Heavy atom enhanced generation of singlet oxygen in novel indenofluorene-based two-photon absorbing chromophores for photodynamic therapy

Tang, Changquan; Hu, Ping; Ma, En; Huang, Mingdong; Zheng, Qingdong

doi:10.1016/j.dyepig.2015.01.019

Cited by 23 publications

(10 citation statements)

References 44 publications

(31 reference statements)

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“…9d), owing to the extended p-conjugation lengths. 168 Fig. 9e showed that all the Br/I-doped TPA PSs caused a much faster absorbance decrease of 1,3-diphenylisobenzofuran (DPBF), which suggested that the doping of heavy atoms could achieve much higher 1 O 2 yield, as well as PDT efficacy.…”

Section: Challenges Of Pdt By Direct Excitationmentioning

confidence: 98%

Overcoming the Achilles' heel of photodynamic therapy

2016

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Photodynamic therapy (PDT) has been applied to treat a wide range of medical conditions, including wet age-related macular degeneration psoriasis, atherosclerosis, viral infection and malignant cancers. However, the tissue penetration limitation of excitation light hinders the widespread clinical use of PDT. To overcome this "Achilles' heel", deep PDT, a novel type of phototherapy, has been developed for the efficient treatment of deep-seated diseases. Based on the different excitation sources, including near-infrared (NIR) light, X-ray radiation, and internal self-luminescence, a series of deep PDT techniques have been explored to demonstrate the advantages of deep cancer therapy over conventional PDT excited by ultraviolet-visible (UV-Vis) light. In particular, the featured applications of deep PDT, such as organelle-targeted deep PDT, hypoxic deep PDT and deep PDT-involved multimodal synergistic therapy are discussed. Finally, the future development and potential challenges of deep PDT are also elucidated for clinical translation. It is highly expected that deep PDT will be developed as a versatile, depth/oxygen-independent and minimally invasive strategy for treating a variety of malignant tumours at deep locations.

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Section: Challenges Of Pdt By Direct Excitationmentioning

confidence: 98%

Overcoming the Achilles' heel of photodynamic therapy

2016

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“…Nevertheless, for efficient production, the sensitizers should possess additional features such as high intersystem crossing (ISC) rates and long triplet lifetimes in order to increase the probability of energy transfer. In terms of molecular design, ISC may be favoured by enhancing the spinorbit coupling (SOC) with the introduction of heavy atoms [12][13][14] or heteroatoms 15,16 or by introducing donor/acceptor units with electron transfer steps. 17,18 In this way, organometallic chromophores containing heavy metals deserve their investigation in this field since they possess high SOC values and the tuneability of their photophysical properties through ligand modification can be easily performed.…”

Section: Introductionmentioning

confidence: 99%

Aggregation of gold(i) complexes: phosphorescence vs. singlet oxygen production

et al. 2022

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“…In the case of NI-H , the most prominent TP absorption wavelength (λ TPA ) was determined to be 444 nm, with a maximum TP absorption cross-section (δ TPA ) of 25 GM. Notably, the incorporation of donor groups into naphthoimidazolium moieties led to a significant enhancement in both the TP absorption wavelength and TP absorption cross-section due to enhanced push–pull as well as the ICT effect. ,, For instance, NI-Cz and NI-Cbz exhibited λ TPA values of 634 and 747 nm, respectively, along with corresponding δ TPA values of 107 and 261 GM. The observed augmentation in the theoretical TP absorption cross-section, progressing from NI-H to NI-Cz and NI-Cbz , demonstrates concordance with empirical findings (Table ).…”

Section: Resultsmentioning

confidence: 98%

“…By incorporating electron-donating groups into imidazolium frameworks, a strong intramolecular charge transfer (ICT) effect can be established. This effect leads to a red shift in both absorption and emission wavelengths , and enhances the two-photon (TP) absorption characteristics, including wavelength (λ TPA ) and absorbance (δ TPA ). , These properties make imidazolium-based PSs particularly attractive for applications in TP-excited PDT and imaging. Another advantageous characteristic of imidazolium salts is their inherent hydrophilicity, which enables them to maintain their fluorescence emission and ROS generation capabilities in aqueous environments. , This hydrophilicity is beneficial for various biomedical applications as it allows for the effective utilization of these PSs in aqueous-based systems.…”

Section: Introductionmentioning

confidence: 99%

Imidazolium-Based Heavy-Atom-Free Photosensitizer for Nucleus-Targeted Fluorescence Bioimaging and Photodynamic Therapy

Pham,

Hoang,

Tran

et al. 2023

ACS Appl. Mater. Interfaces

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The development of heavy-atom-free photosensitizers (PSs) for photodynamic therapy (PDT) has encountered significant challenges in achieving simultaneous high fluorescence emission and reactive oxygen species (ROS) generation. Moreover, the limited water solubility of these PSs imposes further limitations on their biomedical applications. To overcome these obstacles, this study presents a molecular design strategy employing hydrophilic heavy-atom-free PSs based on imidazolium salts. The photophysical properties of these PSs were comprehensively investigated through a combination of experimental and theoretical analyses. Notably, among the synthesized PSs, the ethylcarbazole-naphthoimidazolium (NI-Cz) conjugate exhibited efficient fluorescence emission (Φ F = 0.22) and generation of singlet oxygen (Φ Δ = 0.49), even in highly aqueous environments. The performance of NI-Cz was validated through its application in fluorescence bioimaging and PDT treatment in HeLa cells. Furthermore, NI-Cz holds promise for two-photon excitation and type I ROS generation, nucleus localization, and selective activity against Gram-positive bacteria, thereby expanding its scope for the design of heavy-atom-free PSs and phototheranostic applications.

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Heavy atom enhanced generation of singlet oxygen in novel indenofluorene-based two-photon absorbing chromophores for photodynamic therapy

Cited by 23 publications

References 44 publications

Overcoming the Achilles' heel of photodynamic therapy

Overcoming the Achilles' heel of photodynamic therapy

Aggregation of gold(i) complexes: phosphorescence vs. singlet oxygen production

Imidazolium-Based Heavy-Atom-Free Photosensitizer for Nucleus-Targeted Fluorescence Bioimaging and Photodynamic Therapy

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