Improved radiosynthesis and preliminary in vivo evaluation of the                          11                         C-labeled tetrazine [                         11                         C]AE-1 for pretargeted PET imaging

E. Johanna L. Stéen; Jesper T. Jørgensen; Ida N. Petersen; Kamilla Nørregaard; Szabolcs Lehel; Vladimir Shalgunov; Alexander Birke; Patricia E. Edem; Elina T. L'Estrade; Hanne D. Hansen; Jonas Villadsen; Maria Erlandsson; Tomas Ohlsson; Abdolreza Yazdani; John F. Valliant; Jesper L. Kristensen; Matthias Barz; Gitte M. Knudsen; Andreas Kjær; Matthias M. Herth

doi:10.1016/j.bmcl.2019.02.014

Improved radiosynthesis and preliminary in vivo evaluation of the ¹¹ C-labeled tetrazine [ ¹¹ C]AE-1 for pretargeted PET imaging

E. Johanna L. Stéen, Jesper T. Jørgensen, Ida N. Petersen, Kamilla Nørregaard, Szabolcs Lehel, Vladimir Shalgunov, Alexander Birke, Patricia E. Edem, Elina T. L'Estrade, Hanne D. Hansen, Jonas Villadsen, Maria Erlandsson, Tomas Ohlsson, Abdolreza Yazdani, John F. Valliant, Jesper L. Kristensen, Matthias Barz, Gitte M. Knudsen, Andreas Kjær^*, Matthias M. Herth

^*Corresponding author for this work

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Abstract

Pretargeted nuclear imaging based on the ligation between tetrazines and nano-sized targeting agents functionalized with trans-cyclooctene (TCO) has recently been shown to improve both imaging contrast and dosimetry in nuclear imaging of nanomedicines. Herein, we describe the improved radiosynthesis of a ¹¹ C-labeled tetrazine ([ ¹¹ C]AE-1) and its preliminary evaluation in both mice and pigs. Pretargeted imaging in mice was carried out using both a new TCO-functionalized polyglutamic acid and a previously reported TCO-functionalized bisphosphonate system as targeting agents. Unfortunately, pretargeted imaging was not successful using these targeting agents in pair with [ ¹¹ C]AE-1. However, brain imaging in pig indicated that the tracer crossed the blood-brain-barrier. Hence, we suggest that this tetrazine scaffold could be used as a starting point for the development of pretargeted brain imaging, which has so far been a challenging task.

Original language	English
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	29
Issue number	8
Pages (from-to)	986-990
ISSN	0960-894X
DOIs	https://doi.org/10.1016/j.bmcl.2019.02.014
Publication status	Published - 15 Apr 2019

Keywords

Carbon-11
PET imaging
Pretargeting
Tetrazine
Trans-cyclooctene

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Stéen, E. J. L., Jørgensen, J. T., Petersen, I. N., Nørregaard, K., Lehel, S., Shalgunov, V., Birke, A., Edem, P. E., L'Estrade, E. T., Hansen, H. D., Villadsen, J., Erlandsson, M., Ohlsson, T., Yazdani, A., Valliant, J. F., Kristensen, J. L., Barz, M., Knudsen, G. M., Kjær, A., & Herth, M. M. (2019). Improved radiosynthesis and preliminary in vivo evaluation of the ¹¹ C-labeled tetrazine [ ¹¹ C]AE-1 for pretargeted PET imaging. Bioorganic and Medicinal Chemistry Letters, 29(8), 986-990. https://doi.org/10.1016/j.bmcl.2019.02.014

Improved radiosynthesis and preliminary in vivo evaluation of the ¹¹ C-labeled tetrazine [ ¹¹ C]AE-1 for pretargeted PET imaging. / Stéen, E. Johanna L.; Jørgensen, Jesper T.; Petersen, Ida N. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 29, No. 8, 15.04.2019, p. 986-990.

Research output: Contribution to journal › Journal article › Research › peer-review

Stéen, EJL, Jørgensen, JT, Petersen, IN, Nørregaard, K, Lehel, S, Shalgunov, V, Birke, A, Edem, PE, L'Estrade, ET, Hansen, HD, Villadsen, J, Erlandsson, M, Ohlsson, T, Yazdani, A, Valliant, JF, Kristensen, JL, Barz, M, Knudsen, GM , Kjær, A & Herth, MM 2019, 'Improved radiosynthesis and preliminary in vivo evaluation of the ¹¹ C-labeled tetrazine [ ¹¹ C]AE-1 for pretargeted PET imaging', Bioorganic and Medicinal Chemistry Letters, vol. 29, no. 8, pp. 986-990. https://doi.org/10.1016/j.bmcl.2019.02.014

Stéen EJL, Jørgensen JT, Petersen IN, Nørregaard K, Lehel S, Shalgunov V et al. Improved radiosynthesis and preliminary in vivo evaluation of the ¹¹ C-labeled tetrazine [ ¹¹ C]AE-1 for pretargeted PET imaging. Bioorganic and Medicinal Chemistry Letters. 2019 Apr 15;29(8):986-990. doi: 10.1016/j.bmcl.2019.02.014

Stéen, E. Johanna L. ; Jørgensen, Jesper T. ; Petersen, Ida N. et al. / Improved radiosynthesis and preliminary in vivo evaluation of the ¹¹ C-labeled tetrazine [ ¹¹ C]AE-1 for pretargeted PET imaging. In: Bioorganic and Medicinal Chemistry Letters. 2019 ; Vol. 29, No. 8. pp. 986-990.

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title = "Improved radiosynthesis and preliminary in vivo evaluation of the 11 C-labeled tetrazine [ 11 C]AE-1 for pretargeted PET imaging",

abstract = " Pretargeted nuclear imaging based on the ligation between tetrazines and nano-sized targeting agents functionalized with trans-cyclooctene (TCO) has recently been shown to improve both imaging contrast and dosimetry in nuclear imaging of nanomedicines. Herein, we describe the improved radiosynthesis of a 11 C-labeled tetrazine ([ 11 C]AE-1) and its preliminary evaluation in both mice and pigs. Pretargeted imaging in mice was carried out using both a new TCO-functionalized polyglutamic acid and a previously reported TCO-functionalized bisphosphonate system as targeting agents. Unfortunately, pretargeted imaging was not successful using these targeting agents in pair with [ 11 C]AE-1. However, brain imaging in pig indicated that the tracer crossed the blood-brain-barrier. Hence, we suggest that this tetrazine scaffold could be used as a starting point for the development of pretargeted brain imaging, which has so far been a challenging task. ",

keywords = "Carbon-11, PET imaging, Pretargeting, Tetrazine, Trans-cyclooctene",

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AU - Stéen, E. Johanna L.

AU - Jørgensen, Jesper T.

AU - Petersen, Ida N.

AU - Nørregaard, Kamilla

AU - Lehel, Szabolcs

AU - Shalgunov, Vladimir

AU - Birke, Alexander

AU - Edem, Patricia E.

AU - L'Estrade, Elina T.

AU - Hansen, Hanne D.

AU - Villadsen, Jonas

AU - Erlandsson, Maria

AU - Ohlsson, Tomas

AU - Yazdani, Abdolreza

AU - Valliant, John F.

AU - Kristensen, Jesper L.

AU - Barz, Matthias

AU - Knudsen, Gitte M.

AU - Kjær, Andreas

AU - Herth, Matthias M.

PY - 2019/4/15

Y1 - 2019/4/15

N2 - Pretargeted nuclear imaging based on the ligation between tetrazines and nano-sized targeting agents functionalized with trans-cyclooctene (TCO) has recently been shown to improve both imaging contrast and dosimetry in nuclear imaging of nanomedicines. Herein, we describe the improved radiosynthesis of a 11 C-labeled tetrazine ([ 11 C]AE-1) and its preliminary evaluation in both mice and pigs. Pretargeted imaging in mice was carried out using both a new TCO-functionalized polyglutamic acid and a previously reported TCO-functionalized bisphosphonate system as targeting agents. Unfortunately, pretargeted imaging was not successful using these targeting agents in pair with [ 11 C]AE-1. However, brain imaging in pig indicated that the tracer crossed the blood-brain-barrier. Hence, we suggest that this tetrazine scaffold could be used as a starting point for the development of pretargeted brain imaging, which has so far been a challenging task.

AB - Pretargeted nuclear imaging based on the ligation between tetrazines and nano-sized targeting agents functionalized with trans-cyclooctene (TCO) has recently been shown to improve both imaging contrast and dosimetry in nuclear imaging of nanomedicines. Herein, we describe the improved radiosynthesis of a 11 C-labeled tetrazine ([ 11 C]AE-1) and its preliminary evaluation in both mice and pigs. Pretargeted imaging in mice was carried out using both a new TCO-functionalized polyglutamic acid and a previously reported TCO-functionalized bisphosphonate system as targeting agents. Unfortunately, pretargeted imaging was not successful using these targeting agents in pair with [ 11 C]AE-1. However, brain imaging in pig indicated that the tracer crossed the blood-brain-barrier. Hence, we suggest that this tetrazine scaffold could be used as a starting point for the development of pretargeted brain imaging, which has so far been a challenging task.

KW - Carbon-11

KW - PET imaging

KW - Pretargeting

KW - Tetrazine

KW - Trans-cyclooctene

U2 - 10.1016/j.bmcl.2019.02.014

DO - 10.1016/j.bmcl.2019.02.014

M3 - Journal article

C2 - 30795854

AN - SCOPUS:85061657259

SN - 0960-894X

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SP - 986

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 8

ER -

Improved radiosynthesis and preliminary in vivo evaluation of the 11 C-labeled tetrazine [ 11 C]AE-1 for pretargeted PET imaging

Abstract

Keywords

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Improved radiosynthesis and preliminary in vivo evaluation of the ¹¹ C-labeled tetrazine [ ¹¹ C]AE-1 for pretargeted PET imaging