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 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.
Suchý
Mojmír
M
Department of Chemistry, The University of Western Ontario, London, ON, Canada N6A 5B7.
Li
Alex X
AX
Bartha
Robert
R
Hudson
Robert H E
RH
D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D003287:Contrast Media / Q000138:chemical synthesis* / Q000737:chemistry; D000080027:Cyclams; D003538:Cystamine / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008024:Ligands; D008279:Magnetic Resonance Imaging; D008280:Magnetics; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013379:Substrate Specificity; D013696:Temperature
C534477:(DOTAM-glycyl-phenylalanine)europium(III); C522450:1,4,7,10-tetrakis(carbamoylmethyl)-1,4,7,10-tetraazacyclododecane; D000081:Acetamides; D003287:Contrast Media; D000080027:Cyclams; D004151:Dipeptides; D006571:Heterocyclic Compounds; D006573:Heterocyclic Compounds, 1-Ring; D008024:Ligands; D009942:Organometallic Compounds; C038072:cyclen; D003538:Cystamine