Basic information
- CAS
60239-18-1- Standard SMILES
O=C(O)CN1CCN(CC(=O)O)CCN(CC(=O)O)CCN(CC(=O)O)CC1- InChIKey
WDLRUFUQRNWCPK-UHFFFAOYSA-N- Molecular formula
- C16H28N4O8
- Average molar mass
- 404.42 g/mol
- Monoisotopic mass
- 404.19071386
Overview
DOTA is 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. It has a role as a copper chelator and a chelator. It derives from a hydride of a 1,4,7,10-tetraazacyclododecane.
Names & identifiers
- Preferred name
- Dota
- IUPAC
- 2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
- English name
- DOTA
- Molecular formula
- C16H28N4O8
- Molecular weight
- 404.42
Names & synonyms
DOTATetraxetan60239-18-11,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acidDota acid2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid1,4,7,10-Tetraazacyclododecane-N,N',N'',N'''-tetraacetic acid1,4,7,10-Dota2,2',2'',2'''-(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetraacetic acidDOT-A1HTE449DGZNSC-681107
Show more names
TETRAAZA1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetrakisacetic acid2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetic acid98% DOTADOTADOTANSC 681107
CHEBI:61028DTXSID602089842,2',2'',2'''-(1,4,7,10-TETRAAZACYCLODODECANE-1,4,7,10-TETRYL)TETRAACETIC ACID2-(4,7,10-tris(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl)acetic acidRefChem:188911DTXCID101314751,4,7,10-Tetraazacyclododecane--N,N',N'',N'''-tetraacetic acidMFCD00068657
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- -10.6
- Topological polar surface area
- 162 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 8
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 447
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Chelating Agents
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Physical DescriptionLight yellow hygroscopic powder; [Aldrich MSDS]
Physicochemical properties
- Melting point
- 267 °C · 267 °C
- Boiling point
- 701.6 · 701.6±60.0 °C(Predicted)
- Density
- 1.321 · 1.321
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Water (Slightly, Heated), Methanol (Slightly)
- pka
- 2.16 · 2.16±0.10(Predicted)
- form
- Powder
- color
- white
- BRN
- 1186987 · 1186987
- Stability
- Hygroscopic
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (91.1%): Causes skin irritation [Warning Skin corrosion/irritation]
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, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 56 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 29-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/21563
Hazards SummaryAn irritant; [Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (91.1%)
Safety data
- F
- 3-10-34
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationChemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >1000
Applications
Uses1,4,7,10-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.
UsesBifunctional 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.
Upstream & downstream products
Upstream raw materials
Related reactions
9 records
Compound notes
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