Synthesis and biodistribution of lipophilic and monocationic gallium radiopharmaceuticals derived from N, N′- bis(3-aminopropyl)- N, N′-dimethylethylenediamine: potential agents for PET myocardial imaging with 68Ga
In locations that lack nearby cyclotron facilities for radionuclide production, generator-based 68Ga radiopharmaceuticals might have clinical utility for positron emission tomography (PET) studies of myocardial perfusion and other physiological processes. The lipophilic and monocationic 67Ga-labeled...
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| creator | Hsiao, Yui-May Mathias, Carla J. Wey, Shiaw-Pyng Fanwick, Phillip E. Green, Mark A. |
| description | In locations that lack nearby cyclotron facilities for radionuclide production, generator-based
68Ga radiopharmaceuticals might have clinical utility for positron emission tomography (PET) studies of myocardial perfusion and other physiological processes.
The lipophilic and monocationic
67Ga-labeled gallium chelates of five novel hexadentate
bis(salicylaldimine) ligands the
bis(salicylaldimine),
bis(3-methoxysalicylaldimine),
bis(4-methoxysalicylaldimine),
bis(6-meth,oxysalicylaldimine), and
bis(4,6-dimethoxysalicylaldimine) of
N,
N′-
bis(3-aminopropyl)
-N,
N′
-dimethylethylenediamine (BAPDMEN), were prepared. The structure of the unlabeled [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− salt was determined by X-ray crystallography, and the biodistribution of each of the
67Ga-labeled gallium chelates was determined in rats following intravenous administration and compared with the biodistribution of [
86Rb]rubidium chloride.
The [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− complex exhibited the expected pseudo-octahedral N
4O
2
2− coordination sphere about the Ga
3+ center with a
trans disposition of the phenolate oxygen atoms. All five
67Ga radiopharmaceuticals were found to afford the desired myocardial retention of the radiogallium. The [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+ radiopharmaceutical appears to have the best properties for myocardial imaging, exhibiting 2% of the injected dose in the heart 1 min and 2 h postinjection and very high heart/nontarget ratios (heart/blood ratios of 7.6±1.0 and 54±10 at 1 and 120 min, respectively; heart/liver ratios of 1.8±0.4 and 39±3 at 1 and 120 min, respectively).
Most of these new agents, particularly [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+, would appear superior to previously reported
bis(salicylaldimine) ligands of
N,
N′-
bis(3-aminopropyl)ethylenediamine as candidates for PET imaging of the heart with
68Ga. |
| doi_str_mv | 10.1016/j.nucmedbio.2008.10.010 |
| format | Article |
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68Ga radiopharmaceuticals might have clinical utility for positron emission tomography (PET) studies of myocardial perfusion and other physiological processes.
The lipophilic and monocationic
67Ga-labeled gallium chelates of five novel hexadentate
bis(salicylaldimine) ligands the
bis(salicylaldimine),
bis(3-methoxysalicylaldimine),
bis(4-methoxysalicylaldimine),
bis(6-meth,oxysalicylaldimine), and
bis(4,6-dimethoxysalicylaldimine) of
N,
N′-
bis(3-aminopropyl)
-N,
N′
-dimethylethylenediamine (BAPDMEN), were prepared. The structure of the unlabeled [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− salt was determined by X-ray crystallography, and the biodistribution of each of the
67Ga-labeled gallium chelates was determined in rats following intravenous administration and compared with the biodistribution of [
86Rb]rubidium chloride.
The [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− complex exhibited the expected pseudo-octahedral N
4O
2
2− coordination sphere about the Ga
3+ center with a
trans disposition of the phenolate oxygen atoms. All five
67Ga radiopharmaceuticals were found to afford the desired myocardial retention of the radiogallium. The [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+ radiopharmaceutical appears to have the best properties for myocardial imaging, exhibiting 2% of the injected dose in the heart 1 min and 2 h postinjection and very high heart/nontarget ratios (heart/blood ratios of 7.6±1.0 and 54±10 at 1 and 120 min, respectively; heart/liver ratios of 1.8±0.4 and 39±3 at 1 and 120 min, respectively).
Most of these new agents, particularly [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+, would appear superior to previously reported
bis(salicylaldimine) ligands of
N,
N′-
bis(3-aminopropyl)ethylenediamine as candidates for PET imaging of the heart with
68Ga.</description><identifier>ISSN: 0969-8051</identifier><identifier>EISSN: 1872-9614</identifier><identifier>DOI: 10.1016/j.nucmedbio.2008.10.010</identifier><identifier>PMID: 19181267</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Chelating Agents - chemistry ; Chlorides - chemistry ; Ethylenediamines - chemistry ; Gallium Radioisotopes - chemistry ; Gallium-68 ; Heart - diagnostic imaging ; Male ; Myocardial imaging ; Positron emission tomography, PET ; Positron-Emission Tomography ; Radiochemistry ; Radiopharmaceuticals ; Radiopharmaceuticals - chemical synthesis ; Radiopharmaceuticals - chemistry ; Radiopharmaceuticals - pharmacokinetics ; Rats ; Rubidium - chemistry ; Rubidium Radioisotopes - chemistry ; Tissue Distribution</subject><ispartof>Nuclear medicine and biology, 2009, Vol.36 (1), p.39-45</ispartof><rights>2009 Elsevier Inc.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3180-fef4c78306a246d1ea233d00e7bbee16a02f59a79902a420a603a17804ad17553</citedby><cites>FETCH-LOGICAL-c3180-fef4c78306a246d1ea233d00e7bbee16a02f59a79902a420a603a17804ad17553</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.nucmedbio.2008.10.010$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,4024,27923,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19181267$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hsiao, Yui-May</creatorcontrib><creatorcontrib>Mathias, Carla J.</creatorcontrib><creatorcontrib>Wey, Shiaw-Pyng</creatorcontrib><creatorcontrib>Fanwick, Phillip E.</creatorcontrib><creatorcontrib>Green, Mark A.</creatorcontrib><title>Synthesis and biodistribution of lipophilic and monocationic gallium radiopharmaceuticals derived from N, N′- bis(3-aminopropyl)- N, N′-dimethylethylenediamine: potential agents for PET myocardial imaging with 68Ga</title><title>Nuclear medicine and biology</title><addtitle>Nucl Med Biol</addtitle><description>In locations that lack nearby cyclotron facilities for radionuclide production, generator-based
68Ga radiopharmaceuticals might have clinical utility for positron emission tomography (PET) studies of myocardial perfusion and other physiological processes.
The lipophilic and monocationic
67Ga-labeled gallium chelates of five novel hexadentate
bis(salicylaldimine) ligands the
bis(salicylaldimine),
bis(3-methoxysalicylaldimine),
bis(4-methoxysalicylaldimine),
bis(6-meth,oxysalicylaldimine), and
bis(4,6-dimethoxysalicylaldimine) of
N,
N′-
bis(3-aminopropyl)
-N,
N′
-dimethylethylenediamine (BAPDMEN), were prepared. The structure of the unlabeled [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− salt was determined by X-ray crystallography, and the biodistribution of each of the
67Ga-labeled gallium chelates was determined in rats following intravenous administration and compared with the biodistribution of [
86Rb]rubidium chloride.
The [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− complex exhibited the expected pseudo-octahedral N
4O
2
2− coordination sphere about the Ga
3+ center with a
trans disposition of the phenolate oxygen atoms. All five
67Ga radiopharmaceuticals were found to afford the desired myocardial retention of the radiogallium. The [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+ radiopharmaceutical appears to have the best properties for myocardial imaging, exhibiting 2% of the injected dose in the heart 1 min and 2 h postinjection and very high heart/nontarget ratios (heart/blood ratios of 7.6±1.0 and 54±10 at 1 and 120 min, respectively; heart/liver ratios of 1.8±0.4 and 39±3 at 1 and 120 min, respectively).
Most of these new agents, particularly [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+, would appear superior to previously reported
bis(salicylaldimine) ligands of
N,
N′-
bis(3-aminopropyl)ethylenediamine as candidates for PET imaging of the heart with
68Ga.</description><subject>Animals</subject><subject>Chelating Agents - chemistry</subject><subject>Chlorides - chemistry</subject><subject>Ethylenediamines - chemistry</subject><subject>Gallium Radioisotopes - chemistry</subject><subject>Gallium-68</subject><subject>Heart - diagnostic imaging</subject><subject>Male</subject><subject>Myocardial imaging</subject><subject>Positron emission tomography, PET</subject><subject>Positron-Emission Tomography</subject><subject>Radiochemistry</subject><subject>Radiopharmaceuticals</subject><subject>Radiopharmaceuticals - chemical synthesis</subject><subject>Radiopharmaceuticals - chemistry</subject><subject>Radiopharmaceuticals - pharmacokinetics</subject><subject>Rats</subject><subject>Rubidium - chemistry</subject><subject>Rubidium Radioisotopes - chemistry</subject><subject>Tissue Distribution</subject><issn>0969-8051</issn><issn>1872-9614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFUctu1DAUtRCITgu_AF6C1Ax2knESFpWqqhSkqiBR1taN7SR3lNiRnRmUHd_E57DkS3CYaoAVG9u653GPfAh5ydmaMy7ebNd2pwaja3TrlLEyTteMs0dkxcsiTSrB88dkxSpRJSXb8BNyGsKWRWXO2VNywite8lQUK_Lj82ynzgQMFKym0U9jmDzWuwmdpa6hPY5u7LBH9ZsxOOsULGActND3uBuoB42RBH4AZaJSQR-oNh73RtPGu4HendO7n9--J3FDeJUlMKB1o3fj3L9OjqDGwUzd3B8OazQuPPOWjm4ydkLoKbTxEWjjPP10fU-HOYbxekFwgBZtS7_i1FFR3sAz8qSJOczzh_uMfHl3fX_1Prn9ePPh6vI2URkvWdKYJldFmTEBaS40N5BmmWbMFHVtDBfA0mZTQVFVLIU8ZSBYBrwoWQ6aF5tNdkYuDr7jro6VqBjQQy9HHxP5WTpA-S9isZOt28tURHVeRYPiYKC8C8Gb5qjlTC51y6081i2Xuhcg1h2VL_5e_Uf30G8kXB4IJn7AHo2XQaGxKn6tN2qS2uF_l_wCYDHIdw</recordid><startdate>2009</startdate><enddate>2009</enddate><creator>Hsiao, Yui-May</creator><creator>Mathias, Carla J.</creator><creator>Wey, Shiaw-Pyng</creator><creator>Fanwick, Phillip E.</creator><creator>Green, Mark A.</creator><general>Elsevier Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>5PM</scope></search><sort><creationdate>2009</creationdate><title>Synthesis and biodistribution of lipophilic and monocationic gallium radiopharmaceuticals derived from N, N′- bis(3-aminopropyl)- N, N′-dimethylethylenediamine: potential agents for PET myocardial imaging with 68Ga</title><author>Hsiao, Yui-May ; Mathias, Carla J. ; Wey, Shiaw-Pyng ; Fanwick, Phillip E. ; Green, Mark A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3180-fef4c78306a246d1ea233d00e7bbee16a02f59a79902a420a603a17804ad17553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Animals</topic><topic>Chelating Agents - chemistry</topic><topic>Chlorides - chemistry</topic><topic>Ethylenediamines - chemistry</topic><topic>Gallium Radioisotopes - chemistry</topic><topic>Gallium-68</topic><topic>Heart - diagnostic imaging</topic><topic>Male</topic><topic>Myocardial imaging</topic><topic>Positron emission tomography, PET</topic><topic>Positron-Emission Tomography</topic><topic>Radiochemistry</topic><topic>Radiopharmaceuticals</topic><topic>Radiopharmaceuticals - chemical synthesis</topic><topic>Radiopharmaceuticals - chemistry</topic><topic>Radiopharmaceuticals - pharmacokinetics</topic><topic>Rats</topic><topic>Rubidium - chemistry</topic><topic>Rubidium Radioisotopes - chemistry</topic><topic>Tissue Distribution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hsiao, Yui-May</creatorcontrib><creatorcontrib>Mathias, Carla J.</creatorcontrib><creatorcontrib>Wey, Shiaw-Pyng</creatorcontrib><creatorcontrib>Fanwick, Phillip E.</creatorcontrib><creatorcontrib>Green, Mark A.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Nuclear medicine and biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hsiao, Yui-May</au><au>Mathias, Carla J.</au><au>Wey, Shiaw-Pyng</au><au>Fanwick, Phillip E.</au><au>Green, Mark A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biodistribution of lipophilic and monocationic gallium radiopharmaceuticals derived from N, N′- bis(3-aminopropyl)- N, N′-dimethylethylenediamine: potential agents for PET myocardial imaging with 68Ga</atitle><jtitle>Nuclear medicine and biology</jtitle><addtitle>Nucl Med Biol</addtitle><date>2009</date><risdate>2009</risdate><volume>36</volume><issue>1</issue><spage>39</spage><epage>45</epage><pages>39-45</pages><issn>0969-8051</issn><eissn>1872-9614</eissn><abstract>In locations that lack nearby cyclotron facilities for radionuclide production, generator-based
68Ga radiopharmaceuticals might have clinical utility for positron emission tomography (PET) studies of myocardial perfusion and other physiological processes.
The lipophilic and monocationic
67Ga-labeled gallium chelates of five novel hexadentate
bis(salicylaldimine) ligands the
bis(salicylaldimine),
bis(3-methoxysalicylaldimine),
bis(4-methoxysalicylaldimine),
bis(6-meth,oxysalicylaldimine), and
bis(4,6-dimethoxysalicylaldimine) of
N,
N′-
bis(3-aminopropyl)
-N,
N′
-dimethylethylenediamine (BAPDMEN), were prepared. The structure of the unlabeled [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− salt was determined by X-ray crystallography, and the biodistribution of each of the
67Ga-labeled gallium chelates was determined in rats following intravenous administration and compared with the biodistribution of [
86Rb]rubidium chloride.
The [Ga(4-MeOsal)
2BAPDMEN]
+PF
6
− complex exhibited the expected pseudo-octahedral N
4O
2
2− coordination sphere about the Ga
3+ center with a
trans disposition of the phenolate oxygen atoms. All five
67Ga radiopharmaceuticals were found to afford the desired myocardial retention of the radiogallium. The [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+ radiopharmaceutical appears to have the best properties for myocardial imaging, exhibiting 2% of the injected dose in the heart 1 min and 2 h postinjection and very high heart/nontarget ratios (heart/blood ratios of 7.6±1.0 and 54±10 at 1 and 120 min, respectively; heart/liver ratios of 1.8±0.4 and 39±3 at 1 and 120 min, respectively).
Most of these new agents, particularly [
67/68Ga][Ga(3-MeOsal)
2BAPDMEN]
1+, would appear superior to previously reported
bis(salicylaldimine) ligands of
N,
N′-
bis(3-aminopropyl)ethylenediamine as candidates for PET imaging of the heart with
68Ga.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>19181267</pmid><doi>10.1016/j.nucmedbio.2008.10.010</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0969-8051 |
| ispartof | Nuclear medicine and biology, 2009, Vol.36 (1), p.39-45 |
| issn | 0969-8051 1872-9614 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2655349 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Animals Chelating Agents - chemistry Chlorides - chemistry Ethylenediamines - chemistry Gallium Radioisotopes - chemistry Gallium-68 Heart - diagnostic imaging Male Myocardial imaging Positron emission tomography, PET Positron-Emission Tomography Radiochemistry Radiopharmaceuticals Radiopharmaceuticals - chemical synthesis Radiopharmaceuticals - chemistry Radiopharmaceuticals - pharmacokinetics Rats Rubidium - chemistry Rubidium Radioisotopes - chemistry Tissue Distribution |
| title | Synthesis and biodistribution of lipophilic and monocationic gallium radiopharmaceuticals derived from N, N′- bis(3-aminopropyl)- N, N′-dimethylethylenediamine: potential agents for PET myocardial imaging with 68Ga |
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