Thiadiazoloquinoxaline derivative-based NIR-II organic molecules for NIR-II fluorescence imaging and photothermal therapy

Chen, Yan; Yu, Haoli; Wang, Yuesong; Sun, Pengfei; Fan, Quli; Min, Ji Yun

doi:10.1039/d2bm00283c

Cited by 19 publications

(11 citation statements)

References 70 publications

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“…However, reducing the band gaps of D–A conjugated polymers with absorption located in the NIR-II region remains challenging because few synthetic strategies and strong acceptor units have been developed. The most widely used strong acceptor units include thiadiazole, ,,− imide, , and quinoidal − heterocycles, such as benzobisthiadiazole, thienoisoindigo, thiadiazoloquinoxaline, and their derivatives (Scheme S1, see the Supporting Information, SI). Consequently, it is highly appreciated to design new strong A building blocks for the construction of low-band-gap D–A conjugated polymers.…”

Section: Introductionmentioning

confidence: 99%

Quinoxalineimide-Based Semiconducting Polymer Nanoparticles as an Effective Phototheranostic for the Second Near-Infrared Fluorescence Imaging and Photothermal Therapy

Zhu

Gao

Wang

et al. 2023

ACS Appl. Mater. Interfaces

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Multifunctional theranostics play a critical role in improving the efficacy of photothermal therapy and tumor fluorescence imaging; however, they require the integration of complex components into a single theranostic system, and their response in the second near-infrared (NIR-II) region is constrained by wavelengths of a photosensitizer. To address this issue, we herein developed a novel multifunctional thiazole-fused quinoxalineimide semiconducting polymer (named PQIA−BDTT), which exhibits NIR-II fluorescence and photothermal properties. PQIA−BDTT nanoparticles achieved an impressively high photothermal conversion efficiency (72.6%) in laser (1064 nm)-induced photothermal therapy at a safe maximum permissible exposure, demonstrating their capability as an effective photothermal agent. Moreover, PQIA−BDTT nanoparticles can be used as a reference for NIR-II fluorescence imaging under a low laser fluence. The tumor size and location in 4T1 mice intravenously injected with the PQIA−BDTT nanoparticles could be precisely identified through NIR-II fluorescence imaging, which also exhibited remarkable photothermal antitumor efficacy by in vitro and in vivo therapy. Overall, this study demonstrates that introducing a thiazole-fused quinoxalineimide acceptor unit into a donor− acceptor conjugated polymer is an effective strategy for the synthesis of novel multifunctional theranostic systems, which provides a novel platform for designing theranostic agents for biomedical applications.

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Section: Introductionmentioning

confidence: 99%

Quinoxalineimide-Based Semiconducting Polymer Nanoparticles as an Effective Phototheranostic for the Second Near-Infrared Fluorescence Imaging and Photothermal Therapy

Zhu

Gao

Wang

et al. 2023

ACS Appl. Mater. Interfaces

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“…Moreover, FI in the NIR-II region (1000–1700 nm) possesses better spatial resolution and deeper tissue penetration due to lower tissue scattering and absorption [ 5 – 8 ]. Thus, current research has focused on NIR-II fluorescent materials with photothermal properties [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Transmissible H-aggregated NIR-II fluorophore to the tumor cell membrane for enhanced PTT and synergistic therapy of cancer

Wang

Chen

et al. 2023

Nano Convergence

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Photothermal therapy (PTT) combined with second near-infrared (NIR-II) fluorescence imaging (FI) has received increasing attention owing to its capacity for precise diagnosis and real-time monitoring of the therapeutic effects. It is of great clinical value to study organic small molecular fluorophores with both PTT and NIR-II FI functions. In this work, we report a skillfully fluorescent lipid nanosystem, the RR9 (RGDRRRRRRRRRC) peptide-coated anionic liposome loaded with organic NIR-II fluorophore IR-1061 and chemotherapeutic drug carboplatin, which is named RRIALP-C4. According to the structural interaction between IR-1061 and phospholipid bilayer demonstrated by molecular dynamics simulations, IR-1061 is rationally designed to possess the H-aggregated state versus the free state, thus rendering RRIALP-C4 with the activated dual-channel integrated function of intravital NIR-II FI and NIR-I PTT. Functionalization of RRIALP-C4 with RR9 peptide endows the specifically targeting capacity for αvβ3-overexpressed tumor cells and, more importantly, allows IR-1061 to transfer the H-aggregated state from liposomes to the tumor cell membrane through enhanced membrane fusion, thereby maintaining its PTT effect in tumor tissues. In vivo experiments demonstrate that RRIALP-C4 can effectively visualize tumor tissues and systemic blood vessels with a high sign-to-background ratio (SBR) to realize the synergistic treatment of thermochemotherapy by PTT synergistically with temperature-sensitive drug release. Therefore, the strategy of enhanced PTT through H-aggregation of NIR-II fluorophore in the tumor cell membrane has great potential for developing lipid nanosystems with integrated diagnosis and treatment function.

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“…Fluorescence imaging (FI) in the second near-infrared window (NIR-II, 900–1700 nm) has garnered significant interest. 1 Compared with the traditional first near-infrared region (NIR-I, 700–900 nm), imaging in the NIR-II region offers several advantages such as high resolution, deep tissue penetration and excellent signal-to-noise ratio (SNR). These benefits are due to the inert behavior of biological tissues towards light in this region.…”

Section: Introductionmentioning

confidence: 99%

A diketopyrrolopyrrole-based small molecule with an extended conjugated skeleton and J-aggregation behavior for 808 nm laser triggered phototheranostics

Liu,

Zhang,

et al. 2023

Biomater. Sci.

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Thiadiazoloquinoxaline derivative-based NIR-II organic molecules for NIR-II fluorescence imaging and photothermal therapy

Abstract: NIR-II FI have emerged as a promising imaging tool for in vivo precise diagnosis and visualization towards various diseases, ascribed to its merits of attenuated light scattering and tissue absorption...

Cited by 19 publications

References 70 publications

Quinoxalineimide-Based Semiconducting Polymer Nanoparticles as an Effective Phototheranostic for the Second Near-Infrared Fluorescence Imaging and Photothermal Therapy

Quinoxalineimide-Based Semiconducting Polymer Nanoparticles as an Effective Phototheranostic for the Second Near-Infrared Fluorescence Imaging and Photothermal Therapy

Transmissible H-aggregated NIR-II fluorophore to the tumor cell membrane for enhanced PTT and synergistic therapy of cancer

A diketopyrrolopyrrole-based small molecule with an extended conjugated skeleton and J-aggregation behavior for 808 nm laser triggered phototheranostics

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