| Redox-active magnetic resonance imaging contrast agents: studies with thiol-bearing 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid derivatives. | |
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MedLine Citation:
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PMID: 23148501 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The synthesis and structure-activity relationships of a homologous series of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid gadolinium(III) complexes bearing thiol-terminated alkyl side chains from three to nine carbons in length are reported. The observed binding with human serum albumin (HSA) of the compounds having C-3 through C-7 side chain lengths was inhibited by homocysteine in a manner consistent with single-site binding. The observed binding with HSA of the compounds having C-8 and C-9 side chain lengths was only partly inhibited by homocysteine, consistent with multisite binding. The binding affinity of the C-7 compound could be related to the HSA oxidation state. 2D 1H-1H NMR TOCSY provided evidence of covalent binding of the europium analog of the C-6 compound to HSA-Cys34. The longitudinal water-proton MRI relaxivities of the gadolinium complexes at 7 T increased upon binding to HSA. On the basis of these results, the C-6 and C-7 compounds were identified as promising redox-sensitive MRI contrast agents. |
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Authors:
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Bhumasamudram Jagadish; Gerald P Guntle; Dezheng Zhao; Vijay Gokhale; Tarik J Ozumerzifon; Ali M Ahad; Eugene A Mash; Natarajan Raghunand |
Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2012-11-28 |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 55 ISSN: 1520-4804 ISO Abbreviation: J. Med. Chem. Publication Date: 2012 Dec |
Date Detail:
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Created Date: 2012-12-13 Completed Date: 2013-02-26 Revised Date: 2013-04-16 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: United States |
Other Details:
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Languages: eng Pagination: 10378-86 Citation Subset: IM |
Affiliation:
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Department of Chemistry and Biochemistry, Arizona Cancer Center, University of Arizona, Tucson, Arizona 85721-0041, United States. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Aza Compounds
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chemistry,
pharmacology* Contrast Media / chemistry, pharmacology* Heterocyclic Compounds, 1-Ring / chemistry, pharmacology* Magnetic Resonance Spectroscopy Oxidation-Reduction Spectrometry, Mass, Electrospray Ionization Structure-Activity Relationship Sulfhydryl Compounds / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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P01-CA017094/CA/NCI NIH HHS; P30-CA023074/CA/NCI NIH HHS; R01 CA118359/CA/NCI NIH HHS; R01-CA118359/CA/NCI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/1,4,7,10-tetraazacyclododecane-1,4,7,10-tetracetic acid; 0/Aza Compounds; 0/Contrast Media; 0/Heterocyclic Compounds, 1-Ring; 0/Sulfhydryl Compounds |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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