Chem. J. Chinese Universities ›› 2020, Vol. 41 ›› Issue (2): 191.doi: 10.7503/cjcu20190614
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WU Wenbo,LIU Bin(
)
Received:2019-11-26
Online:2020-02-10
Published:2019-12-31
Contact:
Bin LIU
E-mail:chewwe@nus.edu.sg
Supported by:CLC Number:
TrendMD:
WU Wenbo,LIU Bin. Two-photon Excitable Photosensitizers with Aggregation-induced Emission and Their Biomedical Applications †[J]. Chem. J. Chinese Universities, 2020, 41(2): 191.
Fig.1 Fluorescent photos of solutions or suspensions of perylene(ACQ fluorophore, A) and hexaphenylsilole(AIE fluorophore, B) in THF/water mixtures with different volume fractions of water under UV lamp Reproduced with permission from Ref.[17], Copyright 2015, American Chemical Society.
Fig.2 Difference between one-photon excited and two-photon excited photodynamic therapy Reproduced with permission from Ref.[35], Copyright 2018, Royal Society of Chemistry.
Fig.3 Simplified Jablonski diagram depicting the electron transitions of different types of PSs upon light excitation (A) Traditional PS; (B) AIE PS in aggregated state. ISC from S1 to T1, and energy transfer from T1 to 3O2, generating cytotoxic 1O2. ISC: intersystem crossing, NR: nonradiative decay, FL: fluorescence, 1O2: singlet oxygen, 3O2: normal oxygen. Reproduced with permission from Ref.[20], Copyright 2016, Wiley-VCH.
Fig.4 Design and properties of TPEDC (A) Chemical structure, HOMO and LUMO distributions of TPEDC; (B) UV-Vis spectra of ABDA in the presence of TPEDC NPs under light irradiation(60 mW/cm2, 400—700 nm) in water; (C) two-photon absorption cross section of TPEDC NPs at different wavelengths, the inset shows the two-photon-induced fluorescence spectrum; (D, E) detection of intracellular ROS generation using DCF-DA in HeLa cells incubated with(E) and without(D, control) TPEDC NPs followed by different two-photon scans, λex=488 nm; λem=505—525 nm. Fig.(A) was reproduced with permission from Ref.[45], Copyright 2017, Wiley-VCH; Figures(B—E) were reproduced with permission from Ref.[38], Copyright 2017, Wiley-VCH.
Fig.5 Design and properties of IQ-TPA (A) Chemical structures of TPE-IQ-2O and IQ-TPA; (B) change in fluorescence intensity at 525 nm of TPE-IQ-2O/IQ-TPA and DCFH in PBS upon white light irradiation for different times; (C) two-photon absorption spectrum of IQ-TPA. Reproduced with permission from Ref.[35], Copyright 2018, Royal Society of Chemistry.
Fig.6 Design and properties of DCDPP nanoparticles (A) Preparation of DCDPP-2TPA-encapsulated silica nanoparticles; (B) two-photon fluorescence imaging of HeLa cells after irradiation for 5 min with a 1040 nm fs laser pretreated with DCDPP-2TPA-encapsulated silica NPs(0.018 mg/mL) and DCF-DA(25 μmol/L), or only DCF-DA(25 μmol/L). Reproduced with permission from Ref.[52], Copyright 2018, Wiley-VCH.
Fig.7 Design and properties of Ir1—Ir5 (A) Chemical structures of Ir1—Ir5; (B) Trajectory of Ir3 emission intensity versus water fraction and visual observation of PL; (C) TPA cross-sections of Ir3; (D) 1O2 emission spectra in the presence of Ir3 and irradiation(405 nm laser) in varying fractions of water-DMSO mixture. Reproduced with permission from Ref.[38], Copyright 2018, Royal Society of Chemistry.
Fig.8 Design and properties of PTPEDC2 (A) Chemical structures of TPEDC, PTPEDC1 and PTPEDC2; (B) normalized absorption and photoluminescence(PL) spectra of AIE PS NPs in aqueous media; (C) normalized degradation percentages of ABDA in the presence of PS NPs in aqueous media upon white light irradiation(400—700 nm, 50 mW/cm2); [AIE PS NPs]=10 μmol/L based on AIE PS; [ABDA]=50 μmol/L; (D) two-photon absorption cross-section spectra of AIE PS NPs in aqueous solution. Reproduced with permission from Ref.[60], Copyright 2019, American Chemical Society.
Fig.9 Schematic illustration for the in vitro ROS detection of AIE PS NPs in aqueous media under two-photon excitation(A) and in vitro real-time detection of ROS generation in aqueous solution of PS NPs under two-photon excitation after different scans(B) The image in the last column is the overlay image between the 1th and 5th columns. λex=820 nm, λem: 635—675 nm(red, from PS NPs) and 510—535 nm(green, from DCFH), scanning laser: 820 nm, 6 mW, 5.33 s per scan. Reproduced with permission from Ref.[60], Copyright 2019, American Chemical Society.
Fig.10 PDT results of TPEDC by two-photon(A) and one-photon(B) excited PDT (A) Live/dead staining of TPEDC NPs(10 μg/mL) treated HeLa cells after different two-photon scans. The live cells were stained by calcein(green), while dead cells were stained by propidium iodide(red). The scanned areas(243 μm×243 μm) were shown by white squares[38]. (B) Live/dead staining of TPEDC NPs(5 μg/mL) treated MDA-MB-231 breast cancer cells after 5 min light irradiation(60 mW/cm2, 400—700 nm). The live cells were stained by fluorescein diacetate(green), while dead cells were stained by propidium iodide(red)[61]. Reproduced with permission from Ref.[38,61], Copyright 2017, Royal Society of Chemistry.
Fig.11 Monitoring the mitochondrial change during two-photon PDT by the fluorescence of IQ-TPA Fluorescence images of HeLa cells were incubated with 1 mmol/L of IQ-TPA for 30 min and then followed by two-photon scans: (A, A') 1 scan, (B, B') 33 scans, (C, C') 66 scans, (D, D') 100 scans. The two-photon excitation condition was at 900 nm(fs Ti: sapphire laser, 5 mW) with a scan area of 60 mm×60 mm and a scan speed of 1.02 s per scan. Reproduced with permission from Ref.[35], Copyright 2018, Royal Society of Chemistry.
Fig.12 Chemical structures of TPE-red and PSMA as well as the preparation of AIE-PSMA NPs(A) and transmission images of HeLa cells with different treatment(B) Reproduced with permission from Ref.[65], Copyright 2017, Royal Society of Chemistry.
Fig.13 Two-photon excited PDT results of in PTPEDC2 NPs in zebrafish liver tumor model (A) Schematic illustration of in vivo two-photon excited PDT of PTPEDC2 NPs in zebrafish liver tumor model; (B) the relative increase(in percent) in zebrafish tumor size after different treatments. N.S.: data are not significantly different; double asterisks indicate p<0.01, and n=6. Laser: 820 nm fs laser. Reproduced with permission from Ref.[60], Copyright 2019, American Chemical Society.
Fig.14 Two-photon excited brain-blood-vessel closure results of TPEDC (A, B): 3D reconstruct(A) and Z-projection(B) of two-photon images of brain blood vessels. (C—E): Two-photon images of brain blood vessels at different vertical depths: 70 μm(C), 140 μm(D), and 200 μm(E). (F, G): Pre-irradiation(F) and post-irradiation(G) images of the brain blood vessels of mouse treated with TPEDC NPs(8 mg/kg based on TPEDC) and two-photon excitation. (H, I): Pre-irradiation(H) and post-irradiation(I) images of the brain blood vessels of a mouse treated with Luminicell NPs and two-photon excitation. The scanned areas are highlighted by white squares. Two-photon excitation condition: 800 nm, 30 mW; λex: 800 nm; λem: 590—630 nm. Reproduced with permission from Ref.[38], Copyright 2017, Wiley-VCH.
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