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  Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin

Vibhute, S., Engelmann, J., Verbić, T., Maier, M., Logothetis, N. K., & Angelovski, G. (2013). Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin. Organic & Biomolecular Chemistry, 11(8), 1294-1305. doi:10.1039/C2OB26555A.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-0013-B506-3 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-D1BC-A
Genre: Journal Article

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 Creators:
Vibhute, SM1, 2, Author              
Engelmann, J2, 3, Author              
Verbić, T, Author
Maier, ME, Author
Logothetis, Nikos K1, 2, Author              
Angelovski, G1, 2, Author              
Affiliations:
1Department Physiology of Cognitive Processes, Max Planck Institute for Biological Cybernetics, Max Planck Society, ou_1497798              
2Max Planck Institute for Biological Cybernetics, Max Planck Society, ou_1497794              
3Department High-Field Magnetic Resonance, Max Planck Institute for Biological Cybernetics, Max Planck Society, ou_1497796              

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 Abstract: Responsive or smart contrast agents (SCAs) provide new opportunities in magnetic resonance imaging (MRI) to examine a number of physiological and pathological events. However, their application in vivo remains challenging. Therefore, much research is focused on the optimization of their properties, to enable their use in additional imaging modalities, pre-targeted delivery, or to increase the local concentration of the agent. The key feature in the SCA synthetic modification is the retention of their physicochemical properties related to the specific MR response. Here, we report the preparation and characterization of pH sensitive SCAs appended with a phosphonate pendant arm and either an aliphatic (GdL1) or aromatic linker (GdL2). The longitudinal relaxivity of GdL1 and GdL2 increases by 146 and 31, respectively, while the pH decreases from 9 to 5. These two SCAs were converted to the biotinylated systems GdL3 and GdL4 and their interaction with avidin was investigated. The binding affinity with avidin was assessed with a fluorescence displacement assay and with MRI phantom experiments in a 3T MRI scanner. The fluorometric assay and MRI E-titrations revealed a 3 : 1 binding mode of GdL3–4 to avidin with the binding affinity as high as that of the parent avidin–biotin complex. The high binding affinity was confirmed with MRI by a competitive assay. The avidin–GdL3–4 complexes thus obtained exhibit changes in both r1 and r2 that are pH dependent. The results reveal a new pathway for the modification and improvement of SCAs to make them more suitable for in vivo application.

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 Dates: 2013-02
 Publication Status: Published in print
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 Rev. Type: -
 Identifiers: DOI: 10.1039/C2OB26555A
BibTex Citekey: VibhuteEVMLA2012
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Title: Organic & Biomolecular Chemistry
  Other : Organic and Biomolecular Chemistry
  Abbreviation : Org. Biomol. Chem.
Source Genre: Journal
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Publ. Info: Cambridge : Royal Society of Chemistry
Pages: - Volume / Issue: 11 (8) Sequence Number: - Start / End Page: 1294 - 1305 Identifier: ISSN: 1477-0520
CoNE: https://pure.mpg.de/cone/journals/resource/954925269322