Facile synthesis of a triazine-based porous organic polymer containing thiophene units for effective loading and releasing of temozolomide

Abstract

Suzuki cross-coupling reaction was employed to easily obtain a triazine-based porous organic polymer (2,4,6-tris(5-bromothiophene-2-yl)-1,3,5-triazine [TBrTh]–1,3,5-benzene-triyltriboronic acid pinacol ester [BTBPE]–covalent triazine framework [CTF]) containing thiophene units. The chemical structure of TBrTh–BTBPE–CTF was revealed by solid-state 13C NMR, Fourier-transform infrared, and X-ray photoelectron spectroscopy. TBrTh–BTBPE–CTF with an amorphous structure exhibited excellent thermal stability and intrinsic porosity (373 m2·g−1 of Brunauer–Emmett–Teller surface area). Consequently, temozolomide (TMZ) was used as an oral alkylating agent in melanoma treatment to explore the drug loading and releasing behavior of TBrTh–BTBPE–CTF as a result of the low cytotoxicity of thiophene-based polymers. The successful loading of TMZ within the polymeric structure was suggested by thermogravimetric analysis and N2 sorption isotherms. The release experiments were performed in phosphate-buffered saline at pH values of 5.5 and 7.4, exhibiting good controlled-release properties. These results suggest that the current porous organic polymer is expected to be a drug carrier for the delivery and release of TMZ.

Keywords

• porous organic polymers
• covalent triazine frameworks
• drug loading
• melanoma
• drug releasing