Tetraxetan
[CAS# 60239-18-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Crown ether
• Name: Tetraxetan
• Synonyms: DOTA; 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid
• Molecular Formula: C₁₆H₂₈N₄O₈
• Molecular Weight: 404.42
• CAS Registry Number: 60239-18-1
• EC Number: 611-959-5
• SMILES: C1CN(CCN(CCN(CCN1CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O

Properties

• Density: 1.321±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.532, Calc.^*
• Boiling Point: 701.6±60.0 ºC (760 mmHg), Calc.^*
• Flash Point: 378.1±32.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H317-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Tetraxetan is a chemical compound used primarily in the field of radiopharmaceuticals. It is a ligand that forms stable complexes with metal ions, particularly with radiometals, and is used to create radiolabeled compounds for medical imaging and therapy. The compound is a member of a family of chelating agents, which are molecules that can bind metal ions to form a stable complex.

The primary application of Tetraxetan is in the development of radiopharmaceuticals for positron emission tomography (PET) and single-photon emission computed tomography (SPECT), which are non-invasive imaging techniques used in nuclear medicine. Tetraxetan's ability to form stable complexes with metal ions, such as gallium-68, copper-64, or other radionuclides, makes it an ideal candidate for use in these imaging modalities.

One of the most significant uses of Tetraxetan is in the radiolabeling of biomolecules, such as peptides or antibodies, which can then be tracked inside the body for diagnostic purposes. For instance, Tetraxetan can be attached to a peptide that binds to specific receptors on the surface of tumor cells, allowing for the visualization of tumors via PET or SPECT imaging. This targeted approach is valuable in oncology, where early detection of tumors and accurate imaging of tumor spread is crucial for treatment planning.

Additionally, Tetraxetan-based radiopharmaceuticals are being explored for therapeutic applications. The radiolabeled complexes can deliver radiation directly to cancer cells, offering a form of targeted radiotherapy. This is a promising area of research in nuclear medicine, as it allows for more precise treatment with potentially fewer side effects compared to traditional radiation therapy.

Tetraxetan's stability and versatility in forming complexes with various metal ions, including those used for both diagnostic and therapeutic purposes, make it an important compound in the ongoing development of molecular imaging and targeted radiotherapy.

In conclusion, Tetraxetan is a key component in the development of radiopharmaceuticals, particularly for use in imaging techniques like PET and SPECT. Its ability to bind metal ions and form stable complexes with radionuclides is a valuable tool in the diagnosis and treatment of diseases, especially in oncology.

References

2022. A self-triggered radioligand therapy agent for fluorescence imaging of the treatment response in prostate cancer. European Journal of Nuclear Medicine and Molecular Imaging, 49(8).
DOI: 10.1007/s00259-022-05743-7

2021. Synthesis of DOTA-pyridine chelates for 64Cu coordination and radiolabeling of αMSH peptide. EJNMMI Radiopharmacy and Chemistry, 6(1).
DOI: 10.1186/s41181-020-00119-4

2020. Ultrasonic-Assisted Solid-Phase Peptide Synthesis of DOTA-TATE and DOTA-linker-TATE Derivatives as a Simple and Low-Cost Method for the Facile Synthesis of Chelator-Peptide Conjugates. Bioconjugate Chemistry, 31(7).
DOI: 10.1021/acs.bioconjchem.0c00325