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| Other Sizes |
| Targets |
As a protected chelator, DOTA-tri(t-butyl ester) itself does not have a specific biological target or mechanism of action. Its primary function is as a chemical precursor and a bifunctional chelator. Upon removal of the tert-butyl protecting groups, the resulting DOTA molecule can chelate metal ions with exceptionally high thermodynamic stability and kinetic inertness. This property makes the deprotected DOTA an ideal vehicle for delivering radioactive or paramagnetic metal ions to biological targets when conjugated to targeting vectors such as peptides, antibodies, or small molecules. The compound's utility lies entirely in its chemical reactivity and its role as a building block for creating diagnostic and therapeutic agents.
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| ln Vitro |
In vitro activity is not applicable to DOTA-tri(t-butyl ester) as it is not a biologically active molecule. Its "activity" is chemical, referring to its ability to undergo deprotection reactions and to chelate metal ions after the protecting groups are removed. The compound's performance is assessed by its purity, its reactivity in conjugation and deprotection steps, and the stability of the metal complexes formed from the deprotected product. It is a key raw material for synthesizing nanospherical MRI contrast agents and for labeling peptides with trivalent metallic isotopes for imaging applications.
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| ln Vivo |
In vivo activity is not applicable to DOTA-tri(t-butyl ester) as it is a synthetic intermediate, not a therapeutic or diagnostic agent. Any in vivo effects are associated with the final metal-chelated conjugates synthesized from it, such as MRI contrast agents or radiopharmaceuticals. For example, when conjugated to a targeting antibody and labeled with a radionuclide like 177Lu, the resulting agent can be used for targeted radiotherapy in vivo. The chelator's role is to ensure the stable retention of the metal ion within the body, preventing its release and associated toxicity.
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| Enzyme Assay |
The compound is used as a chemical reagent in organic synthesis. A typical experimental procedure involves its use in peptide conjugation reactions. The DOTA-tri(t-butyl ester) is first activated and coupled to a peptide or other targeting molecule, followed by deprotection of the tert-butyl ester groups using trifluoroacetic acid (TFA). The resulting DOTA-conjugate is then purified and chelated with a metal ion of interest, such as Gd3+ or 177Lu3+, in an appropriate buffer. The chelation efficiency and stability are assessed using analytical techniques like HPLC or radio-TLC.
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| Cell Assay |
Cellular assays are not applicable for DOTA-tri(t-butyl ester) itself. However, the final DOTA-metal complexes and DOTA-conjugates are used in cell-based studies to evaluate their targeting specificity and cellular uptake. For instance, a DOTA-conjugated antibody labeled with a fluorescent or radioactive metal can be incubated with cancer cells expressing the target antigen. The binding and internalization of the conjugate are then assessed using flow cytometry, fluorescence microscopy, or gamma counting.
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| Animal Protocol |
Animal studies are not conducted with the protected chelator DOTA-tri(t-butyl ester). Instead, the final imaging or therapeutic agents containing the deprotected DOTA-metal complex are evaluated in vivo. Typical experiments involve administering the radiolabeled or paramagnetic conjugate to tumor-bearing mice and performing imaging studies (e.g., PET/CT, MRI) or biodistribution analysis. The stability of the metal-chelate complex in vivo is a critical parameter assessed in these studies.
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| ADME/Pharmacokinetics |
DOTA-tri(t-butyl ester) has a molecular weight of 572.73 g/mol and a molecular formula of C28H52N4O8. It is a white to off-white crystalline solid. The compound is soluble in DMSO (50 mg/mL, 87.30 mM) and is typically stored at 4°C, protected from light and under nitrogen for long-term stability. For in vivo formulations, it can be dissolved in a mixture of 10% DMSO, 40% PEG300, 5% Tween-80, and 45% saline, achieving a solubility of ≥2.5 mg/mL (4.37 mM).
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| Toxicity/Toxicokinetics |
As a chemical reagent, DOTA-tri(t-butyl ester) is not intended for human or veterinary use. It should be handled with standard laboratory safety precautions, including the use of appropriate personal protective equipment (PPE) and working in a well-ventilated area. Specific toxicological data for this protected chelator are not typically detailed, as its toxicity is primarily associated with the metal ions it chelates rather than the chelator itself. The compound is classified under WGK Germany 3, indicating it is highly hazardous to water.
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| References | |
| Additional Infomation |
DOTA-tri(t-butyl ester) is a research-grade chemical extensively used in the development of radiopharmaceuticals and MRI contrast agents. It is a key raw material for the synthesis of nanospherical magnetic resonance imaging (MRI) contrast agents used in MR angiography and tumor angiogenesis imaging. The compound's tert-butyl protecting groups provide unique reactivity in non-aqueous solvents, allowing for selective deprotection and conjugation. Compared to other chelating agents, the complexes formed by DOTA and metals are more stable thermodynamically and kinetically, making it suitable for in vivo labeling of peptides and antibodies. It is not an approved drug and is strictly for research purposes.
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| Molecular Formula |
C28H52N4O8
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|---|---|
| Molecular Weight |
572.73
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| Exact Mass |
572.378
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| CAS # |
137076-54-1
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| PubChem CID |
11606627
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| Appearance |
White to off-white solid powder
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| Density |
1.079
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| Boiling Point |
632.1±55.0 °C at 760 mmHg
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| Melting Point |
129-131 ºC
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| Flash Point |
336.1±31.5 °C
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| Vapour Pressure |
0.0±4.0 mmHg at 25°C
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| Index of Refraction |
1.480
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| LogP |
3.76
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
14
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| Heavy Atom Count |
40
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| Complexity |
799
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(C)OC(=O)CN1CCN(CCN(CCN(CC1)CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)CC(=O)O
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| InChi Key |
RVUXZXMKYMSWOM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C28H52N4O8/c1-26(2,3)38-23(35)19-30-12-10-29(18-22(33)34)11-13-31(20-24(36)39-27(4,5)6)15-17-32(16-14-30)21-25(37)40-28(7,8)9/h10-21H2,1-9H3,(H,33,34)
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| Chemical Name |
2-[4,7,10-tris[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 50 mg/mL (87.30 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.37 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.37 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (4.37 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7460 mL | 8.7301 mL | 17.4602 mL | |
| 5 mM | 0.3492 mL | 1.7460 mL | 3.4920 mL | |
| 10 mM | 0.1746 mL | 0.8730 mL | 1.7460 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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