{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/19453"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/19453","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Synthesis and evaluation of fluorine-18 labeled androgens as in vivo imaging agents for prostatic cancer using PET","abstract":"In order to develop androgen receptor (AR) based probes for in vivo imaging of prostatic cancer using positron emission tomography (PET), four pairs of 16$\\beta$- and 16$\\alpha$-fluoro androgens, as well as two 20-fluoro androgens have been synthesized. The fluorination was achieved mainly by nucleophilic fluoride displacement of a triflate or a spirocyclic sulfate precursor, prepared by multistep synthesis.","abstract_html":"In order to develop androgen receptor (AR) based probes for in vivo imaging of prostatic cancer using positron emission tomography (PET), four pairs of 16<span class=\"etd-inline-math\">&beta;</span>- and 16<span class=\"etd-inline-math\">&alpha;</span>-fluoro androgens, as well as two 20-fluoro androgens have been synthesized. The fluorination was achieved mainly by nucleophilic fluoride displacement of a triflate or a spirocyclic sulfate precursor, prepared by multistep synthesis.","abstract_has_math":true,"creators":["Liu, Aijun"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Katzenellenbogen, John A."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2011,"date_issued":"2011-05-07T12:08:02Z","date_published":"2011-05-07T12:08:02Z","updated_at":"2026-07-22T22:25:14Z","subjects":["Chemistry, Organic","Chemistry, Pharmaceutical","Health Sciences, Radiology","Chemistry, Nuclear"],"languages":["eng"],"rights":["Copyright 1991 Liu, Aijun"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9210898","(UMI)AAI9210898"],"render_values":[{"text":"AAI9210898","href":null,"code":true},{"text":"(UMI)AAI9210898","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/19453","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Katzenellenbogen, John A."]},{"key":"dc:creator","label":"Author","values":["Liu, Aijun"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2011-05-07T12:08:02Z","10000-01-01","1991"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic","Chemistry, Pharmaceutical","Health Sciences, Radiology","Chemistry, Nuclear"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 1991 Liu, Aijun"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9210898","(UMI)AAI9210898","http://hdl.handle.net/2142/19453"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["In order to develop androgen receptor (AR) based probes for in vivo imaging of prostatic cancer using positron emission tomography (PET), four pairs of 16$\\beta$- and 16$\\alpha$-fluoro androgens, as well as two 20-fluoro androgens have been synthesized. The fluorination was achieved mainly by nucleophilic fluoride displacement of a triflate or a spirocyclic sulfate precursor, prepared by multistep synthesis.","Of the ten fluorinated androgens, 16$\\beta$-F-DHT (1), 16$\\beta$- and 16$\\alpha$-F-Mib (5 and 6), 16$\\beta$- and 16$\\alpha$-F-MNT (7 and 8), 20-F-Mib (9), as well as 20-F-R1881 (10) were found to have high relative binding affinity for AR, 19%-53% of the potent androgen R1881. In most cases, the fluorination improved the binding selectivity of the androgens to AR vs. other steroid receptors and SBP, and the 16$\\beta$-fluoro androgens have higher affinity than their corresponding 16$\\alpha$-fluoro epimers. Other interesting structure-activity relationships were observed.","Seven of these fluorinated androgens have been prepared in fluorine-18 labeled form, and their in vivo tissue distribution have been studied in estrogen-treated mature male rats. All seven fluorine-18 labeled androgens showed selective and blockable target tissue uptake: the prostate to blood and prostate to muscle ratios (at 4 h) were from 5 (20-F-R1881) to 30 (16$\\alpha$-F-MNT), and the uptake in the unblocked animals were 2.5 (16$\\beta$-F-Mib) to 5.3 (16$\\alpha$-F-MNT and 20-F-MIb) fold higher than that in the blocked animals. Rapid in vivo defluorination was observed with three 16$\\beta$-fluoro androgens (1, 3 and 7). Thus, we have synthesized the first fluorine-18 labeled androgens that have relative high binding affinity and selectivity for AR, and show selective target tissue uptake. It appears that 16$\\beta$-F-F-Mib (5), 16$\\alpha$-F-MNT (8) and 20-F-Mib (9) are the most promising candidates as in vivo imaging agents for prostatic cancer.","Made available in DSpace on 2011-05-07T12:08:02Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9210898.pdf: 6800363 bytes, checksum: 9b818e792adf104faf626a8fa65b4b2c (MD5) Previous issue date: 1991","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:37:04Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:15:10-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"]},{"key":"dc:title","label":"Title","values":["Synthesis and evaluation of fluorine-18 labeled androgens as in vivo imaging agents for prostatic cancer using PET"]}]}],"canonical_facts":{"dc:contributor":["Katzenellenbogen, John A."],"dc:creator":["Liu, Aijun"],"dc:date":["2011-05-07T12:08:02Z","10000-01-01","1991"],"dc:description":["In order to develop androgen receptor (AR) based probes for in vivo imaging of prostatic cancer using positron emission tomography (PET), four pairs of 16$\\beta$- and 16$\\alpha$-fluoro androgens, as well as two 20-fluoro androgens have been synthesized. The fluorination was achieved mainly by nucleophilic fluoride displacement of a triflate or a spirocyclic sulfate precursor, prepared by multistep synthesis.","Of the ten fluorinated androgens, 16$\\beta$-F-DHT (1), 16$\\beta$- and 16$\\alpha$-F-Mib (5 and 6), 16$\\beta$- and 16$\\alpha$-F-MNT (7 and 8), 20-F-Mib (9), as well as 20-F-R1881 (10) were found to have high relative binding affinity for AR, 19%-53% of the potent androgen R1881. In most cases, the fluorination improved the binding selectivity of the androgens to AR vs. other steroid receptors and SBP, and the 16$\\beta$-fluoro androgens have higher affinity than their corresponding 16$\\alpha$-fluoro epimers. Other interesting structure-activity relationships were observed.","Seven of these fluorinated androgens have been prepared in fluorine-18 labeled form, and their in vivo tissue distribution have been studied in estrogen-treated mature male rats. All seven fluorine-18 labeled androgens showed selective and blockable target tissue uptake: the prostate to blood and prostate to muscle ratios (at 4 h) were from 5 (20-F-R1881) to 30 (16$\\alpha$-F-MNT), and the uptake in the unblocked animals were 2.5 (16$\\beta$-F-Mib) to 5.3 (16$\\alpha$-F-MNT and 20-F-MIb) fold higher than that in the blocked animals. Rapid in vivo defluorination was observed with three 16$\\beta$-fluoro androgens (1, 3 and 7). Thus, we have synthesized the first fluorine-18 labeled androgens that have relative high binding affinity and selectivity for AR, and show selective target tissue uptake. It appears that 16$\\beta$-F-F-Mib (5), 16$\\alpha$-F-MNT (8) and 20-F-Mib (9) are the most promising candidates as in vivo imaging agents for prostatic cancer.","Made available in DSpace on 2011-05-07T12:08:02Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9210898.pdf: 6800363 bytes, checksum: 9b818e792adf104faf626a8fa65b4b2c (MD5) Previous issue date: 1991","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:37:04Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:15:10-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"],"dc:identifier":["AAI9210898","(UMI)AAI9210898","http://hdl.handle.net/2142/19453"],"dc:language":["eng"],"dc:rights":["Copyright 1991 Liu, Aijun"],"dc:subject":["Chemistry, Organic","Chemistry, Pharmaceutical","Health Sciences, Radiology","Chemistry, Nuclear"],"dc:title":["Synthesis and evaluation of fluorine-18 labeled androgens as in vivo imaging agents for prostatic cancer using PET"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:25:14Z"}