824984-75-0

Upstream product

• 122555-91-3 1,4,7-tris-tert-butoxycarbonylmethyl-1,4,7,10-tetraazacyclododecane 
• 590-17-0 cyanomethyl bromide 
• 866611-78-1 1-(2-Boc-aminoethyl)-(1,4,7,10-tetraazacyclododecane) 
• 294-90-6 1,4,7,10-tetraazacyclododecan 
• 879999-82-3 1,4,7-tris(tert-butoxycarbonylmethyl)-10-(2-phthalimidoethyl)-1,4,7,10-tetraazacyclododecane 
• 412298-17-0 (4,10-bis-tert-butoxycarbonylmethyl-7-cyanomethyl-1,4,7,10tetraaza-cyclododec-1-yl)-acetic acid tert-butyl ester 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 824984-74-9 1-[N-(benzyloxycarbonyl)-2-aminoethyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid tri(1,1-dimethylethyl ester) 

Downstream Products

• 1198399-89-1 1-[N-[4-(methyloxycarbonylmethylenoxy)benzenesulfonyl]-2-aminoethyl]-1,4,7,10-tetraazacyclododecane-4,7,10-triacetic acid tri(1,1-dimethylethyl ester) 
• 1278587-17-9 C₃₄H₅₃N₇O₁₅ 
• 1278587-15-7 [4,7-bis-butoxycarbonylmethyl-10-(2-(2-((2-(2-(2-(bis(2-tert-butoxy-2-oxoethyl)amino)ethoxy)phenoxy)ethyl)(2-tert-butoxy-2-oxoethyl)amino)acetamido)ethyl)-1,4,7,10-tetraazacyclododec-1-yl]acetic acid tert-butyl ester 
• 1278587-16-8 C₃₀H₄₆N₆O₁₃ 
• 1278587-07-7 [4,7-bis-butoxycarbonylmethyl-10-(2-(2-(2-(2-(bis(2-tert-butoxy-2-oxoethyl)amino)ethoxy)phenoxy)acetamido)ethyl)-1,4,7,10-tetraazacyclododec-1-yl]acetic acid tert-butyl ester 

Relevant academic research and scientific papers

Dimer formation of GdDO3A-arylsulfonamide complexes causes loss of pH-dependency of relaxivity

Gadolinium(iii) complexes with pH-dependent relaxivities have been proposed as responsive magnetic resonance imaging (MRI) contrast agents (CA) for mapping of pH value in living subjects. The latter is clinically relevant because hypoxia-induced reduction of interstitial pH (acidosis) is a hallmark of tumor progression and resistance against chemotherapy. In order to obtain versatile building blocks for integration of a pH-responsive MRI-CA functionality into larger molecular assemblies, such as bioconjugates, micelles or nanoparticles, we equipped the structural motif GdDO3A-ethylene(arylsulfonic acid) with additional carboxylic acid moieties in the aromatic para-position. Two novel compounds were characterized concerning their pH-dependent relaxivity as well as by 17O NMR and 1H NMRD, augmented by determination of luminescence lifetimes of the respective Eu(iii) complexes and structural modelling by density functional theory (TPSSh/LCRECP/6-31G(d)). Unexpected involvement of the peripheral carboxylates into metal ion complexation effected self-assembly of the lanthanide(iii) complexes, resulting in dimeric species comprising two lanthanide ions, two symmetrically bridging ligands, and one coordinated water molecule per Gd(iii) (q = 1). These structures are stable even at low concentrations and in presence of competing anions like phosphate. The pH-sensitive sulfonamide moieties are not involved into Gd(iii) coordination, resulting in virtually constant relaxivities of r1 = 6.7 mM-1 s-1 (298 K, 20 MHz) over the biologically relevant pH range (4 to 9). Since further functionalisation on the peripheral carboxylates would effectively inhibit dimer formation, the compounds are nonetheless suited for the initially envisaged field of application.

Tumor targeting MRI contrast agent and preparation method thereof

The invention provides tumor targeting MRI contrast agent and a preparation method thereof. The contrast agent is characterized by comprising a micromolecule gadolinium chelate part and a targeting carrier part, wherein the micromolecule gadolinium chelate part and the targeting carrier part are coupled through a covalent bond, the micromolecule gadolinium chelate part is Gd-DO3A, and the targeting carrier part contains EBP molecules. The contrast agent is good in relaxation enhancement ability, can be combined with EGFR of tumor cells in a targeting mode, has a strong targeting radiography effect and has strong practicability. Furthermore, the imaging time of the contrast agent in a body is prolonged, and the adding amount of the contrast agent is reduced.

Preparation method of compound

A preparation method of a compound represented by the formula (IV) includes the steps: carrying out addition reaction of a compound represented by the formula (III) with fluorescein isothiocyanate, and further carrying out hydrolysis reaction with trifluoroacetic acid to remove tert-butyl ester to obtain a compound represented by the formula (IV). The reactant obtained by the method only need to be purified by column chromatography to obtain the compound represented by the formula (IV) and having the purity of 95% or more. The preparation method of the compound represented by the formula (IV)has low cost and is suitable for large-scale production. In addition, the invention also discloses a preparation method of the compound represented by the formula (V), wherein the preparation method of the compound represented by the formula (V) includes the preparation method for a compound represented by the formula (IV).

Synthesis of a new family of protected 1,4,7,10-tetraazacyclododecane-1,4, 7-triacetic acid derivatives with thioctic acid pending arms

The synthesis and characterization of a new family of ester protected N-substituted [1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (H3DO3A) derivatives containing a pendant thioctic acid (α lipoic acid, LA) are reported. These compounds (DO3AtBu-NLA, DO3AtBu-NMeNLA, and DO3AtBu-NEtNLA) are suitable for the functionalization of gold surfaces with rare-earth complexes.

Synthesis of chlorin-sensitized near infrared-emitting lanthanide complexes

Lanthanide (Yb3+, Nd3+) complexes equipped with red-absorbing hydroporphyrin (chlorin) antennae were synthesized and characterized. The syntheses are scalable, highly modular, and enable the introduction of different chlorins functionalized with a single reactive group (COOH or NH2). Absorption maxima were dependent on chlorin substitution pattern (monomeso aryl or dimeso aryl) and metalation state (free base or zinc chelate). The complexes benefit from dual chlorin (610-639 nm) and lanthanide (980 or 1065 nm for Yb- or Nd-complexes, respectively) emission in the biologically relevant red and near IR region of the spectrum.

Critical in vitro evaluation of responsive MRI contrast agents for calcium and zinc

The synthesis of two gadolinium(III) complexes that exhibit an increase in proton relaxivity in the presence of added Ca2+ or Zn2+ ions is reported. The complexes increase their hydration state from zero to one following metal-ion bi

Exofacial protein thiols as a route for the internalization of Gd(III)-based complexes for magnetic resonance imaging cell labeling

Four novel MRI Gd(III)-based probes have been synthesized and evaluated for their labeling properties on cultured cell lines K562, C6, and B16. The labeling strategy relies upon the fact that cells display a large number of reactive exofacial protein thio

Poly-β-cyclodextrin based platform for pH mapping via a ratiometric 19F/1H MRI method

The in vitro validation of a new pH mapping MRI method based on a supramolecular poly-β-cyclodextrin-19F-Gd adduct is reported.

10-substituted 1-, 4, 7,-tris (carboxymethyl)-1,4,7,10-tetraazacyclo-dodecane derivative for use as contrast agents

The present invention relates to smart chelating agents suitable for forming stable complexes with lanthanides and/or transition metals.

SYNTHESIS OF TRIS N-ALKYLATED 1,4,7,10-TETRAAZACYCLODODECANES

A directly synthetic method for preparing tris-alkylated 1,4,7,10-tetraazacyclododecanes by the reactions of 1,4,7,10-tetraazacyclododecane (cyclen) and appropriate electrophiles is accomplished in high yield. The method provides operational convenience,