Review: Isomer Separation, Chiral Resolution, and Structure Elucidation Analyses Are the Future of Analytical Supercritical Fluid Chromatography—Mass Spectrometry
In 1822, almost 200 years ago, Baron Charles Cagniard de Latour (1777-1859) discovered the critical phenomena or critical state [1] [2]. At that time, it was described as a curiosity. However, it is now used as an advanced extraction and analytical technology in industry and research. Extraction with supercritical fluids (SFs) was welcome from the very beginning. In the present paper, the application to chromatography of the critical phenomena of compressed gases or overheated liquids as supercritical fluids will be discussed. Supercritical Fluid Chromatography (SFC) received an uneasy welcome, mainly because of the lack of commercially available analytical instruments. Even today, only a small number of industrial companies are manufacturing SFC instrumentation. A very small spectrum of columns is manufactured specially for SFC. SFC is not accepted by Pharmacopeia committees for the analysis of drugs and medical forms to the same extent as Gas Chromatography, High-Performance Liquid Chromatography or even Thin Layer Chromatography. The present status and future perspectives for SFC will be discussed.
References
[1]
de Latour, C.C. (1822) Exposé de Quelques Résultats Obtenupar L’action Combinée de la Chaleur et de la Compression Sur Certains Liquides, Tels Que L’eau, L’alcool, L’ether Sulfurique et L’essence de Pétrole Rectifiée. Annales de Chimieet de Physique, 21, 127-132.
[2]
de Latour, C.C. (1822) Exposé de Quelques Résultats Obtenupar L’action Combinée de la Chaleur et de la Compression Sur Certains Liquides, Tels Que L’eau, L’alcool, L’ether Sulfurique et L’essence de Pétrole Rectifiée. Annales de Chimieet de Physique, 21, 178-182.
[3]
Tswett, M.S. (1903) On a New Category of Adsorption Phenomena and Their Application to Biochemical Analysis. Tr. Varshavskogo obschestva estestvoispytatelei, Otd. Biolol., 14, 1-20 (in Russian).
[4]
Tswett, M.S. (1906) Physikalisch-chemische Studienüber das Chlorophyll. Die Adsorbtionen. Ber.Dtsch. Bot. Ges., 24, 316-323.
[5]
Day, D.T. (1897) Proceedings of the American Philosophical Society, 36, 112-115.
[6]
Day, D.T. (1900) Proceedings of the 1st International Petroleum Congress, Paris, 16-28 August 1900.
[7]
Kutscher, F. and Steudel, H. (1903) Beschreibung eines ?therextraktionsapparates. Mit drei Abbildungen. Zeitschrift fur Physiologische Chemie, 39, 473-474.
[8]
Sch?nbein, F. (1861) übereinigedurch Haarr?hrchenanziehung des Papiershervorgebrachte Trennungswirkungen. Ann Physik u Chemie 2 F (Poggendorffs Ann), 114, 275-280.
[9]
The Bible, Old Testament, Exodus, 15: 25.
[10]
Brondz, I. (2002) Review, Development of Fatty Acid Analysis by High-Performance Liquid Chromatography, Gas Chromatography, and Related Techniques. Analytica Chimica Acta, 21658, 1-37.
[11]
Brondz, I. (2011) In: Brondz, I., Ed., Historical Overview of Chromatography and Related Techniques in Analysis of Antimalarial Drug Primaquine, Nova Science Publishers, Inc., New York.
[12]
Audi, G. (2006) The History of Nuclidicmasses and of Their Evaluation. International Journal of Mass Spectrometry, 251, 85-94.
[13]
Keithley, J.F. (1999) The Story of Electrical and Magnetic Measurements: From 500 BC to the 1940s. John Wiley and Sons, Hoboken, 205.
[14]
Lovelock, J. (1973) Private Communication. W. Bertsch Thesis, University of Houston, Houston.
[15]
Klesper, E., Corwin, A.H. and Turner, D.A. (1962) High Pressure Gas Chromatography above Critical Temperatures. The Journal of Organic Chemistry, 27, 700-701.
[16]
Ibanez, E., Lopez-Sebastian, S., Tabera, J. and Reglero, G. (1998) Separation of Carotenoids by Subcritical Fluid Chromatography with Coated, Packed Capillary Columns and Neat Carbon Dioxide. Journal of Chromatography A, 823, 313-319.
[17]
Alkio, M. (2008) Purification of Pharmaceuticals and Nutraceutical Compounds by Sub- and Supercritical Chromatography and Extraction. Academic Dissertation, Faculty of Pharmacy, University of Helsinki, Helsinki.
http://www.vtt.fi/publications/index.jsp
[18]
Morrissey, M.A. and Hill Jr., H.H. (1988) Metal Selective Flame Ionization Detection after Supercritical Fluid Chro- matography. Journal of High Resolution Chromatography, 11, 375-379.
[19]
Brondz, I., H?iland, K. and Lefler, J. (2007) Supercritical Fluid Chromatography of Secondary Metabolites and Multi-Analysis by Mass Spectrometry-Ultraviolet and Corona Charged Aerosol Detection. 12 Norwegian MS-Winter Meeting, Hafjell, 21-24 January 2007, 63.
[20]
Brondz, I. and H?iland, K. (2008) Chemotaxonomic Differentiation between Cortinarius infractus and Cortinarius subtortus by Supercritical Fluid Chromatography Connected to a Multi-Detection System. Trends in Chromatography, 4, 79-87.
[21]
Brondz, I., Ekeberg, D., Bell, D.S., Hustad, J.A., Svendsen, R., Vlachos, V., Oakley, P., Langley, G.J., Mohini, T., Amaury, C.G. and Mikhalitsyn, F. (2007) Nature of the Main Contaminant in the Drug Primaquine Diphosphate: SFC and SFC-MS Methods of Analysis. Journal of Pharmaceutical and Biomedical Analysis, 43, 937-944.
http://dx.doi.org/10.1016/j.jpba.2006.09.017
[22]
Brondz, I., Ekeberg, D., Annino, A.R. and Palcic, T. (2007) SFC-MS Analyses of Anti-Malaria Drug Primaquine Di- phosphate. Comparison of Techniques and Instrumentation. Proceeding of 12 Norwegian MS-Winter Meeting, Hafjell, 21-24 January 2007, abstr. 42.
[23]
Brondz, I. (2009) Chapter 5, SFC-MS Analysis of Contaminants in Primaquine Diphosphate Tablets and Spectral UV and NMR Characterizing of Primaquine and Quinocide. In: Csizmadia, E. and Kalnoky, I., Eds., Antimalarial Drugs: Costs, Safety and Efficacy, Nova Science Publishers, Inc., Hauppauge, 105-124.
[24]
Brondz, I. (2009) Improved Separation of Quinocide in Primaquine Analysis by Supercritical Fluid Chromatography— Mass Spectrometry. 5th Conference Nordic Separation Science Society, Tallinn, 26-29 August 2009, abstr. PP06.
[25]
Brondz, I. (2009) SFC-MS Analysis of Contaminants in Primaquine Diphosphate Tablets and Spectral UV and NMR Characterizing of Primaquine and Quinocide. 5th Conference Nordic Separation Science Society, Tallinn, 26-29 August 2009, abstr. PP07.
[26]
Brondz, I. and Brondz, A. (2012) The Technology for Preparation of Generic (Monoenantiomeric) Antimalarial Drug Primaquine by Using Supercritical Fluid Chromatography. Separation of Primaquine from Quinocide: Simultaneous Resolution of the Enantiomers of Primaquine and Their Separation from Quinocide in One Run. American Journal of Analytical Chemistry, 3, 884-890. http://dx.doi.org/10.4236/ajac.2012.312A117
[27]
Brondz, I. and Brondz, A. (2012) Supercritical Fluid Chromatography—Mass Spectrometry (SFC-MS) of Heterocyclic Compounds with Trivalent and Pentavalent Nitrogen in Cough Relief Medical Forms Tuxi and Cosylan. American Journal of Analytical Chemistry, 3, 870-876. http://dx.doi.org/10.4236/ajac.2012.312A115
[28]
Brondz, I. (2007) In: Csizmadia, E. and Kalnoky, I., Eds., Antimalarial Drugs: Costs, Safety and Efficiency Chapter V, SFC-MS Analysis of Contaminants in Primaquine Diphosphate Tablets and Spectral UV and NMR Characterising of Primaquine and Quinocide, Nova Science Publishers, Inc., New York, 105, 124.
[29]
Brondz, I. and Klein, U. (2005) Separation of the Positional Isomer Quinocide from the Anti-Malarial Drug Primaquine Using a Discovery? HS F5 HPLC Column. The Reporter, 23, 1.
[30]
Brondz, I., H?iland, K., Bell, D.S. and Annino, A. (2006) Indole Alkaloid Separation Using the Discovery? HS F5, Chemotaxonomic Study of Two Closely Related Brown-Spored Mushrooms. The Reporter, 23, 5-6.
[31]
Baker, T.R. and Pinkston, J.D. (1998) Development and Application of Packed-Column Supercritical Fluid Chromato- graphy/Pneumatically Assisted Electrospray Mass Spectrometry. Journal of the American Society for Mass Spectrometry, 9, 498-509. http://dx.doi.org/10.1016/S1044-0305(98)00006-3
[32]
Se?oráns, F.J., Markides, K.E. and Nyholm, L. (1999) Determination of Tocopherols and Vitamin A in Vegetable Oils Using Packed Capillary Column Supercritical Fluid Chromatography with Electrochemical Detection. Journal of Micro- column Separations, 11, 385-391.
[33]
Carraud, P., Thiebaut, D., Caude, M., Rosset, R., Lafosse, M. and Dreux, M. (1987) Supercritical Fluid Chromatogra- phy/Light-Scattering Detector: A Promising Coupling for Polar Compounds Analysis with Packed Column. Journal of Chromatographic Science, 25, 395-398. http://dx.doi.org/10.1093/chromsci/25.9.395
[34]
Smitha, R.M., Chienthavorna, O., Danksa, N. and Wilsonb, I.D. (1998) Fluorescence Detection in Packed-Column Supercritical Fluid Chromatographic Separations. Journal of Chromatography A, 798, 203-206.
http://dx.doi.org/10.1016/S0021-9673(97)01240-5
[35]
Hoke II, S.H., Pinkston, J.D., Bailey, R.E., Tanguay, S.L. and Eichhold, T.H. (2000) Comparison of Packed-Column Supercritical Fluid Chromatography—Tandem Mass Spectrometry with Liquid Chromatography—Tandem Mass Spec- trometry for Bioanalytical Determination of (R)- and (S)-Ketoprofen in Human Plasma Following Automated 96-Well solid-Phase Extraction. Analytical Chemistry, 72, 4235-4241. http://dx.doi.org/10.1021/ac000068x
[36]
Brondz, I. (2013) Editorial: Analytical Methods in the Quality Control of Scientific Publications Part II: The Authors’, Reviewers’, Editors’ Responsibility, and the Publishers’ Authority. International Journal of Analytical Mass Spectrometry and Chromatography, 1, 81-89. http://dx.doi.org/10.4236/ijamsc.2013.12010
[37]
Stahl, E. (1956) Dünnschicht-Chromatographie; Metthode, Einflussfaktoren und einige Anwendungsbeispiele. Pharmazie, 11, 633-637.
[38]
Mshvidobadze, A.E., Chumburidze, B.I. and Sardzhveladze, O.V. (1963) Luminescent Chromatographic Analysis of Synthetic Antimalarial Preparations. Aptechnoe Delo, 12, 36-39.
[39]
Brondz, I., Ekeberg, D., Bell, D.S., Hustad, J.A., Svendsen, R., Vlachos, V., Oakley, P., Langley, G.J., Mohini, T., Amaury, C.G. and Mikhalitsyn, F. (2007) Nature of the Main Contaminant in the Drug Primaquine Diphosphate: SFC and SFC-MS Methods of Analysis. Journal of Pharmaceutical and Biomedical Analysis, 43, 937-944.
http://dx.doi.org/10.1016/j.jpba.2006.09.017
[40]
Brondz, I., Mantzilas, D., Klein, U., Ekeberg, D., Hvattum, E., Lebedeva, M.N., Mikhailitsyn, F.S., Souleimanov, G.D. and R?e, J. (2004) Nature of the Main Contaminant in the Anti-Malaria Drug Primaquine Diphosphate: A Qualitative Isomer Analysis. Chromatography B: Biomedical Sciences and Applications, 800, 211-223.
[41]
Brondz, I., Ekeberg, D., Karaliova, L., Jennings, I., Hustad, J.A. and Svendsen, R. (2005) Separation of the Positional Isomer Quinocide from the Anti-Malaria Drug Primaquine Using a Discovery? HS-F5 HPLC Column. Trends in Chro- matography, 1, 78-81.
[42]
Brondz, I. and Klein, U. (2006) Separation of the Positional Isomer Quinocide from the Anti-Malarial Drug Primaquine Using a Discovery? HS F5 HPLC Column. Reporter, 19, 3.
[43]
Brondz, I. (2010) In: Quintin, T.J., Ed., Chromatography: Types, Techniques and Methods, Chapter 6, Historical Overview of Chromatography and Related Techniques in Analysis of Antimalarial Drug Primaquine, Nova Science Publishers, Inc., New York, 281-322.
[44]
Brondz, I., Klein, U., Karaliova, L., Vlachos, V., Oakley, P., Leideborg, R. and Mikhalitsyn, F. (2005) Nature of the Main Contaminant in the Drug Primaquine Diphosphate: Comparison of HPLC and SFC Methods. 29th International Symposium on High Performance Liquid Phase Separations and Related Techniques, Stockholm, 26-30 June 2005, abstr. P12:43.
[45]
Brondz, I., Klein, U., Ekeberg, D., Mantzilas, D., Hvattum, E., Schultz, H. and Mikhailitsyn, F.S. (2005) Nature of the Main Contaminant in the Anti-Malaria Drug Primaquine Diphosphate: GC-MS Analysis. Asian Journal of Chemistry, 17, 1678-1688.
[46]
Brondz, I., Fialkov, A.B. and Amirav, A. (2009) Analysis of Quinocide in Unprocessed Primaquine Diphosphate and Primaquine Diphosphate Tablets Using Gas Chromatography—Mass Spectrometry with Supersonic Molecular Beams. Journal of Chromatography A, 1216, 824-829. http://dx.doi.org/10.1016/j.chroma.2008.11.043
[47]
Brondz, I., Greibrokk, T. and Aasen, A.J. (1983) n-1-Alkohols of Hypericum perforatum. Journal of Natural Products, 46, 940-941. http://dx.doi.org/10.1021/np50030a025
[48]
Brondz, I., Olsen, I. and Greibrokk, T. (1983) Direct Analysis of Free Fatty Acids in Bacteria by Gas Chromatography. Journal of Chromatography B, 274, 299-304. http://dx.doi.org/10.1016/S0378-4347(00)84433-3
[49]
Sedunov, B. (2013) The Equilibrium Thermal Physics of Supercritical Fluids. International Journal of Analytical Mass Spectrometry and Chromatography, 1, 103-108.
