kaerner

et al. 2021

J. Am. Soc. Mass Spectrom.

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“…The higher activity of PVA-E-Pz against E. coli may be due to the presence of thinner cell wall than S. aureus [64,65]. PVA-E-Pz's antibacterial properties is due to the presence of piperazine, which affects the cytoplasmic membrane of bacteria, allowing intercellular components to flow out and eventually causing cell lysis [56,66]. To compare the results, antimicrobial activity of ciprofloxacin (10 mg) was measured and it exhibited a zone of inhibition of 45 mm and 46 mm against S. aureus and E. coli, respectively.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

One-Pot Synthesis of Polyvinyl Alcohol-Piperazine Cross-Linked Polymer for Antibacterial Applications

et al. 2022

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The spread of microbes which cause infectious diseases are of great concern on human health. Therefore, a water-soluble cross-linked polymer based on polyvinyl alcohol was synthesized via an economical, facile, and aqueous-based approach. The resultant cross-linked polymer was characterized by different techniques such as FTIR, 1H NMR, 13C NMR, TGA, and DSC. The IR spectrum has been recorded in the range 400–4000 cm−1. From thermal studies, i.e. TGA, cross-linking polymer PVA-E-Pz showed two step degradation and from DSC, glass transition temperature (Tg) was exhibited at 86.05 °C. The antimicrobial properties of the cross-linked polymer were studied using the well-diffusion technique and optical density method against gram-negative bacteria, Escherichia coli and gram-positive bacteria, Staphylococcus aureus. Polymer coated fabric was also evaluated for antimicrobial activity against both the bacteria, even after 25 wash cycles the coated fabric showed about 90% antibacterial activity. Samples showed good antimicrobial activity against both the micro-organisms, but more activity was exhibited against gram-negative bacteria. The coating durability and surface morphology of the coated fabric were also analyzed. Cytotoxicity studies revealed that PVA-E-Pz was non-toxic against human dermal fibroblast cell lines. This material might be a good fit for advanced wound dressing and textile applications. The proposed strategy provides a low-cost, environmentally friendly method for creating a new cross-linked polymer with antimicrobial activity. Graphical Abstract

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“…24 The prevalence of substituted piperazines shows the relevance of N -heterocycles in therapeutic development. 25,26 In the list of FDA-approved pharmaceuticals, piperazine is the third most prevalent saturated N -heterocycle. 27 On this point, we executed and optimized solvent-free mechanochemical procedures for obtaining a library of N -substituted amines under milder reaction conditions in a short reaction time with excellent yields without any further purification.…”

Section: Introductionmentioning

confidence: 99%

Solvent-free mechanochemical grinding facilitates clean synthesis of N-substituted amines

Sharma

Kumar

et al. 2022

Org. Biomol. Chem.

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Piperazine based antimicrobial polymers: a review

Abstract: Mode of action of piperazine based polymers against pathogenic microorganisms.

Cited by 35 publications

References 93 publications

Fragmentation of Polyfunctional Compounds Recorded Using Automated High-Throughput Desorption Electrospray Ionization

Fragmentation of Polyfunctional Compounds Recorded Using Automated High-Throughput Desorption Electrospray Ionization

One-Pot Synthesis of Polyvinyl Alcohol-Piperazine Cross-Linked Polymer for Antibacterial Applications

Solvent-free mechanochemical grinding facilitates clean synthesis of N-substituted amines

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