4.6 Article

Structural effect of NIR-II absorbing charge transfer complexes and its application on cysteine-depletion mediated ferroptosis and phototherapy

Journal

JOURNAL OF MATERIALS CHEMISTRY B
Volume 9, Issue 39, Pages 8300-8307

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1tb01696b

Keywords

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Funding

  1. NNSF of China [61805117, 21975121]
  2. Jiangsu Province Policy Guidance Plan [BZ2019014]
  3. Six talent peak innovation team in Jiangsu Province [TD-SWYY-009]
  4. Natural Science Foundation of Jiangsu Province [BK20190688]
  5. Natural Science Foundation of Shandong Province [ZR2020KB018]
  6. 'Taishan scholars' construction special fund of Shandong Province

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This study successfully prepared NIR-II absorbing PTAs by synthesizing different substituted electron donors and assembling them with electron-deficient F4TCNQ to form charge-transfer complex nanoparticles. Among them, Et-F4 NPs showed the highest NIR-II absorption ability and best photothermal effect, demonstrating potential antitumor efficacy. The research indicated that the photophysical properties of CTCs can be tailored by changing molecular structure and aggregate behaviors.
Second near-infrared (NIR-II) absorbing organic photothermal agents (PTAs) usually suffer from laborious and time-consuming synthesis; therefore, it is of importance to develop a simple and easy-to-handle method for the preparation of NIR-II PTAs. Charge-transfer complexes (CTCs) can be easily used to construct NIR-II absorbing PTAs, although the relationship between their molecular structure and photophysical properties is yet to be uncovered. Herein, three kinds of electron donors with different substitutions (chloroethyl, ethyl, and methyl) were synthesized and assembled with electron-deficient F4TCNQ to afford corresponding CTC nanoparticles (Cl-F4, Et-F4, and Me-F4 NPs). The large energy gap (>0.61 eV) between HOMO of the donor and LUMO of the acceptor made the CTCs exhibit high charge transfer (>0.93) and dramatic differences in photophysical properties. Additionally, Et-F4 NPs possess the highest NIR-II absorption ability and best photothermal effect because of different packing modes (mass extinction coefficient of 11.0 L g(-1) cm(-1) and photothermal conversion efficiency of 40.2% at 1060 nm). The mixed stacking mode formed strong charge-transfer absorption bands, indicating that the photophysical properties of CTCs can be tailored by changing the molecular structure and aggregate behaviors. Furthermore, Et-F4 NPs with cyano groups could specifically react with cysteine to block the intracellular biosynthesis of GSH and result in ROS accumulation and ferroptosis. Et-F4 NPs possess outstanding antitumor efficacy for the combined actions of NIR-II triggered photothermal killing effect and ferroptosis in vivo.

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