Synthesis of Fluorinated and Iodinated Cyanoacrylates and Their Application to Novel Liquid Embolic Compositions

Liquid embolic agents are used for permanent vascular occlusion, but Histoacryl lacks intrinsic radiopacity and exhibits strong microcatheter adhesion. In this study, iodinated and fluorinated cyanoacrylates were investigated for liquid embolic compositions. 2-Iodoethyl 2-cyanoacrylate (IECA) had a calculated iodine concentration of 1100 mg I/mL. Among the fluorinated cyanoacrylates evaluated, 2,2,3,3,3-pentafluoropropyl 2-cyanoacrylate (PFPCA) showed the highest polymerization rate (15.77 ± 1.96 μL/s). The IECA/PFPCA blend containing 67% IECA (IF67) had an iodine concentration of 730 mg I/mL. The optimized formulation, IFO50, containing IF67 and 50% ethyl oleate, showed a polymerization rate of 0.80 ± 0.07 μL/s, an iodine concentration of 370 mg I/mL, and a microcatheter adhesion force of 2.24 ± 0.36 N. In rabbit renal artery embolization, IFO50 was visible under fluoroscopy, and post-embolization digital subtraction angiography showed no contrast-medium opacification of the treated artery. Computed tomography at 7 days showed the embolic cast in the treated kidney without apparent migration to distant organs.