Abstract:
:Synthesis, biochemical and biological testing of the first carborane derivatives of estrogens are described. Estrone 3-carboranylmethyl ether was synthesized in two steps from estrone. Reduction of estrone 3-carboranylmethyl ether with sodium borohydride provided estradiol-17 beta 3-carboranylmethyl ether. Enzyme kinetic measurements showed that estrone 3-carboranylmethyl ether is a substrate for human placental 17 beta-hydroxysteroid dehydrogenase with Km = 5 x 10(-6)M, and Vmax = 0.016 mumol min-1 microgram -1. The relative affinity constant of estradiol-17 beta 3-carboranylmethyl ether for rat uterine estrogen receptor was 0.5 (compared with a value of 100 for estradiol-17 beta). Consistent with its low affinity for estrogen receptor, the dose-dependent uterotropic response to estradiol-17 beta 3-carboranylmethyl ether in castrated female rats was one sixtieth that of estradiol-17 beta. None of the tested rats had a toxic reaction to estradiol-17 beta 3-carboranylmethyl ether. These results demonstrate that exceptionally stable carborane derivatives of estrogens can be synthesized with preservation of their biochemical and biological properties. Boron-containing estrogens may be useful for thermal neutron capture therapy of cancers with estrogen receptors to concentrate boron in the cell nucleus.
journal_name
Steroidsjournal_title
Steroidsauthors
Sweet Fdoi
10.1016/s0039-128x(81)80020-7subject
Has Abstractpub_date
1981-02-01 00:00:00pages
223-38issue
2eissn
0039-128Xissn
1878-5867pii
S0039-128X(81)80020-7journal_volume
37pub_type
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