306776-79-4

Usage

Uses

Used in Magnetic Resonance Imaging (MRI) Applications:
(R,S)-5-(tert-butoxy)-5-oxo-4-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)pentanoic acid is used as a key component in the synthesis of GdDOTAGA(C18)2, an efficient amphiphilic Gd(III) chelate. This chelate is essential for the preparation of self-assembled high relaxivity MRI nanoprobes, which are crucial for enhancing the contrast and resolution of MRI scans, allowing for better detection and diagnosis of various medical conditions.
Used in Radiopharmaceuticals:
In the field of radiopharmaceuticals, (R,S)-5-(tert-butoxy)-5-oxo-4-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)pentanoic acid serves as a bifunctional prochelator for coupling to bioactive peptides. This coupling enables radiometal labeling, which is vital for the development of targeted radiopharmaceuticals used in diagnostic and therapeutic applications, such as positron emission tomography (PET) and therapy of specific diseases.
Used in Chelating Agent Synthesis:
(R,S)-5-(tert-butoxy)-5-oxo-4-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)pentanoic acid is also utilized as a building block for the preparation of DOTAGA-anhydride. (R,S)-5-(tert-butoxy)-5-oxo-4-(4,7,10-tris(2-(tert-butoxy)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)pentanoic acid is a crucial intermediate in the synthesis of DOTA-like chelating agents, which are widely used in various applications, including the development of radiopharmaceuticals and contrast agents for medical imaging.

Upstream product

• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 212771-45-4 (S)-2-bromopentanedioic acid methyl ester 
• 87517-44-0 γ-methyl α-tert-butyl α-bromoglutarate 
• 95352-12-8 2-Bromo-pentanedioic acid 5-methyl ester 
• 1499-55-4 DL-glutamic acid-5-methyl ester 
• 306776-77-2 1-(1-carbobenzyloxy-3-carbotertbutoxypropyl)-1,4,7,10-tetraazacyclododecane 
• 306776-74-9 α-bromoglutaric acid 1-tert-butyl ester 5-benzyl ester 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 306776-78-3 1-(1-carbobenzyloxy-3-carbotertbutoxypropyl)-4,7,10-(carbotertbutoxymethyl)-1,4,7,10-tetraazacyclododecane 

Downstream Products

• 1393934-00-3 C₄₃H₆₉N₁₁O₁₇S 
• 1393934-06-9 C₅₉H₁₀₁N₁₁O₁₇S 

Relevant academic research and scientific papers

Combined Magnetic Resonance Imaging and Photodynamic Therapy Using Polyfunctionalised Nanoparticles Bearing Robust Gadolinium Surface Units

A robust dithiocarbamate tether allows novel gadolinium units based on DOTAGA (q=1) to be attached to the surface of gold nanoparticles (2.6–4.1 nm diameter) along with functional units offering biocompatibility, targeting and photodynamic therapy. A dram

Synthesis and Evaluation of 68Ga- And 177Lu-Labeled (R)- vs (S)-DOTAGA Prostate-Specific Membrane Antigen-Targeting Derivatives

Prostate-specific membrane antigen (PSMA) is overexpressed in prostate cancer cells and therefore is an attractive target for prostate cancer diagnosis and radionuclide therapy. Recently, published results from clinical studies using a new PSMA-targeting PET imaging agent, [68Ga]Ga-PSMA-093 ([68Ga]Ga-HBED-CC-O-carboxymethyl-Tyr-CO-NH-Glu), support the development of this agent for the diagnosis of prostate cancer. In this study, the HBED-CC chelating group in PSMA-093 was replaced by stereoselective (R)- or (S)-DOTAGA. This chelating group serves not only for chelating 68Ga but is also amendable for complexing other radioactive metals for radionuclide therapy. The corresponding optically pure (R)- and (S)-[68Ga/177Lu]-DOTAGA derivatives, (R)-[68Ga/177Lu]-13 and (S)-[68Ga/177Lu]-13, were successfully prepared. Comparison of radiolabeling, binding affinity, cell uptake, and biodistribution between the two isomers was performed. Radiolabeling of (R)-[177Lu]Lu-13 and (S)-[177Lu]Lu-13 at 50 °C suggested that rates of complex formation were time-dependent and the formation of (S)-[177Lu]Lu-13 was distinctly faster. The rates of complex formation for the corresponding 68Ga agents were comparable between structural isomers. The natGa and natLu equivalents showed high binding PSMA affinity (IC50 = 24-111 nM), comparable to that of the parent agent, [natGa]Ga-PSMA-093 (IC50 = 34.0 nM). Results of cell uptake and biodistribution studies in PSMA-expressing PC3-PIP tumor-bearing mice appeared to show no difference between the labeled (R)- and (S)-isomers. This is the first time that a pair of [68Ga/177Lu]-(R)- and (S)-DOTAGA isomers of PSMA agents were evaluated. Results of biological studies between the isomers showed no noticeable difference; however, the distinctions on the rate of Lu complex formation should be considered in the development of new 177Lu-DOTAGA-based radionuclide therapy agents in the future.

A convenient synthesis of novel bifunctional prochelators for coupling to bioactive peptides for radiometal labelling

New DOTA-based bifunctional prochelators, e.g., 1-(1-carboxy-3-carbotertbutoxypropyl)-4,7,10-(carbotertbutoxymethyl)-1,4,7,10 -tetraazacyclodode-cane (DOTAGA(tBu)4), (6d) for a broad application in the modification of biomolecules with metal ions were prepared. The five-step synthesis of 6d has an overall yield of about 20%. The coupling of 6d to a bioactive peptide on solid-phase was exemplified with use of a CCK-B (cholecystokinin) analogue. (C) 2000 Elsevier Science Ltd.