Sulfuric acid-induced fluorescence of corticosteroids

Effects of position substituents on fluorescence

Carl Monder, John Kendall

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The effect of position substituents on sulfuric acid-induced fluorescence of corticosteroids was examined. Of all the steroids tested, 11β,17α-dihydroxy-3-keto-4-androsten-17β-carboxylic acid gave the greatest relative fluorescence intensity with a value approximately four times that of cortisol. All but two steroids yielding relative fluorescence values greater than 2% of that of cortisol had an 11β-OH moiety. The two exceptions were 20α-hydroxy-4-pregnen-3-one and 20β-hydroxy-4-pregnen-3-one. The following characteristics were common to those steroids yielding sulfuric acid-induced fluorescence: All contained an oxygen substituent of carbon 20. At least one hydroxyl group was present on the side chain. If an 11-hydroxyl group occurred an additional hydroxyl oxygen was found at position 17 or 21 or both. If an 11-hydroxylated substituent was absent, then positions 17 and 21 were both devoid of oxygen. The 18-aldehyde group or Δ1 unsaturation strongly suppressed fluorescence.

Original languageEnglish (US)
Pages (from-to)248-254
Number of pages7
JournalAnalytical Biochemistry
Volume68
Issue number1
DOIs
StatePublished - 1975

Fingerprint

Adrenal Cortex Hormones
Fluorescence
Hydroxyl Radical
Steroids
Oxygen
Hydrocortisone
Carboxylic Acids
Aldehydes
Carbon
sulfuric acid

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Sulfuric acid-induced fluorescence of corticosteroids : Effects of position substituents on fluorescence. / Monder, Carl; Kendall, John.

In: Analytical Biochemistry, Vol. 68, No. 1, 1975, p. 248-254.

Research output: Contribution to journalArticle

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abstract = "The effect of position substituents on sulfuric acid-induced fluorescence of corticosteroids was examined. Of all the steroids tested, 11β,17α-dihydroxy-3-keto-4-androsten-17β-carboxylic acid gave the greatest relative fluorescence intensity with a value approximately four times that of cortisol. All but two steroids yielding relative fluorescence values greater than 2{\%} of that of cortisol had an 11β-OH moiety. The two exceptions were 20α-hydroxy-4-pregnen-3-one and 20β-hydroxy-4-pregnen-3-one. The following characteristics were common to those steroids yielding sulfuric acid-induced fluorescence: All contained an oxygen substituent of carbon 20. At least one hydroxyl group was present on the side chain. If an 11-hydroxyl group occurred an additional hydroxyl oxygen was found at position 17 or 21 or both. If an 11-hydroxylated substituent was absent, then positions 17 and 21 were both devoid of oxygen. The 18-aldehyde group or Δ1 unsaturation strongly suppressed fluorescence.",
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