Derringer desirability and kinetic plot LC-column comparison approach for MS-compatible lipopeptide analysis

Journal of Pharmaceutical Analysis

Volumn 4, Issue 3, 2014, Pages 173-182

  D'Hondt, Matthias ^a   Verbeke, Frederick ^a   Stalmans, Sofie ^a   Gevaert, Bert ^a   Wynendaele, Evelien ^a   De Spiegeleer, Bart ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Derringer desirability function; Hierarchical cluster analysis (HCA); Kinetic plot; LC MS; Lipopeptide; Principal component analysis (PCA)

Indexed keywords

ACETONITRILE; AMFOMYCIN; ANIDULAFUNGIN; ANTIFUNGAL AGENT; ARTHROFACTIN; CASPOFUNGIN; CILOFUNGIN; COLISTIN; DALBAVANCIN; DAPTOMYCIN; ECHINOCANDIN B; ELONGATION FACTOR; ELONGATION FACTOR GAMMA; FORMIC ACID; GRAMICIDIN A; ITURIN A DERIVATIVE; LIPOPEPTIDE; MICAFUNGIN; MX 2401; P 3 CSS; PLIPASTATIN; POLYMYXIN B; POLYPEPTIDE ANTIBIOTIC AGENT; RAMOPLANIN; SURFACTIN; SYRINGOMYCIN E; TEICOPLANIN DERIVATIVE; TELAVANCIN; UNCLASSIFIED DRUG;

ANALYTICAL PARAMETERS; AQUEOUS SOLUTION; ARTICLE; CLUSTER ANALYSIS; DERRINGER DESIRABILITY FUNCTION; FLOW RATE; KINETIC PLOT APPROACH; LIPOPEPTIDE ANALYSIS; MASS SPECTROMETRY; PEPTIDE ANALYSIS; PRESSURE GRADIENT; PRINCIPAL COMPONENT ANALYSIS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84901264401     PISSN: 20951779     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpha.2013.09.001     Document Type: Article

References (47)

1. J.M. Raaijmakers, I. de Bruijn, and O. Nybroe et al. Natural functions of lipopeptides from Bacillus and Pseudomonas: more than surfactants and antibiotics FEMS Microbiol. Rev. 34 2010 1037 1062
2. G. Pirri, A. Giuliani, and S.F. Nicoletto et al. Lipopeptides as anti-infectives: a practical perspective Cent. Eur. J. Biol. 4 2009 258 273
3. T.M. Arnold, G.N. Forrest, and K.J. Messmer Polymyxin antibiotics for gram-negative infections Am. J. Health-Syst. Pharm. 64 2007 819 826
4. C.F. Carpenter, and H. Chambers Daptomycin: another novel agent for treating infections due to drug-resistant gram-positive pathogens Clin. Infect. Dis. 38 2004 994 1000
5. C.J. Balibar, F.H. Vaillancourt, and C.T. Walsh Generation of D amino acid residues in assembly of arthrofactin by dual condensation/epimerization domains Chem. Biol. 12 2005 1189 1200
6. C.S. Taft, T. Start, and C.P. Selitrennikoff Cilofungin (LY121019) inhibits Candida albicans (1-3)-beta-D-glucan synthase activity Antimicrob. Agents Chemother. 32 1988 1901 1903
7. P. Vitovic, M. Weis, and P. Tomcik et al. Maxwell displacement current allows to study structural changes of gramicidin A in monolayers at the air-water interface Bioelectrochemistry 70 2007 469 480
8. G.Y. Yu, J.B. Sinclair, and G.L. Hartman et al. Production of iturin A by Baccilus amyloliquefaciens suppressing Rhizoctonia solani Soil Biol. Biochem. 34 2002 955 963
9. T.U. Vogel, B.E. Beer, and J.Z. Megede et al. Induction of anti-simian immunodeficiency virus cellular and humoral immune responses in rhesus macaques by peptide immunogens: correlation of CTL activity and reduction of cell-associated but not plasma virus load following challenge J. Gen. Virol. 83 2002 81 91
10. N. Roongsawang, J. Thaniyavarn, and S. Thaniyavarn et al. Isolation and characterization of halotolerant Bacillus subtilis BBK-1 which produces three kinds of lipopeptides: Bacillomycin L, Plipastatin, and Surfactin Extremophilis 6 2002 499 506
11. E.A. Somner, and P.E. Reynolds Inhibition of peptidoglycan biosynthesis by ramoplanin Antimicrob. Agents Chemother. 34 1990 413 419
12. M. Anselmi, T. Eliseo, and L. Zanetti-Polzi et al. Structure of the lipodepsipeptide syringomycin E in phospholipids and sodium dodecylsulphate micelle studied by circular dichroism, NMR spectroscopy and molecular dynamics Biochim. Biophys. Acta 1808 2011 2102 2110
13. F. Parenti Structure and mechanism of action of teicoplanin J. Hosp. Infect. 7 1986 79 83
14. S.S. Cameotra, and R.S. Makkar Recent applications of biosurfactants as biological and immunological molecules Curr. Opin. Mircobiol. 7 2004 262 266
15. A.-B.M. Abdel-Aal, K. Al-Isae, and M. Zaman et al. Simple synthetic toll-like receptor 2 ligands Bioorg. Med. Chem. Lett. 21 2011 5863 5865
16. G. Henry, M. Deleu, and E. Jourdan et al. The bacterial lipopeptide surfactin targets the lipid fraction of the plant plasma membrane to trigger immune-related defence responses Cell. Microbiol. 13 2011 1824 1837
17. H.D. Brightbill, D.H. Libraty, and S.R. Krutzik et al. Host defense mechanisms triggered by microbial lipoproteins through toll-like receptors Nature 732 1999 732 736
18. K. Langel, S. Lindberg, and D. Copolovici et al. Novel fatty acid modifications of Transportan 10 Int. J. Pept. Res. Ther. 16 2010 247 255
19. J.S. Lee, and C.-H. Tung Enhanced cellular uptake and metabolic stability of lipo-oligoarginine peptides Pept. Sci. 96 2011 772 779
20. A.R. Nelson, L. Borland, and N.L. Allbritton et al. Myristoyl-based transport of peptides into living cells Biochemistry 46 2007 14771 14781
21. J.-F. Dubern, B.J.J. Lugtenberg, and G.V. Bloemberg The ppuI-rsaL-ppuR quorum-sensing system regulates biofilm formation of pseudomonas putida PCL1445 by controlling biosynthesis of the cyclic lipopeptides Putisolvins I and II J. Bacteriol. 188 2006 2898 2906
22. M. Okada, H. Yamaguchi, and I. Sato et al. Chemical structure of posttranslational modification with a farnesyl group on tryptophan Biosci. Biotechnol. Biochem. 72 2008 914 918
23. F. Tsuji, K. Kobayashi, and M. Okada et al. The geranyl-modified tryptophan residue is crucial for comXRO-E-2 pheromone biological activity Bioorganic Med. Chem. Lett. 21 2011 4041 4044
24. E. Wynendaele, A. Bronselaer, and J. Nielandt et al. Quorumpeps database: chemical space, microbial origin and functionality of quorum sensing peptides Nucleic Acids Res. 41 2013 D655 D659
25. M. D'Hondt, B. Gevaert, and S. Stalmans et al. Reversed-phase fused-core HPLC modeling of peptides J. Pharmaceut. Anal. 3 2013 93 101
26. J.A. Orwa, A. Van Gerven, and E. Roets et al. Liquid chromatography of polymyxin B sulfate J. Chromatogr. A 870 2000 237 243
27. European Directorate for the Quality of Medicines & Healthcare European Pharmacopoeia seventh ed., Strassbourg, France, 2011, pp. 70-77
28. V. Mageshwaran, S. Walia, and K. Annapurna Isolation and partial characterization of antibacterial lipopeptide produced by Paenibacillus polymyxa HKA-15 against phytopathogen Xantomonas campestris pv. Phaseoli M-5 World J. Microbiol. Biotechnol. 28 2012 909 917
29. Y. Deng, Z. Lu, and F. Lu et al. Identification of LI-F type antibiotics and di-n-butyl phthalate produced by Paenibacillus polymyxa J. Microbiol. Methods 85 2010 175 182
30. E. Gikas, F.N. Bazoti, and P. Fanourgiakis et al. Development and validation of a UPLC-UV method for the determination of daptomycin in rabbit plasma Biomed. Chromatogr. 24 2009 522 527
31. C. Sivapathasekaran, S. Mukherjee, and R. Samanta et al. High-performance liquid chromatography purification of biosurfactant isoforms produced by a marine bacterium Anal. Bioanal. Chem. 395 2009 845 854
32. Y. Wang, Z. Lu, and X. Bie et al. Separation and extraction of antimicrobial lipopeptides produced by bacillus amyololiquefaciens ES-2 with macroporous resin Eur. Food. Res. Technol. 231 2010 189 196
33. S.A. Gustavsson, J. Samskog, and K. Markides et al. Studies of signal suppression in liquid chromatography - electrospray ionization mass spectrometry using volatile ion-pairing reagents J. Chromatogr. A 937 2001 41 47
34. S. Van Dorpe, V. Vergote, and A. Pezeshki et al. Hydrophilic interaction LC of peptides: columns comparison and clustering J. Sep. Sci. 33 2010 728 739
35. K. Broeckhoven, D. Cabooter, and F. Lynen et al. The kinetic plot method applied to gradient chromatography: theoretical framework and experimental validation J. Chromatogr. A. 1217 2010 2787 2795
36. K. Broeckhoven, D. Cabooter, and S. Eeltink et al. Kinetic plot based comparison of the efficiency and peak capacity of high-performance liquid chromatography columns: theoretical background and selected examples J. Chromatogr. A 1228 2012 20 30
37. S. Eeltink, W. Decrop, and F. Steiner et al. Use of kinetic plots for the optimization of the separation time in ultra-high pressure LC J. Sep. Sci. 33 2010 2629 2635
38. A. Fanigliulo, D. Cabooter, and G. Bellazzi et al. Comparison of performance of high-performance liquid chromatography columns packed with superficially and fully porous 2.5 μm particles using kinetic plots J. Sep. Sci. 33 2010 3655 3665
39. A. Fanigliulo, D. Cabooter, and G. Bellazzi et al. Kinetic performance of reversed-phase C18 high-performance liquid chromatography columns compared by meanse of the kinetic plot method in pharmaceutically relevant application J. Chromatogr. A 1218 2011 3351 3359
40. K. Broeckhoven, D. Cabooter, and G. Desmet Kinetic performance comparison of fully and superficially porous particles with sizes ranging between 2.7μm and 5 μm: intrinsic evaluation and application to a pharmaceutical test compound J. Pharm. Anal. 3 2013 313 323
41. E.E. Bolton, Y. Wang, and P.A. Thiessen et al. Chapter 12 PubChem: integrated platform of small molecules and biological activities Anu. Rep. Comput. Chem. 4 2008 217 241
42. HyperChem. HyperChem Reference Manual Vol. 1, Chapter 8: Chemical Calculations - QSAR Properties, first ed., Hypercube Inc., USA, 2002, pp. 450-458.
43. First Choice Column for Method Development, 〈http://www.ymc.de/ ymceurope/products/analyticalLC/analyticalColumns/YMC-Triart-C18-19.htm〉 (accessed on 03.04.12).
44. Comparison Guide to C18 Reversed Phase HPLC Columns, 〈http://www.mz- at.de/pdf/ace-comparison-guide.pdf〉 (accessed 03.04.12).
45. D.M. Fast, P.H. Culbreth, and E.J. Sampson Multivariate and univariate optimization studies of liquid-chromatographic separation of steroid mixtures Clin. Chem. 28 1982 444 448
46. G. Derringer, and R.J. Suich Simultaneous optimization of several response variables J. Qual. Technol. 12 1980 214 219
47. B.L. Karger, M. Martin, and G. Guiochon Role of column parameters and injection volume on detection limits in liquid chromatography Anal. Chem. 46 1974 1640 1647