Peptidyl Molecular Imaging Contrast Agents Using a New Solid Phase Peptide Synthesis Approach
Identifieur interne : 000235 ( Pmc/Corpus ); précédent : 000234; suivant : 000236Peptidyl Molecular Imaging Contrast Agents Using a New Solid Phase Peptide Synthesis Approach
Auteurs : Byunghee Yoo ; Mark D. PagelSource :
- Bioconjugate chemistry [ 1043-1802 ] ; 2007.
Abstract
A versatile method is disclosed for solid phase peptide synthesis (SPPS) of molecular imaging contrast agents. A DO3A moiety was derivatized to introduce a CBZ-protected amino group and then coupled to a polymeric support. CBZ cleavage with Et2AlCl/thioanisole was optimized for SPPS. Amino acids were then coupled to the aminoDOTA loaded resin using conventional step-wise Fmoc SPPS to create a product with DOTA coupled to the C-terminus of the peptide. In a second study, the DO3A moiety was coupled to a glycine-loaded polymeric support, and amino acids were then coupled to the amino-DOTA-peptide loaded resin using SPPS, to incorporate DOTA within the peptide sequence. The peptide-(Tm3+-DOTA) amide showed a PARAmagnetic Chemical Exchange Saturation Transfer (PARACEST) effect, which demonstrated the utility of this contrast agent for molecular imaging. These results demonstrate the advantages of exploiting SPPS methodologies through the development of unique DOTA derivatives to create peptide-based molecular imaging contrast agents.
Url:
DOI: 10.1021/bc060250q
PubMed: 17330953
PubMed Central: 2584118
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PMC:2584118Le document en format XML
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<author><name sortKey="Pagel, Mark D" sort="Pagel, Mark D" uniqKey="Pagel M" first="Mark D." last="Pagel">Mark D. Pagel</name>
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<series><title level="j">Bioconjugate chemistry</title>
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<front><div type="abstract" xml:lang="en"><p id="P1">A versatile method is disclosed for solid phase peptide synthesis (SPPS) of molecular imaging contrast agents. A DO3A moiety was derivatized to introduce a CBZ-protected amino group and then coupled to a polymeric support. CBZ cleavage with Et<sub>2</sub>
AlCl/thioanisole was optimized for SPPS. Amino acids were then coupled to the aminoDOTA loaded resin using conventional step-wise Fmoc SPPS to create a product with DOTA coupled to the C-terminus of the peptide. In a second study, the DO3A moiety was coupled to a glycine-loaded polymeric support, and amino acids were then coupled to the amino-DOTA-peptide loaded resin using SPPS, to incorporate DOTA within the peptide sequence. The peptide-(Tm<sup>3+</sup>
-DOTA) amide showed a PARAmagnetic Chemical Exchange Saturation Transfer (PARACEST) effect, which demonstrated the utility of this contrast agent for molecular imaging. These results demonstrate the advantages of exploiting SPPS methodologies through the development of unique DOTA derivatives to create peptide-based molecular imaging contrast agents.</p>
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<front><journal-meta><journal-id journal-id-type="nlm-journal-id">9010319</journal-id>
<journal-id journal-id-type="pubmed-jr-id">1061</journal-id>
<journal-id journal-id-type="nlm-ta">Bioconjug Chem</journal-id>
<journal-title>Bioconjugate chemistry</journal-title>
<issn pub-type="ppub">1043-1802</issn>
<issn pub-type="epub">1520-4812</issn>
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<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
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<title-group><article-title>Peptidyl Molecular Imaging Contrast Agents Using a New Solid Phase Peptide Synthesis Approach</article-title>
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<contrib-group><contrib contrib-type="author"><name><surname>Yoo</surname>
<given-names>Byunghee</given-names>
</name>
<email>bxy20@case.edu</email>
</contrib>
<contrib contrib-type="author"><name><surname>Pagel</surname>
<given-names>Mark D.</given-names>
</name>
<email>mpagel@case.edu</email>
<xref ref-type="corresp" rid="cor1">*</xref>
</contrib>
<aff id="A1">Case Center of Imaging Research and Department of Biomedical Engineering, Case Western Reserve University 10900 Euclid Avenue, Cleveland, OHIO 44106</aff>
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<author-notes><corresp id="cor1"><label>*</label>
To whom correspondence should be addressed. Mark (Marty) Pagel, Ph.D., Case Center for Imaging Research, Assistant Professor of Biomedical Engineering, Case Western Reserve University, Tel.: +216 368 8519. Fax: 216 368 4969. E-mail: <email>mpagel@case.edu</email>
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<pub-date pub-type="nihms-submitted"><day>6</day>
<month>8</month>
<year>2008</year>
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<pub-date pub-type="epub"><day>2</day>
<month>3</month>
<year>2007</year>
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<pub-date pub-type="ppub"><year>2007</year>
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<pub-date pub-type="pmc-release"><day>17</day>
<month>11</month>
<year>2008</year>
</pub-date>
<volume>18</volume>
<issue>3</issue>
<fpage>903</fpage>
<lpage>911</lpage>
<abstract><p id="P1">A versatile method is disclosed for solid phase peptide synthesis (SPPS) of molecular imaging contrast agents. A DO3A moiety was derivatized to introduce a CBZ-protected amino group and then coupled to a polymeric support. CBZ cleavage with Et<sub>2</sub>
AlCl/thioanisole was optimized for SPPS. Amino acids were then coupled to the aminoDOTA loaded resin using conventional step-wise Fmoc SPPS to create a product with DOTA coupled to the C-terminus of the peptide. In a second study, the DO3A moiety was coupled to a glycine-loaded polymeric support, and amino acids were then coupled to the amino-DOTA-peptide loaded resin using SPPS, to incorporate DOTA within the peptide sequence. The peptide-(Tm<sup>3+</sup>
-DOTA) amide showed a PARAmagnetic Chemical Exchange Saturation Transfer (PARACEST) effect, which demonstrated the utility of this contrast agent for molecular imaging. These results demonstrate the advantages of exploiting SPPS methodologies through the development of unique DOTA derivatives to create peptide-based molecular imaging contrast agents.</p>
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<kwd-group><kwd>DOTA</kwd>
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<contract-num rid="DK1">P30 DK027651-259018</contract-num>
<contract-sponsor id="DK1">National Institute of Diabetes and Digestive and Kidney Diseases : NIDDK</contract-sponsor>
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