Photocrosslinkable Trehalose Derivatives Carrying Mesogenic Groups: Synthesis, Characterization, and in Vitro Evaluation for Fibroblast Attachment

Shinya Yano; Naozumi Teramoto; Toshiaki Shimasaki; Mitsuhiro Shibata

doi:10.3390/jfb7030024

Photocrosslinkable Trehalose Derivatives Carrying Mesogenic Groups: Synthesis, Characterization, and in Vitro Evaluation for Fibroblast Attachment

J Funct Biomater. 2016 Sep 10;7(3):24. doi: 10.3390/jfb7030024.

Authors

Shinya Yano¹, Naozumi Teramoto², Toshiaki Shimasaki³, Mitsuhiro Shibata⁴

Affiliations

¹ Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. shinya.y08232@gmail.com.
² Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. teramoto.naozumi@it-chiba.ac.jp.
³ Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. shimasaki.toshiaki@it-chiba.ac.jp.
⁴ Department of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. mitsuhiro.shibata@p.chibakoudai.jp.

Abstract

A photocrosslinkable trehalose derivative carrying mesogenic groups was synthesized by esterification reactions. The derivative (TC-HBPHA) was synthesized by the reaction of partially cinnamoyl-modified trehalose (TC4) with 4-(4-hexyloxybenzoyloxy)phenoxy-6-oxohexanoic acid (HBPHA) as a mesogenic unit. TC-HBPHA showed a nematic liquid crystalline mesophase at a temperature range from 150 °C to 175 °C in the heating process under observation with a polarized optical microscope. The dimerization of the cinnamoyl groups of TC-HBPHA by ultraviolet (UV) light irradiation was monitored by ultraviolet-visible (UV-Vis) spectroscopy and Fourier transform infrared (FT-IR) spectroscopy. The photocrosslinked film was obtained after the UV irradiation of TC-HBPHA, and it kept the liquid crystalline mesophase at almost the same temperature range. Fibroblast cells cultured on the photocrosslinked TC-HBPHA proliferated as well as on the polystyrene culture plate, indicating that the film has no toxicity. Interestingly, some cells on photocrosslinked TC-HBPHA had a spindle shape and aligned characteristically.

Keywords: cell growth; cinnamoyl; fibroblast; liquid crystal; mesogen; photocrosslinking; trehalose.