Synthesis and NMR studies of new DOTP-like lanthanide(III) complexes containing a hydrophobic substituent on one phosphonate side arm.
Identifieur interne : 000719 ( PubMed/Curation ); précédent : 000718; suivant : 000720Synthesis and NMR studies of new DOTP-like lanthanide(III) complexes containing a hydrophobic substituent on one phosphonate side arm.
Auteurs : X. Li [États-Unis] ; S. Zhang ; P. Zhao ; Z. Kovacs ; A D SherrySource :
- Inorganic chemistry [ 0020-1669 ] ; 2001.
Descripteurs français
- KwdFr :
- Animaux, Chimie physique, Coeur (), Composés organiques du phosphore (), Conformation moléculaire, Hydrolyse, Lanthanides (), Lanthanides (synthèse chimique), Ligands, Mâle, Nitrobenzènes, Phosphonates (), Phosphonates (synthèse chimique), Rat Sprague-Dawley, Rats, Sodium (), Spectroscopie par résonance magnétique, Structure moléculaire, Stéréoisomérie, Techniques in vitro, Thulium (), Ytterbium ().
- MESH :
- synthèse chimique : Lanthanides, Phosphonates.
- Animaux, Chimie physique, Coeur, Composés organiques du phosphore, Conformation moléculaire, Hydrolyse, Lanthanides, Ligands, Mâle, Nitrobenzènes, Phosphonates, Rat Sprague-Dawley, Rats, Sodium, Spectroscopie par résonance magnétique, Structure moléculaire, Stéréoisomérie, Techniques in vitro, Thulium, Ytterbium.
English descriptors
- KwdEn :
- Animals, Chemistry, Physical, Heart (drug effects), Hydrolysis, In Vitro Techniques, Lanthanoid Series Elements (chemical synthesis), Lanthanoid Series Elements (chemistry), Ligands, Magnetic Resonance Spectroscopy, Male, Molecular Conformation, Molecular Structure, Nitrobenzenes, Organophosphonates (chemical synthesis), Organophosphonates (chemistry), Organophosphorus Compounds (chemistry), Physicochemical Phenomena, Rats, Rats, Sprague-Dawley, Sodium (chemistry), Stereoisomerism, Thulium (chemistry), Ytterbium (chemistry).
- MESH :
- chemical , chemical synthesis : Lanthanoid Series Elements, Organophosphonates.
- chemical , chemistry : Lanthanoid Series Elements, Organophosphonates, Organophosphorus Compounds, Sodium, Thulium, Ytterbium.
- drug effects : Heart.
- Animals, Chemistry, Physical, Hydrolysis, In Vitro Techniques, Ligands, Magnetic Resonance Spectroscopy, Male, Molecular Conformation, Molecular Structure, Nitrobenzenes, Physicochemical Phenomena, Rats, Rats, Sprague-Dawley, Stereoisomerism.
Abstract
Three derivatives of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylene phosphonic acid) (DOTP) containing a hydrophobic substituent on one side chain were prepared and their lanthanide complexes examined by NMR. The new ligands include 1-(1-octyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (C(8)-DOTP), 1-(1-undecyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (C(11)-DOTP), and 1-(1-4-nitro-phenyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (NO(2)-Ph-DOTP). (1)H NMR spectra of the ytterbium(III) complexes were assigned by using a combination of COSY spectroscopy and a fitting procedure that matches experimental NMR hyperfine shifts with those estimated from a MMX-derived structure. The analysis showed that a single isomer is present in solution and that the bulky hydrophobic substituent occupies the less sterically demanding H(6) equatorial position in the YbL(5)(-) complexes. Although the YbL(5)(-) complexes have lower symmetry due to the added substituent, the average (1)H hyperfine shifts are 5-10% larger in these complexes compared to YbDOTP(5)(-). This was magnified further in the hyperfine (23)Na NMR shifts of ion-paired sodium ions where the extracellular Na(+) signal in perfused rat hearts displayed a 28% larger hyperfine shift in the presence of Tm(C(11)-DOTP)(5)(-) than with an equivalent amount of TmDOTP(5)(-).
PubMed: 11735465
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and NMR studies of new DOTP-like lanthanide(III) complexes containing a hydrophobic substituent on one phosphonate side arm.</title><author><name sortKey="Li, X" sort="Li, X" uniqKey="Li X" first="X" last="Li">X. Li</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Texas at Dallas, Richardson, Texas 75083, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, University of Texas at Dallas, Richardson, Texas 75083</wicri:regionArea></affiliation></author><author><name sortKey="Zhang, S" sort="Zhang, S" uniqKey="Zhang S" first="S" last="Zhang">S. Zhang</name></author><author><name sortKey="Zhao, P" sort="Zhao, P" uniqKey="Zhao P" first="P" last="Zhao">P. Zhao</name></author><author><name sortKey="Kovacs, Z" sort="Kovacs, Z" uniqKey="Kovacs Z" first="Z" last="Kovacs">Z. Kovacs</name></author><author><name sortKey="Sherry, A D" sort="Sherry, A D" uniqKey="Sherry A" first="A D" last="Sherry">A D Sherry</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2001">2001</date><idno type="RBID">pubmed:11735465</idno><idno type="pmid">11735465</idno><idno type="wicri:Area/PubMed/Corpus">000719</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000719</idno><idno type="wicri:Area/PubMed/Curation">000719</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000719</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis and NMR studies of new DOTP-like lanthanide(III) complexes containing a hydrophobic substituent on one phosphonate side arm.</title><author><name sortKey="Li, X" sort="Li, X" uniqKey="Li X" first="X" last="Li">X. Li</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Texas at Dallas, Richardson, Texas 75083, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry, University of Texas at Dallas, Richardson, Texas 75083</wicri:regionArea></affiliation></author><author><name sortKey="Zhang, S" sort="Zhang, S" uniqKey="Zhang S" first="S" last="Zhang">S. Zhang</name></author><author><name sortKey="Zhao, P" sort="Zhao, P" uniqKey="Zhao P" first="P" last="Zhao">P. Zhao</name></author><author><name sortKey="Kovacs, Z" sort="Kovacs, Z" uniqKey="Kovacs Z" first="Z" last="Kovacs">Z. Kovacs</name></author><author><name sortKey="Sherry, A D" sort="Sherry, A D" uniqKey="Sherry A" first="A D" last="Sherry">A D Sherry</name></author></analytic><series><title level="j">Inorganic chemistry</title><idno type="ISSN">0020-1669</idno><imprint><date when="2001" type="published">2001</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Chemistry, Physical</term><term>Heart (drug effects)</term><term>Hydrolysis</term><term>In Vitro Techniques</term><term>Lanthanoid Series Elements (chemical synthesis)</term><term>Lanthanoid Series Elements (chemistry)</term><term>Ligands</term><term>Magnetic Resonance Spectroscopy</term><term>Male</term><term>Molecular Conformation</term><term>Molecular Structure</term><term>Nitrobenzenes</term><term>Organophosphonates (chemical synthesis)</term><term>Organophosphonates (chemistry)</term><term>Organophosphorus Compounds (chemistry)</term><term>Physicochemical Phenomena</term><term>Rats</term><term>Rats, Sprague-Dawley</term><term>Sodium (chemistry)</term><term>Stereoisomerism</term><term>Thulium (chemistry)</term><term>Ytterbium (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Chimie physique</term><term>Coeur ()</term><term>Composés organiques du phosphore ()</term><term>Conformation moléculaire</term><term>Hydrolyse</term><term>Lanthanides ()</term><term>Lanthanides (synthèse chimique)</term><term>Ligands</term><term>Mâle</term><term>Nitrobenzènes</term><term>Phosphonates ()</term><term>Phosphonates (synthèse chimique)</term><term>Rat Sprague-Dawley</term><term>Rats</term><term>Sodium ()</term><term>Spectroscopie par résonance magnétique</term><term>Structure moléculaire</term><term>Stéréoisomérie</term><term>Techniques in vitro</term><term>Thulium ()</term><term>Ytterbium ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Lanthanoid Series Elements</term><term>Organophosphonates</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Lanthanoid Series Elements</term><term>Organophosphonates</term><term>Organophosphorus Compounds</term><term>Sodium</term><term>Thulium</term><term>Ytterbium</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Heart</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Lanthanides</term><term>Phosphonates</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Chemistry, Physical</term><term>Hydrolysis</term><term>In Vitro Techniques</term><term>Ligands</term><term>Magnetic Resonance Spectroscopy</term><term>Male</term><term>Molecular Conformation</term><term>Molecular Structure</term><term>Nitrobenzenes</term><term>Physicochemical Phenomena</term><term>Rats</term><term>Rats, Sprague-Dawley</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Chimie physique</term><term>Coeur</term><term>Composés organiques du phosphore</term><term>Conformation moléculaire</term><term>Hydrolyse</term><term>Lanthanides</term><term>Ligands</term><term>Mâle</term><term>Nitrobenzènes</term><term>Phosphonates</term><term>Rat Sprague-Dawley</term><term>Rats</term><term>Sodium</term><term>Spectroscopie par résonance magnétique</term><term>Structure moléculaire</term><term>Stéréoisomérie</term><term>Techniques in vitro</term><term>Thulium</term><term>Ytterbium</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Three derivatives of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylene phosphonic acid) (DOTP) containing a hydrophobic substituent on one side chain were prepared and their lanthanide complexes examined by NMR. The new ligands include 1-(1-octyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (C(8)-DOTP), 1-(1-undecyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (C(11)-DOTP), and 1-(1-4-nitro-phenyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (NO(2)-Ph-DOTP). (1)H NMR spectra of the ytterbium(III) complexes were assigned by using a combination of COSY spectroscopy and a fitting procedure that matches experimental NMR hyperfine shifts with those estimated from a MMX-derived structure. The analysis showed that a single isomer is present in solution and that the bulky hydrophobic substituent occupies the less sterically demanding H(6) equatorial position in the YbL(5)(-) complexes. Although the YbL(5)(-) complexes have lower symmetry due to the added substituent, the average (1)H hyperfine shifts are 5-10% larger in these complexes compared to YbDOTP(5)(-). This was magnified further in the hyperfine (23)Na NMR shifts of ion-paired sodium ions where the extracellular Na(+) signal in perfused rat hearts displayed a 28% larger hyperfine shift in the presence of Tm(C(11)-DOTP)(5)(-) than with an equivalent amount of TmDOTP(5)(-).</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">11735465</PMID><DateCreated><Year>2001</Year><Month>12</Month><Day>12</Day></DateCreated><DateCompleted><Year>2002</Year><Month>02</Month><Day>05</Day></DateCompleted><DateRevised><Year>2014</Year><Month>11</Month><Day>20</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0020-1669</ISSN><JournalIssue CitedMedium="Print"><Volume>40</Volume><Issue>26</Issue><PubDate><Year>2001</Year><Month>Dec</Month><Day>17</Day></PubDate></JournalIssue><Title>Inorganic chemistry</Title><ISOAbbreviation>Inorg Chem</ISOAbbreviation></Journal><ArticleTitle>Synthesis and NMR studies of new DOTP-like lanthanide(III) complexes containing a hydrophobic substituent on one phosphonate side arm.</ArticleTitle><Pagination><MedlinePgn>6572-9</MedlinePgn></Pagination><Abstract><AbstractText>Three derivatives of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylene phosphonic acid) (DOTP) containing a hydrophobic substituent on one side chain were prepared and their lanthanide complexes examined by NMR. The new ligands include 1-(1-octyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (C(8)-DOTP), 1-(1-undecyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (C(11)-DOTP), and 1-(1-4-nitro-phenyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane (NO(2)-Ph-DOTP). (1)H NMR spectra of the ytterbium(III) complexes were assigned by using a combination of COSY spectroscopy and a fitting procedure that matches experimental NMR hyperfine shifts with those estimated from a MMX-derived structure. The analysis showed that a single isomer is present in solution and that the bulky hydrophobic substituent occupies the less sterically demanding H(6) equatorial position in the YbL(5)(-) complexes. Although the YbL(5)(-) complexes have lower symmetry due to the added substituent, the average (1)H hyperfine shifts are 5-10% larger in these complexes compared to YbDOTP(5)(-). This was magnified further in the hyperfine (23)Na NMR shifts of ion-paired sodium ions where the extracellular Na(+) signal in perfused rat hearts displayed a 28% larger hyperfine shift in the presence of Tm(C(11)-DOTP)(5)(-) than with an equivalent amount of TmDOTP(5)(-).</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Li</LastName><ForeName>X</ForeName><Initials>X</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Texas at Dallas, Richardson, Texas 75083, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>S</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Zhao</LastName><ForeName>P</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Kovacs</LastName><ForeName>Z</ForeName><Initials>Z</Initials></Author><Author ValidYN="Y"><LastName>Sherry</LastName><ForeName>A D</ForeName><Initials>AD</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>HL-34557</GrantID><Acronym>HL</Acronym><Agency>NHLBI NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>RR-02584</GrantID><Acronym>RR</Acronym><Agency>NCRR NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013487">Research Support, U.S. Gov't, P.H.S.</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Inorg Chem</MedlineTA><NlmUniqueID>0366543</NlmUniqueID><ISSNLinking>0020-1669</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C444781">1-(1-4-nitro-phenyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C444783">1-(1-octyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C444782">1-(1-undecyl-methyl-phosphonic acid)-4,7,10-tris(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D028581">Lanthanoid Series Elements</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D008024">Ligands</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009578">Nitrobenzenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D063065">Organophosphonates</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009943">Organophosphorus Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>65F5KPT4JK</RegistryNumber><NameOfSubstance UI="C082084">1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylenephosphonic acid)</NameOfSubstance></Chemical><Chemical><RegistryNumber>8RKC5ATI4P</RegistryNumber><NameOfSubstance UI="D013932">Thulium</NameOfSubstance></Chemical><Chemical><RegistryNumber>9NEZ333N27</RegistryNumber><NameOfSubstance UI="D012964">Sodium</NameOfSubstance></Chemical><Chemical><RegistryNumber>MNQ4O4WSI1</RegistryNumber><NameOfSubstance UI="D015018">Ytterbium</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N" UI="D000818">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D002627">Chemistry, Physical</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D006321">Heart</DescriptorName><QualifierName MajorTopicYN="N" UI="Q000187">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D006868">Hydrolysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D066298">In Vitro Techniques</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D028581">Lanthanoid Series Elements</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000138">chemical synthesis</QualifierName><QualifierName MajorTopicYN="Y" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D008024">Ligands</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D009682">Magnetic Resonance Spectroscopy</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D008297">Male</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D008968">Molecular Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D015394">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D009578">Nitrobenzenes</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D063065">Organophosphonates</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000138">chemical synthesis</QualifierName><QualifierName MajorTopicYN="N" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D009943">Organophosphorus Compounds</DescriptorName><QualifierName MajorTopicYN="Y" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D055605">Physicochemical Phenomena</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D051381">Rats</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D017207">Rats, Sprague-Dawley</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D012964">Sodium</DescriptorName><QualifierName MajorTopicYN="N" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D013237">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D013932">Thulium</DescriptorName><QualifierName MajorTopicYN="N" UI="Q000737">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N" UI="D015018">Ytterbium</DescriptorName><QualifierName MajorTopicYN="N" UI="Q000737">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2001</Year><Month>12</Month><Day>12</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2002</Year><Month>2</Month><Day>6</Day><Hour>10</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2001</Year><Month>12</Month><Day>12</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">11735465</ArticleId><ArticleId IdType="pii">ic010291s</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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