J Am Chem Soc. 2009 Mar 25;131(11):4027-30.

Caged progesterone: a new tool for studying rapid nongenomic actions of progesterone.

Kilic F, Kashikar ND, Schmidt R, Alvarez L, Dai L, Weyand I, Wiesner B, Goodwin N, Hagen V, Kaupp UB.

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Leibniz-Institut für Molekulare Pharmakologie, Berlin, Germany.

Abstract

Ketalization of the biomolecule progesterone with (6-bromo-7-hydroxycoumarin-4-yl)ethane-1,2-diol gives the photolabile progesterone derivatives 3 and 4. These compounds display dramatically reduced bioactivity and release progesterone upon irradiation with UV/vis or IR light. In particular, 4 can be used to perform concentration-jump experiments with high temporal and spatial resolution that allows one to study elegantly the mechanisms of rapid nongenomic cellular events evoked by progesterone. The usefulness of 4 was demonstrated by measurement of changes in swimming behavior of single human sperm caused by progesterone-induced Ca(2+) influx in the sperm flagellum.

PMID:: 19256499; [PubMed - indexed for MEDLINE]

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