Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [ 11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents
A series of [ 11C]methyl-halo-CGS 27023A analogs (2-F, 1a; 4-F, 1b; 2-Cl, 1c; 3-Cl, 1d; 4-Cl, 1e; 2-Br, 1f; 3-Br, 1g; 4-Br, 1h; 4-I, 1i), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast canc...
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| Veröffentlicht in: | Nuclear medicine and biology 2002-10, Vol.29 (7), p.761-770 |
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| creator | Zheng, Qi-Huang Fei, Xiangshu Liu, Xuan Wang, Ji-Quan Bin Sun, Hui Mock, Bruce H Lee Stone, K Martinez, Tanya D Miller, Kathy D Sledge, George W Hutchins, Gary D |
| description | A series of [
11C]methyl-halo-CGS 27023A analogs (2-F,
1a; 4-F,
1b; 2-Cl,
1c; 3-Cl,
1d; 4-Cl,
1e; 2-Br,
1f; 3-Br,
1g; 4-Br,
1h; 4-I,
1i), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents. The precursors halo-CGS 27023A analogs (2-F,
6a; 4-F,
6b; 2-Cl,
6c; 3-Cl,
6d; 4-Cl,
6e; 2-Br,
6f; 3-Br,
6g; 4-Br,
6h; 4-I,
6i) for radiolabeling were obtained in four steps from starting material amino acid D-valine with moderate to excellent chemical yields. Precursors were labeled by [
11C]methyl triflate through
11C-O-methylation method at the aminohydroxyl position under basic conditions and isolated by solid-phase extraction (SPE) purification to produce pure target compounds in 40–60% radiochemical yields (decay corrected to end of bombardment), in 20–25 min synthesis time. |
| doi_str_mv | 10.1016/S0969-8051(02)00338-4 |
| format | Article |
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11C]methyl-halo-CGS 27023A analogs (2-F,
1a; 4-F,
1b; 2-Cl,
1c; 3-Cl,
1d; 4-Cl,
1e; 2-Br,
1f; 3-Br,
1g; 4-Br,
1h; 4-I,
1i), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents. The precursors halo-CGS 27023A analogs (2-F,
6a; 4-F,
6b; 2-Cl,
6c; 3-Cl,
6d; 4-Cl,
6e; 2-Br,
6f; 3-Br,
6g; 4-Br,
6h; 4-I,
6i) for radiolabeling were obtained in four steps from starting material amino acid D-valine with moderate to excellent chemical yields. Precursors were labeled by [
11C]methyl triflate through
11C-O-methylation method at the aminohydroxyl position under basic conditions and isolated by solid-phase extraction (SPE) purification to produce pure target compounds in 40–60% radiochemical yields (decay corrected to end of bombardment), in 20–25 min synthesis time.</description><identifier>ISSN: 0969-8051</identifier><identifier>EISSN: 1872-9614</identifier><identifier>DOI: 10.1016/S0969-8051(02)00338-4</identifier><identifier>PMID: 12381456</identifier><language>eng</language><publisher>Amsterdam: Elsevier Inc</publisher><subject>[ 11C]Methyl-halo-CGS 27023A analogs ; Animals ; Biological and medical sciences ; Biomarkers, Tumor ; Breast cancer ; Breast Neoplasms - diagnostic imaging ; Carbon Radioisotopes - pharmacokinetics ; Carbon-11 ; Humans ; Hydroxamic Acids ; Matrix metalloproteinase inhibitor ; Medical sciences ; Metalloendopeptidases - antagonists & inhibitors ; Metalloendopeptidases - metabolism ; Positron emission tomography ; Protease Inhibitors - chemical synthesis ; Protease Inhibitors - pharmacokinetics ; Pyrazines ; Radiopharmaceuticals - pharmacokinetics ; Radiotracer ; Sulfonamides ; Tomography, Emission-Computed - methods</subject><ispartof>Nuclear medicine and biology, 2002-10, Vol.29 (7), p.761-770</ispartof><rights>2002 Elsevier Science Inc.</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c457t-adc527c6bd4ddd0cf9e817d0528670ec55aee521a50f2f0bc43616b96ea618a93</citedby><cites>FETCH-LOGICAL-c457t-adc527c6bd4ddd0cf9e817d0528670ec55aee521a50f2f0bc43616b96ea618a93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0969-8051(02)00338-4$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13977535$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12381456$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zheng, Qi-Huang</creatorcontrib><creatorcontrib>Fei, Xiangshu</creatorcontrib><creatorcontrib>Liu, Xuan</creatorcontrib><creatorcontrib>Wang, Ji-Quan</creatorcontrib><creatorcontrib>Bin Sun, Hui</creatorcontrib><creatorcontrib>Mock, Bruce H</creatorcontrib><creatorcontrib>Lee Stone, K</creatorcontrib><creatorcontrib>Martinez, Tanya D</creatorcontrib><creatorcontrib>Miller, Kathy D</creatorcontrib><creatorcontrib>Sledge, George W</creatorcontrib><creatorcontrib>Hutchins, Gary D</creatorcontrib><title>Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [ 11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents</title><title>Nuclear medicine and biology</title><addtitle>Nucl Med Biol</addtitle><description>A series of [
11C]methyl-halo-CGS 27023A analogs (2-F,
1a; 4-F,
1b; 2-Cl,
1c; 3-Cl,
1d; 4-Cl,
1e; 2-Br,
1f; 3-Br,
1g; 4-Br,
1h; 4-I,
1i), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents. The precursors halo-CGS 27023A analogs (2-F,
6a; 4-F,
6b; 2-Cl,
6c; 3-Cl,
6d; 4-Cl,
6e; 2-Br,
6f; 3-Br,
6g; 4-Br,
6h; 4-I,
6i) for radiolabeling were obtained in four steps from starting material amino acid D-valine with moderate to excellent chemical yields. Precursors were labeled by [
11C]methyl triflate through
11C-O-methylation method at the aminohydroxyl position under basic conditions and isolated by solid-phase extraction (SPE) purification to produce pure target compounds in 40–60% radiochemical yields (decay corrected to end of bombardment), in 20–25 min synthesis time.</description><subject>[ 11C]Methyl-halo-CGS 27023A analogs</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Biomarkers, Tumor</subject><subject>Breast cancer</subject><subject>Breast Neoplasms - diagnostic imaging</subject><subject>Carbon Radioisotopes - pharmacokinetics</subject><subject>Carbon-11</subject><subject>Humans</subject><subject>Hydroxamic Acids</subject><subject>Matrix metalloproteinase inhibitor</subject><subject>Medical sciences</subject><subject>Metalloendopeptidases - antagonists & inhibitors</subject><subject>Metalloendopeptidases - metabolism</subject><subject>Positron emission tomography</subject><subject>Protease Inhibitors - chemical synthesis</subject><subject>Protease Inhibitors - pharmacokinetics</subject><subject>Pyrazines</subject><subject>Radiopharmaceuticals - pharmacokinetics</subject><subject>Radiotracer</subject><subject>Sulfonamides</subject><subject>Tomography, Emission-Computed - methods</subject><issn>0969-8051</issn><issn>1872-9614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkVFrFDEUhQdR7Fr9CUpeFAVHk8wkM_MkZWmr0GJh65NIuJPcmY3MJNsk27J_x19q2l3so08XLt8593JOUbxm9BOjTH5e0U52ZUsFe0_5B0qrqi3rJ8WCtQ0vO8nqp8XiH3JUvIjxN826mtHnxRHjVctqIRfFn9XOpTVGGwk4QzYBJztbB2FHeusnP1oNE8FbmLaQrHfED-Ty8opYt7a9TT6QAMb6FEBjiOQnYWz5a8a03k3lGiZfLs9XhDeUVyf5QF6M8SNxeEc2PqFLNptfnV6TPiDERDS4bEPsDKN1I4ExI_Fl8WyAKeKrwzwufpydXi-_lhffz78tTy5KXYsmlWC04I2WvamNMVQPHbasMVTwVjYUtRCAKDgDQQc-0F7XlWSy7ySCZC101XHxbu-7Cf5mizGp2UaN0wQO_TaqhrNs2MkMij2og48x4KA2Ib8cdopRdV-OeihH3SevKFcP5ag6694cDmz7Gc2j6tBGBt4eAIg59iHkOGx85KquaUQlMvdlz2GO49ZiUFFbzNEZG1AnZbz9zyt_Ae00rVE</recordid><startdate>20021001</startdate><enddate>20021001</enddate><creator>Zheng, Qi-Huang</creator><creator>Fei, Xiangshu</creator><creator>Liu, Xuan</creator><creator>Wang, Ji-Quan</creator><creator>Bin Sun, Hui</creator><creator>Mock, Bruce H</creator><creator>Lee Stone, K</creator><creator>Martinez, Tanya D</creator><creator>Miller, Kathy D</creator><creator>Sledge, George W</creator><creator>Hutchins, Gary D</creator><general>Elsevier Inc</general><general>Elsevier</general><scope>IQODW</scope><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>20021001</creationdate><title>Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [ 11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents</title><author>Zheng, Qi-Huang ; Fei, Xiangshu ; Liu, Xuan ; Wang, Ji-Quan ; Bin Sun, Hui ; Mock, Bruce H ; Lee Stone, K ; Martinez, Tanya D ; Miller, Kathy D ; Sledge, George W ; Hutchins, Gary D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-adc527c6bd4ddd0cf9e817d0528670ec55aee521a50f2f0bc43616b96ea618a93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>[ 11C]Methyl-halo-CGS 27023A analogs</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Biomarkers, Tumor</topic><topic>Breast cancer</topic><topic>Breast Neoplasms - diagnostic imaging</topic><topic>Carbon Radioisotopes - pharmacokinetics</topic><topic>Carbon-11</topic><topic>Humans</topic><topic>Hydroxamic Acids</topic><topic>Matrix metalloproteinase inhibitor</topic><topic>Medical sciences</topic><topic>Metalloendopeptidases - antagonists & inhibitors</topic><topic>Metalloendopeptidases - metabolism</topic><topic>Positron emission tomography</topic><topic>Protease Inhibitors - chemical synthesis</topic><topic>Protease Inhibitors - pharmacokinetics</topic><topic>Pyrazines</topic><topic>Radiopharmaceuticals - pharmacokinetics</topic><topic>Radiotracer</topic><topic>Sulfonamides</topic><topic>Tomography, Emission-Computed - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Qi-Huang</creatorcontrib><creatorcontrib>Fei, Xiangshu</creatorcontrib><creatorcontrib>Liu, Xuan</creatorcontrib><creatorcontrib>Wang, Ji-Quan</creatorcontrib><creatorcontrib>Bin Sun, Hui</creatorcontrib><creatorcontrib>Mock, Bruce H</creatorcontrib><creatorcontrib>Lee Stone, K</creatorcontrib><creatorcontrib>Martinez, Tanya D</creatorcontrib><creatorcontrib>Miller, Kathy D</creatorcontrib><creatorcontrib>Sledge, George W</creatorcontrib><creatorcontrib>Hutchins, Gary D</creatorcontrib><collection>Pascal-Francis</collection><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>Zheng, Qi-Huang</au><au>Fei, Xiangshu</au><au>Liu, Xuan</au><au>Wang, Ji-Quan</au><au>Bin Sun, Hui</au><au>Mock, Bruce H</au><au>Lee Stone, K</au><au>Martinez, Tanya D</au><au>Miller, Kathy D</au><au>Sledge, George W</au><au>Hutchins, Gary D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [ 11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents</atitle><jtitle>Nuclear medicine and biology</jtitle><addtitle>Nucl Med Biol</addtitle><date>2002-10-01</date><risdate>2002</risdate><volume>29</volume><issue>7</issue><spage>761</spage><epage>770</epage><pages>761-770</pages><issn>0969-8051</issn><eissn>1872-9614</eissn><abstract>A series of [
11C]methyl-halo-CGS 27023A analogs (2-F,
1a; 4-F,
1b; 2-Cl,
1c; 3-Cl,
1d; 4-Cl,
1e; 2-Br,
1f; 3-Br,
1g; 4-Br,
1h; 4-I,
1i), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents. The precursors halo-CGS 27023A analogs (2-F,
6a; 4-F,
6b; 2-Cl,
6c; 3-Cl,
6d; 4-Cl,
6e; 2-Br,
6f; 3-Br,
6g; 4-Br,
6h; 4-I,
6i) for radiolabeling were obtained in four steps from starting material amino acid D-valine with moderate to excellent chemical yields. Precursors were labeled by [
11C]methyl triflate through
11C-O-methylation method at the aminohydroxyl position under basic conditions and isolated by solid-phase extraction (SPE) purification to produce pure target compounds in 40–60% radiochemical yields (decay corrected to end of bombardment), in 20–25 min synthesis time.</abstract><cop>Amsterdam</cop><pub>Elsevier Inc</pub><pmid>12381456</pmid><doi>10.1016/S0969-8051(02)00338-4</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Nuclear medicine and biology, 2002-10, Vol.29 (7), p.761-770 |
| issn | 0969-8051 1872-9614 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | [ 11C]Methyl-halo-CGS 27023A analogs Animals Biological and medical sciences Biomarkers, Tumor Breast cancer Breast Neoplasms - diagnostic imaging Carbon Radioisotopes - pharmacokinetics Carbon-11 Humans Hydroxamic Acids Matrix metalloproteinase inhibitor Medical sciences Metalloendopeptidases - antagonists & inhibitors Metalloendopeptidases - metabolism Positron emission tomography Protease Inhibitors - chemical synthesis Protease Inhibitors - pharmacokinetics Pyrazines Radiopharmaceuticals - pharmacokinetics Radiotracer Sulfonamides Tomography, Emission-Computed - methods |
| title | Synthesis and preliminary biological evaluation of MMP inhibitor radiotracers [ 11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents |
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