175854-39-4

Basic information

• Product Name: 1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane
• Synonyms: 1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane;1,4,7-Tri-Boc-1,4,7,10-tetraazacyclododecane;Tri-tert-butyl 1,4,7,10-tetraazacyclotetradecane-1,4,7-tricarboxylate;N,N',N''-tris-Boc-cyclen;1,4,7,10-Tetraazacyclododecane-1,4,7-tricarboxylic acid, tris(1,1-diMethylethyl) ester;TriBoc-Cyclen;Tri-tert-Butyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate;1,4,7,10-Tetraazacyclododecane-1,4,7-tricarboxylic acid, 1,4,7-tris(1,1-dimethylethyl) ester
• CAS NO: 175854-39-4
• Molecular Formula: C₂₃H₄₄N₄O₆
• Molecular Weight: 472.63
• Mol File: 175854-39-4.mol
• Article Data: 44

Chemical Properties

• Melting Point: 72-73℃
• Boiling Point: 541.1°Cat760mmHg
• Flash Point: 281°C
• Appearance: /
• Density: 1.065
• Vapor Pressure: 9E-12mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: 2-8°C
• PKA: 9.52±0.20(Predicted)
• Sensitive: Hygroscopic
• CAS DataBase Reference: 1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane(175854-39-4)
• EPA Substance Registry System: 1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane(175854-39-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 175854-39-4(Hazardous Substances Data)

Usage

Description

1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane is a white powder chemical compound that serves as a crucial building block in the synthesis of various molecular structures. It is particularly useful for attaching the Cyclen azacrown to a molecular scaffold and for creating a trifold cyclen Zn complex that acts as a phosphate dianion receptor in aqueous solutions.

Uses

Used in Chemical Synthesis:
1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane is used as a building block for attaching the Cyclen azacrown to a molecular scaffold. This application is essential for creating complex molecular structures with specific functions and properties.
Used in Coordination Chemistry:
In coordination chemistry, 1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane is used as a building block for a trifold cyclen Zn complex. This complex serves as a phosphate dianion receptor in aqueous solutions, making it a valuable tool for studying and manipulating interactions between metal ions and biological molecules.
Used in Pharmaceutical Industry:
The compound may also find applications in the pharmaceutical industry, where it can be utilized in the development of new drugs or drug delivery systems that target specific biological receptors or pathways.
Used in Material Science:
1,4,7-tris-Boc-1,4,7,10-tetraaza-cyclododecane could potentially be used in material science to create novel materials with unique properties, such as improved stability or selectivity in chemical reactions.

InChI:InChI=1/C23H44N4O6/c1-21(2,3)18(28)33-27-13-11-24-10-12-25(19(29)31-22(4,5)6)14-15-26(16-17-27)20(30)32-23(7,8)9/h24H,10-17H2,1-9H3

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 188903-14-2 1-benzyloxycarbonyl-4,7,10-tris-tert-butoxycarbonyl-1,4,7,10-tetraazacyclododecane 
• 52667-88-6 cyclen tetratosylate 
• 10045-25-7 1,4,7,10-tetraazacyclododecane tetrahydrochloride 

Downstream Products

• 175854-41-8 1,1'-phthaloylbis<4,7,10-tris(tert-butyloxycarbonyl)-1,4,7,10-tetraazacyclododecane> 
• 188903-14-2 1-benzyloxycarbonyl-4,7,10-tris-tert-butoxycarbonyl-1,4,7,10-tetraazacyclododecane 
• 390362-13-7 1,3-bis(1,4,7-tris[tert-butyloxycarbonyl]-1,4,7,10-tetraaza-cyclododecan-1-yl)-4,6-dinitro-benzene 
• 1349904-86-4 1,1,3,3-tetraphenylyloxy-5,5-bis[4-(1,4,7,10-(1,4,7-tricarboxylic acid tri-tert-butyl)tetraazacyclododecanyl)methylphenoxy]cyclotriphosphazene 
• 1369793-87-2 C₆₃H₁₀₄N₈O₁₄ 
• 1369793-88-3 C₆₄H₁₀₆N₈O₁₄ 
• 1369793-91-8 C₆₅H₁₀₈N₈O₁₄ 
• 1369793-93-0 C₆₆H₁₁₀N₈O₁₄ 
• 1266708-40-0 10-(4-{2-[(4-benzothiazol-2-yl-phenyl)methylamino]ethoxy}-6-chloro-[1,3,5]triazin-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylic acid tri-tert-butyl ester 

Relevant articles and documents

Fuel-Selective Transient Activation of Nanosystems for Signal Generation

The transient activation of function using chemical fuels is common in nature, but much less in synthetic systems. Progress towards the development of systems with a complexity similar to that of natural ones requires chemical fuel selectivity. Here, we show that a self-assembled nanosystem, composed of monolayer-protected gold nanoparticles and a fluorogenic peptide, is activated for transient signal generation only in case the chemical fuel matches the recognition site present at the nanoparticle surface. A modification of the recognition site in the nanosystem completely changes the chemical fuel selectivity. When two nanosystems are simultaneously present, the selectivity expressed by the system depends on the concentration of nucleotide added.

Dinuclear macrocyclic polyamine zinc(II) complexes linked with flexible spacers: Synthesis, characterization, and DNA cleavage

Dinuclear macrocyclic polyamine zinc(II) complexes, which have two cyclen groups linked by flexible spacers, have been synthesized as DNA cleavage agents. The structures of these new dinuclear complexes are consistent with the data obtained from elemental analysis, MS and 1H NMR spectroscopy. The catalytic activity of these dinuclear complexes on DNA cleavage was studied. The results showed that the dinuclear zinc(II) complexes can catalyze the cleavage of supercoiled DNA (pUC 19 plasmid DNA) (Form I) under physiological conditions to produce selectively nicked DNA (Form II).

Synthesis of calix[4]arene-cyclen conjugates

Novel calix[4]arene derivatives constrained in the cone or 1,3-alternate conformations, bearing one or two cyclen (1,4,7,10-tetraazacyclododecane) moieties directly connected to the upper rim, have been synthesized using Buchwald-Hartwig coupling reaction. The complexation ability and hydrolytic activities of selected Zn(II) complexes of these calixarenes were studied. Although the attempts to hydrolyze activated phosphodiester bonds were unsuccessful, the NMR titration experiments revealed binding affinity for chloride, acetate, and benzoate anions in defined stoichiometry.

Vesicles and micelles from amphiphilic Zinc(II)-cyclen complexes as highly potent promoters of hydrolytic DNA cleavage

Phosphate esters are essential to any living organism and their specific hydrolysis plays an important role in many metabolic processes. As phosphodiester bonds can be extraordinary stable, as in DNA, great effort has been put into mimicking the active sites of hydrolytic enzymes which can easily cleave these linkages and were often found to contain one or more coordinated metal ions. With this in mind, we report micellar and vesicular Zn(II)-cyclen complexes which considerably promote the hydrolytic cleavage of native DNA and the activated model substrate bis(4-nitrophenyl)phosphate (BNPP). They are formed by self-assembly from amphiphilic derivatives of previously employed complexes in aqueous solution and therefore allow a simple and rapid connection of multiple active metal sites without great synthetic effort. Considering the hydrolytic cleavage of BNPP at 25 °C and pH 8, the micellar and vesicular metal catalysts show an increase of second-order rate constants (k2) by 4-7 orders of magnitude compared to the unimolecular complexes under identical conditions. At neutral pH, they produce the highest k2 values reported so far. For pBR322 plasmid DNA, both a conversion of the supercoiled to the relaxed and linear form, and also a further degradation into smaller fragments by double strand cleavages could be observed after incubation with the vesicular Zn(II)-complexes. Finally, even the cleavage of nonactivated single-stranded oligonucleotides could be considerably promoted compared to background reaction.

Coordination chemistry of a mono-dibenzofuran derivative of 1,4,7,10-tetraazacyclododecane

Copper(II) and cadmium(II) complex of a mono-dibenzofuran derivative of 1,4,7,10-tetraazacyclododecane (cyclen), L1, have been prepared by reaction of the mono-dibenzofuran-substituted cyclen with either copper(II) or cadmium(II) perchlorate in acetonitrile. This yielded the corresponding divalent metal complexes, [Cu(L1)](ClO4)2·H2O (C1) and [Cd(L1)](ClO4)2·H2O (C2), which were isolated as single crystals suitable for X-ray crystallography by diffusing diethyl ether into an acetonitrile solution of each complex. For the copper(II) complex, C1, the X-ray crystal structure revealed a distorted square pyramidal Cu(II) coordination sphere occupied by four amine nitrogens from the cyclen ring and one oxygen from the amide linkage present in L1. On the other hand, the metal center in the cadmium complex is seven coordinate, with two weakly bound acetonitrile molecules occupying two additional coordination sites about the Cd(II) center; these bind cis to the amide oxygen. The coordination geometry is best described as monocapped trigonal prismatic. In both complexes, the secondary amine nitrogens on the cyclen macrocycle form hydrogen bonds with perchlorate counterions present in the crystal lattice. Titration of L1 with various metal ions (Mn2+, Co2+, Ni2+, Cu2+, Zn2+, and Cd2+) in acetonitrile revealed a gradual quenching of the benzofuran emission with increasing [M2+] consistent with formation of metal complexes with a 1: 1 M2+: L1 stoichiometry. From the emission data, the conditional stability constant was determined to be 10-20 times higher for the Cu(II) complex than the other divalent metal complexes investigated.

Cooperative self-assembly of adenosine and uridine nucleotides on a 2D synthetic template

(Figure Presented) Double plane: Base pairing mediates sterically induced, cooperative self-assembly of complementary nucleotides on a template formed from amphiphilic bis(ZnII-cyclen) derivatives ordered on thiolated surface. Real-time monitoring of binding events proved precise harboring of equal amounts of A and U nucleotides from their arbitrary combinations in solution into planar bilayers (see picture).

Cu(II)-Based Paramagnetic Probe to Study RNA-Protein Interactions by NMR

Paramagnetic NMR techniques allow for studying three-dimensional structures of RNA-protein complexes. In particular, paramagnetic relaxation enhancement (PRE) data can provide valuable information about long-range distances between different structural components. For PRE NMR experiments, oligonucleotides are typically spin-labeled using nitroxide reagents. The current work describes an alternative approach involving a Cu(II) cyclen-based probe that can be covalently attached to an RNA strand in the vicinity of the protein's binding site using "click" chemistry. The approach has been applied to study binding of HIV-1 nucleocapsid protein 7 (NCp7) to a model RNA pentanucleotide, 5′-ACGCU-3′. Coordination of the paramagnetic metal to glutamic acid residue of NCp7 reduced flexibility of the probe, thus simplifying interpretation of the PRE data. NMR experiments showed attenuation of signal intensities from protein residues localized in proximity to the paramagnetic probe as the result of RNA-protein interactions. The extent of the attenuation was related to the probe's proximity allowing us to construct the protein's contact surface map.

DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX

To provide a metal complex that has high cancer cell toxicity and has DNA target and cyclen.SOLUTION: The present disclosure provides a dinuclear metal complex represented by the following formula (IV).SELECTED DRAWING: None

PET bone imaging agent precursor and synthesis method thereof

The invention discloses a PET bone imaging agent precursor, wherein a linking agent tripolyethanol is introduced between a macrocyclic polyamine ligand and a targeting carrier diphosphonic acid, and the diphosphonic acid bone-seeking group with targeting effect can form the macrocyclic polyamine cooperation group of a stable chelate with a plurality of metal nuclides so as to form a bone imaging agent. According to the present invention, the synthesized precursor compound contains the bone-seeking group (diphosphonic acid) and the cooperation group (DOTA), and the two functional groups are linked by PFG3, such that the precursor compound has remarkable structural characteristics; the precursor compound has strong bone-seeking property, and can form a complex (marker) with kinetic and thermodynamic stability with metal nuclides; the marker formed by marking the precursor with different metal nuclides can be used as a bone imaging agent (marked with Cu, Ga and other positron emission metal nuclides) with powerful functions, and can further be used as an ideal bone tumor treatment drug (marked with In, Y, Zr, Sm and other radioactive treatment metal nuclides).