The study of salting-out thin-layer chromatography and their application on QSRR/QSAR of some macrolide antibiotics

Ciura, Krzesimir; Nowakowska, Joanna; Rudnicka-Litka, Kaja; Kawczak, Piotr; Bączek, Tomasz; Markuszewski, Michał J.

doi:10.1007/s00706-015-1606-5

Cited by 13 publications

(6 citation statements)

References 29 publications

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“…The most significant ones are a relatively low bioavailability and high costs of production [ 1 , 2 ]. A lot of attention has been paid to designing new analogues: shorter compounds containing the sequence crucial for antimicrobial action or designing novel compounds basing on native AMPs as well as new high throughput methods for their assessment [ 3 , 4 , 5 ]. To obtain compounds with improved stability, several approaches have been applied: advanced drug formulation or modification of chemical structure of compounds, such as introduction of D-amino acid or fatty acid residues into the molecule [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

In Vitro Evaluation of Cytotoxicity and Permeation Study on Lysine- and Arginine-Based Lipopeptides with Proven Antimicrobial Activity

et al. 2017

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Owing to their excellent antimicrobial activities with a relatively low cost of production, lipopeptides are being intensively investigated as potential alternatives to popular antimicrobials. However, a critical obstacle for their application is a relatively high toxicity, hence a lot of attention has been paid to designing new molecules with optimal properties. In this study we synthesized the following lipopeptides: C16-KK-NH2, C16-KεK-NH2, C16-KKK-NH2, C16-KRK-NH2, C16-RR-NH2, C16-RRR-NH2, (C10)2-KKKK-NH2 and (C12)2-KKKK-NH2. Their antimicrobial activity against representative strains of Gram-positive bacteria, Gram-negative bacteria and fungi has been confirmed. The compounds have been evaluated with regard to the safety of their application in dermatology. The cytotoxicity was determined in HaCaT keratinocytes using MTT assay, whereas Strat M membranes placed in Franz diffusion cells were used to assess their ability to skin permeation. The compounds containing one hexadecanoic acid chain turned out to be very toxic towards human keratinocytes, while lipopeptides containing two fatty acid chains (decanoic and dodecanoic) demonstrated much lower cytotoxicity. For the most promising lipopeptide, (C10)2-KKKK-NH2, the measured IC50 on HaCaT keratinocytes was few times higher as compared to MICs obtained for the tested bacteria. Both groups of lipopeptides did not permeate the model membranes and therefore lack of permeation through human skin could be expected. The results of this work encourage further research on the potential application of lipopeptides with two fatty acids as novel antimicrobials.

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Section: Introductionmentioning

confidence: 99%

In Vitro Evaluation of Cytotoxicity and Permeation Study on Lysine- and Arginine-Based Lipopeptides with Proven Antimicrobial Activity

et al. 2017

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“…A particular example of QSPR is a quantitative structure–retention relationship (QSRR) where the properties are defined as chromatographic parameters. The QSRR/QSAR approach was successfully applied to predict antimicrobial activities of others class of antibiotics (Ciura et al 2016 ).…”

Section: Introductionmentioning

confidence: 99%

Characterization of antimicrobial and hemolytic properties of short synthetic cationic lipopeptides based on QSAR/QSTR approach

et al. 2017

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In this study, we investigated the influence of molecular descriptors of cationic lipopeptides on their antimicrobial activity and hemolytic properties. The quantitative structure–activity relationship and quantitative structure–property relationship models were constructed. The antimicrobial, hemolytic and retention data were used as dependent variable and structural parameters as the independent ones. The obtained results suggest that the chromatographic indexes can be employed for prediction of antibacterial activity and that lipopeptides present nonspecific interaction between erythrocytes and bacterial membranes.Electronic supplementary materialThe online version of this article (10.1007/s00726-017-2530-2) contains supplementary material, which is available to authorized users.

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“…191 Ledbetter et al 192 have correlated structural fragments obtained from 64 aliphatic and aromatic compounds with log k for these compounds found by IAM-HPLC and have used this to predict log k. They obtained an R 2 value of 0.97 between experimental and predicted log k values. TLC studies using QSRR to predict retention behavior have included RP-TLC with a C8 SP applied to guanidine and imidazoline derivatives, 193 the use of QSRR to predict lipophilicity (and hence antimicrobial properties) for some macrolide antibiotics, 194 the correlation of C18 or CN highperformance TLC retention data with antimalarial activity of 1,2,4,5-mixed tetraoxanes by QSRR 196 (ref 189), and the application of QSRR to prediction of molecular lipophilicity of 12 2,4-dioxotetrahydro-1,3-thiazole derivatives. 195 Filipic et al 197 have applied QSRR using MLR and PLS to investigate the correlations between isocratic retention times (obtained at 5 different percentages of 2-propanol in the MP) and extrapolated retention parameters (log k w values) and they have attempted to interpret the relevance of the chosen descriptors to the separation mechanism.…”

Section: ■ Prediction Of Retention In Icmentioning

confidence: 99%

Prediction of Analyte Retention Time in Liquid Chromatography

2020

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The study of salting-out thin-layer chromatography and their application on QSRR/QSAR of some macrolide antibiotics

Cited by 13 publications

References 29 publications

In Vitro Evaluation of Cytotoxicity and Permeation Study on Lysine- and Arginine-Based Lipopeptides with Proven Antimicrobial Activity

In Vitro Evaluation of Cytotoxicity and Permeation Study on Lysine- and Arginine-Based Lipopeptides with Proven Antimicrobial Activity

Characterization of antimicrobial and hemolytic properties of short synthetic cationic lipopeptides based on QSAR/QSTR approach

Prediction of Analyte Retention Time in Liquid Chromatography

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