Analogs of Eu3+ DOTAM-Gly-Phe-OH and Tm3+ DOTAM-Gly-Lys-OH: synthesis and magnetic properties of potential PARACEST MRI contrast agents.
Identifieur interne : 001222 ( Main/Exploration ); précédent : 001221; suivant : 001223Analogs of Eu3+ DOTAM-Gly-Phe-OH and Tm3+ DOTAM-Gly-Lys-OH: synthesis and magnetic properties of potential PARACEST MRI contrast agents.
Auteurs : Mojmír Such [Canada] ; Alex X. Li ; Robert Bartha ; Robert H E. HudsonSource :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2008.
Descripteurs français
- KwdFr :
- Acétamides (synthèse chimique), Composés hétérocycliques (synthèse chimique), Composés hétéromonocycliques (synthèse chimique), Dipeptides (synthèse chimique), Europium, Glycine (), Imagerie par résonance magnétique, Ligands, Lysine (), Phénylalanine (), Produits de contraste (synthèse chimique), Spectrométrie de masse ESI, Spectroscopie par résonance magnétique, Thulium.
- MESH :
English descriptors
- KwdEn :
- Acetamides (chemical synthesis), Contrast Media (chemical synthesis), Dipeptides (chemical synthesis), Europium, Glycine (chemistry), Heterocyclic Compounds (chemical synthesis), Heterocyclic Compounds, 1-Ring (chemical synthesis), Ligands, Lysine (chemistry), Magnetic Resonance Imaging, Magnetic Resonance Spectroscopy, Phenylalanine (chemistry), Spectrometry, Mass, Electrospray Ionization, Thulium.
- MESH :
- chemical , chemical synthesis : Acetamides, Contrast Media, Dipeptides, Heterocyclic Compounds, Heterocyclic Compounds, 1-Ring.
- chemical , chemistry : Glycine, Lysine, Phenylalanine.
- chemical : Europium, Ligands, Thulium.
- Magnetic Resonance Imaging, Magnetic Resonance Spectroscopy, Spectrometry, Mass, Electrospray Ionization.
Abstract
Chelated lanthanide ions, especially gadolinium, have found wide use as contrast agents in magnetic resonance imaging. A new paradigm for generating contrast, termed PARACEST, was recently described that requires the slow exchange of water or other exchangeable protons present in the ligand framework. In previous work, we have described a synthetic method for the preparation of dipeptide conjugates of DOTAM for use as PARACEST agents. Two compounds possessed interesting magnetic properties: the Eu(3+) complex of DOTAM-Gly-Phe-OH and the Tm(3+) complex of DOTAM-Gly-Lys-OH. To understand the relationship between the structure of these complexes and their magnetic properties, we have expanded our synthetic methodology and prepared several new complexes. Ligands have been prepared in which the terminal phenylalanine moieties have been replaced with tryptophan or tyrosine, the distance to the amino acid residue possessing an alpha-substituent has been changed, or phenylalanine and lysine have been combined in the peptide sequence. The preparation of lanthanide(III) complexes of these ligands has been achieved and their PARACEST properties have been determined.
DOI: 10.1016/j.bmc.2008.04.038
PubMed: 18457955
Affiliations:
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Li</name></author><author><name sortKey="Bartha, Robert" sort="Bartha, Robert" uniqKey="Bartha R" first="Robert" last="Bartha">Robert Bartha</name></author><author><name sortKey="Hudson, Robert H E" sort="Hudson, Robert H E" uniqKey="Hudson R" first="Robert H E" last="Hudson">Robert H E. Hudson</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2008">2008</date><idno type="doi">10.1016/j.bmc.2008.04.038</idno><idno type="RBID">pubmed:18457955</idno><idno type="pmid">18457955</idno><idno type="wicri:Area/PubMed/Corpus">000583</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000583</idno><idno type="wicri:Area/PubMed/Curation">000583</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000583</idno><idno type="wicri:Area/PubMed/Checkpoint">000583</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000583</idno><idno type="wicri:Area/Ncbi/Merge">000235</idno><idno type="wicri:Area/Ncbi/Curation">000235</idno><idno type="wicri:Area/Ncbi/Checkpoint">000235</idno><idno type="wicri:Area/Main/Merge">001258</idno><idno type="wicri:Area/Main/Curation">001222</idno><idno type="wicri:Area/Main/Exploration">001222</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Analogs of Eu3+ DOTAM-Gly-Phe-OH and Tm3+ DOTAM-Gly-Lys-OH: synthesis and magnetic properties of potential PARACEST MRI contrast agents.</title><author><name sortKey="Such, Mojmir" sort="Such, Mojmir" uniqKey="Such M" first="Mojmír" last="Such">Mojmír Such</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, The University of Western Ontario, Chemistry Building, Room 209, London, Ont., Canada N6A 5B7.</nlm:affiliation><country>Canada</country><wicri:regionArea>Department of Chemistry, The University of Western Ontario, Chemistry Building, Room 209, London, Ont.</wicri:regionArea><wicri:noRegion>Ont.</wicri:noRegion></affiliation></author><author><name sortKey="Li, Alex X" sort="Li, Alex X" uniqKey="Li A" first="Alex X" last="Li">Alex X. Li</name></author><author><name sortKey="Bartha, Robert" sort="Bartha, Robert" uniqKey="Bartha R" first="Robert" last="Bartha">Robert Bartha</name></author><author><name sortKey="Hudson, Robert H E" sort="Hudson, Robert H E" uniqKey="Hudson R" first="Robert H E" last="Hudson">Robert H E. Hudson</name></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="eISSN">1464-3391</idno><imprint><date when="2008" type="published">2008</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acetamides (chemical synthesis)</term><term>Contrast Media (chemical synthesis)</term><term>Dipeptides (chemical synthesis)</term><term>Europium</term><term>Glycine (chemistry)</term><term>Heterocyclic Compounds (chemical synthesis)</term><term>Heterocyclic Compounds, 1-Ring (chemical synthesis)</term><term>Ligands</term><term>Lysine (chemistry)</term><term>Magnetic Resonance Imaging</term><term>Magnetic Resonance Spectroscopy</term><term>Phenylalanine (chemistry)</term><term>Spectrometry, Mass, Electrospray Ionization</term><term>Thulium</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acétamides (synthèse chimique)</term><term>Composés hétérocycliques (synthèse chimique)</term><term>Composés hétéromonocycliques (synthèse chimique)</term><term>Dipeptides (synthèse chimique)</term><term>Europium</term><term>Glycine ()</term><term>Imagerie par résonance magnétique</term><term>Ligands</term><term>Lysine ()</term><term>Phénylalanine ()</term><term>Produits de contraste (synthèse chimique)</term><term>Spectrométrie de masse ESI</term><term>Spectroscopie par résonance magnétique</term><term>Thulium</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Acetamides</term><term>Contrast Media</term><term>Dipeptides</term><term>Heterocyclic Compounds</term><term>Heterocyclic Compounds, 1-Ring</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Glycine</term><term>Lysine</term><term>Phenylalanine</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Europium</term><term>Ligands</term><term>Thulium</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Acétamides</term><term>Composés hétérocycliques</term><term>Composés hétéromonocycliques</term><term>Dipeptides</term><term>Produits de contraste</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Magnetic Resonance Imaging</term><term>Magnetic Resonance Spectroscopy</term><term>Spectrometry, Mass, Electrospray Ionization</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Europium</term><term>Glycine</term><term>Imagerie par résonance magnétique</term><term>Ligands</term><term>Lysine</term><term>Phénylalanine</term><term>Spectrométrie de masse ESI</term><term>Spectroscopie par résonance magnétique</term><term>Thulium</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Chelated lanthanide ions, especially gadolinium, have found wide use as contrast agents in magnetic resonance imaging. A new paradigm for generating contrast, termed PARACEST, was recently described that requires the slow exchange of water or other exchangeable protons present in the ligand framework. In previous work, we have described a synthetic method for the preparation of dipeptide conjugates of DOTAM for use as PARACEST agents. Two compounds possessed interesting magnetic properties: the Eu(3+) complex of DOTAM-Gly-Phe-OH and the Tm(3+) complex of DOTAM-Gly-Lys-OH. To understand the relationship between the structure of these complexes and their magnetic properties, we have expanded our synthetic methodology and prepared several new complexes. Ligands have been prepared in which the terminal phenylalanine moieties have been replaced with tryptophan or tyrosine, the distance to the amino acid residue possessing an alpha-substituent has been changed, or phenylalanine and lysine have been combined in the peptide sequence. The preparation of lanthanide(III) complexes of these ligands has been achieved and their PARACEST properties have been determined.</div></front></TEI><affiliations><list><country><li>Canada</li></country></list><tree><noCountry><name sortKey="Bartha, Robert" sort="Bartha, Robert" uniqKey="Bartha R" first="Robert" last="Bartha">Robert Bartha</name><name sortKey="Hudson, Robert H E" sort="Hudson, Robert H E" uniqKey="Hudson R" first="Robert H E" last="Hudson">Robert H E. Hudson</name><name sortKey="Li, Alex X" sort="Li, Alex X" uniqKey="Li A" first="Alex X" last="Li">Alex X. Li</name></noCountry><country name="Canada"><noRegion><name sortKey="Such, Mojmir" sort="Such, Mojmir" uniqKey="Such M" first="Mojmír" last="Such">Mojmír Such</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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