Skip to main content
Log in

Exploration of biocompatible AIEgens from human trichochrome

由人类毛发红素结构改造的生物相容性聚集诱导发 光体系

  • Letters
  • Published:
Science China Materials Aims and scope Submit manuscript

摘要

人类毛发红素(HTC)是一类生物安全性高、环境友好、性能稳 定的天然色素, 然而HTC的核心结构BBTD在溶解状态和固态下均无荧 光发射. 通过结构测试结合理论计算, 我们揭示了该化合物独特的双重 暗态光物理特性的内在机理. 在深刻理解机理的基础上, 我们利用化学 修饰的手段改造了BBTD母核, 设计合成了一系列具有聚集诱导发射光 性质的BBTD衍生物, 并成功将其应用于溶酶体靶向成像以及DNA定量 检测领域.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. Ferreira ESB, Hulme AN, McNab H, et al. The natural constituents of historical textile dyes. Chem Soc Rev, 2004, 33: 329–336

    Article  CAS  Google Scholar 

  2. Cramér G, Isaksson B. Quantitative determination of quinidine in plasma. Scand J Clin Lab Investigation, 1963, 15: 553–556

    Article  Google Scholar 

  3. Schramm S, Karothu DP, Raj G, et al. Turning on solid-state fluorescence with light. Angew Chem Int Ed, 2018, 57: 9538–9542

    Article  CAS  Google Scholar 

  4. Sharma DK, AdamsJr. ST, Liebmann KL, et al. Rapid access to a broad range of 6′-substituted firefly luciferin analogues reveals surprising emitters and inhibitors. Org Lett, 2017, 19: 5836–5839

    Article  CAS  Google Scholar 

  5. Evans MS, Chaurette JP, AdamsJr ST, et al. A synthetic luciferin improves bioluminescence imaging in live mice. Nat Methods, 2014, 11: 393–395

    Article  CAS  Google Scholar 

  6. Gao M, Liu YJ. Photoluminescence rainbow from coelenteramide—A theoretical study. Photochem Photobiol, 2019, 95: 563–571

    Article  CAS  Google Scholar 

  7. Zhu DY, Jiang YH, Jiang HF, et al. Marine fluorescent natural products. Chin J Mar Drugs, 2019, 38: 58–64

    Google Scholar 

  8. Sethna SM, Shah NM. The chemistry of coumarins. Chem Rev, 1945, 36: 1–62

    Article  CAS  Google Scholar 

  9. Shinde R, Perkins J, Contag CH. Luciferin derivatives for enhanced in vitro and in vivo bioluminescence assays. Biochemistry, 2006, 45: 11103–11112

    Article  CAS  Google Scholar 

  10. Wu W, Su J, Tang C, et al. cybLuc: An effective aminoluciferin derivative for deep bioluminescence imaging. Anal Chem, 2017, 89: 4808–4816

    Article  CAS  Google Scholar 

  11. Naghdi T, Faham S, Mahmoudi T, et al. Phytochemicals toward green (bio)sensing. ACS Sens, 2020, 5: 3770–3805

    Article  CAS  Google Scholar 

  12. Mei J, Leung NLC, Kwok RTK, et al. Aggregation-induced emission: Together we shine, united we soar! Chem Rev, 2015, 115: 11718–11940

    Article  CAS  Google Scholar 

  13. Zhao Q, Sun JZ. Red and near infrared emission materials with AIE characteristics. J Mater Chem C, 2016, 4: 10588–10609

    Article  CAS  Google Scholar 

  14. Jiang N, Wang Y, Qin A, et al. Effective enhancement of the emission efficiency of tetraphenylporphyrin in solid state by tetraphenylethene modification. Chin Chem Lett, 2019, 30: 143–148

    Article  CAS  Google Scholar 

  15. Feng G, Liu B. Aggregation-induced emission (AIE) dots: Emerging theranostic nanolights. Acc Chem Res, 2018, 51: 1404–1414

    Article  CAS  Google Scholar 

  16. Xu Y, Li C, Xu R, et al. Tuning molecular aggregation to achieve highly bright AIE dots for NIR-II fluorescence imaging and NIR-I photo-acoustic imaging. Chem Sci, 2020, 11: 8157–8166

    Article  CAS  Google Scholar 

  17. Han W, Du Y, Song M, et al. Fluorescent nanorods based on 9,10-distyrylanthracene (DSA) derivatives for efficient and long-term bioimaging. J Mater Chem B, 2020, 8: 9544–9554

    Article  CAS  Google Scholar 

  18. Han W, Zhang S, Deng R, et al. Self-assembled nanostructured photosensitizer with aggregation-induced emission for enhanced photodynamic anticancer therapy. Sci China Mater, 2020, 63: 136–146

    Article  CAS  Google Scholar 

  19. Liu Z, Wang Q, Zhu Z, et al. AIE-based nanoaggregate tracker: High-fidelity visualization of lysosomal movement and drug-escaping processes. Chem Sci, 2020, 11: 12755–12763

    Article  CAS  Google Scholar 

  20. Li D, Qin W, Xu B, et al. AIE nanoparticles with high stimulated emission depletion efficiency and photobleaching resistance for long-term super-resolution bioimaging. Adv Mater, 2017, 29: 1703643

    Article  Google Scholar 

  21. Thomson RH. The pigments of reddish hair and feathers. Angew Chem Int Ed Engl, 1974, 13: 305–312

    Article  CAS  Google Scholar 

  22. Napolitano A, Panzella L, Leone L, et al. Red hair benzothiazines and benzothiazoles: Mutation-inspired chemistry in the quest for functionality. Acc Chem Res, 2013, 46: 519–528

    Article  CAS  Google Scholar 

  23. Kaul BL. Studies on heterocyclic colouring matters part II: Δ2,2′-Bi(2H-1,4-benzothiazines). Helv Chim Acta, 1974, 57: 2664–2678

    Article  CAS  Google Scholar 

  24. Wang X, Liu H, Wu J, et al. Synthesis and photovoltaic properties of new conjugated polymers based on red hair pigment skeleton. Dyes Pigments, 2019, 160: 823–829

    Article  CAS  Google Scholar 

  25. Leone L, Crescenzi O, Napolitano A, et al. The Δ2,2′-bi(2H-1,4-benzothiazine) structural motif of red hair pigments revisited: Photochromism and acidichromism in a unique four-state system. Eur J Org Chem, 2012, 2012(27): 5136–5140

    Article  CAS  Google Scholar 

  26. Jangir R, Gadre S, Argade N. Sulfuryl chloride promoted gem-dichlorination-dehydrochlorination in alkyl benzothiazinylacetates: Synthesis of the skeleton of trichochrome pigments. Synthesis, 2015, 47: 2631–2634

    Article  CAS  Google Scholar 

  27. Leung NLC, Xie N, Yuan W, et al. Restriction of intramolecular motions: The general mechanism behind aggregation-induced emission. Chem Eur J, 2014, 20: 15349–15353

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (22021715 and 52150222) and the Major Scientific and Technological Project of the Department of Science & Technology, Zhejiang Province (2020C03030). Zhang HK thanks the support from the Open Fund of Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates and the South China University of Technology (2019B030301003).

Author information

Authors and Affiliations

Authors

Contributions

Zang Q and Zhang J carried out the molecular design and synthesis, structure characterization, photophysical property measurements and data analyses, and manuscript preparation. Huang C conducted the cell incubation, confocal-image taking and treatment under the guidance of Liu J; Zhang H helped with the theoretical calculations and mechanism analysis. Sun JZ managed the research projects, and guided the mechanism understanding and manuscript writing. Tang BZ assisted in the project and AIE mechanism analysis.

Corresponding authors

Correspondence to Jing Zhi Sun  (孙景志) or Ben Zhong Tang  (唐本忠).

Additional information

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary information

Experimental details and supporting data are available in the online version of the paper.

Qiguang Zang received his bachelor’s degree and master degree from the Central South University. He got his PhD degree from the South China University of Technology (SCUT) in 2018, under the supervision of Prof. Ben Zhong Tang and Prof. Rongrong Hu. He has been a postdoctor at Zhejiang University (ZJU) since 2020. His research interests focus on exploring the mechanism of molecular luminescence and developing novel AIE-active materials.

Jie Zhang received her bachelor’s degree from SCUT in 2014. She got her PhD degree in material science and engineering from ZJU in 2019, under the supervision of Prof. Ben Zhong Tang, Prof. Anjun Qin and Prof. Jing Zhi Sun. She has been a postdoctor at ZJU since 2019. Her research interests focus on the novel polymerization methodology based on green monomers.

Jing Zhi Sun received his bachelor’s, MSc and PhD degrees from Jilin University majored in chemistry. He was a postdoctoral fellow (1999) and then worked as an associated (2001) and full professor (2006) at ZJU. His research interests focus on the synthesis of functional polymers with triple-bond monomers and organic/polymeric luminescent materials with aggregation-induced emission property for chemical, environmental, biological and medical sensors.

Ben Zhong Tang received his BSc and PhD degrees from SCUT and Kyoto University, respectively. He conducted postdoctoral research at the University of Toronto. He joined Hong Kong University of Science and Technology (HKUST) as an assistant professor in 1994 and was promoted to chair professor in 2008. Now he is the presidential chair professor at The Chinese University of Hong Kong, Shenzhen (CUHK-SZ) and an adjunct professor at HKUST. His research interests include materials science, macromolecular chemistry, and biomedical theranostics. He is a pioneer of the concept of aggregation-induced emission (AIE).

Supporting Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zang, Q., Zhang, J., Huang, C. et al. Exploration of biocompatible AIEgens from human trichochrome. Sci. China Mater. 65, 3175–3181 (2022). https://doi.org/10.1007/s40843-022-2137-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40843-022-2137-4

Navigation