Hydrophilic polyphosphoester-conjugated fluorinated chlorin as an entirely biodegradable nano-photosensitizer for reliable and efficient photodynamic therapy

Li, Yong; Wu, Meng-Si; Xue, Yudong; Chen, Chao; Wurm, Frederik R.; Lan, Minbo

doi:10.1039/d0cc00142b

Cited by 16 publications

(13 citation statements)

References 35 publications

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“…Inspired by the structure of bacteriochlorins, an analogue of bacteriochlorin, FBC, was synthesized via one-step diimide reduction of TFPP. TFPP could be directly obtained by the original reactive agents of pentafluoro benzaldehyde and pyrrole, according to previous works 41,42 . As shown in Scheme S1 (ESI †), TFPP was carefully mixed with p-toluenesulfonyl hydrazide (TSH) by grinding, and then the mixture was heated under vacuum to produce FBC after 2 h of vacuuming.…”

Section: Resultsmentioning

confidence: 99%

“…TFPP could be directly obtained using the original reactive agents pentafluorobenzaldehyde and pyrrole, according to previous studies. 41,42 As shown in Scheme S1 (ESI†), TFPP was carefully mixed with p -toluenesulfonyl hydrazide (TSH) by grinding, and then the mixture was heated under vacuum to produce FBC after 2 h of vacuuming. FBC was characterized with 1 H-NMR and 19 F-NMR spectra (Fig.…”

Section: Resultsmentioning

confidence: 99%

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An ultra-stable bio-inspired bacteriochlorin analogue for hypoxia-tolerant photodynamic therapy

2021

Chem. Sci.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

An ultra-stable bio-inspired bacteriochlorin analogue for hypoxia-tolerant photodynamic therapy

2021

Chem. Sci.

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“…As previously reported, [46] we first synthesized (TFPP) from 2,3,4,5,6-pentafluorobenzaldehyde and pyrrole ( 1 H NMR and 19 F NMR were shown in Figures S1 and S2, Supporting Informa-tion), and then the TFPP was reduced into FBC by the solid phase reduction, as shown in Scheme S1 (Supporting Information). FBC was characterized by 1 H NMR and 19 F NMR, respectively.…”

Section: Synthesis and Characterization Of Nir Light Absorption Photo...mentioning

confidence: 99%

RAFT Polymerization of Semifluorinated Monomers Mediated by a NIR Fluorinated Photocatalyst

Wang

Zhang

et al. 2022

Macromol. Rapid Commun.

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Near‐infrared (NIR) light plays an increasingly important role in the field of photoinduced electron/energy transfer‐reversible addition–fragmentation chain transfer (PET‐RAFT) polymerization due to its unique properties. Yet, the NIR photocatalyst with good stability for PET‐RAFT polymerization remains promising. Here, a strategy of NIR PET‐RAFT polymerization of semifluorinated monomers using fluorophenyl bacteriochlorin as a photocatalyst with strong absorption at the NIR light region (710–780 nm) is reported. In which, the F atoms are used to modify reduced tetraphenylporphyrin structure with enhanced photostability of photocatalyst. Under the irradiation of NIR light (λmax = 740 nm), the PET‐RAFT polymerization of semifluorinated methylacrylic monomers presents living/control characteristics and temporal modulation. By the PET‐RAFT polymerization‐induced self‐assembly (PISA) strategy, stable fluorine‐containing micelles are constructed in various solvents. In addition, the fluorinated hydrophobic surface is fabricated via a surface‐initiated PET‐RAFT (SI‐PET‐RAFT) polymerization using silicon wafer bearing RAFT agents with tunable surface hydrophobicity. This strategy not only enlightens the application of further modified compounds based on porphyrin structure in photopolymerization, but also shows promising potential for the construction of well‐defined functional fluoropolymers.

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“…64 The biodegradable nanogel conjugate of 7,8-dihydro-5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphine (TFPC) with polyphosphoesters (PPE) (TFPC-PPE NPS) accumulates in 4T1 carcinoma cells of mice and exhibits tremendous regression of tumor growth with 665 nm laser irradiation. 65 Polymer-conjugated NPSs can be trapped inside the polymer micelle, matrix, and network. These NPs ensure biocompatibility and bioavailability and enhance the NPS accumulation in the carcinoma cells due to the EPR effect.…”

Section: Types Of Nanophotosensitizers In Pdtmentioning

confidence: 99%

Photodynamic Nanophotosensitizers: Promising Materials for Tumor Theranostics

Keerthiga

Zhao

Pei

et al. 2020

ACS Biomater. Sci. Eng.

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Photodynamic theranostics/therapy (PDT) is a potential strategy for selectively imaging malignant sites and treating cancer via a non-invasive therapeutic method. Photosensitizers, the crucial components of PDT, enable colocalization of photons and light, and photon/light therapy in the therapeutic window of 400–900 nm exhibits photocytotoxicity to tumor cells. Due to their high biostability and photocytotoxicity, nanophotosensitizers (NPSs) are of much interest for malignant tumor theranostics at present. NPS-activated photons transfer energy through the absorption of a photon and convert molecular oxygen to the singlet reactive oxygen species, which leads to apoptosis and necrosis. Moreover, NPSs modified by polymers, including PLGA, PEG-PLA, PDLLA, PVCL-g-PLA, and P(VCL-co-VIM)-g-PLA, exhibit excellent biocompatibility, and a tumor-targeting molecule linked on the nanoparticle surface can precisely deliver NPSs into the tumor region. The development of NPSs will accelerate the progress in tumor theranostics through the photon/light pathway.

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Hydrophilic polyphosphoester-conjugated fluorinated chlorin as an entirely biodegradable nano-photosensitizer for reliable and efficient photodynamic therapy

Abstract: An entirely biodegradable nano-photosensitizer platform (PPE-FP2) was fabricated to avoid residual nanoparticles, thus realizing reliable and effective photodynamic therapy.

Cited by 16 publications

References 35 publications

An ultra-stable bio-inspired bacteriochlorin analogue for hypoxia-tolerant photodynamic therapy

An ultra-stable bio-inspired bacteriochlorin analogue for hypoxia-tolerant photodynamic therapy

RAFT Polymerization of Semifluorinated Monomers Mediated by a NIR Fluorinated Photocatalyst

Photodynamic Nanophotosensitizers: Promising Materials for Tumor Theranostics

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