Lanthanide(III) complexes of pyridine-tetraacetic acid-glycoconjugates: Synthesis and luminescence studies of mono and divalent derivatives

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• 作者：Sé ; bastien G. Gouin^a ; ^b ; ^{sebastien.gouin@univ-nantes.fr} ; Mé ; lissa Roger^a ; Nadine Leygue^c ; ^d ; David Deniaud^a ; Karine Julienne^a ; Eric Benoist^c ; ^d ; Claude Picard^c ; ^d ; José ; Kovensky^b ; Chantal Galaup^c ; ^d ;
• 关键词：Glycoconjugates ; Chelating agents ; Lanthanides ; Luminescence ; Click chemistry
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2012
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：15 April, 2012
• 卷：22
• 期：8
• 页码：2684-2688
• 文件大小：405 K

摘要

A potent lanthanide chelate, fulfilling the requirements for the development of MRI contrast agents or luminescent probes, was armed with alkyne groups. We then implemented a click methodology to graft the bifunctional ligand to azide-containing glucoside and maltoside scaffolds. The resulting hydrophilic glycoconjugates retained the ligand binding capacity for Eu³⁺ or Tb³⁺ ion as evidenced by the number of bound water molecules to the lanthanide ion. Divalent Eu³⁺ and Tb³⁺ complexes were shown to double the brightness of the emitted fluorescent signal compared to its monovalent derivatives. Designing multivalent lanthanide luminescent probes would enable the fluorescent signal of labeled biomolecules to be enhanced.