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Synthesis of 2‐[ 11 C]methoxy‐3,17β‐estradiol to measure the pharmacokinetics of an antitumor drug candidate, 2‐methoxy‐3,17β‐estradiol
Author(s) -
Mun Jiyoung,
Voll Ronald J.,
Goodman Mark M.
Publication year - 2006
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1131
Subject(s) - chemistry , pharmacokinetics , metabolite , estrogen , estrone , prostate cancer , cytotoxicity , distribution (mathematics) , pharmacology , stereochemistry , cancer , in vitro , medicine , hormone , biochemistry , mathematical analysis , mathematics
2‐Methoxy‐3,17β‐estradiol, an endogenous estrogen metabolite, showed cytotoxicity in various cancer cell lines and also has antiangiogenic and proapoptotic activities. Clinical I and II trials of 2‐methoxy‐3,17β‐estradiol for multiple myeloma, advanced solid tumors, metastatic breast and prostate cancer are underway. We prepared 2‐[ 11 C]methoxy‐3,17β‐estradiol to measure the pharmacokinetics and organ distribution of 2‐methoxy‐3,17β‐estradiol in clinical trials. 2‐[ 11 C]Methoxy‐3,17β‐estradiol was synthesized from a precursor, 2‐hydroxy‐3,17β‐ O ‐bis(methoxymethyl)estradiol, in two steps with over 99% radiochemical purity. The overall reaction time was 45 min and the decay‐corrected radiochemical yield was 32.9%. The distribution coefficient (logP 7.4 ) of 2‐[ 11 C]methoxy‐3,17β‐estradiol at pH 7.4 was measured as 2.95. Copyright © 2006 John Wiley & Sons, Ltd.