Challenging core-shell stationary phases with the separation of closely related anti-cancer compounds: Performance studies and application to drug quantitation in cell cultures with multi-well plate clean-up

Journal of Chromatography A

Volumn 1364, Issue , 2014, Pages 83-95

  González Ruiz, Víctor ^a   Olives, Ana I ^a   Martín, M Antonia ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Core shell particles; Green chromatography; High throughput clean up; Kinetic performance; Sustainable analytical chemistry; Topoisomerase inhibitors

Indexed keywords

CELL CULTURE; CHROMATOGRAPHY; DISEASES; EFFICIENCY; ENVIRONMENTAL IMPACT; KINETICS; SEPARATION; WASTE TREATMENT;

CORE SHELL PARTICLES; EXPERIMENTAL CONDITIONS; FUNCTIONALIZATIONS; GREEN CHROMATOGRAPHIES; HIGH THROUGHPUT; INTRINSIC EFFICIENCY; SAMPLE PRETREATMENT; TOPOISOMERASES;

SHELLS (STRUCTURES);

ACETONITRILE; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; CHEMICAL COMPOUND; LUOTONIN A; METHANOL; OCTADECYL DERIVATIVE; ORGANIC SOLVENT; PENTAFLUOROPHENYL PROPYL DERIVATIVE; PHENYL HEXYL DERIVATIVE; UNCLASSIFIED DRUG; MICROSPHERE;

ACCURACY; ANALYTICAL PARAMETERS; ANIMAL CELL; ARTICLE; BIOSEPARATION; CELL CULTURE; CHEMICAL FUNCTIONALIZATION; CHEMICAL PROCEDURES; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CORE SHELL PARTICLE; DENSITY GRADIENT; DRUG DETERMINATION; DRUG STRUCTURE; EMBRYO; ENTHALPY; ENTROPY; FULLY POROUS PARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTERMETHOD COMPARISON; KINETIC PLOT; LIQUID CHROMATOGRAPHY; MATERIAL STATE; METHOD SELECTIVITY; MULTI WELL PLATE CLEAN UP; NONHUMAN; PARTICLE SIZE; PERMEABILITY; PHYSICAL PHASE; PLOTS AND CURVES; STATIONARY PHASE; TEMPERATURE; TIME; VAN DEEMTER PLOT; ANIMAL; DEVICES; DRUG EFFECTS; FIBROBLAST; ISOLATION AND PURIFICATION; KINETICS; METABOLISM; MOUSE; POROSITY; PROCEDURES; THERMODYNAMICS;

ANIMALS; ANTINEOPLASTIC AGENTS; CELLS, CULTURED; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FIBROBLASTS; KINETICS; MICE; MICROSPHERES; PERMEABILITY; POROSITY; THERMODYNAMICS;

EID: 84922070016     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2014.08.054     Document Type: Article

References (81)

1. Chen S.H., Chan N.-L., Hsieh T.-S. New mechanistic and functional insights into DNA topoisomerases. Annu. Rev. Biochem. 2013, 82:139-170.
2. Avendaño C., Menéndez J.C. Medicinal Chemistry of Anticancer Drugs 2008, Elsevier, Amsterdam. 1st ed.
3. Pommier Y. DNA Topoisomerases and Cancer 2012, Springer, New York.
4. Adams V.R., Burke T.G. Camptothecins in Cancer Therapy 2005, Springer, Totowa.
5. Leppard J.B., Champoux J.J. Human DNA topoisomerase I: relaxation, roles, and damage control. Chromosoma 2005, 114:75-85.
6. Liang J.L., Cha H.C., Jahng Y. Recent advances in the studies on luotonins. Molecules 2011, 16:4861-4883.
7. Sridharan V., Ribelles P., Ramos M.T., Menéndez J.C. Cerium(IV) ammonium nitrate is an excellent, general catalyst for the Friedländer and Friedländer-Borsche quinoline syntheses: very efficient access to the antitumor alkaloid luotonin A. J. Org. Chem. 2009, 74:5715-5718.
8. Cagir A., Jones S., Eisenhauer B., Gao R., Hecht S. Synthesis and biochemical properties of E-ring modified luotonin A derivatives. Bioorg. Med. Chem. Lett. 2004, 14:2051-2054.
9. Cagir A., Eisenhauer B.M., Gao R., Thomas S.J., Hecht S.M. Synthesis and topoisomerase I inhibitory properties of luotonin a analogues. Bioorg. Med. Chem. 2004, 12:6287-6299.
10. Cagir A., Jones S.H., Gao R., Eisenhauer B.M., Hecht S.M., Luotonin A. A naturally occurring human DNA topoisomerase I poison. J. Am. Chem. Soc. 2003, 125:13628-13629.
11. Nacro K., Zha C.C., Guzzo P.R., Herr R.J., Peace D., Friedrich T.D. Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives. Bioorg. Med. Chem. 2007, 15:4237-4246.
12. Tseng M.-C., Chu Y.-W., Tsai H.-P., Lin C.-M., Hwang J., Chu Y.-H. One-pot synthesis of luotonin A and its analogues. Org. Lett. 2011, 13:920-923.
13. Dallavalle S., Merlini L., Beretta G.L., Tinelli S., Zunino F. Synthesis and cytotoxic activity of substituted luotonin A derivatives. Bioorg. Med. Chem. Lett. 2004, 14:5757-5761.
14. Nussbaumer S., Bonnabry P., Veuthey J.-L., Fleury-Souverain S. Analysis of anticancer drugs: a review. Talanta 2011, 85:2265-2289.
15. Ramesh M., Ahlawat P., Srinivas N.R. Irinotecan and its active metabolite, SN-38: review of bioanalytical methods and recent update from clinical pharmacology perspectives. Biomed. Chromatogr. 2010, 24:104-123.
16. Aaron J.J., Trajkovska S. Fluorescence studies of anti-cancer drugs-analytical and biomedical applications. Curr. Drug Targets 2006, 7:1067-1081.
17. Tsakalozou E., Horn J., Leggas M. An HPLC assay for the lipophilic camptothecin analog AR-67 carboxylate and lactone in human whole blood. Biomed. Chromatogr. 2010, 24:1045-1051.
18. Baylatry M.-T., Joly A.-C., Pelage J.-P., Bengrine-Lefevre L., Prugnaud J.-L., Laurent A., Fernandez C. Simple liquid chromatography method for the quantification of irinotecan and SN38 in sheep plasma: application to in vivo pharmacokinetics after pulmonary artery chemoembolization using drug eluting beads. J. Chromatogr. B 2010, 878:738-742.
19. Bansal T., Awasthi A., Jaggi M., Khar R.K., Talegaonkar S. Development and validation of reversed phase liquid chromatographic method utilizing ultraviolet detection for quantification of irinotecan (CPT-11) and its active metabolite, SN-38, in rat plasma and bile samples: application to pharmacokinetic studies. Talanta 2008, 76:1015-1021.
20. Pistolozzi M., Varchi G., Degli Esposti A., Guerrini A., Sotgiu G., Ballestri M., Ferroni C., Venturini A., Bertucci C. Camptothecin and thiocamptothecin: the role of sulfur in shifting the hydrolysis equilibrium towards the closed lactone form. ChemMedChem. 2011, 6:1706-1714.
21. Badaloni E., Cabri W., Ciogli A., D'Acquarica I., Deias R., Gasparrini F., Giorgi F., Kotoni D., Villani C. Extending the use of inverted chirality columns approach for enantiomeric excess determination in absence of reference samples: application to a water-soluble camptothecin derivative. J. Chromatogr. A 2010, 1217:1024-1032.
22. González-Ruiz V., González-Cuevas Y., Arunachalam S., Martín M.A., Olives A.I., Ribelles P., Ramos M.T., Menéndez J.C. Fluorescence properties of the anti-tumour alkaloid luotonin A and new synthetic analogues: pH modulation as an approach to their fluorimetric quantitation in biological samples. J. Lumin. 2012, 132:2468-2475.
23. Miskolczy Z., Biczók L. Effect of hydrogen bonding and complexation with metal ions on the fluorescence of luotonin A. Photochem. Photobiol. Sci. 2013, 12:936-943.
24. González-Ruiz V., Mussardo P., Corda E., Girotti S., Olives A.I., Martín M.A. Liquid chromatographic analysis of the anticancer alkaloid luotonin A and some new derivatives in human serum samples. J. Sep. Sci. 2010, 33:2086-2093.
25. Lee S., Lee J., Jahng Y., Jeong T.C., Kim D.H. Characterization of in vitro metabolites of luotonin A in human liver microsomes using electrospray/tandem mass spectrometry. Xenobiotica 2013, 43:527-533.
26. Ahmed A., Abdelmagid W., Ritchie H., Myers P., Zhang H. Investigation on synthesis of spheres-on-sphere silica particles and their assessment for high performance liquid chromatography applications. J. Chromatogr. A 2012, 1270:194-203.
27. Chaudhuri R.G., Paria S. Core/shell nanoparticles: classes, properties, synthesis mechanisms, characterization, and applications. Chem. Rev. 2012, 112:2373-2433.
28. Gritti F., Guiochon G. Mass transfer kinetics, band broadening and column efficiency. J. Chromatogr. A 2012, 1221:2-40.
29. Gritti F., Guiochon G. Shell particles, trials, tribulations and triumphs. J. Chromatogr. A 2011, 1218:1915-1938.
30. Gritti F., Guiochon G. Speed-resolution properties of columns packed with new 4.6μm Kinetex-C(18) core-shell particles. J. Chromatogr. A 2013, 1280:35-50.
31. Cunliffe J.M., Maloney T.D. Fused-core particle technology as an alternative to sub-2-microm particles to achieve high separation efficiency with low backpressure. J. Sep. Sci. 2007, 30:3104-3109.
32. Fekete S., Oláh E., Fekete J. Fast liquid chromatography: the domination of core-shell and very fine particles. J. Chromatogr. A 2012, 1228:57-71.
33. Fekete S., Veuthey J.L., Guillarme D. New trends in reversed-phase liquid chromatographic separations of therapeutic peptides and proteins: theory and applications. J. Pharm. Biomed. Anal. 2012, 69:9-27.
34. Guillarme D., Ruta J., Rudaz S., Veuthey J.L. New trends in fast and high-resolution liquid chromatography: a critical comparison of existing approaches. Anal. Bioanal. Chem. 2010, 397:1069-1082.
35. Ali I., Al-Othman Z.A., Al-Za'abi M. Superficially porous particles columns for super fast HPLC separations. Biomed. Chromatogr. 2012, 26:1001-1008.
36. Salisbury J.J. Fused-core particles: a practical alternative to sub-2 micron particles. J. Chromatogr. Sci. 2008, 46:883-886.
37. Vinci G., Antonelli M.L., Preti R. Rapid determination of polycyclic aromatic hydrocarbons in rainwater by liquid-liquid microextraction and LC with core-shell particles column and fluorescence detection. J. Sep. Sci. 2013, 36:461-468.
38. Wu J., Qian Y., Mao P., Chen L., Lu Y., Wang H. Separation and identification of phenolic compounds in canned artichoke by LC/DAD/ESI-MS using core-shell C18 column: a comparative study. J. Chromatogr. B 2013, 927:173-180.
39. Chocholouš P., Vacková J., Šrámková I., Šatínský D., Solich P. Advantages of core-shell particle columns in sequential injection chromatography for determination of phenolic acids. Talanta 2012, 103:221-227.
40. Rostagno M.A., Manchón N., D'Arrigo M., Guillamón E., Villares A., García-Lafuente A., Ramos A., Martínez J.A. Fast and simultaneous determination of phenolic compounds and caffeine in teas, mate, instant coffee, soft drink and energetic drink by high-performance liquid chromatography using a fused-core column. Anal. Chim. Acta 2011, 685:204-211.
41. Gavina J.M.A., Priem J., Wood C.M., Xiao C.W., Feng Y.L. Determination of isoflavones in rat serum using liquid chromatography-tandem mass spectrometry with a highly efficient core-shell column. Anal. Bioanal. Chem. 2013, 405:2643-2651.
42. DeGrasse S.L., DeGrasse J.A., Reuter K. Solid core column technology applied to HPLC-FD of paralytic shellfish toxins. Toxicon 2011, 57:179-182.
43. Ruta J., Zurlino J.D., Grivel C., Heinisch S., Veuthey J.L., Guillarme D. Evaluation of columns packed with shell particles with compounds of pharmaceutical interest. J. Chromatogr. A 2012, 1228:221-231.
44. Dziadosz M., Lessig R., Bartels H. Protein kinase inhibitor analysis with the core-shell separation technique. Anal. Bioanal. Chem. 2012, 404:2083-2086.
45. Tölgyesi A., Sharma V.K., Fekete S., Lukonics D., Fekete J. Simultaneous determination of eight corticosteroids in bovine tissues using liquid chromatography-tandem mass spectrometry. J. Chromatogr. B 2012, 906:75-84.
46. Roth M.J., Plymire D.A., Chang A.N., Kim J., Maresh E.M., Larson S.E., Patrie S.M. Sensitive and reproducible intact mass analysis of complex protein mixtures with superficially porous capillary reversed-phase liquid chromatography mass spectrometry. Anal. Chem. 2011, 83:9586-9592.
47. Whiley L., Godzien J., Ruperez F.J., Legido-Quigley C., Barbas C. In-vial dual extraction for direct LC-MS analysis of plasma for comprehensive and highly reproducible metabolic fingerprinting. Anal. Chem. 2012, 84:5992-5999.
48. Martins S.M., Wendling T., Gonçalves V.M.F., Sarmento B., Ferreira D.C. Development and validation of a simple reversed-phase HPLC method for the determination of camptothecin in animal organs following administration in solid lipid nanoparticles. J. Chromatogr. B 2012, 880:100-107.
49. Zhao Y.X., Gao J.Q., Qiao H.L., Chen H.L., Liang W.Q. Development and validation of a sensitive reversed-phase HPLC method to determine intracellular accumulation of hydroxycamptothecin. J. Pharm. Biomed. Anal. 2006, 41:1007-1010.
50. Vuckovic D. High-throughput solid-phase microextraction in multi-well-plate format. Trend. Anal. Chem. 2013, 45:136-153.
51. Fekete S., Kohler I., Rudaz S., Guillarme D. Importance of instrumentation for fast liquid chromatography in pharmaceutical analysis. J. Pharm. Biomed. Anal. 2014, 87:105-119.
52. McCalley D.V. Instrumental considerations for the effective operation of short, highly efficient fused-core columns. Investigation of performance at high flow rates and elevated temperatures. J. Chromatogr. A 2010, 1217:4561-4567.
53. Alexander A.J., Waeghe T.J., Himes K.W., Tomasella F.P., Hooker T.F. Modifying conventional high-performance liquid chromatography systems to achieve fast separations with fused-core columns: a case study. J. Chromatogr. A 2011, 1218:5456-5469.
54. Gritti F., Guiochon G. Overload behavior and apparent efficiencies in chromatography. J. Chromatogr. A 2012, 1254:30-42.
55. McCalley D.V. Some practical comparisons of the efficiency and overloading behaviour of sub-2μm porous and sub-3μm shell particles in reversed-phase liquid chromatography. J. Chromatogr. A 2011, 1218:2887-2897.
56. Fallas M.M., Buckenmaier S.M.C., McCalley D.V. A comparison of overload behaviour for some sub 2μm totally porous and sub 3μm shell particle columns with ionised solutes. J. Chromatogr. A 2012, 1235:49-59.
57. K.J. Fountain, P.C. Iraneta, Instrumentation and columns for UHPLC separations, in: D. Guillarme, J.-L. Veuthey (Eds.), UHPLC in Life Sciences, Royal Society of Chemistry, Cambridge, 2012, pp. 29-66.
58. Desmet G., Clicq D., Gzil P. Geometry-independent plate height representation methods for the direct comparison of the kinetic performance of LC supports with a different size or morphology. Anal. Chem. 2005, 77:4058-4070.
59. Thompson J.W., Kaiser T.J., Jorgenson J.W. Viscosity measurements of methanol-water and acetonitrile-water mixtures at pressures up to 3500bar using a novel capillary time-of-flight viscometer. J. Chromatogr. A 2006, 1134:201-209.
60. Sanchez A.C., Anspach J.A., Farkas T. Performance optimizing injection sequence for minimizing injection band broadening contributions in high efficiency liquid chromatographic separations. J. Chromatogr. A 2012, 1228:338-348.
61. European Medicines Agency, Guideline on Bioanalytical Method Validation, 21st ed., EMEA/CHMP/EWP/192217/2009, Committee for Medicinal Products for Human Use (CHMP), European Medicines Agency, London, 2011, pp. 1-22.
62. International Conference on Harmonisation, Validation of Analytical Procedures: Text and Methodology Q2(R1), 2007, pp. 1-17.
63. Ellison S., Thompson M. Harmonized guidelines for single-laboratory validation of methods of analysis (IUPAC Technical Report). Pure Appl. Chem. 2002, 74:835.
64. Zheng W., Wang S., Barnes L., Guan Y., Louis E. Determination of harmane and harmine in human blood using reversed-phased high-performance liquid chromatography and fluorescence detection. Anal. Biochem. 2000, 279:125-129.
65. Snyder L.R., Dolan J.W., Carr P.W. The hydrophobic-subtraction model of reversed-phase column selectivity. J. Chromatogr. A 2004, 1060:77-116.
66. Poole C.F. The Essence of Chromatography 2003, Elsevier, Amsterdam.
67. Gritti F., Guiochon G. Adsorption mechanisms and effect of temperature in reversed-phase liquid chromatography. Meaning of the classical Van't Hoff plot in chromatography. Anal. Chem. 2006, 78:4642-4653.
68. Wu N., Liu Y., Lee M.L. Sub-2μm porous and nonporous particles for fast separation in reversed-phase high performance liquid chromatography. J. Chromatogr. A 2006, 1131:142-150.
69. Gritti F., Guiochon G. A chromatographic estimate of the degree of heterogeneity of RPLC packing materials. 1. Non-endcapped polymeric C30-bonded stationary phase. J. Chromatogr. A 2006, 1103:43-56.
70. Bell D.S., Cramer H.M., Jones A.D. Rational method development strategies on a fluorinated liquid chromatography stationary phase: mobile phase ion concentration and temperature effects on the separation of ephedrine alkaloids. J. Chromatogr. A 2005, 1095:113-118.
71. Doyle C.A., Vickers T.J., Mann C.K., Dorsey J.G. Characterization of C18-bonded liquid chromatographic stationary phases by Raman spectroscopy: the effect of temperature. J. Chromatogr. A 2000, 877:41-59.
72. Gritti F., Guiochon G. Accurate measurements of peak variances: importance of this accuracy in the determination of the true corrected plate heights of chromatographic columns. J. Chromatogr. A 2011, 1218:4452-4461.
73. Sanchez A.C., Friedlander G., Fekete S., Anspach J., Guillarme D., Chitty M., Farkas T. Pushing the performance limits of reversed-phase ultra high performance liquid chromatography with 1.3μm core-shell particles. J. Chromatogr. A 2013, 1311:90-97.
74. Gritti F., Guiochon G. Accurate measurements of the true column efficiency and of the instrument band broadening contributions in the presence of a chromatographic column. J. Chromatogr. A 2014, 1327:49-56.
75. Fekete S., Fekete J. The impact of extra-column band broadening on the chromatographic efficiency of 5cm long narrow-bore very efficient columns. J. Chromatogr. A 2011, 1218:5286-5291.
76. Destefano J.J., Langlois T.J., Kirkland J.J. Characteristics of superficially-porous silica particles for fast HPLC: some performance comparisons with sub-2-μm particles. J. Chromatogr. Sci. 2008, 46:254-260.
77. Fekete S., Fekete J., Ganzler K. Shell and small particles; evaluation of new column technology. J. Pharm. Biomed. Anal. 2009, 49:64-71.
78. Poppe H. Some reflections on speed and efficiency of modern chromatographic methods. J. Chromatogr. A 1997, 778:3-21.
79. Knox J.H. Theoretical aspects of LC with packed and open small-bore columns. J. Chromatogr. Sci. 1980, 18:453-461.
80. Carr P.W., Wang X., Stoll D.R. Effect of pressure, particle size and time on optimizing performance in liquid chromatography. Anal. Chem. 2009, 81:5342-5353.
81. González-Ruiz V., Pascua I., Fernández-Marcelo T., Ribelles P., Bianchini G., Sridharan V., Iniesta P., Ramos M.T., Olives A.I., Martín M.A., Menéndez J.C. B-ring-aryl substituted luotonin A analogues with a new binding mode to the topoisomerase 1-DNA complex show enhanced cytotoxic activity. PloS One 2014, 9:e95998. 10.1371/journal.pone.0095998.