Synthesis, Relaxometric and Photophysical Properties of a New pH-Responsive MRI Contrast Agent: The Effect of Other Ligating Groups on Dissociation of a p-Nitrophenolic Pendant Arm
Two gadolinium(III) chelates, GdNP-DO3A (1-methlyene-(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-tri Acetate) and GdNP-DO3AM (1-methlyene(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-triacetAMide), containing a single nitrophenolic pendant arm plus either three acetate or three ami...
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| Veröffentlicht in: | Journal of the American Chemical Society 2004-08, Vol.126 (30), p.9248-9256 |
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| creator | Woods, Mark Kiefer, Garry E Bott, Simon Castillo-Muzquiz, Aminta Eshelbrenner, Carrie Michaudet, Lydie McMillan, Kenneth Mudigunda, Siva D. K Ogrin, Doug Tircsó, Gyula Zhang, Shanrong Zhao, Piyu Sherry, A. Dean |
| description | Two gadolinium(III) chelates, GdNP-DO3A (1-methlyene-(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-tri Acetate) and GdNP-DO3AM (1-methlyene(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-triacetAMide), containing a single nitrophenolic pendant arm plus either three acetate or three amide pendant arms were synthesized and characterized. The properties of the gadolinium, terbium, and dysprosium complexes of these ligands were examined as a function of pH. The extent and mechanism of the changes in water relaxivity with pH of each gadolinium complex was found to differ substantially for the two complexes. The water relaxivity of Gd(NP-DO3A) increases from 4.1 mM-1 s-1 at pH 9 to 7.0 mM-1 s-1 at pH 5 as a result of acid-catalyzed dissociation of the nitrophenol from the lanthanide. The nitrophenol group in Gd(NP-DO3AM) does not dissociate from the metal center even at pH 5; therefore, the very modest increase in relaxivity in this complex must be ascribed to an increase in prototropic exchange rate of the bound water and/or phenolic protons. |
| doi_str_mv | 10.1021/ja048299z |
| format | Article |
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K ; Ogrin, Doug ; Tircsó, Gyula ; Zhang, Shanrong ; Zhao, Piyu ; Sherry, A. Dean</creator><creatorcontrib>Woods, Mark ; Kiefer, Garry E ; Bott, Simon ; Castillo-Muzquiz, Aminta ; Eshelbrenner, Carrie ; Michaudet, Lydie ; McMillan, Kenneth ; Mudigunda, Siva D. K ; Ogrin, Doug ; Tircsó, Gyula ; Zhang, Shanrong ; Zhao, Piyu ; Sherry, A. Dean</creatorcontrib><description>Two gadolinium(III) chelates, GdNP-DO3A (1-methlyene-(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-tri Acetate) and GdNP-DO3AM (1-methlyene(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-triacetAMide), containing a single nitrophenolic pendant arm plus either three acetate or three amide pendant arms were synthesized and characterized. The properties of the gadolinium, terbium, and dysprosium complexes of these ligands were examined as a function of pH. The extent and mechanism of the changes in water relaxivity with pH of each gadolinium complex was found to differ substantially for the two complexes. The water relaxivity of Gd(NP-DO3A) increases from 4.1 mM-1 s-1 at pH 9 to 7.0 mM-1 s-1 at pH 5 as a result of acid-catalyzed dissociation of the nitrophenol from the lanthanide. The nitrophenol group in Gd(NP-DO3AM) does not dissociate from the metal center even at pH 5; therefore, the very modest increase in relaxivity in this complex must be ascribed to an increase in prototropic exchange rate of the bound water and/or phenolic protons.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja048299z</identifier><identifier>PMID: 15281814</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Amines - chemistry ; Biological and medical sciences ; Chemistry ; Condensed matter: structure, mechanical and thermal properties ; Contrast Media - chemical synthesis ; Contrast Media - chemistry ; Contrast media. Radiopharmaceuticals ; Coordination compounds ; Crystallography, X-Ray ; Exact sciences and technology ; Gadolinium - chemistry ; Hydrogen-Ion Concentration ; Inorganic chemistry and origins of life ; Inorganic compounds ; Kinetics ; Luminescent Measurements ; Magnetic Resonance Imaging ; Magnetic Resonance Spectroscopy ; Medical sciences ; Metal complexes ; Molecular Structure ; Nitrophenols - chemical synthesis ; Nitrophenols - chemistry ; Organometallic Compounds - chemical synthesis ; Organometallic Compounds - chemistry ; Pharmacology. Drug treatments ; Photochemistry ; Physics ; Preparations and properties ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids</subject><ispartof>Journal of the American Chemical Society, 2004-08, Vol.126 (30), p.9248-9256</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a535t-de0fe8fc7275479109f18f16d56e4abb4e1bdb509fc1ac0c46fcf8c8984c20bc3</citedby><cites>FETCH-LOGICAL-a535t-de0fe8fc7275479109f18f16d56e4abb4e1bdb509fc1ac0c46fcf8c8984c20bc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja048299z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja048299z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15990186$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15281814$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Woods, Mark</creatorcontrib><creatorcontrib>Kiefer, Garry E</creatorcontrib><creatorcontrib>Bott, Simon</creatorcontrib><creatorcontrib>Castillo-Muzquiz, Aminta</creatorcontrib><creatorcontrib>Eshelbrenner, Carrie</creatorcontrib><creatorcontrib>Michaudet, Lydie</creatorcontrib><creatorcontrib>McMillan, Kenneth</creatorcontrib><creatorcontrib>Mudigunda, Siva D. K</creatorcontrib><creatorcontrib>Ogrin, Doug</creatorcontrib><creatorcontrib>Tircsó, Gyula</creatorcontrib><creatorcontrib>Zhang, Shanrong</creatorcontrib><creatorcontrib>Zhao, Piyu</creatorcontrib><creatorcontrib>Sherry, A. Dean</creatorcontrib><title>Synthesis, Relaxometric and Photophysical Properties of a New pH-Responsive MRI Contrast Agent: The Effect of Other Ligating Groups on Dissociation of a p-Nitrophenolic Pendant Arm</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Two gadolinium(III) chelates, GdNP-DO3A (1-methlyene-(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-tri Acetate) and GdNP-DO3AM (1-methlyene(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-triacetAMide), containing a single nitrophenolic pendant arm plus either three acetate or three amide pendant arms were synthesized and characterized. The properties of the gadolinium, terbium, and dysprosium complexes of these ligands were examined as a function of pH. The extent and mechanism of the changes in water relaxivity with pH of each gadolinium complex was found to differ substantially for the two complexes. The water relaxivity of Gd(NP-DO3A) increases from 4.1 mM-1 s-1 at pH 9 to 7.0 mM-1 s-1 at pH 5 as a result of acid-catalyzed dissociation of the nitrophenol from the lanthanide. The nitrophenol group in Gd(NP-DO3AM) does not dissociate from the metal center even at pH 5; therefore, the very modest increase in relaxivity in this complex must be ascribed to an increase in prototropic exchange rate of the bound water and/or phenolic protons.</description><subject>Amines - chemistry</subject><subject>Biological and medical sciences</subject><subject>Chemistry</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>Contrast Media - chemical synthesis</subject><subject>Contrast Media - chemistry</subject><subject>Contrast media. Radiopharmaceuticals</subject><subject>Coordination compounds</subject><subject>Crystallography, X-Ray</subject><subject>Exact sciences and technology</subject><subject>Gadolinium - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Inorganic chemistry and origins of life</subject><subject>Inorganic compounds</subject><subject>Kinetics</subject><subject>Luminescent Measurements</subject><subject>Magnetic Resonance Imaging</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Metal complexes</subject><subject>Molecular Structure</subject><subject>Nitrophenols - chemical synthesis</subject><subject>Nitrophenols - chemistry</subject><subject>Organometallic Compounds - chemical synthesis</subject><subject>Organometallic Compounds - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Photochemistry</subject><subject>Physics</subject><subject>Preparations and properties</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptks1uEzEUhS0EoiGw4AWQNyAhMWBP5rcLpCptk0ohjdKwtjye64zDxB5spzSs2PJEvA9PgkOitEisrOv7-ZxrHyP0kpL3lMT0w4qTpIjL8vsj1KNpTKKUxtlj1COExFFeZIMT9My5VSiTuKBP0UmAClrQpId-3Wy1b8Ap9w7PoeV3Zg3eKoG5rvGsMd50zdYpwVs8s6YD6xU4bCTmeArfcDeO5uA6o526BfxpfoWHRnvLncdnS9D-9PePn3jRAL6QEoTfHbwOdhZP1JJ7pZd4ZM2mC4oanyvnjFBhOxR_HbpoqnxwbUCbNsw0A11zHaTt-jl6Innr4MVh7aPPlxeL4TiaXI-uhmeTiKeD1Ec1EAmFFHmcp0leUlJKWkia1WkGCa-qBGhVV2nYFpQLIpJMClmIoiwSEZNKDPro416321RrqAXsbteyzqo1t1tmuGL_drRq2NLcsjhPKKFxEHhzELDm6wacZ2vlBLQt12A2jmVZnpQlSQL4dg8Ka5yzII8mlLBdzOwYc2BfPZzqnjzkGoDXB4C7kJ20XAvlHnDBkoaP0UfRnlPOw92xz-0XluWDPGWL2Q1bzOl4dJ5esum9LheOrczG6vD4_xnwD1Yt0G8</recordid><startdate>20040804</startdate><enddate>20040804</enddate><creator>Woods, Mark</creator><creator>Kiefer, Garry E</creator><creator>Bott, Simon</creator><creator>Castillo-Muzquiz, Aminta</creator><creator>Eshelbrenner, Carrie</creator><creator>Michaudet, Lydie</creator><creator>McMillan, Kenneth</creator><creator>Mudigunda, Siva D. K</creator><creator>Ogrin, Doug</creator><creator>Tircsó, Gyula</creator><creator>Zhang, Shanrong</creator><creator>Zhao, Piyu</creator><creator>Sherry, A. Dean</creator><general>American Chemical Society</general><scope>BSCLL</scope><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><scope>5PM</scope></search><sort><creationdate>20040804</creationdate><title>Synthesis, Relaxometric and Photophysical Properties of a New pH-Responsive MRI Contrast Agent: The Effect of Other Ligating Groups on Dissociation of a p-Nitrophenolic Pendant Arm</title><author>Woods, Mark ; Kiefer, Garry E ; Bott, Simon ; Castillo-Muzquiz, Aminta ; Eshelbrenner, Carrie ; Michaudet, Lydie ; McMillan, Kenneth ; Mudigunda, Siva D. K ; Ogrin, Doug ; Tircsó, Gyula ; Zhang, Shanrong ; Zhao, Piyu ; Sherry, A. Dean</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a535t-de0fe8fc7275479109f18f16d56e4abb4e1bdb509fc1ac0c46fcf8c8984c20bc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Amines - chemistry</topic><topic>Biological and medical sciences</topic><topic>Chemistry</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>Contrast Media - chemical synthesis</topic><topic>Contrast Media - chemistry</topic><topic>Contrast media. Radiopharmaceuticals</topic><topic>Coordination compounds</topic><topic>Crystallography, X-Ray</topic><topic>Exact sciences and technology</topic><topic>Gadolinium - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Inorganic chemistry and origins of life</topic><topic>Inorganic compounds</topic><topic>Kinetics</topic><topic>Luminescent Measurements</topic><topic>Magnetic Resonance Imaging</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Metal complexes</topic><topic>Molecular Structure</topic><topic>Nitrophenols - chemical synthesis</topic><topic>Nitrophenols - chemistry</topic><topic>Organometallic Compounds - chemical synthesis</topic><topic>Organometallic Compounds - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Photochemistry</topic><topic>Physics</topic><topic>Preparations and properties</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Woods, Mark</creatorcontrib><creatorcontrib>Kiefer, Garry E</creatorcontrib><creatorcontrib>Bott, Simon</creatorcontrib><creatorcontrib>Castillo-Muzquiz, Aminta</creatorcontrib><creatorcontrib>Eshelbrenner, Carrie</creatorcontrib><creatorcontrib>Michaudet, Lydie</creatorcontrib><creatorcontrib>McMillan, Kenneth</creatorcontrib><creatorcontrib>Mudigunda, Siva D. K</creatorcontrib><creatorcontrib>Ogrin, Doug</creatorcontrib><creatorcontrib>Tircsó, Gyula</creatorcontrib><creatorcontrib>Zhang, Shanrong</creatorcontrib><creatorcontrib>Zhao, Piyu</creatorcontrib><creatorcontrib>Sherry, A. Dean</creatorcontrib><collection>Istex</collection><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><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Woods, Mark</au><au>Kiefer, Garry E</au><au>Bott, Simon</au><au>Castillo-Muzquiz, Aminta</au><au>Eshelbrenner, Carrie</au><au>Michaudet, Lydie</au><au>McMillan, Kenneth</au><au>Mudigunda, Siva D. K</au><au>Ogrin, Doug</au><au>Tircsó, Gyula</au><au>Zhang, Shanrong</au><au>Zhao, Piyu</au><au>Sherry, A. Dean</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Relaxometric and Photophysical Properties of a New pH-Responsive MRI Contrast Agent: The Effect of Other Ligating Groups on Dissociation of a p-Nitrophenolic Pendant Arm</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2004-08-04</date><risdate>2004</risdate><volume>126</volume><issue>30</issue><spage>9248</spage><epage>9256</epage><pages>9248-9256</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Two gadolinium(III) chelates, GdNP-DO3A (1-methlyene-(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-tri Acetate) and GdNP-DO3AM (1-methlyene(p-NitroPhenol)-1,4,7,10-tetraazacycloDOdecane-4,7,10-triacetAMide), containing a single nitrophenolic pendant arm plus either three acetate or three amide pendant arms were synthesized and characterized. The properties of the gadolinium, terbium, and dysprosium complexes of these ligands were examined as a function of pH. The extent and mechanism of the changes in water relaxivity with pH of each gadolinium complex was found to differ substantially for the two complexes. The water relaxivity of Gd(NP-DO3A) increases from 4.1 mM-1 s-1 at pH 9 to 7.0 mM-1 s-1 at pH 5 as a result of acid-catalyzed dissociation of the nitrophenol from the lanthanide. The nitrophenol group in Gd(NP-DO3AM) does not dissociate from the metal center even at pH 5; therefore, the very modest increase in relaxivity in this complex must be ascribed to an increase in prototropic exchange rate of the bound water and/or phenolic protons.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15281814</pmid><doi>10.1021/ja048299z</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Amines - chemistry Biological and medical sciences Chemistry Condensed matter: structure, mechanical and thermal properties Contrast Media - chemical synthesis Contrast Media - chemistry Contrast media. Radiopharmaceuticals Coordination compounds Crystallography, X-Ray Exact sciences and technology Gadolinium - chemistry Hydrogen-Ion Concentration Inorganic chemistry and origins of life Inorganic compounds Kinetics Luminescent Measurements Magnetic Resonance Imaging Magnetic Resonance Spectroscopy Medical sciences Metal complexes Molecular Structure Nitrophenols - chemical synthesis Nitrophenols - chemistry Organometallic Compounds - chemical synthesis Organometallic Compounds - chemistry Pharmacology. Drug treatments Photochemistry Physics Preparations and properties Structure of solids and liquids crystallography Structure of specific crystalline solids |
| title | Synthesis, Relaxometric and Photophysical Properties of a New pH-Responsive MRI Contrast Agent: The Effect of Other Ligating Groups on Dissociation of a p-Nitrophenolic Pendant Arm |
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