ISSN:
0268-2605
Keywords:
bioorganometallic
;
ruthenocene
;
organometallic oestrogen
;
radiopharmaceutical
;
Chemistry
;
Industrial Chemistry and Chemical Engineering
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of 17α-ruthenocenyl-17β-oestradiol and results of biochemical tests to determine its suitability as a radiopharmaceutical agent, are reported. 17α-Ruthenocyl-17β-oestradiol was obtained, in an overall yield of 29%, by addition of ruthenocenyl-lithium (prepared by treatment of ruthenocene with t-butyl-lithium) to the ketone function of protected oestrone, followed by the deprotection of the 3-OH function. It was characterized by X-ray crystallography: space group P 21 (monoclinic), a=9.150(2) Å, b=11.806(4) Å, c=12.193(3) Å, β=94.56(2)°, V=1313(2) Å3, Z=2. The relative binding affinity (RBA) of this complex for the oestradiol-specific receptor was compared with that of oestradiol. 17α-Ruthenocyl-17β-oestradiol is still recognized by the oestradiol receptor with an RBA of 2%. Unlike its analogue, 17α-propynyl-Co2(CO)6-17β-oestradiol, it does not act as an affinity marker for the oestradiol receptor. This may be explained by the relative stability of the carbenium ion generated from it, which has a pKR+ value of +0.73. 17α-Ruthenocyl-17β-oestradiol is however of potential interest as a radiopharmaceutical agent since ruthenium has radioactive isotopes emitting β- and γ-radiation useful in nuclear medicine. © 1997 John Wiley & Sons, Ltd.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
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