157599-02-5

Basic information

• Product Name: 1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane
• Synonyms: 1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane;2,2',2'',2'''-(1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetrayl)tetraacetamide;1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetamide
• CAS NO: 157599-02-5
• Molecular Formula: C16H32N8O4
• Molecular Weight: 400.48
• Mol File: 157599-02-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 767.394 °C at 760 mmHg
• Flash Point: 417.905 °C
• Appearance: /
• Density: 1.211 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Water (Slightly, Heated, Sonicated)
• PKA: 15.76±0.40(Predicted)
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane(157599-02-5)
• EPA Substance Registry System: 1,4,7,10-Tetrakis(aminocarbonylmethyl)-1,4,7,10-tetraazacyclododecane(157599-02-5)

Safety Data

• Hazardous Substances Data: 157599-02-5(Hazardous Substances Data)

Usage

Uses

DOTAM, can be used in the prepataion of Gadolinium(III) Complexes for Magnetic Resonance Imaging (MRI).

InChI:InChI=1/C16H32N8O4/c17-13(25)9-21-1-2-22(10-14(18)26)5-6-24(12-16(20)28)8-7-23(4-3-21)11-15(19)27/h1-12H2,(H2,17,25)(H2,18,26)(H2,19,27)(H2,20,28)

Upstream product

• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 79-07-2 Chloroacetamide 
• 683-57-8 bromo-acetic acid amide 

Relevant articles and documents

The amide oxygen as a donor group. Metal ion complexing properties of tetra-N-acetamide substituted cyclen: A crystallographic, NMR, molecular mechanics, and thermodynamic study

The syntheses of the octadentate ligand DOTAM (1,4,7,10-tetrakis(acetamido)-1,4,7,10-cyclododecane) and its complexes with Zn(II), Cd(II), and Ca(II) are described. Crystal structures of [Cd(DOTAM)](ClO4)2 · 1.5H2O (1), [Ca(DOTAM)](ClO4)2 · 2.5H2O (2), and [Zn(DOTAM)](ClO4)2 · H2O (3) are reported. Crystal data: (1) monoclinic, space group Cc, a = 11.908(2) A?, b = 21.237(3) A?, c = 11.445(2) A?, β= 102.15(1)° (2) monoclinic, P21/c, a = 14.031(9) A?, b = 11.469(8) A?, c = 17.448 A?, β = 92.10(1)°; (3) triclinic, space group P1, a = 9.490(1) A?, b = 12.464(2) A?, c = 12.998(2) A?, α = 99.070(1)°, β= 107.67(1)°, and γ = 108.24(1)°. There is an unusual distortion in the coordination geometry of the complexes. There are two sets of metal-to-oxygen bond lengths for each complex; Zn(II) has two oxygens, placed opposite each other in the approximately square arrangement defined by the four oxygen donor atoms at about 2.19 A? and two at 3.23 A, Cd(II) has two at 2.34 and two at 2.64 A?, and Ca(II) has two at 2.40 A? and two at 2.42 A?. Molecular mechanics calculations suggest the Cd(II) and Zn(II) structures represent six coordination of four nitrogens and two of the oxygens, while the two long bonds represent van der Waals contacts with a possible electrostatic component. Approach of the oxygen donors to the metal ion is controlled by the van der Waals radii of the oxygens. 13C NMR studies give rates of helicity interchange of the complexes Zn(II) > Hg(II) > Cd(II) > Ca(II) ? Pb(II). This order is discussed in terms of the difference in bond lengths between the two sets of oxygen donors. A stability constant study gave logK1 values in 0.1 M NaNO3 and 25 °C: Cu(II), 16.3; Zn(II), 10.47; Ca(II), 7.54; Sr(II), 6.67; Ba(II), 5.35; Hg(II), 14.53; La(III), 10.35; Gd(III), 10.05. For Cd(II) and Pb(II), the complexes were fully formed even at pH 0.3, and only a lower limit of 19 for logK1 could be set. Selectivity of DOTAM for metal ions is discussed in terms of coordinating properties of the amide oxygen donor and geometric requirements of the DOTAM ligand.

DOTA-Branched Organic Frameworks as Giant and Potent Metal Chelators

Multinuclear complexes as metallo-agents for clinical use have caught extensive attention. In this paper, using 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) as both a functioning unit and a constructing junction, we build a series of DOTA-branched organic frameworks with multiple chelating holes by organizing DOTA layer by layer. These giant chelators are well characterized, which reveals their nanosized and soft structures. Further experiments demonstrate that they could efficiently hold abundant metal ions with much higher kinetic stabilities than the conventional small DOTA chelator. Their corresponding polynuclear complexes containing Gd3+, Tb3+, or both show superior imaging properties, excellent feasibility for peripheral modification, and unusual kinetic stability. This work can be easily extended to the fabrication of diverse homomultinuclear complexes and core/shell heteromultinuclear complexes with multifunctional properties. We expect that this new type of giant molecules and the ligand-branching strategy would open up a new avenue for the design and construction of next-generation polymetallic agents with high performance and stabilities for biomedical applications.

Stability Enhancement of Heavy-metal-Macrocycle Complexes via Pendant Amide Coordination

Formation of the pendant-arm macrocyclic ligand 1,4,7,10-tetrakis(carbamoylmethyl)-1,4,7,10-tetraazacyclododecane L and subsequent generation of its cadmium(II) complex indicates very significant stabilisation of the complex, compared to that observed for related macrocyclic cadmium(II) complexes, which either lack pendant donors altogether, or have other types of neutral oxygen donors attached to the macrocycle, and compared to complexes of L with lighter metal ions.

Modulation of the lifetime of water bound to lanthanide metal ions in complexes with ligands derived from 1,4,7,10-tetraazacyclododecane tetraacetate (DOTA)

A series of di- and tetraamide derivatives of DOTA were synthesized, and their lanthanide(III) complexes were examined by multinuclear 1H-, 13C-, and 17O-NMR spectroscopy, and compared with literature data of similar, know