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86734

Sigma-Aldrich

1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid

≥97.0% (CHN)

Synonym(s):

DOTA

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About This Item

Empirical Formula (Hill Notation):
C16H28N4O8 · xH2O
CAS Number:
60239-18-1
Molecular Weight:
404.42 (anhydrous basis)
Beilstein:
1186987
MDL number:
MFCD00068657
UNSPSC Code:
12352005
PubChem Substance ID:
57653192
NACRES:
NA.22

Quality Level

100

Assay

≥97.0% (CHN)

form

powder

functional group

carboxylic acid

SMILES string

OC(=O)CN1CCN(CCN(CCN(CC1)CC(O)=O)CC(O)=O)CC(O)=O

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)

InChI key

WDLRUFUQRNWCPK-UHFFFAOYSA-N

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Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0148
BCCJ4712
BCCD5753
BCBV9132
BCBP6598V

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Preparation of carbon nanotube bioconjugates for biomedical applications.
Liu Z, et al.
Nature Protocols, 4(9), 1372-1372 (2009)
GdIII complexes with fast water exchange and high thermodynamic stability: potential building blocks for high-relaxivity MRI contrast agents.
Laus S, et al.
Chemistry?A European Journal , 9(15), 3555-3566 (2003)
An improved method for conjugating monoclonal antibodies with N-hydroxysulfosuccinimidyl DOTA.
Lewis MR, et al.
Bioconjugate Chemistry, 12(2), 320-324 (2001)
The synthesis and chelation chemistry of DOTA- peptide conjugates.
De Leon-Rodriguez LM and Kovacs Z
Bioconjugate Chemistry, 19(2), 391-402 (2007)
Luca Garbuio et al.
The journal of physical chemistry. B, 117(11), 3145-3153 (2013-02-28)
We present the first example of chemoselective site-specific spin labeling of a monomeric protein with two spectroscopically orthogonal spin labels: a gadolinium(III) chelate complex and a nitroxide radical. A detailed analysis of the performance of two commercially available Gd(III) ligands
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