79944-44-8

Upstream product

• 35453-19-1 2,4,6-triiodo-5-aminoisophthalic acid 
• 99-31-0 5-aminoisophthalic acid 
• 37441-29-5 5-amino-2,4,6-triiodoisophthalic acid dichloride 
• 1663-67-8 malonoyl dichloride 

Downstream Products

• 1187316-83-1 tetra-tert-butyl [({5,5′-[malonylbis(azanediyl)]bis(2,4,6-triiodoisophthaloyl)}tetrakis(azanediyl))tetrakis(ethane-2,1-diyl)]tetracarbamate 
• 915228-77-2 C₇₅H₈₀I₆N₁₀O₂₂ 

Relevant academic research and scientific papers

Synthesis and Preclinical Characterization of a Cationic Iodinated Imaging Contrast Agent (CA4+) and Its Use for Quantitative Computed Tomography of Ex Vivo Human Hip Cartilage

Contrast agents that go beyond qualitative visualization and enable quantitative assessments of functional tissue performance represent the next generation of clinically useful imaging tools. An optimized and efficient large-scale synthesis of a cationic iodinated contrast agent (CA4+) is described for imaging articular cartilage. Contrast-enhanced CT (CECT) using CA4+ reveals significantly greater agent uptake of CA4+ in articular cartilage compared to that of similar anionic or nonionic agents, and CA4+ uptake follows Donnan equilibrium theory. The CA4+ CECT attenuation obtained from imaging ex vivo human hip cartilage correlates with the glycosaminoglycan content, equilibrium modulus, and coefficient of friction, which are key indicators of cartilage functional performance and osteoarthritis stage. Finally, preliminary toxicity studies in a rat model show no adverse events, and a pharmacokinetics study documents a peak plasma concentration 30 min after dosing, with the agent no longer present in vivo at 96 h via excretion in the urine.

Effect of contrast agent charge on visualization of articular cartilage using computed tomography: Exploiting electrostatic interactions for improved sensitivity

(Chemical Equation Presented) The synthesis and evaluation of a new class of cationic iodinated contrast agents for the imaging of cartilage using computed tomography (CT) are described. In direct comparisons with anionic contrast agents, the cationic contrast agents afforded higher equilibrium concentrations in the articular cartilage of ex vivo rabbit femurs and thus greater imaging sensitivity. Variations in CT intensity across the sample reflected the inhomogeneous distribution of glycosaminoglycans in the tissue as confirmed by histological analysis. We anticipate that this work represents the first step in the development of sensitive, nondestructive CT-based methods to characterize the biochemical properties of cartilage using cationic contrast agents.

Synthesis and evaluation of potential CT (computer tomography) contrast agents for bone structure and microdamage analysis

The design and synthesis of several novel X-ray contrast agents 1-3, developed for targeting bone structures, and in particularly microcracks in bones, using CT (Computer Tomography) detection is described. These contrast agents are based on the use of the well known triiodobenzene platform, which was conjugated into one or more phenyliminodiacetate moieties, which can be used to 'lock' onto bone matrices. Compounds 1-3 were all tested for their ability to visualise cracks in bone structures (bovine bones) using μ-CT imaging. The Royal Society of Chemistry 2006.

Highly-iodinated fullerene as a contrast agent for X-ray imaging

The first fullerene-based X-ray contrast agent (CA) has been designed, synthesized, and characterized. The new CA is an externally functionalized derivative of C60 that is conceptually based on contemporary X-ray CA, all of which use iodine as the X-ray attenuating vehicle and are based on the 2,4,6-triiodinated-benzene-ring substructure. Using a modified Bingel-type reaction, a single addend containing 6 iodine atoms and 8 protected hydroxyl groups was appended to C60 followed by the addition of 4 more addends each containing 4 protected hydroxyl groups. Final deprotection afforded the highly water-soluble (>460 mg/mL), non-ionic, highly-iodinated (24% I) fullerene for application as an X-ray contrast agent.

Toward fullerene-based X-ray contrast agents: Design and synthesis of non-ionic, highly-iodinated derivatives of C60

An X-ray contrast agent precursor based on C60 has been designed, synthesized, and characterized. The compound is the monoadduct of a malonodiamide containing six iodine atoms and eight acetal-protected alcohols with multiple hindered rotations

Nonionic X-ray contrast agents, compositions and methods

Triiodinated isophthalamide derivatives, useful as X-ray contrast agents, having at least one amide group derived from the amino-alcohol, 3-(N-2-hydroxyethyl)amino-1,2-propanediol, which provides high water solubility and low mammalian toxicity, and methods of preparing them. Methods of preparing 3-(N-2-hydroxyethyl)amino-1,2-propanediol are provided.

Novel amino-dioxepane intermediates for the synthesis of new non-ionic contrast media

Novel intermediates for non-ionic polyiodo amino-substituted benzenepolyamides having polyol substituents on the amide nitrogens are provided which are 5-amino-6-hydroxy-1,3-dioxepanes. The compounds provide an economic and efficient route to novel contrast media having excellent chemical and physiological properties. Also provided are methods for preparing the subject compounds.