Iodinated polyesters as a versatile platform for radiopaque biomaterials

Abstract

The design of polymeric biomaterials with long‐lasting X‐ray contrast could advance safe and effective implants and contrast agents. Herein, a new set of wholly aliphatic, iodinated polyesters are synthesized and evaluated as high‐contrast biomaterials and nanoparticle contrast agents for general computed tomography imaging. A single iodinated monomer is used to synthesize a variety of aliphatic polyesters with tunable thermal and mechanical properties. These iodinated polyesters are end‐functionalized with a photocurable methacrylate group, which allows easy processability. The resulting materials exhibit no cytotoxicity and are radiopaque, containing over 40% iodine by weight after processing. The polymers can be formulated into lipid–polymer hybrid nanoparticles using a modified nanoprecipitation method. Initial studies indicate that these nanoparticles show good continual contrast over 60 minutes with no uptake into the kidneys. The work presented here illustrates a novel platform for iodinated polyesters that exhibit high radiopacity and processability, low cost, and no cytotoxicity. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 2171–2177

Organic Nanoplatforms for Iodinated Contrast Media in CT Imaging

“…The main strategies based on polymerization technologies for combining polymer and ICMs to prepare macromolecular contrast media are shown in Figure 3 . The macromolecular contrast media can be prepared by free radical polymerization, condensation polymerization or ring-opening polymerization of iodine-containing monomers [ 36 , 37 , 38 , 39 ]. For example, triiodobenzoate-containing vinylic monomers, such as 3-(methacryloy-lamidoacetamido)-2,4,6-triiodobenzoic acid (MABTIB) [ 40 ], 2-hydroxy-3-methacryloyloxypropyl (2,3,5-triiodobenzoate) (HMTIB) [ 41 , 42 ] and 2-methacryloyloxyethyl (2,3,5-triiodobenzoate) (MAOETIB) [ 36 , 43 ] were widely used to prepare radiopaque polymers by homo-polymerization or copolymerization with other vinylic monomers.…”

“…It is worth pointing out that some iodine-containing vinylic monomers, such as triiodophenyl methacrylate, only can be used to obtain low molecular weight polymers (oligomers), due to the steric hinderance effect of the iodinated aromatic nucleus [ 44 ]. In addition, some iodine-containing diol monomers, such as 2,2-bis(iodomethyl)-1,3-propanediol [ 38 ] and 2,2-bis(hydroxymethyl)propane-1,3-diyl bis(2,3,5-triiodobenzoate) [ 45 ], were used to undergo condensation polymerization with diacids to prepare iodinated polyesters as a versatile platform for radiopaque biomaterials. Moreover, ring-opening polymerization also can be applied to prepare iodinated macromolecular contrast media.…”

“…To meet increasingly rigorous requirements for clinical use, a great number of approaches have been explored to effectively surmount these drawbacks [ 8 , 9 , 21 , 22 , 23 , 61 , 62 , 66 , 67 ]. The strategies and applications of organic NPs with desirable functions and excellent performances for medical imaging have gained an enormous amount of attention [ 3 , 32 , 33 , 34 , 38 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 ]. This is due to the fact that organic NPs possess a great number of desirable physicochemical properties, such as simplicity for drug loading, high biocompatibility, desirable biodegradation, facile synthesis, low cost as well as great flexibility and versatility in modification or functionalization [ 28 , 34 , 61 , 62 , 65 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 ].…”

Radiopaque Chitosan Ducts Fabricated by Extrusion-Based 3D Printing to Promote Healing After Pancreaticoenterostomy

“…In future clinical applications, postoperative follow-up observation of patients is very important. X-ray imaging technology is an effective and convenient method for detecting and evaluating the position and shape of implant materials (Sang et al, 2014;Houston et al, 2017). Traditional polymer molecules should be endowed with radiopaque properties to meet medical requirements.…”

Light Weight, Easy Formable and Non-Toxic Polymer-Based Composites for Hard X-ray Shielding: A Theoretical and Experimental Study

“…The second solution is represented by organic materials in which the number of electrons by volume unit is increased by adding iodine atoms to polymeric chains: mostly, isoprenic rubber is synthesized with monomers that have iodine atoms covalently bound. Examples of these monomers are iopanoic acid 3-(3-amino-2,4,6-triiodophenyl)-2-ethyl propanoic acid and iothalamic acid (5-acetamido-2,4,6-triiodo-N-methyl iso-phthalamic acid) and 2,4,6-triiodobenzoic acid [4][5][6].…”