Redox properties and in vivo magnetic resonance imaging of cyclodextrin-polynitroxides contrast agents
This paper reports the synthesis, characterization and in vivo application of water-soluble supramolecular contrast agents (Mw:5-5.6 kDa) for MRI obtained from β-cyclodextrin functionalized with different kinds of nitroxide radicals, both with piperidine structure (CD2 and CD3) and with pyrrolidine...
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| Published in | Chemphyschem Vol. 24; no. 19; p. e202300100 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | This paper reports the synthesis, characterization and in vivo application of water-soluble supramolecular contrast agents (Mw:5-5.6 kDa) for MRI obtained from β-cyclodextrin functionalized with different kinds of nitroxide radicals, both with piperidine structure (CD2 and CD3) and with pyrrolidine structure (CD4 and CD5). As to the stability of the radicals in presence of ascorbic acid, CD4 and CD5 have low second order kinetic constants (≤0.06 M-1 s-1) compared to CD2 (3.5 M-1 s-1) and CD3 (0.73 M-1s-1). Relaxivity (r1) measurements on compounds CD3-CD5 were carried out at different magnetic field strength (0.7, 3, 7 and 9.4 T). At 0.7 T, r1 values comprised between 1.5 mM-1s-1 and 1.9 mM-1s-1 were found while a significant reduction was observed at higher fields (r1≈0.6-0.8 mM-1 s-1 at 9.4 T). Tests in vitro on HEK293 human embryonic kidney cells, L929 mouse fibroblasts and U87 glioblastoma cells indicated that all compounds were non-cytotoxic at concentrations below 1 µmol mL-1. MRI in vivo was carried out at 9.4 T on glioma-bearing rats and using the compounds CD3-CD5. The experiments showed a good lowering of T1 relaxation in tumor with a retention of the contrast for at least 60 mins confirming improved stability also in vivo conditions. |
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| AbstractList | Abstract
This paper reports the synthesis, characterization and
in vivo
application of water‐soluble supramolecular contrast agents (Mw: 5–5.6 kDa) for MRI obtained from β‐cyclodextrin functionalized with different kinds of nitroxide radicals, both with piperidine structure (
CD2
and
CD3
) and with pyrrolidine structure (
CD4
and
CD5
). As to the stability of the radicals in presence of ascorbic acid,
CD4
and
CD5
have low second order kinetic constants (≤0.05 M
−1
s
−1
) compared to
CD2
(3.5 M
−1
s
−1
) and
CD3
(0.73 M
−1
s
−1
). Relaxivity (r
1
) measurements on compounds
CD3
‐
CD5
were carried out at different magnetic field strength (0.7, 3, 7 and 9.4 T). At 0.7 T, r
1
values comprised between 1.5 mM
−1
s
−1
and 1.9 mM
−1
s
−1
were found while a significant reduction was observed at higher fields (r
1
≈0.6‐0.9 mM
−1
s
−1
at 9.4 T). Tests
in vitro
on HEK293 human embryonic kidney cells, L929 mouse fibroblasts and U87 glioblastoma cells indicated that all compounds were non‐cytotoxic at concentrations below 1 μmol mL
−1
. MRI
in vivo
was carried out at 9.4 T on glioma‐bearing rats using the compounds
CD3
‐
CD5
. The experiments showed a good lowering of T
1
relaxation in tumor with a retention of the contrast for at least 60 mins confirming improved stability also in vivo conditions. This paper reports the synthesis, characterization and in vivo application of water‐soluble supramolecular contrast agents (Mw: 5–5.6 kDa) for MRI obtained from β‐cyclodextrin functionalized with different kinds of nitroxide radicals, both with piperidine structure (CD2 and CD3) and with pyrrolidine structure (CD4 and CD5). As to the stability of the radicals in presence of ascorbic acid, CD4 and CD5 have low second order kinetic constants (≤0.05 M−1 s−1) compared to CD2 (3.5 M−1 s−1) and CD3 (0.73 M−1 s−1). Relaxivity (r1) measurements on compounds CD3‐CD5 were carried out at different magnetic field strength (0.7, 3, 7 and 9.4 T). At 0.7 T, r1 values comprised between 1.5 mM−1 s−1 and 1.9 mM−1 s−1 were found while a significant reduction was observed at higher fields (r1≈0.6‐0.9 mM−1 s−1 at 9.4 T). Tests in vitro on HEK293 human embryonic kidney cells, L929 mouse fibroblasts and U87 glioblastoma cells indicated that all compounds were non‐cytotoxic at concentrations below 1 μmol mL−1. MRI in vivo was carried out at 9.4 T on glioma‐bearing rats using the compounds CD3‐CD5. The experiments showed a good lowering of T1 relaxation in tumor with a retention of the contrast for at least 60 mins confirming improved stability also in vivo conditions. This paper reports the synthesis, characterization and in vivo application of water-soluble supramolecular contrast agents (Mw:5-5.6 kDa) for MRI obtained from β-cyclodextrin functionalized with different kinds of nitroxide radicals, both with piperidine structure (CD2 and CD3) and with pyrrolidine structure (CD4 and CD5). As to the stability of the radicals in presence of ascorbic acid, CD4 and CD5 have low second order kinetic constants (≤0.06 M-1 s-1) compared to CD2 (3.5 M-1 s-1) and CD3 (0.73 M-1s-1). Relaxivity (r1) measurements on compounds CD3-CD5 were carried out at different magnetic field strength (0.7, 3, 7 and 9.4 T). At 0.7 T, r1 values comprised between 1.5 mM-1s-1 and 1.9 mM-1s-1 were found while a significant reduction was observed at higher fields (r1≈0.6-0.8 mM-1 s-1 at 9.4 T). Tests in vitro on HEK293 human embryonic kidney cells, L929 mouse fibroblasts and U87 glioblastoma cells indicated that all compounds were non-cytotoxic at concentrations below 1 µmol mL-1. MRI in vivo was carried out at 9.4 T on glioma-bearing rats and using the compounds CD3-CD5. The experiments showed a good lowering of T1 relaxation in tumor with a retention of the contrast for at least 60 mins confirming improved stability also in vivo conditions. |
| Author | Hyppönen, Viivi Isse, Abdirisak Ahmed Kettunen, Mikko Rosa, Jessica Olsson, Venla Melone, Lucio Altomare, Lina Franco, Lorenzo Barbon, Antonio |
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| Snippet | This paper reports the synthesis, characterization and in vivo application of water-soluble supramolecular contrast agents (Mw:5-5.6 kDa) for MRI obtained from... Abstract This paper reports the synthesis, characterization and in vivo application of water‐soluble supramolecular contrast agents (Mw: 5–5.6 kDa) for MRI... This paper reports the synthesis, characterization and in vivo application of water‐soluble supramolecular contrast agents (Mw: 5–5.6 kDa) for MRI obtained... |
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| SubjectTerms | Ascorbic acid Contrast agents Cyclodextrins Fibroblasts Field strength Glioma In vivo methods and tests Magnetic properties Magnetic resonance imaging Piperidine |
| Title | Redox properties and in vivo magnetic resonance imaging of cyclodextrin-polynitroxides contrast agents |
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