Journal of East China Normal University(Natural Science) >

2023 , Vol. 2023 >Issue 1: 186 - 193

DOI: https://doi.org/10.3969/j.issn.1000-5641.2023.01.019

Green Chemical Analysis

Preparation and photothermal studies on a cucurbit[8]uril-based near-infrared organic supramolecular photothermal agent

  • Wenyan CAI ,
  • Yue PAN ,
  • Qiwei ZHANG ,
  • Yang TIAN
Expand
  • Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai　200062, China

Received date: 2022-08-09

  Accepted date: 2022-09-30

  Online published: 2023-01-07

Fold

Abstract

Photothermal therapy has attracted attention as a novel cancer treatment with high specificity, minimal invasiveness, and low toxicity. In this study, a facile, effective, and green method was developed to prepare a novel supramolecular photothermal material. Grinding a commercial dye, dibenzotetrathiafulvalene (DBTTF, with absorption <400 nm) with cucurbit[8]uril (CB[8]) in air with a small amount of water leads to the oxidation of DBTTF to radical cations. Furthermore, DBTTF dimerizes, assembles into the cavity of CB[8], and forms a ternary supramolecular complex with strong absorption in the visible and near-infrared regions, where the longest absorption wavelength exceeds 1000 nm. The photothermal conversion efficiency of the supramolecular system is 18.7%. The system exhibits good photothermal stability and biocompatibility, and has been successfully applied in the photothermal ablation of live tumor cells. This supramolecular material has potential applications in photothermal therapy and other photothermal conversion fields.

Key words： supramolecular complex; self-assembly; cucurbituril; dibenzotetrathiafulvalene; near-infrared; photothermal therapy; photothermal conversion

Cite this article

Wenyan CAI , Yue PAN , Qiwei ZHANG , Yang TIAN . Preparation and photothermal studies on a cucurbit[8]uril-based near-infrared organic supramolecular photothermal agent[J]. Journal of East China Normal University(Natural Science), 2023 , 2023(1) : 186 -193 . DOI: 10.3969/j.issn.1000-5641.2023.01.019

References

1 LI X, YONG T, WEI Z, et al. Reversing insufficient photothermal therapy-induced tumor relapse and metastasis by regulating cancer-associated fibroblasts. Nature Communications, 2022, 13 (1): 2794- 2813.
2 CHEN C, PAN Y, LI D, et al. An intramolecular charge transfer-forster resonance energy transfer integrated unimolecular platform for two-photon ratiometric fluorescence sensing of methionine sulfoxide reductases in live-neurons and mouse brain tissues. Analytical Chemistry, 2022, 94 (16): 6289- 6296.
3 MEI Y, LIU Z, LIU M, et al. Two-photon fluorescence imaging and ratiometric quantification of mitochondrial monoamine oxidase-A in neurons. Chemical Communications, 2022, 58 (46): 6657- 6660.
4 WANG H, XUE K F, YANG Y, et al. In situ hypoxia-induced supramolecular perylene diimide radical anions in tumors for photothermal therapy with improved specificity. Journal of the American Chemical Society, 2022, 144 (5): 2360- 2367.
5 LIU S, ZHOU X, ZHANG H, et al. Molecular motion in aggregates: Manipulating tict for boosting photothermal theranostics. Journal of the American Chemical Society, 2019, 141 (13): 5359- 5368.
6 XU G, LI C, CHI C, et al. A supramolecular photosensitizer derived from an Arene-Ru(Ⅱ) complex self-assembly for NIR activated photodynamic and photothermal therapy. Nature Communications, 2022, 13 (1): 3064.
7 YOU C, LI Y, DONG Y, et al. Low-temperature trigger nitric oxide nanogenerators for enhanced mild photothermal therapy. ACS Biomaterials Science & Engineering, 2020, 6 (3): 1535- 1542.
8 ZHANG D, WU T, QIN X, et al. Intracellularly generated immunological gold nanoparticles for combinatorial photothermal therapy and immunotherapy against tumor. Nano Letters, 2019, 19 (9): 6635- 6646.
9 FU J J, ZHANG J Y, LI S P, et al. CuS nanodot-loaded thermosensitive hydrogel for anticancer photothermal therapy. Molecular Pharmaceutics, 2018, 15 (10): 4621- 4631.
10 ZHOU T, XIE S, ZHOU C, et al. All-in-one second near-infrared light-responsive drug delivery system for synergistic chemo-photothermal therapy. ACS Applied Bio Materials, 2022, 5 (8): 3841- 3849.
11 LEI S, ZHAO F, ZHANG J, et al. Metallo-dye-based supramolecular nanoassembly for NIR-Ⅱ cancer theranostics. Analytical Chemistry, 2022, 94 (23): 8399- 8408.
12 WU F, LU Y, MU X, et al. Intriguing H-aggregates of heptamethine cyanine for imaging-guided photothermal cancer therapy. ACS Applied Materials & Interfaces, 2020, 12 (29): 32388- 32396.
13 ZHANG W, LIN W, LI C, et al. Rational design of BODIPY-diketopyrrolopyrrole conjugated polymers for photothermal tumor ablation. ACS Applied Materials & Interfaces, 2019, 11 (36): 32720- 32728.
14 WU C, HUANG X, TANG Y, et al. Pyrrolopyrrole aza-BODIPY near-infrared photosensitizer for dual-mode imaging-guided photothermal cancer therapy. Chemical Communications, 2019, 55 (6): 790- 793.
15 ZOU Q, ABBAS M, ZHAO L, et al. Biological photothermal nanodots based on self-assembly of peptide-porphyrin conjugates for antitumor therapy. Journal of the American Chemical Society, 2017, 139 (5): 1921- 1927.
16 HU H, WANG H, YANG Y, et al. A bacteria-responsive porphyrin for adaptable photodynamic/photothermal therapy. Angewandte Chemie-International Edition, 2022, 61 (23): e202200799.
17 DUAN X, ZHANG Q, JIANG Y, et al. Semiconducting polymer nanoparticles with intramolecular motion-induced photothermy for tumor phototheranostics and tooth root canal therapy. Advanced Materials, 2022, 34 (17): e2200179.
18 CHEN P, MA Y, ZHENG Z, et al. Facile syntheses of conjugated polymers for photothermal tumour therapy. Nature Communications, 2019, 10 (1): 1192.
19 ZHANG Q, TIAN H. Effective integrative supramolecular polymerization. Angewandte Chemie-International Edition, 2014, 53 (40): 10582- 10584.
20 TANG B, LI W L, CHANG Y, et al. A supramolecular radical dimer: High-efficiency NIR-Ⅱ photothermal conversion and therapy. Angewandte Chemie-International Edition, 2019, 58 (43): 15526- 15531.
21 ZIGANSHINA A Y, KO Y H, JEON W S, et al. Stable π-dimer of a tetrathiafulvalene cation radical encapsulated in the cavity of cucurbit[8]uril. Chemical Communications, 2004, (7): 806- 807.
22 LI D, FENG Z, HAN Y, et al. Time-resolved encryption via a kinetics-tunable supramolecular photochromic system . Advanced Science, 2022, 9 (6): e2104790.
23 LI D, HAN Y, JIANG Y, et al. Achieving adjustable multifunction based on host-guest interaction-manipulated reversible molecular conformational switching. ACS Applied Materials & Interfaces, 2022, 14 (1): 1807- 1816.
24 ZHANG Q W, LI D, LI X, et al. Multicolor photoluminescence including white-light emission by a single host-guest complex. Journal of the American Chemical Society, 2016, 138 (41): 13541- 13550.
Options
Outlines

/

〈 〉