Among polymer materials used for drug delivery systems (DDS), radiopaque polymers are attractive materials for noninvasive precise monitoring of the drug location in human body after injection. To realize the high radiopacity, iodine has been generally utilized in functional polymers such as cross-linked polyvinyl alcohol. For the more accurate DDS control of drug release, introducing biodegradability into such radiopaque polymers has been urgently required. In this study, biodegradable/radiopaque polymers with poly(glycerol adipate) (PGA) backbones were synthesized (Fig). PGA was obtained by enzymatic polymerization of glycerol and divinyl adipate. Secondary hydroxyl groups of glycerol took part in transesterification and the branch degree was calculated from 1H NMR analysis. PGA was then iodinated by condensation with iodoacetic acid (IA), 2-iodobenzoic acid (IBA), or 2,3,5-triiodobenzoic acid (TIBA), and the synthesized polymers were named as PGA-I, PGA-IB, or PGA-3IB, respectively. PGA-3IB was obtained as a rubbery material because branching points of PGA effectively behaved as crosslinking. The elastomeric feature of this new type of iodinated PGA could be effectively utilized for the applications in DDS. To evaluate the thermal property of iodinated PGAs, differential scanning calorimetry (DSC) analysis was conducted. The glass transition temperature (Tg) was increased by iodination, reaching maximum Tg for PGA-3IB. The sufficient radiopacity of the iodinated PGAs was also confirmed by CT scan. These results indicated that the synthesized iodinated PGAs could become a prospective candidate for DDS in IVR as a new biodegradable/radiopaque polymer.

Synthesis of iodinated poly(glycerol adipate) for drug delivery systems in interventional radiology (IVR)

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