Synthesis and biological studies of nociceptin derivatives containing the DTPA chelating group for further labeling with therapeutic radionuclides.
Identifieur interne : 002C01 ( Main/Exploration ); précédent : 002C00; suivant : 002C02Synthesis and biological studies of nociceptin derivatives containing the DTPA chelating group for further labeling with therapeutic radionuclides.
Auteurs : RBID : pubmed:15949634English descriptors
- KwdEn :
- Animals, Biological Assay, Chelating Agents (chemistry), Dimerization, Guanosine 5'-O-(3-Thiotriphosphate) (metabolism), Indium Radioisotopes (chemistry), Isotope Labeling, Male, Mice, Mice, Inbred Strains, Opioid Peptides (chemical synthesis), Opioid Peptides (chemistry), Opioid Peptides (pharmacology), Pentetic Acid (chemistry), Peptide Fragments (chemical synthesis), Peptide Fragments (pharmacology), Radiopharmaceuticals (chemistry), Rats, Rats, Wistar, Receptors, Opioid (agonists), Receptors, Opioid (chemistry), Technetium (chemistry), Vas Deferens (drug effects).
- MESH :
- chemical , agonists : Receptors, Opioid.
- chemical , chemical synthesis : Opioid Peptides, Peptide Fragments.
- chemical , chemistry : Chelating Agents, Indium Radioisotopes, Opioid Peptides, Pentetic Acid, Radiopharmaceuticals, Receptors, Opioid, Technetium.
- chemical , metabolism : Guanosine 5'-O-(3-Thiotriphosphate).
- chemical , pharmacology : Opioid Peptides, Peptide Fragments.
- drug effects : Vas Deferens.
- Animals, Biological Assay, Dimerization, Isotope Labeling, Male, Mice, Mice, Inbred Strains, Rats, Rats, Wistar.
Abstract
Nociceptin is an endogenous anti-opiate heptadecapeptide primarily interacting with the nociceptin (NOP) receptor. This neuropeptide-receptor system is involved in pain regulation, tolerance to and dependence on opiates as well as many other physiological and pathophysiological events. The role and mechanisms of nociceptin in pathological conditions is not clearly known yet. In an attempt to have a radiopharmaceutical labeled either with 99mTc or (111)In, we incorporated diethylenetriaminepentaacetic acid (DTPA) as chelator into the structure of [Arg14,Lys15]nociceptin(1-17)-NH2 at the epsilon-amino group of Lys15. Such a radiopeptide may be useful in imaging for diagnostical purposes. Preparation of the peptide ligands was carried out by solid phase synthesis. Two peptides containing DTPA were obtained and purified. The products were [Arg14,Lys(DTPA)15]nociceptin(1-17)-NH2 and its cross-linked dimer on the basis of mass spectrometric analysis. In (115)In3+ binding experiments the conjugates exhibited preserved indium ion chelating properties, indicating the potential use of radiolabeled DTPA-nociceptin derivatives as radiopharmaceutical. Biological properties of these compounds were studied in rat brain membrane preparations by radioligand binding, functional biochemical [35S]GTPgammaS binding assays and mouse vas deferens (MVD) bioassay. Besides the similar in vitro binding characteristics to nociceptin receptor, both of the DTPA-chelated compounds were more potent and efficient than nociceptin in functional biochemical and mouse vas deferens bioassays. Our further aim is to radiolabel these compounds in order to get a radiopharmaceutical which can be used diagnostically.
DOI: 10.1016/j.peptides.2005.01.018
PubMed: 15949634
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and biological studies of nociceptin derivatives containing the DTPA chelating group for further labeling with therapeutic radionuclides.</title><author><name sortKey="Ligeti, Melinda" uniqKey="Ligeti M">Melinda Ligeti</name><affiliation wicri:level="1"><nlm:affiliation>Research Group of Peptide Chemistry, Eötvös University and Hungarian Academy of Sciences, Budapest, Hungary.</nlm:affiliation><country xml:lang="fr">Hongrie</country><wicri:regionArea>Research Group of Peptide Chemistry, Eötvös University and Hungarian Academy of Sciences, Budapest</wicri:regionArea></affiliation></author><author><name sortKey="G Nd Z, Ozge" uniqKey="G Nd Z O">Ozge Gündüz</name></author><author><name sortKey="Magyar, Anna" uniqKey="Magyar A">Anna Magyar</name></author><author><name sortKey="Kat, Erzsebet" uniqKey="Kat E">Erzsébet Kató</name></author><author><name sortKey="R Nai, Andr S Z" uniqKey="R Nai A">András Z Rónai</name></author><author><name sortKey="Vita, Claudio" uniqKey="Vita C">Claudio Vita</name></author><author><name sortKey="Varga, Imre" uniqKey="Varga I">Imre Varga</name></author><author><name sortKey="Hudecz, Ferenc" uniqKey="Hudecz F">Ferenc Hudecz</name></author><author><name sortKey="T Th, Geza" uniqKey="T Th G">Géza Tóth</name></author><author><name sortKey="Borsodi, Anna" uniqKey="Borsodi A">Anna Borsodi</name></author><author><name sortKey="Benyhe, S Ndor" uniqKey="Benyhe S">Sándor Benyhe</name></author></titleStmt><publicationStmt><date when="2005">2005</date><idno type="doi">10.1016/j.peptides.2005.01.018</idno><idno type="RBID">pubmed:15949634</idno><idno type="pmid">15949634</idno><idno type="wicri:Area/Main/Corpus">002E75</idno><idno type="wicri:Area/Main/Curation">002E75</idno><idno type="wicri:Area/Main/Exploration">002C01</idno></publicationStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Biological Assay</term><term>Chelating Agents (chemistry)</term><term>Dimerization</term><term>Guanosine 5'-O-(3-Thiotriphosphate) (metabolism)</term><term>Indium Radioisotopes (chemistry)</term><term>Isotope Labeling</term><term>Male</term><term>Mice</term><term>Mice, Inbred Strains</term><term>Opioid Peptides (chemical synthesis)</term><term>Opioid Peptides (chemistry)</term><term>Opioid Peptides (pharmacology)</term><term>Pentetic Acid (chemistry)</term><term>Peptide Fragments (chemical synthesis)</term><term>Peptide Fragments (pharmacology)</term><term>Radiopharmaceuticals (chemistry)</term><term>Rats</term><term>Rats, Wistar</term><term>Receptors, Opioid (agonists)</term><term>Receptors, Opioid (chemistry)</term><term>Technetium (chemistry)</term><term>Vas Deferens (drug effects)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="agonists" xml:lang="en"><term>Receptors, Opioid</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Opioid Peptides</term><term>Peptide Fragments</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Chelating Agents</term><term>Indium Radioisotopes</term><term>Opioid Peptides</term><term>Pentetic Acid</term><term>Radiopharmaceuticals</term><term>Receptors, Opioid</term><term>Technetium</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Guanosine 5'-O-(3-Thiotriphosphate)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Opioid Peptides</term><term>Peptide Fragments</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Vas Deferens</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Biological Assay</term><term>Dimerization</term><term>Isotope Labeling</term><term>Male</term><term>Mice</term><term>Mice, Inbred Strains</term><term>Rats</term><term>Rats, Wistar</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Nociceptin is an endogenous anti-opiate heptadecapeptide primarily interacting with the nociceptin (NOP) receptor. This neuropeptide-receptor system is involved in pain regulation, tolerance to and dependence on opiates as well as many other physiological and pathophysiological events. The role and mechanisms of nociceptin in pathological conditions is not clearly known yet. In an attempt to have a radiopharmaceutical labeled either with 99mTc or (111)In, we incorporated diethylenetriaminepentaacetic acid (DTPA) as chelator into the structure of [Arg14,Lys15]nociceptin(1-17)-NH2 at the epsilon-amino group of Lys15. Such a radiopeptide may be useful in imaging for diagnostical purposes. Preparation of the peptide ligands was carried out by solid phase synthesis. Two peptides containing DTPA were obtained and purified. The products were [Arg14,Lys(DTPA)15]nociceptin(1-17)-NH2 and its cross-linked dimer on the basis of mass spectrometric analysis. In (115)In3+ binding experiments the conjugates exhibited preserved indium ion chelating properties, indicating the potential use of radiolabeled DTPA-nociceptin derivatives as radiopharmaceutical. Biological properties of these compounds were studied in rat brain membrane preparations by radioligand binding, functional biochemical [35S]GTPgammaS binding assays and mouse vas deferens (MVD) bioassay. Besides the similar in vitro binding characteristics to nociceptin receptor, both of the DTPA-chelated compounds were more potent and efficient than nociceptin in functional biochemical and mouse vas deferens bioassays. Our further aim is to radiolabel these compounds in order to get a radiopharmaceutical which can be used diagnostically.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">15949634</PMID><DateCreated><Year>2005</Year><Month>06</Month><Day>13</Day></DateCreated><DateCompleted><Year>2005</Year><Month>10</Month><Day>14</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0196-9781</ISSN><JournalIssue CitedMedium="Print"><Volume>26</Volume><Issue>7</Issue><PubDate><Year>2005</Year><Month>Jul</Month></PubDate></JournalIssue><Title>Peptides</Title><ISOAbbreviation>Peptides</ISOAbbreviation></Journal><ArticleTitle>Synthesis and biological studies of nociceptin derivatives containing the DTPA chelating group for further labeling with therapeutic radionuclides.</ArticleTitle><Pagination><MedlinePgn>1159-66</MedlinePgn></Pagination><Abstract><AbstractText>Nociceptin is an endogenous anti-opiate heptadecapeptide primarily interacting with the nociceptin (NOP) receptor. This neuropeptide-receptor system is involved in pain regulation, tolerance to and dependence on opiates as well as many other physiological and pathophysiological events. The role and mechanisms of nociceptin in pathological conditions is not clearly known yet. In an attempt to have a radiopharmaceutical labeled either with 99mTc or (111)In, we incorporated diethylenetriaminepentaacetic acid (DTPA) as chelator into the structure of [Arg14,Lys15]nociceptin(1-17)-NH2 at the epsilon-amino group of Lys15. Such a radiopeptide may be useful in imaging for diagnostical purposes. Preparation of the peptide ligands was carried out by solid phase synthesis. Two peptides containing DTPA were obtained and purified. The products were [Arg14,Lys(DTPA)15]nociceptin(1-17)-NH2 and its cross-linked dimer on the basis of mass spectrometric analysis. In (115)In3+ binding experiments the conjugates exhibited preserved indium ion chelating properties, indicating the potential use of radiolabeled DTPA-nociceptin derivatives as radiopharmaceutical. Biological properties of these compounds were studied in rat brain membrane preparations by radioligand binding, functional biochemical [35S]GTPgammaS binding assays and mouse vas deferens (MVD) bioassay. Besides the similar in vitro binding characteristics to nociceptin receptor, both of the DTPA-chelated compounds were more potent and efficient than nociceptin in functional biochemical and mouse vas deferens bioassays. Our further aim is to radiolabel these compounds in order to get a radiopharmaceutical which can be used diagnostically.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ligeti</LastName><ForeName>Melinda</ForeName><Initials>M</Initials><Affiliation>Research Group of Peptide Chemistry, Eötvös University and Hungarian Academy of Sciences, Budapest, Hungary.</Affiliation></Author><Author ValidYN="Y"><LastName>Gündüz</LastName><ForeName>Ozge</ForeName><Initials>O</Initials></Author><Author ValidYN="Y"><LastName>Magyar</LastName><ForeName>Anna</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Kató</LastName><ForeName>Erzsébet</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Rónai</LastName><ForeName>András Z</ForeName><Initials>AZ</Initials></Author><Author ValidYN="Y"><LastName>Vita</LastName><ForeName>Claudio</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Varga</LastName><ForeName>Imre</ForeName><Initials>I</Initials></Author><Author ValidYN="Y"><LastName>Hudecz</LastName><ForeName>Ferenc</ForeName><Initials>F</Initials></Author><Author ValidYN="Y"><LastName>Tóth</LastName><ForeName>Géza</ForeName><Initials>G</Initials></Author><Author ValidYN="Y"><LastName>Borsodi</LastName><ForeName>Anna</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Benyhe</LastName><ForeName>Sándor</ForeName><Initials>S</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType><PublicationType>Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2005</Year><Month>03</Month><Day>02</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Peptides</MedlineTA><NlmUniqueID>8008690</NlmUniqueID><ISSNLinking>0196-9781</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Chelating Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Indium Radioisotopes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Opioid Peptides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Peptide Fragments</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Radiopharmaceuticals</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Receptors, Opioid</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>nociceptin</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>nociceptin (1-17)amide, Arg(14)-Lys(DTPA)(15)-</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>nociceptin receptor</NameOfSubstance></Chemical><Chemical><RegistryNumber>37589-80-3</RegistryNumber><NameOfSubstance>Guanosine 5'-O-(3-Thiotriphosphate)</NameOfSubstance></Chemical><Chemical><RegistryNumber>7440-26-8</RegistryNumber><NameOfSubstance>Technetium</NameOfSubstance></Chemical><Chemical><RegistryNumber>7A314HQM0I</RegistryNumber><NameOfSubstance>Pentetic Acid</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Biological Assay</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Chelating Agents</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Dimerization</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Guanosine 5'-O-(3-Thiotriphosphate)</DescriptorName><QualifierName MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Indium Radioisotopes</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Isotope Labeling</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Male</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Mice</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Mice, Inbred Strains</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Opioid Peptides</DescriptorName><QualifierName MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName MajorTopicYN="Y">chemistry</QualifierName><QualifierName MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Pentetic Acid</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Peptide Fragments</DescriptorName><QualifierName MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Radiopharmaceuticals</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Rats</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Rats, Wistar</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Receptors, Opioid</DescriptorName><QualifierName MajorTopicYN="Y">agonists</QualifierName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Technetium</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Vas Deferens</DescriptorName><QualifierName MajorTopicYN="N">drug effects</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2004</Year><Month>11</Month><Day>29</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2005</Year><Month>1</Month><Day>25</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2005</Year><Month>1</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="aheadofprint"><Year>2005</Year><Month>3</Month><Day>2</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2005</Year><Month>6</Month><Day>14</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2005</Year><Month>10</Month><Day>15</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2005</Year><Month>6</Month><Day>14</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pii">S0196-9781(05)00033-1</ArticleId><ArticleId IdType="doi">10.1016/j.peptides.2005.01.018</ArticleId><ArticleId IdType="pubmed">15949634</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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