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New method for the selective determination of corticosteroids by means of difference CD spectroscopy

XI. Application of chiroptical methods in drug analysis

Neues Verfahren zur selektiven Bestimmung von Corticosteroiden mit Hilfe der Differential-CD-Spektroskopie

XI. Anwendung chiro-optischer Methoden in der Arzneimittelanalyse

  • Original Papers
  • Determination of Drugs
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Zusammenfassung

Eine differenz-CD-spektroskopische Bestimmung von 21-Hydroxy- und 21-Acetoxy-Corticosteroiden, die auf der Oxidation mit Periodsäure beruht, wird beschrieben. 21-Hydroxy-Corticosteroide können mit Periodsäure zu einer 17β-Carbonsäure und Formaldehyd umgesetzt werden. C21-Ester der Corticosteroide reagieren mit Periodsäure nur nach alkalischer Hydrolyse. Die 20-Ketogruppe der 17β-Ketol-Seitenkette weist im Bereich von 270–300 nm eine optisch aktive Absorptionsbande auf und im CD-Spektrum beobachtet man einen positiven Cotton Effekt. Nach Oxidation mit Periodsäure verschwindet diese Bande.

Die quantitative Bestimmung beruht auf der deutlichen Differenz zwischen der Elliptizität vor und nach der Oxidation. Die Elliptizität der neun geprüften Corticosteroide ändert sich linear mit der Konzentration im Bereich von 5–250 μg/ml. Die Korrelationsgleichung und die Statistik der Genauigkeit werden gegeben.

Summary

A difference CD spectroscopic determination of 21-hydroxy- and 21-acetoxy-corticosteroids, based on periodic acid oxidation is described. With periodic acid, 21-hydroxy-corticosteroid compounds can be transformed into a 17β-carboxylic acid and formaldehyde. The corticosteroid C21 esters react with periodic acid only after alkaline hydrolysis. The 20-keto group of the 17β-ketol side chain has an optically active absorbance band in the interval 270–300 nm, and an intensive positive Cotton effect is observed in the CD spectra. Following periodate oxidation, this band is no longer present.

The quantitative determination is based on the considerable difference between the ellipticities before and after oxidation. For the nine corticosteroids examined the ellipticity (m°) varies linearly with the concentration in the interval 5–250 μg/ml. The regressional equation and statistics of accuracy are given.

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References

  1. House HO (1972) Modern synthetic reaction. The Benjamin Cummings Publishing Company, Menlo Park, California p 353

    Google Scholar 

  2. Pesez M, Bartos J (1974) Colorimetric and fluorimetric analysis of organic compounds and drugs. Marcel Dekker, Inc., New York, a p 540, b p 504

    Google Scholar 

  3. Görög S, Szász Gy (1978) Analysis of steroid hormone drugs. Akadémiai Kiadó, Budapest, p 345

    Google Scholar 

  4. Mason HL, Hoehn WM, McKenzie BF, Kendall EC (1937) J Biol Chem 120:719

    Google Scholar 

  5. Higuchi T, Brochmann-Hanssenm E (1961) Pharmaceutical analysis. Interscience Publishers, New York, London, p 77

    Google Scholar 

  6. Corcoran AC, Page IH (1948) J Lab Clin Med 33:1326

    Google Scholar 

  7. Desgrez P, Haas J, Weinmann SH (1957) Ann Biol Clin 15:289

    Google Scholar 

  8. MacFadyen DA (1945) J Biol Chem 158:197

    Google Scholar 

  9. Pesez M, Bartos J (1967) Talanta 14:1097

    Google Scholar 

  10. Merits I (1962) J Lipid Res 3:126

    Google Scholar 

  11. Kittinger GW (1964) Steroids 3:21

    Google Scholar 

  12. Kittinger GW (1964) Steroids 4:539

    Google Scholar 

  13. Kittinger GW (1968) Steroids 11:47

    Google Scholar 

  14. Cassim JY, Yang JT (1969) Biochemistry 8:1947

    Google Scholar 

  15. Toshio Konno, Hiroshi Meguro, Katura Tuzimura (1975) Anal Biochem 67:226

    Google Scholar 

  16. Gergely A, Szász Gy (1983) Acta Pharm Hung 53:280

    Google Scholar 

  17. Duvivier J (1965) J Chromatogr 19:352

    Google Scholar 

  18. Velluz L, Petit A, Pesez M, Berret R (1947) Bull Soc Chim Fr 123

  19. Guttmann DE, Meister PD (1958) J Am Pharm Assoc (Sci. Ed.) 47:773

    Google Scholar 

  20. Görög S (1969) J Pharm Pharmacol 21: Suppl 465

    Google Scholar 

  21. Gergely A, Szász Gy, Soós J (1984) Unpublished results

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Author information

Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Semmelweis MedicalUniversity, Hőgyes E. u. 9, H-1092, Budapest, Hungary

    A. Gergely & Gy. Szász

  2. Biophysics Institute, Szeged Biological Research Centre of the Hungarian Academy of Sciences, Odesszai krt. 62, H-6721, Szeged, Hungary

    J. Soós

Authors
  1. A. Gergely
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  2. Gy. Szász
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  3. J. Soós
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Additional information

For part X see J Pharm Biomed Anal (in press)

For part IX see Fresenius Z Anal Chem (1984) 318:528

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Gergely, A., Szász, G. & Soós, J. New method for the selective determination of corticosteroids by means of difference CD spectroscopy. Z. Anal. Chem. 323, 157–161 (1986). https://doi.org/10.1007/BF01172910

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  • DOI: https://doi.org/10.1007/BF01172910

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