Caged progesterone: a new tool for studying rapid nongenomic actions of progesterone.
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.
Kilic
Funda
F
Leibniz-Institut für Molekulare Pharmakologie, Berlin, Germany.
Kashikar
Nachiket D
ND
Schmidt
Reinhard
R
Alvarez
Luis
L
Dai
Luru
L
Weyand
Ingo
I
Wiesner
Burkhard
B
Goodwin
Normann
N
Hagen
Volker
V
Kaupp
U Benjamin
UB
D000438:Alcohols; D002118:Calcium / Q000378:metabolism; D005407:Flagella / Q000187:drug effects; D006801:Humans; D008027:Light; D008297:Male; D055668:Photochemical Processes; D011374:Progesterone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology* / Q000528:radiation effects; D012107:Research Design; D013094:Spermatozoa / Q000187:drug effects
D000438:Alcohols; D011374:Progesterone; D002118:Calcium