A new synthesis of cystamine modified Eu3+ DOTAM-Gly-Phe-OH: a conjugation ready temperature sensitive MRI contrast agent

Several approaches towards asymmetrically derivatized peptide-decorated cyclens that yield lanthanide metal chelators, in which three of the nitrogen atoms of-cyclen share a common substituent and the fourth nitrogen atom is differentially Substituted, have been evaluated. The most effective route c...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 6; no. 19; pp. 3588 - 3596
Main Authors Suchy, Mojmir, Li, Alex X., Bartha, Robert, Hudson, Robert H. E.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.10.2008
Subjects
Acetamides - chemical synthesis
Acetamides - chemistry
Alkylation
Chemistry
Chemistry, Organic
Contrast Media - chemical synthesis
Contrast Media - chemistry
Cystamine - chemistry
Dipeptides - chemical synthesis
Dipeptides - chemistry
Heterocyclic Compounds - chemistry
Heterocyclic Compounds, 1-Ring - chemical synthesis
Heterocyclic Compounds, 1-Ring - chemistry
Ligands
Magnetic Resonance Imaging
Magnetics
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Physical Sciences
Science & Technology
Substrate Specificity
Temperature
DIE FORMYLGRUPPE
CYCLEN
PROTECTION
SCHUTZGRUPPE FUR PEPTIDSYNTHESEN
COMPLEXES
CELL-PENETRATING PEPTIDES
SELECTIVITY
BINDING
1,4,7,10-TETRAAZACYCLODODECANE
DELIVERY
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Summary:Several approaches towards asymmetrically derivatized peptide-decorated cyclens that yield lanthanide metal chelators, in which three of the nitrogen atoms of-cyclen share a common substituent and the fourth nitrogen atom is differentially Substituted, have been evaluated. The most effective route consisted of selective monoalkylation followed by peralkylation with a second different electrophile. The unique substituent also possessed a masked sulfanyl group that was suitable for subsequent chemoselective conjugation chemistry.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/b808282k