DOTA Chemical Properties

Melting point:

267 °C

Boiling point:

701.6±60.0 °C(Predicted)

Density 

1.321

storage temp. 

Sealed in dry,Room Temperature

solubility 

Water (Slightly, Heated), Methanol (Slightly)

pka

2.16±0.10(Predicted)

form 

Powder

color 

white

BRN 

1186987

Stability:

Hygroscopic

InChI

InChI=1S/C16H28N4O8/c21-13(22)9-17-1-2-18(10-14(23)24)5-6-20(12-16(27)28)8-7-19(4-3-17)11-15(25)26/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28)

InChIKey

WDLRUFUQRNWCPK-UHFFFAOYSA-N

SMILES

N1(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

3-10-34

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

DOTA Usage And Synthesis

Chemical Properties

Colourless crystals

Uses

1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) is a macrocyclic complexing agent.

• It has been used for radiolabeling of carbon nanotube bioconjugates by chelating ⁶⁴Cu radioisotope.
• DOTA can be activated with N-hydroxysulfosuccinimidyl for conjugation with monoclonal antibodies in clinical radioimmunotherapy.
• It can form complexes with gadolinium for application as MRI contrast agents.
• Metal complexes of DOTA-peptide conjugates can be used as therapeutic radiopharmaceuticals.

Uses

Bifunctional DOTA aconjugates to peptides and has become an established strategy for constructing target-specific metal containing agents including targeted MRI contrast agents and diagnostic and ther apeutic radiopharmaceuticals.

Definition

ChEBI: An azamacrocyle in which four nitrogen atoms at positions 1, 4, 7 and 10 of a twelve-membered ring are each substituted with a carboxymethyl group.

Synthesis

To a three-necked flask, 1,4,7,10-tetraazacyclododecane (100 g, 0.58 mol) and 10 ml of deionized water were added and mixed with stirring. The pH of the reaction system was adjusted to 8.5 by slow dropwise addition of 30% potassium hydroxide solution.Subsequently, chloroacetic acid (263 g, 2.78 mol) was added and the pH was adjusted again to 8.5 using 30% potassium hydroxide solution.The reaction mixture was heated to 80 °C and kept for 24 h, during which time the pH was continually monitored and adjusted to maintain a pH value between 8.5 and 9. After completion of the reaction, it was cooled to room temperature and the pH was adjusted to 2 by adding concentrated hydrochloric acid, at which time a white precipitate was produced. The precipitate was collected by filtration and the filter cake was recrystallized from a mixed water-ethanol solution. The resulting crystals were washed with ethanol and ether in turn, and 183 g of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) crystals were obtained after drying with a yield of 78%.

References

[1] Journal of Labelled Compounds and Radiopharmaceuticals, 2003, vol. 46, # 3, p. 197 - 209
[2] Dalton Transactions, 2016, vol. 45, # 23, p. 9553 - 9564
[3] Patent: WO2014/114664, 2014, A1. Location in patent: Page/Page column 28-29
[4] Patent: WO2015/117911, 2015, A1. Location in patent: Paragraph 0081; 0082; 0083; 0084
[5] Patent: CN104447598, 2017, B. Location in patent: Paragraph 0096; 0098; 0099

DOTA(60239-18-1)Related Product Information

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