Literature DB >> 6889575

Methodology for the synthesis and specific activity determination of 16 alpha-[77Br]-bromoestradiol-17 beta and 16 alpha-[77Br]-11 beta-methoxyestradiol-17 beta, two estrogen receptor-binding radiopharmaceuticals.

S G Senderoff, K D McElvany, K E Carlson, D F Heiman, J A Katzenellenbogen, M J Welch.   

Abstract

16 alpha-[77 Br]-Bromoestradiol-17 beta (3a) has been synthesized from estrone enol diacetate (1) by bromination with Na77Br and hydrogen peroxide-acetic acid, followed by reduction with lithium aluminum hydride to give a mixture of 16 alpha-[77 Br]-bromoestradiol-17 beta (3a) and 16 alpha-[77Br]-bromoestradiol-17 alpha (3b) from which the desired epimer (3a) can be obtained in 50% overall radiochemical yield (from Na77Br) by HPLC. Analogous procedures can be used in the preparation of 16 alpha-[77Br]-bromo-11 beta-methoxyestradiol-17 beta. (4a) The effective specific activities of these radiopharmaceuticals, determined by binding to the uterine estrogen receptor, are 900-1500 Ci/mmol. Both have affinity and good binding selectivity for the estrogen receptor and are useful as imaging agents for mammary tumors.

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Year:  1982        PMID： 6889575     DOI： 10.1016/0020-708x(82)90010-2

Source DB:  PubMed          Journal:  Int J Appl Radiat Isot        ISSN： 0020-708X


  7 in total

1.  Evaluation of a bromine-76-labeled progestin 16alpha,17alpha-dioxolane for breast tumor imaging and radiotherapy: in vivo biodistribution and metabolic stability studies.

Authors:  Dong Zhou; Terry L Sharp; Nicole M Fettig; Hsiaoju Lee; Jason S Lewis; John A Katzenellenbogen; Michael J Welch
Journal:  Nucl Med Biol       Date:  2008-06-30       Impact factor: 2.408

2.  Synthesis and biological evaluation of two agents for imaging estrogen receptor β by positron emission tomography: challenges in PET imaging of a low abundance target.

Authors:  Jae Hak Lee; Olaf Peters; Lutz Lehmann; Carmen S Dence; Terry L Sharp; Kathryn E Carlson; Dong Zhou; M Jeyakumar; Michael J Welch; John A Katzenellenbogen
Journal:  Nucl Med Biol       Date:  2012-06-30       Impact factor: 2.408

3.  Optimization of the preparation of fluorine-18-labeled steroid receptor ligands 16alpha-[18F]fluoroestradiol (FES), [18F]fluoro furanyl norprogesterone (FFNP), and 16beta-[18F]fluoro-5alpha-dihydrotestosterone (FDHT) as radiopharmaceuticals.

Authors:  Dong Zhou; Mai Lin; Norio Yasui; Mohammed H Al-Qahtani; Carmen S Dence; Sally Schwarz; John A Katzenellenbogen
Journal:  J Labelled Comp Radiopharm       Date:  2014-02-17       Impact factor: 1.921

4.  Synthesis and biodistribution of fluorine-18-labeled fluorocyclofenils for imaging the estrogen receptor.

Authors:  Jai Woong Seo; Dae Yoon Chi; Carmen S Dence; Michael J Welch; John A Katzenellenbogen
Journal:  Nucl Med Biol       Date:  2007-03-30       Impact factor: 2.408

5.  Bromination from the macroscopic level to the tracer radiochemical level: (76)Br radiolabeling of aromatic compounds via electrophilic substitution.

Authors:  Dong Zhou; Haibing Zhou; Carl C Jenks; Jason S Lewis; John A Katzenellenbogen; Michael J Welch
Journal:  Bioconjug Chem       Date:  2009-04       Impact factor: 4.774

Review 6.  PET Imaging Agents (FES, FFNP, and FDHT) for Estrogen, Androgen, and Progesterone Receptors to Improve Management of Breast and Prostate Cancers by Functional Imaging.

Authors:  John A Katzenellenbogen
Journal:  Cancers (Basel)       Date:  2020-07-23       Impact factor: 6.639

Review 7.  The quest for improving the management of breast cancer by functional imaging: The discovery and development of 16α-[18F]fluoroestradiol (FES), a PET radiotracer for the estrogen receptor, a historical review.

Authors:  John A Katzenellenbogen
Journal:  Nucl Med Biol       Date:  2020-02-22       Impact factor: 2.408
  7 in total

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