Introduction of Peripheral Carboxylates to Decrease the Charge on Tm(3+) DOTAM-Alkyl Complexes: Implications for Detection Sensitivity and in Vivo Toxicity of PARACEST MRI Contrast Agents.
Identifieur interne : 000138 ( Main/Exploration ); précédent : 000137; suivant : 000139Introduction of Peripheral Carboxylates to Decrease the Charge on Tm(3+) DOTAM-Alkyl Complexes: Implications for Detection Sensitivity and in Vivo Toxicity of PARACEST MRI Contrast Agents.
Auteurs : Mojmír Such [Canada] ; Mark Milne [Canada] ; Adam A H. Elmehriki [Canada] ; Nevin Mcvicar [Canada] ; Alex X. Li [Canada] ; Robert Bartha [Canada] ; Robert H E. Hudson [Canada]Source :
- Journal of medicinal chemistry [ 1520-4804 ] ; 2015.
Descripteurs français
- KwdFr :
- Acide aspartique (), Acides carboxyliques (), Acides carboxyliques (pharmacologie), Animaux, Composés organométalliques (synthèse chimique), Composés organométalliques (toxicité), Imagerie par résonance magnétique, Produits de contraste (synthèse chimique), Produits de contraste (toxicité), Rein (anatomie et histologie), Souris, Souris de lignée C57BL, Spectroscopie de résonance de spin électronique, Thulium ().
- MESH :
- anatomie et histologie : Rein.
- pharmacologie : Acides carboxyliques.
- synthèse chimique : Composés organométalliques, Produits de contraste.
- toxicité : Composés organométalliques, Produits de contraste.
- Acide aspartique, Acides carboxyliques, Animaux, Imagerie par résonance magnétique, Souris, Souris de lignée C57BL, Spectroscopie de résonance de spin électronique, Thulium.
English descriptors
- KwdEn :
- Animals, Aspartic Acid (chemistry), Carboxylic Acids (chemistry), Carboxylic Acids (pharmacology), Contrast Media (chemical synthesis), Contrast Media (toxicity), Electron Spin Resonance Spectroscopy, Kidney (anatomy & histology), Magnetic Resonance Imaging, Mice, Mice, Inbred C57BL, Organometallic Compounds (chemical synthesis), Organometallic Compounds (toxicity), Thulium (chemistry).
- MESH :
- chemical , chemical synthesis : Contrast Media, Organometallic Compounds.
- chemical , chemistry : Aspartic Acid, Carboxylic Acids, Thulium.
- chemical , pharmacology : Carboxylic Acids.
- chemical , toxicity : Contrast Media, Organometallic Compounds.
- anatomy & histology : Kidney.
- Animals, Electron Spin Resonance Spectroscopy, Magnetic Resonance Imaging, Mice, Mice, Inbred C57BL.
Abstract
A series of structurally modified Tm(3+) DOTAM-alkyl complexes as potential PARACEST MRI contrast agents has been synthesized with the aim to decrease the overall positive charge associated with these molecules and increase their biocompatibility. Two types of structural modification have been performed, an introduction of terminal carboxylate arms to the alkyl side chains and a conjugation of one of the alkyl side chains with aspartic acid. Detailed evaluation of the magnetic resonance imaging chemical exchange contrast associated with the structurally modified contrast agents has been performed. In contrast to the acutely toxic Tm(3+) DOTAM-alkyl complexes, the structurally modified compounds were found to be tolerated well during in vivo MRI studies in mice; however, only the aspartic acid modified chelates produced an amide proton-based PARACEST signal.
DOI: 10.1021/acs.jmedchem.5b00621
PubMed: 26214576
Affiliations:
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Elmehriki</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, The University of Western Ontario , Chemistry Building, London, Ontario N6A 5B7, Canada.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Department of Chemistry, The University of Western Ontario , Chemistry Building, London, Ontario N6A 5B7</wicri:regionArea><wicri:noRegion>Ontario N6A 5B7</wicri:noRegion></affiliation></author><author><name sortKey="Mcvicar, Nevin" sort="Mcvicar, Nevin" uniqKey="Mcvicar N" first="Nevin" last="Mcvicar">Nevin Mcvicar</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medical Biophysics, The University of Western Ontario , London, Ontario N6A 5K8, Canada.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Department of Medical Biophysics, The University of Western Ontario , London, Ontario N6A 5K8</wicri:regionArea><wicri:noRegion>Ontario N6A 5K8</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><affiliation wicri:level="1"><nlm:affiliation>Department of Medical Biophysics, The University of Western Ontario , London, Ontario N6A 5K8, Canada.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Department of Medical Biophysics, The University of Western Ontario , London, Ontario N6A 5K8</wicri:regionArea><wicri:noRegion>Ontario N6A 5K8</wicri:noRegion></affiliation></author><author><name sortKey="Bartha, Robert" sort="Bartha, Robert" uniqKey="Bartha R" first="Robert" last="Bartha">Robert Bartha</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medical Biophysics, The University of Western Ontario , London, Ontario N6A 5K8, Canada.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Department of Medical Biophysics, The University of Western Ontario , London, Ontario N6A 5K8</wicri:regionArea><wicri:noRegion>Ontario N6A 5K8</wicri:noRegion></affiliation></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><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, The University of Western Ontario , Chemistry Building, London, Ontario N6A 5B7, Canada.</nlm:affiliation><country xml:lang="fr">Canada</country><wicri:regionArea>Department of Chemistry, The University of Western Ontario , Chemistry Building, London, Ontario N6A 5B7</wicri:regionArea><wicri:noRegion>Ontario N6A 5B7</wicri:noRegion></affiliation></author></analytic><series><title level="j">Journal of medicinal chemistry</title><idno type="eISSN">1520-4804</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Aspartic Acid (chemistry)</term><term>Carboxylic Acids (chemistry)</term><term>Carboxylic Acids (pharmacology)</term><term>Contrast Media (chemical synthesis)</term><term>Contrast Media (toxicity)</term><term>Electron Spin Resonance Spectroscopy</term><term>Kidney (anatomy & histology)</term><term>Magnetic Resonance Imaging</term><term>Mice</term><term>Mice, Inbred C57BL</term><term>Organometallic Compounds (chemical synthesis)</term><term>Organometallic Compounds (toxicity)</term><term>Thulium (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acide aspartique ()</term><term>Acides carboxyliques ()</term><term>Acides carboxyliques (pharmacologie)</term><term>Animaux</term><term>Composés organométalliques (synthèse chimique)</term><term>Composés organométalliques (toxicité)</term><term>Imagerie par résonance magnétique</term><term>Produits de contraste (synthèse chimique)</term><term>Produits de contraste (toxicité)</term><term>Rein (anatomie et histologie)</term><term>Souris</term><term>Souris de lignée C57BL</term><term>Spectroscopie de résonance de spin électronique</term><term>Thulium ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Contrast Media</term><term>Organometallic Compounds</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Aspartic Acid</term><term>Carboxylic Acids</term><term>Thulium</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Carboxylic Acids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Contrast Media</term><term>Organometallic Compounds</term></keywords><keywords scheme="MESH" qualifier="anatomie et histologie" xml:lang="fr"><term>Rein</term></keywords><keywords scheme="MESH" qualifier="anatomy & histology" xml:lang="en"><term>Kidney</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Acides carboxyliques</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Composés organométalliques</term><term>Produits de contraste</term></keywords><keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>Composés organométalliques</term><term>Produits de contraste</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Electron Spin Resonance Spectroscopy</term><term>Magnetic Resonance Imaging</term><term>Mice</term><term>Mice, Inbred C57BL</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acide aspartique</term><term>Acides carboxyliques</term><term>Animaux</term><term>Imagerie par résonance magnétique</term><term>Souris</term><term>Souris de lignée C57BL</term><term>Spectroscopie de résonance de spin électronique</term><term>Thulium</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of structurally modified Tm(3+) DOTAM-alkyl complexes as potential PARACEST MRI contrast agents has been synthesized with the aim to decrease the overall positive charge associated with these molecules and increase their biocompatibility. Two types of structural modification have been performed, an introduction of terminal carboxylate arms to the alkyl side chains and a conjugation of one of the alkyl side chains with aspartic acid. Detailed evaluation of the magnetic resonance imaging chemical exchange contrast associated with the structurally modified contrast agents has been performed. In contrast to the acutely toxic Tm(3+) DOTAM-alkyl complexes, the structurally modified compounds were found to be tolerated well during in vivo MRI studies in mice; however, only the aspartic acid modified chelates produced an amide proton-based PARACEST signal.</div></front></TEI><affiliations><list><country><li>Canada</li></country></list><tree><country name="Canada"><noRegion><name sortKey="Such, Mojmir" sort="Such, Mojmir" uniqKey="Such M" first="Mojmír" last="Such">Mojmír Such</name></noRegion><name sortKey="Bartha, Robert" sort="Bartha, Robert" uniqKey="Bartha R" first="Robert" last="Bartha">Robert Bartha</name><name sortKey="Elmehriki, Adam A H" sort="Elmehriki, Adam A H" uniqKey="Elmehriki A" first="Adam A H" last="Elmehriki">Adam A H. Elmehriki</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><name sortKey="Mcvicar, Nevin" sort="Mcvicar, Nevin" uniqKey="Mcvicar N" first="Nevin" last="Mcvicar">Nevin Mcvicar</name><name sortKey="Milne, Mark" sort="Milne, Mark" uniqKey="Milne M" first="Mark" last="Milne">Mark Milne</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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