Synthesis and Radiolabeling of a polar [125 I]I-1,2,4,5-Tetrazine

Natasha Bidesi; Vladimir Shalgunov; Umberto Maria Battisti; Lars Hvass; Jesper Tranekjaer Jørgensen; Christian B M Poulie; Andreas I Jensen; Andreas Kjaer; Matthias M Herth

doi:10.1002/jlcr.4009

Synthesis and Radiolabeling of a polar [125 I]I-1,2,4,5-Tetrazine

Natasha Bidesi, Vladimir Shalgunov, Umberto Maria Battisti, Lars Hvass, Jesper Tranekjaer Jørgensen, Christian B M Poulie, Andreas I Jensen, Andreas Kjaer, Matthias M Herth^*

^*Corresponding author for this work

Department of Clinical Physiology, Nuclear Medicine & PET

Abstract

Pretargeting imaging has gained a lot of prominence, due to its excellent bioorthogonality and improved imaging contrast compared to conventional imaging. A new iodo tetrazine (Tz) derivative has been synthesized and further developed into the corresponding iodine-125 (125 I) analog (12), via the trimethylstannane precursor. Radiolabeling with either N-chlorosuccinimide or chloramine-T, in either MeCN or MeOH proceeded with a radiochemical conversion (RCC) of >80%. Subsequent deprotection only proved successful, among the tested conditions, when the radiolabeled Tz was stirred in 6-M HCl(aq.) at 60°C for 2.5 h. To the best of our knowledge, this is the first H-tetrazine labeled with iodine. In vivo investigations on the pretargeting ability of 12 are currently under way.

Original language	English
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	66
Issue number	1
Pages (from-to)	22-30
Number of pages	9
ISSN	0362-4803
DOIs	https://doi.org/10.1002/jlcr.4009
Publication status	Published - Jan 2023

Keywords

Cell Line, Tumor
Click Chemistry/methods
Heterocyclic Compounds
Iodine Radioisotopes
Radiopharmaceuticals
idodine-125
pretargeting
click chemistry
bioorthogonal
tetrazine

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title = "Synthesis and Radiolabeling of a polar [125 I]I-1,2,4,5-Tetrazine",

abstract = "Pretargeting imaging has gained a lot of prominence, due to its excellent bioorthogonality and improved imaging contrast compared to conventional imaging. A new iodo tetrazine (Tz) derivative has been synthesized and further developed into the corresponding iodine-125 (125 I) analog (12), via the trimethylstannane precursor. Radiolabeling with either N-chlorosuccinimide or chloramine-T, in either MeCN or MeOH proceeded with a radiochemical conversion (RCC) of >80%. Subsequent deprotection only proved successful, among the tested conditions, when the radiolabeled Tz was stirred in 6-M HCl(aq.) at 60°C for 2.5 h. To the best of our knowledge, this is the first H-tetrazine labeled with iodine. In vivo investigations on the pretargeting ability of 12 are currently under way.",

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author = "Natasha Bidesi and Vladimir Shalgunov and Battisti, {Umberto Maria} and Lars Hvass and J{\o}rgensen, {Jesper Tranekjaer} and Poulie, {Christian B M} and Jensen, {Andreas I} and Andreas Kjaer and Herth, {Matthias M}",

year = "2023",

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doi = "10.1002/jlcr.4009",

language = "English",

volume = "66",

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AU - Bidesi, Natasha

AU - Shalgunov, Vladimir

AU - Battisti, Umberto Maria

AU - Hvass, Lars

AU - Jørgensen, Jesper Tranekjaer

AU - Poulie, Christian B M

AU - Jensen, Andreas I

AU - Kjaer, Andreas

AU - Herth, Matthias M

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N2 - Pretargeting imaging has gained a lot of prominence, due to its excellent bioorthogonality and improved imaging contrast compared to conventional imaging. A new iodo tetrazine (Tz) derivative has been synthesized and further developed into the corresponding iodine-125 (125 I) analog (12), via the trimethylstannane precursor. Radiolabeling with either N-chlorosuccinimide or chloramine-T, in either MeCN or MeOH proceeded with a radiochemical conversion (RCC) of >80%. Subsequent deprotection only proved successful, among the tested conditions, when the radiolabeled Tz was stirred in 6-M HCl(aq.) at 60°C for 2.5 h. To the best of our knowledge, this is the first H-tetrazine labeled with iodine. In vivo investigations on the pretargeting ability of 12 are currently under way.

AB - Pretargeting imaging has gained a lot of prominence, due to its excellent bioorthogonality and improved imaging contrast compared to conventional imaging. A new iodo tetrazine (Tz) derivative has been synthesized and further developed into the corresponding iodine-125 (125 I) analog (12), via the trimethylstannane precursor. Radiolabeling with either N-chlorosuccinimide or chloramine-T, in either MeCN or MeOH proceeded with a radiochemical conversion (RCC) of >80%. Subsequent deprotection only proved successful, among the tested conditions, when the radiolabeled Tz was stirred in 6-M HCl(aq.) at 60°C for 2.5 h. To the best of our knowledge, this is the first H-tetrazine labeled with iodine. In vivo investigations on the pretargeting ability of 12 are currently under way.

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KW - Iodine Radioisotopes

KW - Radiopharmaceuticals

KW - idodine-125

KW - pretargeting

KW - click chemistry

KW - bioorthogonal

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JO - Journal of Labelled Compounds and Radiopharmaceuticals

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Synthesis and Radiolabeling of a polar [125 I]I-1,2,4,5-Tetrazine

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Keywords

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