Chromatographic and computational lipophilicity assessment of novel antibiofilm agents

References

• Paulino, B. N.; Pessôa, M. G.; Mano, M. C.; Molina, G.; Neri-Numa, I. A.; Pastore, G. M. Current Status in Biotechnological Production and Applications of Glycolipid Biosurfactants. Appl. Microbiol. Biotechnol. 2016, 100, 10265–10293. DOI: 10.1007/s00253-016-7980-z.
   PubMed Web of Science ®Google Scholar
• Abdel-Mawgoud, A. M.; Lépine, F.; Déziel, E. Rhamnolipids: diversity of Structures, Microbial Origins and Roles. Appl. Microbiol. Biotechnol. 2010, 86, 1323–1336. DOI: 10.1007/s00253-010-2498-2.
   PubMed Web of Science ®Google Scholar
• Haba, E.; Pinazo, A.; Jáuregui, O.; Espuny, M. J.; Infante, M. R.; Manresa, A. Physicochemical Characterization and Antimicrobial Properties of Rhamnolipids Produced by Pseudomonas aeruginosa 47T2 NCBIM 40044. Biotechnol. Bioeng. 2003, 81, 316–322. DOI: 10.1002/bit.10474.
   PubMed Web of Science ®Google Scholar
• McClure, C. D.; Schiller, N. L. Effects of Pseudomonas aeruginosa Rhamnolipids on Human Monocyte-Derived Macrophages. J. Leukoc. Biol. 1992, 51, 97–102. DOI: 10.1002/jlb.51.2.97.
   PubMed Web of Science ®Google Scholar
• Jiang, L.; Shen, C.; Long, X.; Zhang, G.; Meng, Q. Rhamnolipids Elicit the Same Cytotoxic Sensitivity between Cancer Cell and Normal Cell by Reducing Surface Tension of Culture Medium. Appl. Microbiol. Biotechnol. 2014, 98, 10187–10196. DOI: 10.1007/s00253-014-6065-0.
   PubMed Web of Science ®Google Scholar
• Irie, Y.; O'toole, G. A.; Yuk, M. H. Pseudomonas aeruginosa Rhamnolipids Disperse Bordetella bronchiseptica Biofilms. FEMS Microbiol. Lett. 2005, 250, 237–243. DOI: 10.1016/j.femsle.2005.07.012.
   PubMed Web of Science ®Google Scholar
• Yan, J.; Nadell, C. D.; Stone, H. A.; Wingreen, N. S.; Bassler, B. L. Extracellular-Matrix-Mediated Osmotic Pressure Drives Vibrio cholerae Biofilm Expansion and Cheater Exclusion. Nat. Commun. 2017, 8, 1–11. DOI: 10.1038/s41467-017-00401-1.
   PubMed Web of Science ®Google Scholar
• Bjarnsholt, T. The Role of Bacterial Biofilms in Chronic Infections. APMIS. 2013, 121, 1–58. DOI: 10.1111/apm.12099.
   PubMed Web of Science ®Google Scholar
• Jovanovic, M.; Radivojevic, J.; O'Connor, K.; Blagojevic, S.; Begovic, B.; Lukic, V.; Nikodinovic-Runic, J.; Savic, V. Rhamnolipid Inspired Lipopeptides Effective in Preventing Adhesion and Biofilm Formation of Candida albicans. Bioorg. Chem. 2019, 87, 209–217. DOI: 10.1016/j.bioorg.2019.03.023.
   PubMed Web of Science ®Google Scholar
• Yang, Y.; Engkvist, O.; Llinàs, A.; Chen, H. Beyond Size, Ionization State, and Lipophilicity: influence of Molecular Topology on Absorption, Distribution, Metabolism, Excretion, and Toxicity for Druglike Compounds. J. Med. Chem. 2012, 55, 3667–3677. DOI: 10.1021/jm201548z.
   PubMed Web of Science ®Google Scholar
• Milošević, N. P.; Dimova, V. B.; Perišić-Janjić, N. U. RP TLC Data in Correlation Studies with in Silico Pharmacokinetic Properties of Benzimidazole and Benztriazole Derivatives. Eur. J. Pharm. Sci. 2013, 49, 10–17. DOI: 10.1016/j.ejps.2013.01.018.
   PubMed Web of Science ®Google Scholar
• Sangster, J. Octanol-water Partition Coefficients of Simple Organic Compounds. J. Phys. Chem. Ref. Data. 1989, 18, 1111–1229. DOI: 10.1063/1.555833
   Google Scholar
• De Bruijn, J.; Busser, F.; Seinen, W.; Hermens, J. Determination of Octanol/Water Partition Coefficients for Hydrophobic Organic Chemicals with the “Slow-Stirring” Method. Environ. Toxicol. Chem. 1989, 8, 499–512. DOI: 10.1002/etc.5620080607
   Google Scholar
• Casoni, D.; Kot-Wasik, A.; Namieśnik, J.; Sârbu, C. Lipophilicity Data for Some Preservatives Estimated by Reversed-Phase Liquid Chromatography and Different Computation Methods. J Chromatogr A. 2009, 1216, 2456–2465. DOI: 10.1016/j.chroma.2009.01.029.
   PubMed Web of Science ®Google Scholar
• Snyder, L. R.; Kirkland, J. J.; Glajch, J. L. Practical HPLC Method Development. John Wiley & Sons, Inc.: New Jersey, USA, 2012.
   Google Scholar
• Liang, C.; Lian, H. Z. Recent Advances in Lipophilicity Measurement by Reversed-Phase High-Performance Liquid Chromatography. Trac, Trends Anal. Chem. 2015, 68, 28–36. DOI: 10.1016/j.trac.2015.02.009.
   Web of Science ®Google Scholar
• Héberger, K. Sum of Ranking Differences Compares Methods or Models Fairly. Trac, Trends Anal. Chem. 2010, 29, 101–109. DOI: 10.1016/j.trac.2009.09.009.
   Web of Science ®Google Scholar
• Haber, P.; Baczek, T.; Kaliszan, R.; Snyder, L. R.; Dolan, J. W.; Wehr, C. T. Computer Simulation for the Simultaneous Optimization of Any Two Variables and Any Chromatographic Procedure. J. Chromatogr. Sci. 2000, 38, 386–392. DOI: 10.1093/chromsci/38.9.386.
   PubMed Web of Science ®Google Scholar
• Mannhold, R.; Poda, G. I.; Ostermann, C.; Tetko, I. V. Calculation of Molecular Lipophilicity: State-of-the-Art and Comparison of Log P Methods on More than 96,000 Compounds. J. Pharm. Sci. 2009, 98, 861–893. DOI: 10.1002/jps.21494.
   PubMed Web of Science ®Google Scholar
• Kollár-Hunek, K.; Héberger, K. Method and Model Comparison by Sum of Ranking Differences in Cases of Repeated Observations (Ties). Chemomet. Intell. Lab. Syst. 2013, 127, 139–146. DOI: 10.1016/j.chemolab.2013.06.007.
   Web of Science ®Google Scholar
• Héberger, K.; Rácz, A.; Bajusz, D. Which Performance Parameters Are Best Suited to Assess the Predictive Ability of Models? In Advances in QSAR Modeling; Roy, K., Ed. Springer, International Publishing: New York, USA, 2017; pp. 89–104.
   Google Scholar
• Šegan, S.; Božinović, N.; Opsenica, I.; Andrić, F. Consensus-Based Comparison of Chromatographic and Computationally Estimated Lipophilicity of Benzothiepino[3,2-c]pyridine Derivatives as Potential Antifungal Drugs. J. Sep. Sci. 2017, 40, 2089–2096. DOI: 10.1002/jssc.201601442.
   PubMed Web of Science ®Google Scholar
• Andrić, F.; Héberger, K. Towards Better Understanding of Lipophilicity: Assessment of in Silico and Chromatographic logP Measures for Pharmaceutically Important Compounds by Nonparametric Rankings. J. Pharm. Biomed. Anal. 2015, 115, 183–191. DOI: 10.1016/j.jpba.2015.07.006.
   PubMed Web of Science ®Google Scholar
• Sima, I. A.; Kot-Wasik, A.; Wasik, A.; Namieśnik, J.; Sârbu, C. Assessment of Lipophilicity Indices Derived from Retention Behavior of Antioxidant Compounds in RP-HPLC. Molecules 2017, 22, 550. DOI: 10.3390/molecules22040550.
   Web of Science ®Google Scholar
• Pitucha, M.; Matysiak, J.; Senczyna, B. Synthesis and RP HPLC Studies of Biologically Active Semicarbazides and Their Cyclic Analogues 1,2,4-triazol-3-ones. Monatsh. Chem. 2012, 143, 657–667. DOI: 10.1007/s00706-011-0715-z.
   PubMed Web of Science ®Google Scholar
• Platts, J. A.; Oldfield, S. P.; Reif, M. M.; Palmucci, A.; Gabano, E.; Osella, D. The RP-HPLC Measurement and QSPR Analysis of LogP(o/w) Values of Several Pt(II) Complexes. J. Inorg. Biochem. 2006, 100, 1199–1207. DOI: 10.1016/j.jinorgbio.2006.01.035.
   PubMed Web of Science ®Google Scholar
• Paneth, A.; Hawrył, A.; Plech, T.; Hawrył, M.; Świeboda, R.; Janowska, D.; Wujec, M.; Paneth, P. Lipophilicity Studies on Thiosemicarbazide Derivatives. Molecules. 2017, 22, 952. DOI: 10.3390/molecules22060952.
   PubMed Web of Science ®Google Scholar
• Ghose, A. K.; Viswanadhan, V. N.; Wendoloski, J. J. Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods. J. Phys. Chem. A. 1998, 102, 3762–3772. DOI: 10.1021/jp980230o.
   Web of Science ®Google Scholar
• Andrić, F.; Héberger, K. Chromatographic and Computational Assessment of Lipophilicity Using Sum of Ranking Differences and Generalized Pair-Correlation. J Chromatogr A. 2015, 1380, 130–138. DOI: 10.1016/j.chroma.2014.12.073.
   PubMed Web of Science ®Google Scholar
• Flieger, J.; Pizoń, M.; Plech, T. Chromatographic Behavior of New Antiepileptic Active Compounds on Different Reversed-Phase Materials. J Chromatogr A. 2014, 1338, 188–196. DOI: 10.1016/j.chroma.2014.02.054.
   PubMed Web of Science ®Google Scholar
• Didziapetris, R.; Reynolds, D. P.; Japertas, P.; Zmuidinavicius, D.; Petrauskas, A. In Silico Technology for Identification of Potentially Toxic Compounds in Drug Discovery. CAD. 2006, 2, 95–103. DOI: 10.2174/157340906777441708.
   Web of Science ®Google Scholar
• Tsopelas, F.; Giaginis, C.; Tsantili-Kakoulidou, A. Lipophilicity and Biomimetic Properties to Support Drug Discovery. Expert Opin. Drug Discov. 2017, 12, 885–896. DOI: 10.1080/17460441.2017.1344210.
   PubMed Web of Science ®Google Scholar
• Gao, Y.; Ge Senberg, C.; Zheng, W. Oral Formulations for Preclinical Studies: Principle, Design, and Development Considerations. In Developing Solid Oral Dosage Forms; Yihong, Q., Yisheng, C., Geoff, Z., Eds.; Academic Press: Cambridge, 2017; pp 455–495.
   Google Scholar
• Waring, M. J. Lipophilicity in Drug Discovery. Expert Opin. Drug Discov. 2010, 5, 235–248. DOI: 10.1517/17460441003605098.
   PubMed Web of Science ®Google Scholar