Photoreversibility and Biocompatibility of Polydimethylsiloxane‐Coumarin as Adjustable Intraocular Lens Material

Abstract

Polydimethylsiloxane (PDMS) constitutes an interesting material for a variety of biomedical applications, especially as intraocular lenses (IOLs), for its excellent transparency. In this work, a photoreversible PDMS-coumarin network, whose shape and properties can be adjusted postoperatively in a noninvasive manner, is developed. The synthesis of PDMS-coumarin is achieved by amidation of a coumarin acid chloride derivative with amine-functionalized PDMSs. Under exposure of λ > 300 nm, these polymers can be cured by dimerization of coumarin. The cured polymers can be uncrosslinked via photocleavage of cyclobutane dimers upon illumination at λ < 290 nm. The diffusion of linear PDMSs in a crosslinked network and the controlled shape modification are studied, which demonstrate that these polymers are good candidates for adjustable IOL application. IOL disks prepared from these materials show high hydrophobicity and good transparency. In vitro cytotoxicity, lens epithelial cell adhesion assays, and rabbit host reaction against implanted disks demonstrate the biocompatibility of the polymer.

Recent Advances of Intraocular Lens Materials and Surface Modification in Cataract Surgery

“…This represents better protection for the eyes. On this basis, Jellali et al (2017) synthesized a silicone-coumarin phototunable intraocular lens and tested the photosensitivity and biocompatibility. Ultraviolet-visible light spectroscopy showed that irradiation above 300 nm occurred crosslinking, and the process was reversed under light below 245 nm.…”

“… (A) Schematic of photoreversible crosslinking of PDSM-coumarin polymer. (B) Schematic of designed IOL from Jellali et al (2017) , with the permission of Wiley. …”

Recent Advances in Functional Polymers Containing Coumarin Chromophores

“…The [2πs + 2πs] photocycloaddition of coumarin derivatives upon irradiation with UV light (>300 nm), to generate cyclobutane derivatives with itself or even with another double bond in the reaction medium, has been widely employed in the synthesis of polymeric networks [ 41 , 62 , 63 , 64 , 65 , 66 , 67 , 68 ]. The advantages of this method are the creation of a network without extra monomers or photoinitiators [ 66 ] and the possibility to reverse the process (by regenerating the double bonds using radiation wavelength <290 nm).…”

Room temperature crystallization of amorphous polysiloxane using photodimerization

“…Diffusion of polymer chains against a photo-induced crosslinking gradient has been previously reported for the preparation of heterogeneously swollen lms. 50,51 Diffusion in our samples was studied using pulsed eld gradient (PFG) 1 H NMR spectroscopy. 52,53 The translational diffusion coefficient (D t ) and rotational time play important roles in crystallization events, governing the rates of mass transport and reorientation to the growing crystal facets respectively.…”