Synthesis of D-A-type groups modified aza-BODIPY fluorescent dye encapsulated by amphiphilic polypeptide nanoparticles for NIR-II phototheranostics

• Published in: Talanta (Oxford) 2024-11, Vol.279, p.126633, Article 126633
• Main Authors: Xie, Kai, Yin, Dalong, Yan, Lifeng
• Format: Article
• Language: English
• Subjects: Animals; Aza-BODIPY; Boron Compounds - chemistry; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Humans; Infrared Rays; Mice; Mice, Inbred BALB C; Nanoparticles - chemistry; Peptides - chemistry; Phototherapy; Photothermal Therapy; Polypeptide; Second near-infrared fluorescence (NIR-II); Theranostic Nanomedicine - methods; Theranostics
• ISSN: 0039-9140; 1873-3573; 1873-3573
• DOI: 10.1016/j.talanta.2024.126633

An innovative organic small molecule with a D-A structure was synthesized by connecting triphenylamine to BODIPY via a thiophene bridge. Triphenylamine and thiophene units ingeniously modulate the balance between steric hindrance and π-π interactions around the flat aza-BODIPY core. The molecule exhibits near-infrared fluorescence absorption and emits at roughly 1100 nm, featuring a significant Stokes shift. Both the molecule and its nanoparticles demonstrate high stability and achieve a remarkable 35 % photothermal conversion efficiency when conjugated with the P(OEGMA)20-P(Asp)14 copolymer. In vitro assessments show low dark toxicity and outstanding biocompatibility. Moreover, in vivo studies and photothermal therapy in mice indicate substantial tumor shrinkage and reduced recurrence, confirming its potential in cancer treatment. These results highlight the promise of this organic molecule and its nanoparticles for NIR-II imaging-guided photothermal therapy, introducing a novel approach to phototheranostic applications for cancer management. [Display omitted] •D-A structure NIR-II dye based on the strong electron-withdrawing nature of aza-BODIPY has been syntheized.•The molecule exhibits near-infrared fluorescence absorption and emits at roughly 1100 nm.•Nanoaprticles of the dye display remarkable photothermal conversion efficiency and fluorescence.•The nanoparticles showed efficent NIR-II imaging-guided PTT.