Supramolecular Engineering Cascade Regulates NIR-II J-aggregates to Improve Photodynamic Therapy

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2024 Jul 26

PMID 39055007

Authors

Huizhe Wang

Huijia Liu

Wenqing Li

Shuai Li

Jiaqi Zhang

Jingzhe Zang

Li Liu

Peng Wang

Affiliations

Soon will be listed here.

Abstract

Rational design of small organic molecule-based NIR-II photosensitizers (PSs) with high singlet oxygen quantum yield in aqueous solution for deep tissue imaging and cancer therapy still presents challenges. Herein, we devised a general synthesis strategy to obtain six NIR-II region PSs with tunable aggregation states by adjusting the steric effect, and all PSs possess longer NIR absorption/emission wavelengths with tails extending beyond 1200 nm. Notably, ATX-6 possessed a singlet oxygen quantum yield of 38.2% and exhibited concentration-dependent J-aggregation properties upon self-assembly in an aqueous solution. What's more, supramolecular engineering with DSPE-PEG further enhanced its degree of J-aggregation, which was attributed to the dimer-excited reduction of the energy levels of the single-linear/triple-linear states and the facilitation of intersystem crossover processes. In addition, ATX-6 NPs showed superior photodynamic therapy effects and great potential in high-contrast bioimaging of the NIR-II region. These results provide valuable insights for achieving the diagnostic and therapeutic integration of tumors.

References

Tang Z, Liu Y, He M, Bu W . Chemodynamic Therapy: Tumour Microenvironment-Mediated Fenton and Fenton-like Reactions. Angew Chem Int Ed Engl. 2018; 58(4):946-956. DOI: 10.1002/anie.201805664. View

Tian Y, Yin D, Yan L . J-aggregation strategy of organic dyes for near-infrared bioimaging and fluorescent image-guided phototherapy. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2022; 15(1):e1831. DOI: 10.1002/wnan.1831. View

Zhao H, Chen K, Liu M, Wang Z, Li L, Li M . A Mitochondria-Targeted NIR-II Molecule Fluorophore for Precise Cancer Phototheranostics. J Med Chem. 2023; 67(1):467-478. DOI: 10.1021/acs.jmedchem.3c01677. View

Wen K, Tan H, Peng Q, Chen H, Ma H, Wang L . Achieving Efficient NIR-II Type-I Photosensitizers for Photodynamic/Photothermal Therapy upon Regulating Chalcogen Elements. Adv Mater. 2021; 34(7):e2108146. DOI: 10.1002/adma.202108146. View

Li S, Fu L, Xiao X, Geng H, Liao Q, Liao Y . Regulation of Thermally Activated Delayed Fluorescence to Room-Temperature Phosphorescent Emission Channels by Controlling the Excited-States Dynamics via J- and H-Aggregation. Angew Chem Int Ed Engl. 2021; 60(33):18059-18064. DOI: 10.1002/anie.202103192. View

Li K, Duan X, Jiang Z, Ding D, Chen Y, Zhang G . J-aggregates of meso-[2.2]paracyclophanyl-BODIPY dye for NIR-II imaging. Nat Commun. 2021; 12(1):2376. PMC: 8062432. DOI: 10.1038/s41467-021-22686-z. View

Zheng Y, Li Q, Wu J, Luo Z, Zhou W, Li A . All-in-one mitochondria-targeted NIR-II fluorophores for cancer therapy and imaging. Chem Sci. 2021; 12(5):1843-1850. PMC: 8179124. DOI: 10.1039/d0sc04727a. View

Lv Q, Yang X, Wang M, Yang J, Qin Z, Kan Q . Mitochondria-targeted prostate cancer therapy using a near-infrared fluorescence dye-monoamine oxidase A inhibitor conjugate. J Control Release. 2018; 279:234-242. DOI: 10.1016/j.jconrel.2018.04.038. View

Wang S, Liu J, Goh C, Ng L, Liu B . NIR-II-Excited Intravital Two-Photon Microscopy Distinguishes Deep Cerebral and Tumor Vasculatures with an Ultrabright NIR-I AIE Luminogen. Adv Mater. 2019; 31(44):e1904447. DOI: 10.1002/adma.201904447. View

10.

Bian H, Ma D, Zhang X, Xin K, Yang Y, Peng X . Tailored Engineering of Novel Xanthonium Polymethine Dyes for Synergetic PDT and PTT Triggered by 1064 nm Laser toward Deep-Seated Tumors. Small. 2021; 17(21):e2100398. DOI: 10.1002/smll.202100398. View

11.

Lee K, Gao Y, Wei W, Tan J, Wan Y, Feng Z . Anti-Quenching NIR-II J-Aggregates of Benzo[c]thiophene Fluorophore for Highly Efficient Bioimaging and Phototheranostics. Adv Mater. 2023; 35(20):e2211632. DOI: 10.1002/adma.202211632. View

12.

Liu Y, Teng L, Lou X, Zhang X, Song G . "Four-In-One" Design of a Hemicyanine-Based Modular Scaffold for High-Contrast Activatable Molecular Afterglow Imaging. J Am Chem Soc. 2023; 145(9):5134-5144. DOI: 10.1021/jacs.2c11466. View

13.

Hu X, Zhu C, Sun F, Chen Z, Zou J, Chen X . J-Aggregation Strategy toward Potentiated NIR-II Fluorescence Bioimaging of Molecular Fluorophores. Adv Mater. 2023; 36(1):e2304848. DOI: 10.1002/adma.202304848. View

14.

Wu C, Li E, Chou P . Reducing the internal reorganization energy symmetry controlled π-electron delocalization. Chem Sci. 2022; 13(24):7181-7189. PMC: 9214956. DOI: 10.1039/d2sc01851a. View

15.

Zhou Y, Zhu L, Liu B, Xu W, Yang X, Liu Y . Tailored Zwitterionic Hemicyanine Reporters for Early Diagnosis and Prognostic Assessment of Acute Renal Failure. Angew Chem Int Ed Engl. 2023; 62(52):e202315457. DOI: 10.1002/anie.202315457. View

16.

Liu S, Ou H, Li Y, Zhang H, Liu J, Lu X . Planar and Twisted Molecular Structure Leads to the High Brightness of Semiconducting Polymer Nanoparticles for NIR-IIa Fluorescence Imaging. J Am Chem Soc. 2020; 142(35):15146-15156. DOI: 10.1021/jacs.0c07193. View

17.

de Silva A, Gunaratne H, Gunnlaugsson T, Huxley A, McCoy C, Rademacher J . Signaling Recognition Events with Fluorescent Sensors and Switches. Chem Rev. 1997; 97(5):1515-1566. DOI: 10.1021/cr960386p. View

18.

Xiao H, Wu G, Tan S, Tan X, Yang Q . Recent Progress on Tumor Microenvironment-Activated NIR-II Phototheranostic Agents with Simultaneous Activation for Diagnosis and Treatment. Chem Asian J. 2024; 19(4):e202301036. DOI: 10.1002/asia.202301036. View

19.

Tian Y, Yin D, Cheng Q, Dang H, Teng C, Yan L . Supramolecular J-aggregates of aza-BODIPY by steric and π-π nteractions for NIR-II phototheranostics. J Mater Chem B. 2022; 10(10):1650-1662. DOI: 10.1039/d1tb02820k. View

20.

Li Y, Ma T, Jiang H, Li W, Tian D, Zhu J . Anionic Cyanine J-Type Aggregate Nanoparticles with Enhanced Photosensitization for Mitochondria-Targeting Tumor Phototherapy. Angew Chem Int Ed Engl. 2022; 61(24):e202203093. DOI: 10.1002/anie.202203093. View