Silicone hydrogels grafted with natural amino acids for ophthalmological application.
In this report, protein repelling silicone hydrogels with improved hydrophilicity were prepared by photo-polymerization of silicone-containing monomer and glycidyl methacrylate followed by grafting zwitterionic amino acids. The grafted silicone hydrogels possessed excellent hydrophilic surfaces due to the enrichment of amino acids, which was confirmed by attenuated total reflectance Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, contact angle, and equilibrium water content measurements. Remarkable resistance to bovine serum albumin and lysozyme fouling was observed for the silicone hydrogels immobilized with neutrally charged amino acids because of the formation of zwitterionic surfaces with pairs of protonated secondary ammonium cations and deprotonated carboxyl anions. Meanwhile, the silicone hydrogels grafted with positively or negatively charged amino acids were able to repulse same charged protein with reduced deposition and attract oppositely charged protein with increased adsorption. Preliminary cytotoxicity test indicated that the zwitterionic silicone hydrogels were non-cytotoxic. Similarly, three types of natural amino acids, including serine, aspartic acid and histidine, modified silicone hydrogel contact lenses exhibited excellent hydrophilicity and non-damage to the rabbit's eyes, but only serine modified zwitterionic contact lens showed superior protein fouling resistance compared with the current commercial hydrogel contact lens, which may have great potential application in ophthalmology.
a School of Chemistry and Chemical Engineering , Southeast University , Nanjing , China.
Chen
C
Xu
a School of Chemistry and Chemical Engineering , Southeast University , Nanjing , China.
Ruiyu
R
He
a School of Chemistry and Chemical Engineering , Southeast University , Nanjing , China.
Binbin
B
Xie
a School of Chemistry and Chemical Engineering , Southeast University , Nanjing , China.
Muhammad
M
Ismail
a School of Chemistry and Chemical Engineering , Southeast University , Nanjing , China.
Chen
C
Yao
b Department of Ophthalmology , Zhongda Hospital Southeast University , Nanjing , China.
Jie
J
Luan
a School of Chemistry and Chemical Engineering , Southeast University , Nanjing , China.
Xinsong
X
Li
D000327:Adsorption; D000596:Amino Acids / Q000737:chemistry*; D000818:Animals; D002417:Cattle; D002460:Cell Line; D002470:Cell Survival; D003263:Contact Lenses, Hydrophilic; D004852:Epoxy Compounds / Q000737:chemistry*; D020100:Hydrogels / Q000138:chemical synthesis* / Q000633:toxicity; D057927:Hydrophobic and Hydrophilic Interactions; D008027:Light; D008689:Methacrylates / Q000737:chemistry*; D051379:Mice; D009113:Muramidase / Q000737:chemistry; D058105:Polymerization; D011817:Rabbits; D012710:Serum Albumin, Bovine / Q000737:chemistry; D012828:Silicones / Q000737:chemistry*; D013499:Surface Properties; D014867:Water; D017155:Wettability
D000596:Amino Acids; D004852:Epoxy Compounds; D020100:Hydrogels; D008689:Methacrylates; D012828:Silicones; D014867:Water; D012710:Serum Albumin, Bovine; D009113:Muramidase; C007870:glycidyl methacrylate
Silicone hydrogel; amino acid; contact lens; grafting; protein resistance