Thieno[3,2-b]thiophene-DPP based near-infrared nanotheranostic agent for dual imaging-guided photothermal/photodynamic synergistic therapy

Abstract

Diketopyrrolopyrrole (DPP) based organic molecules have drawn significant research attention as phototheranostic agents. Herein, based on thieno[3,2-b]thienyl-DPP (TT-DPP), a near-infrared small molecule photosensitizer diethyl 3,3′-((((2,5-bis(2-decyltetradecyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(thieno[3,2-b]thiophene-5,2-diyl))bis-(4,1-phenylene))bis(7-bromo-10H-phenothiazine-10,3-diyl))(2E,2′E)-diacrylate (PDBr), with a high singlet oxygen (¹O₂) quantum yield of 67%, was developed. After nano-precipitation, the hydrophilic PDBr NPs present an encouraging photothermal conversion efficiency of 35.7% and excellent fluorescence/infrared-thermal imaging performance. In vitro studies disclosed the high phototoxicity but low dark cytotoxicity of PDBr NPs to tumor cells. Furthermore, PDBr NPs can effectively impede the tumor growth without noticeable side effects in living mice through imaging-guided synergistic photothermal/photodynamic therapy. Therefore, PDBr NPs could be a promising nanotheranostic agent for imaging-guided synergistic photothermal and photodynamic therapy in the clinic.