ThuliumV1, PubMed, Checkpoint, bibRecord, 000554

The thulium complex of 1,4,7,10-tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami) as a ParaCEST contrast agent.

Identifieur interne : 000554 ( PubMed/Checkpoint ); précédent : 000553; suivant : 000555

The thulium complex of 1,4,7,10-tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami) as a ParaCEST contrast agent.

Auteurs : Dirk Burdinski ; Johan Lub ; Jeroen A. Pikkemaat ; Sander Langereis ; Holger Grüll ; Wolter Ten Hoeve

Source :

Chemistry & biodiversity [ 1612-1880 ] ; 2008.

RBID : pubmed:18729087

Descripteurs français

English descriptors

KwdEn :
- Amides (chemistry), Amines (chemistry), Contrast Media (chemical synthesis), Contrast Media (chemistry), Hydrogen Bonding, Hydrogen-Ion Concentration, Ligands, Magnetic Resonance Spectroscopy (methods), Magnetic Resonance Spectroscopy (standards), Molecular Structure, Organometallic Compounds (chemical synthesis), Organometallic Compounds (chemistry), Protons, Reference Standards, Stereoisomerism, Thulium (chemistry).
MESH :
- chemical , chemical synthesis : Contrast Media, Organometallic Compounds.
- chemical , chemistry : Amides, Amines, Contrast Media, Organometallic Compounds, Thulium.
- methods : Magnetic Resonance Spectroscopy.
- standards : Magnetic Resonance Spectroscopy.
- Hydrogen Bonding, Hydrogen-Ion Concentration, Ligands, Molecular Structure, Protons, Reference Standards, Stereoisomerism.

Abstract

1,4,7,10-Tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami), a tetra(1H-imidazol-2-yl) derivative of the well-studied octadentate 1,4,7,10-tetrakis[(carbamoyl)methyl]-1,4,7,10-tetraazacyclododecane (dotam) ligand, was synthesized by reaction of 1,4,7,10-tetraazacyclododecane with N-(1H-imidazol-2-yl)chloroacetamide in high yield. Its tricationic thulium complex was isolated as a water-soluble chloride salt. The detection of the mildly acidic amide and amine protons by direct proton NMR in aqueous solution was unsuccessful, but such exchangeable protons could be detected via their chemical exchange-dependent saturation transfer (CEST) effect. The observed CEST effect was distinctly different from that found for respective dotam complexes and is, therefore, ascribed to exchangeable protons associated with the imidazole substituent.

DOI: 10.1002/cbdv.200890139
PubMed: 18729087

Affiliations:

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pubmed:18729087

Le document en format XML

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<author><name sortKey="Burdinski, Dirk" sort="Burdinski, Dirk" uniqKey="Burdinski D" first="Dirk" last="Burdinski">Dirk Burdinski</name>
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<author><name sortKey="Lub, Johan" sort="Lub, Johan" uniqKey="Lub J" first="Johan" last="Lub">Johan Lub</name>
</author>
<author><name sortKey="Pikkemaat, Jeroen A" sort="Pikkemaat, Jeroen A" uniqKey="Pikkemaat J" first="Jeroen A" last="Pikkemaat">Jeroen A. Pikkemaat</name>
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<author><name sortKey="Langereis, Sander" sort="Langereis, Sander" uniqKey="Langereis S" first="Sander" last="Langereis">Sander Langereis</name>
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<author><name sortKey="Grull, Holger" sort="Grull, Holger" uniqKey="Grull H" first="Holger" last="Grüll">Holger Grüll</name>
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<author><name sortKey="Ten Hoeve, Wolter" sort="Ten Hoeve, Wolter" uniqKey="Ten Hoeve W" first="Wolter" last="Ten Hoeve">Wolter Ten Hoeve</name>
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<author><name sortKey="Burdinski, Dirk" sort="Burdinski, Dirk" uniqKey="Burdinski D" first="Dirk" last="Burdinski">Dirk Burdinski</name>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amides (chemistry)</term>
<term>Amines (chemistry)</term>
<term>Contrast Media (chemical synthesis)</term>
<term>Contrast Media (chemistry)</term>
<term>Hydrogen Bonding</term>
<term>Hydrogen-Ion Concentration</term>
<term>Ligands</term>
<term>Magnetic Resonance Spectroscopy (methods)</term>
<term>Magnetic Resonance Spectroscopy (standards)</term>
<term>Molecular Structure</term>
<term>Organometallic Compounds (chemical synthesis)</term>
<term>Organometallic Compounds (chemistry)</term>
<term>Protons</term>
<term>Reference Standards</term>
<term>Stereoisomerism</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Amides ()</term>
<term>Amines ()</term>
<term>Composés organométalliques ()</term>
<term>Composés organométalliques (synthèse chimique)</term>
<term>Concentration en ions d'hydrogène</term>
<term>Liaison hydrogène</term>
<term>Ligands</term>
<term>Normes de référence</term>
<term>Produits de contraste ()</term>
<term>Produits de contraste (synthèse chimique)</term>
<term>Protons</term>
<term>Spectroscopie par résonance magnétique ()</term>
<term>Spectroscopie par résonance magnétique (normes)</term>
<term>Structure moléculaire</term>
<term>Stéréoisomérie</term>
<term>Thulium ()</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Contrast Media</term>
<term>Organometallic Compounds</term>
</keywords>
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<term>Amines</term>
<term>Contrast Media</term>
<term>Organometallic Compounds</term>
<term>Thulium</term>
</keywords>
<keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Magnetic Resonance Spectroscopy</term>
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<keywords scheme="MESH" qualifier="normes" xml:lang="fr"><term>Spectroscopie par résonance magnétique</term>
</keywords>
<keywords scheme="MESH" qualifier="standards" xml:lang="en"><term>Magnetic Resonance Spectroscopy</term>
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<term>Produits de contraste</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Hydrogen Bonding</term>
<term>Hydrogen-Ion Concentration</term>
<term>Ligands</term>
<term>Molecular Structure</term>
<term>Protons</term>
<term>Reference Standards</term>
<term>Stereoisomerism</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Amides</term>
<term>Amines</term>
<term>Composés organométalliques</term>
<term>Concentration en ions d'hydrogène</term>
<term>Liaison hydrogène</term>
<term>Ligands</term>
<term>Normes de référence</term>
<term>Produits de contraste</term>
<term>Protons</term>
<term>Spectroscopie par résonance magnétique</term>
<term>Structure moléculaire</term>
<term>Stéréoisomérie</term>
<term>Thulium</term>
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<front><div type="abstract" xml:lang="en">1,4,7,10-Tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami), a tetra(1H-imidazol-2-yl) derivative of the well-studied octadentate 1,4,7,10-tetrakis[(carbamoyl)methyl]-1,4,7,10-tetraazacyclododecane (dotam) ligand, was synthesized by reaction of 1,4,7,10-tetraazacyclododecane with N-(1H-imidazol-2-yl)chloroacetamide in high yield. Its tricationic thulium complex was isolated as a water-soluble chloride salt. The detection of the mildly acidic amide and amine protons by direct proton NMR in aqueous solution was unsuccessful, but such exchangeable protons could be detected via their chemical exchange-dependent saturation transfer (CEST) effect. The observed CEST effect was distinctly different from that found for respective dotam complexes and is, therefore, ascribed to exchangeable protons associated with the imidazole substituent.</div>
</front>
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<ArticleTitle>The thulium complex of 1,4,7,10-tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami) as a ParaCEST contrast agent.</ArticleTitle>
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<Abstract><AbstractText>1,4,7,10-Tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami), a tetra(1H-imidazol-2-yl) derivative of the well-studied octadentate 1,4,7,10-tetrakis[(carbamoyl)methyl]-1,4,7,10-tetraazacyclododecane (dotam) ligand, was synthesized by reaction of 1,4,7,10-tetraazacyclododecane with N-(1H-imidazol-2-yl)chloroacetamide in high yield. Its tricationic thulium complex was isolated as a water-soluble chloride salt. The detection of the mildly acidic amide and amine protons by direct proton NMR in aqueous solution was unsuccessful, but such exchangeable protons could be detected via their chemical exchange-dependent saturation transfer (CEST) effect. The observed CEST effect was distinctly different from that found for respective dotam complexes and is, therefore, ascribed to exchangeable protons associated with the imidazole substituent.</AbstractText>
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<tree><noCountry><name sortKey="Burdinski, Dirk" sort="Burdinski, Dirk" uniqKey="Burdinski D" first="Dirk" last="Burdinski">Dirk Burdinski</name>
<name sortKey="Grull, Holger" sort="Grull, Holger" uniqKey="Grull H" first="Holger" last="Grüll">Holger Grüll</name>
<name sortKey="Langereis, Sander" sort="Langereis, Sander" uniqKey="Langereis S" first="Sander" last="Langereis">Sander Langereis</name>
<name sortKey="Lub, Johan" sort="Lub, Johan" uniqKey="Lub J" first="Johan" last="Lub">Johan Lub</name>
<name sortKey="Pikkemaat, Jeroen A" sort="Pikkemaat, Jeroen A" uniqKey="Pikkemaat J" first="Jeroen A" last="Pikkemaat">Jeroen A. Pikkemaat</name>
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The thulium complex of 1,4,7,10-tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami) as a ParaCEST contrast agent.

The thulium complex of 1,4,7,10-tetrakis{[N-(1H-imidazol-2-yl)carbamoyl]methyl}-1,4,7,10-tetraazacyclododecane (dotami) as a ParaCEST contrast agent.

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Abstract

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