Synthetic Strategy to Prepare DOTA-Based Bifunctional Chelating Agent Ready to Bind Biomolecular Probes

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• 作者：Enrica Calce (1)
  Luca Monfregola (1)
  Stefania De Luca (1)
  
• 关键词：DOTA ; Bifunctional chelating agent ; Biological probe ; Peptide labeling
• 刊名：International Journal of Peptide Research and Therapeutics
• 出版年：2013
• 出版时间：September 2013
• 年：2013
• 卷：19
• 期：3
• 页码：199-202
• 全文大小：292KB
• 参考文献：1. Barge A, Cappelletti E, Cravotto G, Ferrigato A, Lattuada L, Marinoni F, Tei L (2009) Synthesis of functionalised HP-DO3A chelating agents for conjugation to biomolecules. Org Biomol Chem 7:3810鈥?816 10.1039/b905369g">CrossRef
  2. Bernhard C, Moreau M, Lhenry D, Goze C, Boschetti F, Rousselin Y, Brunotte F, Denat F (2012) DOTAGA-anhydride: a valuable building block for the preparation of DOTA-like chelating agents. Chem Eur J 18:7834鈥?841 10.1002/chem.201200132">CrossRef
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  4. Jamous M, Haberkorn U, Mier W (2012) DOTA-tris(OPp ester) as a bifunctional prochelator for the preparation of DOTA-peptide conjugates. Tetrahedron Lett 53:6810鈥?814 10.1016/j.tetlet.2012.10.007">CrossRef
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• 作者单位：Enrica Calce (1)
  Luca Monfregola (1)
  Stefania De Luca (1)
  
  1. Institute of Biostructure and Bioimaging, National Research Council, Via Mezzocannone 16, 80138, Naples, Italy
  

文摘

Due to the continued interest in new bifunctional chelating agents (BFCA), we focused on the development of a convenient synthesis of 1,4,7,10-tetraazacyclododecane-1,4,7-tris(acetic acid)-10-butyrate mono (N-hydroxysuccinimidyl ester). It consists in the macrocycle DO3A derivatized with an aliphatic linker containing an active ester that requires selective and mild conditions to react with the targeting biomolecule. It is important to underlay the versatility of the obtained BFCA, which can be conjugated both to a biomolecule (protein, Fab fragment) or to a synthetic molecule. In a subsequent step, the developed chelator was successfully conjugated to a peptide sequence.