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Near-infrared Aza-BODIPY Dyes Through Molecular Surgery for Enhanced Photothermal and Photodynamic Antibacterial Therapy

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Chemical Research in Chinese Universities Aims and scope

Abstract

The widespread use of high-dose antibiotics will not only lead to the rapid acquisition of antibiotic resistance and increased incidence of drug-resistant bacterial infections, but also produce toxic side effects on normal tissues. Herein, two near-infrared dyes BDP-4PTZ and BDP-4DPA were synthesized, and the electron donors of diphenylamine and phenothiazine with the only difference of sulphur(S)-lock between the two phenyl rings were introduced onto the electron acceptor aza-dipyrromethene boron difluoride(aza-BODIPY) through molecular surgery. Through co-precipitation into nanoparticles(NPs), BDP-4PTZ NPs and BDP-4DPA NPs were fabricated with good biocompatibility. Upon 660 nm photoirradiation, BDP-4PTZ NPs and BDP-4DPA NPs showed excellent photothermal conversion efficiency(43% and 50%, respectively) and reactive oxygen species(ROS) production performance(ca. 3.6 and 6 times higher than that of indocyanine green, respectively). In vitro antibacterial experiments indicated that both NPs could effectively destroy the bacteria’s membrane to eradicate drug-resistant bacteria. Furthermore, the bacterial abscess was effectively eliminated after treatment with BDP-4DPA NPs under 660 nm photoirradiation without adverse effects. Thus, through molecular surgery, BDP-4DPA without the S-lock demonstrates synergistic photothermal and photodynamic antimicrobial activities, which is promising for further molecular design towards effective neo-antimicrobial phototherapy.

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Acknowledgements

This work was supported by the the Natural Science Foundation of Jiangsu Province, China(Nos.BK20200092, BK20200710).

We are also grateful to the High-performance Computing Center in Nanjing Tech University, China for supporting the computational resources.

Author information

Authors and Affiliations

  1. Key Laboratory of Flexible Electronics(KLOFE) & Institute of Advanced Materials(IAM), Nanjing Tech University, Nanjing, 210009, P. R. China

    Qing Yu, Xuan Huang, Tian Zhang, Weili Wang, Dongliang Yang, Jinjun Shao & Xiaochen Dong

Authors
  1. Qing Yu
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  2. Xuan Huang
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  3. Tian Zhang
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  4. Weili Wang
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  5. Dongliang Yang
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  6. Jinjun Shao
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  7. Xiaochen Dong
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Correspondence to Jinjun Shao or Xiaochen Dong.

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40242_2021_1190_MOESM1_ESM.pdf

Near-Infrared Aza-BODIPY Dyes through Molecular Surgery for Enhanced Photothermal and Photodynamic Antibacterial Therapy

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Yu, Q., Huang, X., Zhang, T. et al. Near-infrared Aza-BODIPY Dyes Through Molecular Surgery for Enhanced Photothermal and Photodynamic Antibacterial Therapy. Chem. Res. Chin. Univ. 37, 951–959 (2021). https://doi.org/10.1007/s40242-021-1190-7

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  • DOI: https://doi.org/10.1007/s40242-021-1190-7

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