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Journal of Lipid Research, Vol 32, 1755-1767, Copyright © 1991 by Lipid Research, Inc.
S Schneider, U Schramm, A Schreyer, HP Buscher, W Gerok and G Kurz
In order to visualize bile salt transport, fluorescent bile salt
derivatives were synthesized by introduction of the relatively small
fluorescent 4-nitrobenzo-2-oxa-1,3-diazol (NBD)-amino group in either the
3-, 7-, or 12-position of the steroid structure, thus providing a complete
set of diastereomeric derivatives, 3 alpha-NBD-amino-7 alpha,12
alpha-dihydroxy-5 beta-cholan-24-oic acid, 3 beta-NBD-amino-7 alpha,12
alpha-dihydroxy-5 beta-cholan-24-oic acid, 7 alpha-NBD-amino-3 alpha,12
alpha-dihydroxy-5 beta-cholan-24-oic acid, 7 beta-NBD-amino-3 alpha,12
alpha-dihydroxy-5 beta-cholan-24-oic acid, 12 alpha-NBD-amino- 3 alpha,7
alpha-dihydroxy-5 beta-cholan-24-oic acid, 12 beta-NBD-amino- 3 alpha,7
alpha-dihydroxy-5 beta-cholan-24-oic acid, as well as their taurine
conjugates. Their optical properties with absorption maxima at about 490 nm
and emission maxima at 550 nm make them suitable for fluorescent
microscopic studies. Fluorescence of the NBD-derivatives is strongly
dependent on polarity of the solvent, on the concentration of the bile salt
derivatives, and only slightly on temperature.
ARTICLES
Fluorescent derivatives of bile salts. I. Synthesis and properties of NBD-amino derivatives of bile salts
Institut fur Organische Chemie und Biochemie Universitat Freiburg, Germany.
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