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

Authorized Users Only
2013
Authors
Vibhute, Sandip M.
Engelmann, Joern
Verbić, Tatjana
Maier, Martin E.
Logothetis, Nikos K.
Angelovski, Goran
Article (Published version)
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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 r(1) and r(2) 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.

Source:
Organic and Biomolecular Chemistry, 2013, 11, 8, 1294-1305
Publisher:
  • Royal Soc Chemistry, Cambridge
Funding / projects:
  • German Ministry for Education and Research (BMBF) [FKZ: 01EZ0813]
  • Max-Planck Society
  • German Research Foundation (DFG) [AN 716/2-1]
Note:
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3532

DOI: 10.1039/c2ob26555a

ISSN: 1477-0520

PubMed: 23223612

WoS: 000314368200005

Scopus: 2-s2.0-84875841582
[ Google Scholar ]
19
17
URI
https://cherry.chem.bg.ac.rs/handle/123456789/1595
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Vibhute, Sandip M.
AU  - Engelmann, Joern
AU  - Verbić, Tatjana
AU  - Maier, Martin E.
AU  - Logothetis, Nikos K.
AU  - Angelovski, Goran
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1595
AB  - 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 r(1) and r(2) 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.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic and Biomolecular Chemistry
T1  - Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin
VL  - 11
IS  - 8
SP  - 1294
EP  - 1305
DO  - 10.1039/c2ob26555a
UR  - Kon_2426
ER  - 
@article{
author = "Vibhute, Sandip M. and Engelmann, Joern and Verbić, Tatjana and Maier, Martin E. and Logothetis, Nikos K. and Angelovski, Goran",
year = "2013",
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 r(1) and r(2) 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.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic and Biomolecular Chemistry",
title = "Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin",
volume = "11",
number = "8",
pages = "1294-1305",
doi = "10.1039/c2ob26555a",
url = "Kon_2426"
}
Vibhute, S. M., Engelmann, J., Verbić, T., Maier, M. E., Logothetis, N. K.,& Angelovski, G.. (2013). Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin. in Organic and Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 11(8), 1294-1305.
https://doi.org/10.1039/c2ob26555a
Kon_2426
Vibhute SM, Engelmann J, Verbić T, Maier ME, Logothetis NK, Angelovski G. Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin. in Organic and Biomolecular Chemistry. 2013;11(8):1294-1305.
doi:10.1039/c2ob26555a
Kon_2426 .
Vibhute, Sandip M., Engelmann, Joern, Verbić, Tatjana, Maier, Martin E., Logothetis, Nikos K., Angelovski, Goran, "Synthesis and characterization of pH-sensitive, biotinylated MRI contrast agents and their conjugates with avidin" in Organic and Biomolecular Chemistry, 11, no. 8 (2013):1294-1305,
https://doi.org/10.1039/c2ob26555a .,
Kon_2426 .

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