Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression
Although several COX-2 inhibitors have recently been radiolabeled, their potential for imaging COX-2 expression remains unclear. In particular, the sulfonamide moiety of COX-2 inhibitors may cause slow blood clearance of the radiotracer, due to its affinity for carbonic anhydrase (CA) in erythrocyte...
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| creator | Kuge, Yuji Katada, Yumiko Shimonaka, Sayaka Temma, Takashi Kimura, Hiroyuki Kiyono, Yasushi Yokota, Chiaki Minematsu, Kazuo Seki, Koh-ichi Tamaki, Nagara Ohkura, Kazue Saji, Hideo |
| description | Although several COX-2 inhibitors have recently been radiolabeled, their potential for imaging COX-2 expression remains unclear. In particular, the sulfonamide moiety of COX-2 inhibitors may cause slow blood clearance of the radiotracer, due to its affinity for carbonic anhydrase (CA) in erythrocytes. Thus, we designed a methyl sulfone-type analogue, 5-(4-iodophenyl)-1-[4-(methylsulfonyl)phenyl]-3-trifluoromethyl-1
H-pyrazole (IMTP). In this study, the potential of radioiodinated IMTP was assessed in comparison with a
125I-labeled celecoxib analogue with a sulfonamide moiety (
125I-IATP).
The COX inhibitory potency was assessed by measuring COX-catalyzed oxidation by hydrogen peroxide. The biodistribution of
125I-IMTP and
125I-IATP was determined by the ex vivo tissue counting method in rats. Distribution of the labeled compounds to rat blood cells was measured.
The COX-2 inhibitory potency of IMTP (IC
50=5.16 μM) and IATP (IC
50=8.20 μM) was higher than that of meloxicam (IC
50=29.0 μM) and comparable to that of SC-58125 (IC
50=1.36 μM). The IC
50 ratios (COX-1/COX-2) indicated the high isoform selectivity of IMTP and IATP for COX-2. Significant levels of
125I-IMTP and
125I-IATP were observed in the kidneys and the brain (organs known to express COX-2). The blood clearance of
125I-IMTP was much faster than that of
125I-IATP. Distribution of
125I-IATP to blood cells (88.0%) was markedly higher than that of
125I-IMTP (18.1%), which was decreased by CA inhibitors.
Our results showed a high inhibitory potency and selectivity of IMTP for COX-2. The substitution of a sulfonamide moiety to a methyl sulfone moiety effectively improved the blood clearance of the compound, indicating the loss of the cross reactivity with CA in
125I-IMTP.
123I-IMTP may be a potential SPECT radiopharmaceutical for COX-2 expression. |
| doi_str_mv | 10.1016/j.nucmedbio.2005.10.004 |
| format | Article |
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H-pyrazole (IMTP). In this study, the potential of radioiodinated IMTP was assessed in comparison with a
125I-labeled celecoxib analogue with a sulfonamide moiety (
125I-IATP).
The COX inhibitory potency was assessed by measuring COX-catalyzed oxidation by hydrogen peroxide. The biodistribution of
125I-IMTP and
125I-IATP was determined by the ex vivo tissue counting method in rats. Distribution of the labeled compounds to rat blood cells was measured.
The COX-2 inhibitory potency of IMTP (IC
50=5.16 μM) and IATP (IC
50=8.20 μM) was higher than that of meloxicam (IC
50=29.0 μM) and comparable to that of SC-58125 (IC
50=1.36 μM). The IC
50 ratios (COX-1/COX-2) indicated the high isoform selectivity of IMTP and IATP for COX-2. Significant levels of
125I-IMTP and
125I-IATP were observed in the kidneys and the brain (organs known to express COX-2). The blood clearance of
125I-IMTP was much faster than that of
125I-IATP. Distribution of
125I-IATP to blood cells (88.0%) was markedly higher than that of
125I-IMTP (18.1%), which was decreased by CA inhibitors.
Our results showed a high inhibitory potency and selectivity of IMTP for COX-2. The substitution of a sulfonamide moiety to a methyl sulfone moiety effectively improved the blood clearance of the compound, indicating the loss of the cross reactivity with CA in
125I-IMTP.
123I-IMTP may be a potential SPECT radiopharmaceutical for COX-2 expression.</description><identifier>ISSN: 0969-8051</identifier><identifier>EISSN: 1872-9614</identifier><identifier>DOI: 10.1016/j.nucmedbio.2005.10.004</identifier><identifier>PMID: 16459255</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Cyclooxygenase 2 - metabolism ; Cyclooxygenase 2 Inhibitors - pharmacokinetics ; Cyclooxygenase-2 (COX-2) ; Feasibility Studies ; Inhibitor ; Iodine Radioisotopes ; Isotope Labeling - methods ; Male ; Metabolic Clearance Rate ; Organ Specificity ; Pyrazoles - chemistry ; Pyrazoles - pharmacokinetics ; Radioiodination ; Radiopharmaceutical ; Radiopharmaceuticals - chemical synthesis ; Radiopharmaceuticals - pharmacokinetics ; Rats ; Rats, Sprague-Dawley ; SPECT ; Sulfonamides - chemistry ; Sulfonamides - pharmacokinetics ; Sulfones - chemistry ; Sulfones - pharmacokinetics ; Tissue Distribution ; Tomography, Emission-Computed, Single-Photon - methods</subject><ispartof>Nuclear medicine and biology, 2006, Vol.33 (1), p.21-27</ispartof><rights>2006 Elsevier Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c435t-7e057793b0814b938e75f9a0a71362b1ea62aa4af7f901eb9ca5b1581eab3863</citedby><cites>FETCH-LOGICAL-c435t-7e057793b0814b938e75f9a0a71362b1ea62aa4af7f901eb9ca5b1581eab3863</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.2005.10.004$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3549,4023,27922,27923,27924,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16459255$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kuge, Yuji</creatorcontrib><creatorcontrib>Katada, Yumiko</creatorcontrib><creatorcontrib>Shimonaka, Sayaka</creatorcontrib><creatorcontrib>Temma, Takashi</creatorcontrib><creatorcontrib>Kimura, Hiroyuki</creatorcontrib><creatorcontrib>Kiyono, Yasushi</creatorcontrib><creatorcontrib>Yokota, Chiaki</creatorcontrib><creatorcontrib>Minematsu, Kazuo</creatorcontrib><creatorcontrib>Seki, Koh-ichi</creatorcontrib><creatorcontrib>Tamaki, Nagara</creatorcontrib><creatorcontrib>Ohkura, Kazue</creatorcontrib><creatorcontrib>Saji, Hideo</creatorcontrib><title>Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression</title><title>Nuclear medicine and biology</title><addtitle>Nucl Med Biol</addtitle><description>Although several COX-2 inhibitors have recently been radiolabeled, their potential for imaging COX-2 expression remains unclear. In particular, the sulfonamide moiety of COX-2 inhibitors may cause slow blood clearance of the radiotracer, due to its affinity for carbonic anhydrase (CA) in erythrocytes. Thus, we designed a methyl sulfone-type analogue, 5-(4-iodophenyl)-1-[4-(methylsulfonyl)phenyl]-3-trifluoromethyl-1
H-pyrazole (IMTP). In this study, the potential of radioiodinated IMTP was assessed in comparison with a
125I-labeled celecoxib analogue with a sulfonamide moiety (
125I-IATP).
The COX inhibitory potency was assessed by measuring COX-catalyzed oxidation by hydrogen peroxide. The biodistribution of
125I-IMTP and
125I-IATP was determined by the ex vivo tissue counting method in rats. Distribution of the labeled compounds to rat blood cells was measured.
The COX-2 inhibitory potency of IMTP (IC
50=5.16 μM) and IATP (IC
50=8.20 μM) was higher than that of meloxicam (IC
50=29.0 μM) and comparable to that of SC-58125 (IC
50=1.36 μM). The IC
50 ratios (COX-1/COX-2) indicated the high isoform selectivity of IMTP and IATP for COX-2. Significant levels of
125I-IMTP and
125I-IATP were observed in the kidneys and the brain (organs known to express COX-2). The blood clearance of
125I-IMTP was much faster than that of
125I-IATP. Distribution of
125I-IATP to blood cells (88.0%) was markedly higher than that of
125I-IMTP (18.1%), which was decreased by CA inhibitors.
Our results showed a high inhibitory potency and selectivity of IMTP for COX-2. The substitution of a sulfonamide moiety to a methyl sulfone moiety effectively improved the blood clearance of the compound, indicating the loss of the cross reactivity with CA in
125I-IMTP.
123I-IMTP may be a potential SPECT radiopharmaceutical for COX-2 expression.</description><subject>Animals</subject><subject>Cyclooxygenase 2 - metabolism</subject><subject>Cyclooxygenase 2 Inhibitors - pharmacokinetics</subject><subject>Cyclooxygenase-2 (COX-2)</subject><subject>Feasibility Studies</subject><subject>Inhibitor</subject><subject>Iodine Radioisotopes</subject><subject>Isotope Labeling - methods</subject><subject>Male</subject><subject>Metabolic Clearance Rate</subject><subject>Organ Specificity</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacokinetics</subject><subject>Radioiodination</subject><subject>Radiopharmaceutical</subject><subject>Radiopharmaceuticals - chemical synthesis</subject><subject>Radiopharmaceuticals - pharmacokinetics</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>SPECT</subject><subject>Sulfonamides - chemistry</subject><subject>Sulfonamides - pharmacokinetics</subject><subject>Sulfones - chemistry</subject><subject>Sulfones - pharmacokinetics</subject><subject>Tissue Distribution</subject><subject>Tomography, Emission-Computed, Single-Photon - methods</subject><issn>0969-8051</issn><issn>1872-9614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEFvEzEQhS0EoqHwF8Anbhvs3bW9PlZRC0iVQGru1tg7Sx1t7GB7q-bIP8dRIjhw4DTSvPfN0zxCPnC25ozLT7t1WNweR-vjumVM1O2asf4FWfFBtY2WvH9JVkxL3QxM8CvyJucdq2TP2WtyVafQrRAr8uvhGMojZp8phJHiE8wLFB8DjRNNMPro4-gDFBypO7o5xufjDwyQsWmpD4_e-hJThTM9xIKheJjpw_fbzZaWBA6rNMX0L4rPh4Q516C35NUEc8Z3l3lNtne3282X5v7b56-bm_vG9Z0ojUImlNKdZQPvre4GVGLSwEDxTraWI8gWoIdJTZpxtNqBsFwMVbDdILtr8vF89pDizwVzMXufHc4zBIxLNlLJrtOyr0Z1NroUc044mUPye0hHw5k5lW925k_55lT-SajlV_L9JWKxVf7LXdquhpuzAeufTx6Tyc5jcDj6hK6YMfr_hvwG4OmdLw</recordid><startdate>2006</startdate><enddate>2006</enddate><creator>Kuge, Yuji</creator><creator>Katada, Yumiko</creator><creator>Shimonaka, Sayaka</creator><creator>Temma, Takashi</creator><creator>Kimura, Hiroyuki</creator><creator>Kiyono, Yasushi</creator><creator>Yokota, Chiaki</creator><creator>Minematsu, Kazuo</creator><creator>Seki, Koh-ichi</creator><creator>Tamaki, Nagara</creator><creator>Ohkura, Kazue</creator><creator>Saji, Hideo</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>7X8</scope></search><sort><creationdate>2006</creationdate><title>Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression</title><author>Kuge, Yuji ; Katada, Yumiko ; Shimonaka, Sayaka ; Temma, Takashi ; Kimura, Hiroyuki ; Kiyono, Yasushi ; Yokota, Chiaki ; Minematsu, Kazuo ; Seki, Koh-ichi ; Tamaki, Nagara ; Ohkura, Kazue ; Saji, Hideo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c435t-7e057793b0814b938e75f9a0a71362b1ea62aa4af7f901eb9ca5b1581eab3863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Cyclooxygenase 2 - metabolism</topic><topic>Cyclooxygenase 2 Inhibitors - pharmacokinetics</topic><topic>Cyclooxygenase-2 (COX-2)</topic><topic>Feasibility Studies</topic><topic>Inhibitor</topic><topic>Iodine Radioisotopes</topic><topic>Isotope Labeling - methods</topic><topic>Male</topic><topic>Metabolic Clearance Rate</topic><topic>Organ Specificity</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacokinetics</topic><topic>Radioiodination</topic><topic>Radiopharmaceutical</topic><topic>Radiopharmaceuticals - chemical synthesis</topic><topic>Radiopharmaceuticals - pharmacokinetics</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>SPECT</topic><topic>Sulfonamides - chemistry</topic><topic>Sulfonamides - pharmacokinetics</topic><topic>Sulfones - chemistry</topic><topic>Sulfones - pharmacokinetics</topic><topic>Tissue Distribution</topic><topic>Tomography, Emission-Computed, Single-Photon - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuge, Yuji</creatorcontrib><creatorcontrib>Katada, Yumiko</creatorcontrib><creatorcontrib>Shimonaka, Sayaka</creatorcontrib><creatorcontrib>Temma, Takashi</creatorcontrib><creatorcontrib>Kimura, Hiroyuki</creatorcontrib><creatorcontrib>Kiyono, Yasushi</creatorcontrib><creatorcontrib>Yokota, Chiaki</creatorcontrib><creatorcontrib>Minematsu, Kazuo</creatorcontrib><creatorcontrib>Seki, Koh-ichi</creatorcontrib><creatorcontrib>Tamaki, Nagara</creatorcontrib><creatorcontrib>Ohkura, Kazue</creatorcontrib><creatorcontrib>Saji, Hideo</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Nuclear medicine and biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuge, Yuji</au><au>Katada, Yumiko</au><au>Shimonaka, Sayaka</au><au>Temma, Takashi</au><au>Kimura, Hiroyuki</au><au>Kiyono, Yasushi</au><au>Yokota, Chiaki</au><au>Minematsu, Kazuo</au><au>Seki, Koh-ichi</au><au>Tamaki, Nagara</au><au>Ohkura, Kazue</au><au>Saji, Hideo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression</atitle><jtitle>Nuclear medicine and biology</jtitle><addtitle>Nucl Med Biol</addtitle><date>2006</date><risdate>2006</risdate><volume>33</volume><issue>1</issue><spage>21</spage><epage>27</epage><pages>21-27</pages><issn>0969-8051</issn><eissn>1872-9614</eissn><abstract>Although several COX-2 inhibitors have recently been radiolabeled, their potential for imaging COX-2 expression remains unclear. In particular, the sulfonamide moiety of COX-2 inhibitors may cause slow blood clearance of the radiotracer, due to its affinity for carbonic anhydrase (CA) in erythrocytes. Thus, we designed a methyl sulfone-type analogue, 5-(4-iodophenyl)-1-[4-(methylsulfonyl)phenyl]-3-trifluoromethyl-1
H-pyrazole (IMTP). In this study, the potential of radioiodinated IMTP was assessed in comparison with a
125I-labeled celecoxib analogue with a sulfonamide moiety (
125I-IATP).
The COX inhibitory potency was assessed by measuring COX-catalyzed oxidation by hydrogen peroxide. The biodistribution of
125I-IMTP and
125I-IATP was determined by the ex vivo tissue counting method in rats. Distribution of the labeled compounds to rat blood cells was measured.
The COX-2 inhibitory potency of IMTP (IC
50=5.16 μM) and IATP (IC
50=8.20 μM) was higher than that of meloxicam (IC
50=29.0 μM) and comparable to that of SC-58125 (IC
50=1.36 μM). The IC
50 ratios (COX-1/COX-2) indicated the high isoform selectivity of IMTP and IATP for COX-2. Significant levels of
125I-IMTP and
125I-IATP were observed in the kidneys and the brain (organs known to express COX-2). The blood clearance of
125I-IMTP was much faster than that of
125I-IATP. Distribution of
125I-IATP to blood cells (88.0%) was markedly higher than that of
125I-IMTP (18.1%), which was decreased by CA inhibitors.
Our results showed a high inhibitory potency and selectivity of IMTP for COX-2. The substitution of a sulfonamide moiety to a methyl sulfone moiety effectively improved the blood clearance of the compound, indicating the loss of the cross reactivity with CA in
125I-IMTP.
123I-IMTP may be a potential SPECT radiopharmaceutical for COX-2 expression.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>16459255</pmid><doi>10.1016/j.nucmedbio.2005.10.004</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0969-8051 |
| ispartof | Nuclear medicine and biology, 2006, Vol.33 (1), p.21-27 |
| issn | 0969-8051 1872-9614 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67633964 |
| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | Animals Cyclooxygenase 2 - metabolism Cyclooxygenase 2 Inhibitors - pharmacokinetics Cyclooxygenase-2 (COX-2) Feasibility Studies Inhibitor Iodine Radioisotopes Isotope Labeling - methods Male Metabolic Clearance Rate Organ Specificity Pyrazoles - chemistry Pyrazoles - pharmacokinetics Radioiodination Radiopharmaceutical Radiopharmaceuticals - chemical synthesis Radiopharmaceuticals - pharmacokinetics Rats Rats, Sprague-Dawley SPECT Sulfonamides - chemistry Sulfonamides - pharmacokinetics Sulfones - chemistry Sulfones - pharmacokinetics Tissue Distribution Tomography, Emission-Computed, Single-Photon - methods |
| title | Synthesis and evaluation of radioiodinated cyclooxygenase-2 inhibitors as potential SPECT tracers for cyclooxygenase-2 expression |
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