Boron‐Fluorine Photosensitizers for Photodynamic Therapy

Yao, Liang; Xiao, Shuzhang; Dan, Feijun

doi:10.1155/2013/697850

Cited by 22 publications

(10 citation statements)

References 59 publications

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“…For instance, protonation or incorporation of metal ions or halogen atoms in the macrocycle changes the balance between fluorescence and intersystem crossing and can influence many photophysical parameters [ 21 – 24 ]. It is generally recognized that molecules bearing fluorine, chlorine or other halogen atoms display enhanced photoinduced cytotoxic properties [ 25 – 27 ]. This is assigned to the “heavy atom effect” resulting from the increased spin-orbit coupling in the presence of atoms with higher atomic number and, consequently, higher spin-orbit coupling constants that enable efficient intersystem crossing, large triplet quantum yields and the generation of ROS with high yields [ 16 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

Properties of halogenated and sulfonated porphyrins relevant for the selection of photosensitizers in anticancer and antimicrobial therapies

et al. 2017

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The impact of substituents on the photochemical and biological properties of tetraphenylporphyrin-based photosensitizers for photodynamic therapy of cancer (PDT) as well as photodynamic inactivation of microorganisms (PDI) was examined. Spectroscopic and physicochemical properties were related with therapeutic efficacy in PDT of cancer and PDI of microbial cells in vitro. Less polar halogenated, sulfonamide porphyrins were most readily taken up by cells compared to hydrophilic and anionic porphyrins. The uptake and PDT of a hydrophilic porphyrin was significantly enhanced with incorporation in polymeric micelles (Pluronic L121). Photodynamic inactivation studies were performed against Gram-positive (S. aureus, E. faecalis), Gram-negative bacteria (E. coli, P. aeruginosa, S. marcescens) and fungal yeast (C. albicans). We observed a 6 logs reduction of S. aureus after irradiation (10 J/cm2) in the presence of 20 μM of hydrophilic porphyrin, but this was not improved with incorporation in Pluronic L121. A 2–3 logs reduction was obtained for E. coli using similar doses, and a decrease of 3–4 logs was achieved for C. albicans. Rational substitution of tetraphenylporphyrins improves their photodynamic properties and informs on strategies to obtain photosensitizers for efficient PDT and PDI. However, the design of the photosensitizers must be accompanied by the development of tailored drug formulations.

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Section: Introductionmentioning

confidence: 99%

Properties of halogenated and sulfonated porphyrins relevant for the selection of photosensitizers in anticancer and antimicrobial therapies

et al. 2017

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“…Accordingly, progressive exploration of metal-free organic photosensitizers in DSP systems capable of harvesting visible-to-NIR regions are worth studying. However, there are a few reports of photocatalytic hydrogen production using panchromatic photosensitizers. , 4,4-Difluoro-4-bora-3 a ,4 a -diaza- s -indacene (BODIPY) dyes − exhibit outstanding photophysical properties, such as high molar extinction coefficients (ε) of absorbance, high-fluorescence quantum yields, and high photostabilities, leading to their use in bioprobes, , photodynamic therapy, − organic light-emitting diode, solar devices, photodetectors, etc . In addition, the robust properties made use as photosensitizers possible for applications in DSP or dye-sensitized photoelectrochemical cells .…”

Section: Introductionmentioning

confidence: 99%

Visible-to-Near-Infrared Light-Driven Photocatalytic Hydrogen Production Using Dibenzo-BODIPY and Phenothiazine Conjugate as Organic Photosensitizer

Suryani

Higashino

Sato

et al. 2018

ACS Appl. Energy Mater.

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A novel visible-to-near-infrared (visible-to-NIR) light-driven photocatalyst was prepared by loading a dibenzo-BODIPY-phenothiazine conjugate dye 1 as a panchromatic photosensitizer on hierarchical porous TiO2 (HPT) semiconductor. The sensitizer 1, which absorbed visible light at 638 and 440 nm with molecular extinction coefficients (ε) of 1.23 × 105 and 1.80 × 104 M–1 cm–1, respectively, in THF due to the dibenzo-BODIPY and phenothiazine-based D−π–A systems, respectively, showed panchromatic absorption up to 780 nm when deposited on the Pt/HPT photocatalyst to produce Pt/HPT500/1. The photocatalytic activities were investigated in the presence of ascorbic acid as a sacrificial agent in phosphate buffer solution under irradiation with λ > 400 nm using a 300 W Xe lamp at 100 mW cm–2 light intensity. After 10-h irradiation, the system achieved a remarkable catalytic activity for the production of H2 with a turnover number (TON) value of 11100. The sustained activity was suggestive after two sequences of 10-h illumination-period, whereas we found somewhat decrease in the photoactivity for the third run, although a TON value of 5650 still remained. The apparent quantum yields were evaluated by monitoring H2 production for each monochromatic light irradiation (λ = 420, 530, 600, 670, 700, and 750 nm). They were found to be consistent with the absorption profile, proving the panchromatic hydrogen generation sensitized by 1. The active absorption band of dye 1 in the entire visible-to-NIR spectrum led to production of a dye-sensitized photocatalytic system with a light-to-fuel efficiency of 6.96% in the initial irradiation period. This study provides important information for the development of metal-free organic photosensitizers with a wide spectral response up to the NIR region for photocatalytic water-splitting H2 production.

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“…Though a variety of small organic PSs including porphyrin structures, synthetic dyes, and natural products have been used in clinics, most of them can only show limited PDT efficacy against cancers due to their inherent features, including poor water solubility, insufficient photostability, low extinction coefficient, low absorption in the near‐infrared (NIR) region, insufficient 1 O 2 quantum yield, and poor cancer selectivity. [ 8 , 12 ] Therefore, it is highly desirable to develop new PSs capable of overcoming the limitations of currently used organic PSs, thus augmenting therapeutic outcomes against cancers.…”

Section: Introductionmentioning

confidence: 99%

Inorganic Nanomaterials with Intrinsic Singlet Oxygen Generation for Photodynamic Therapy

Younis

et al. 2021

Advanced Science

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Inorganic nanomaterials with intrinsic singlet oxygen (1O2) generation capacity, are emerged yet dynamically developing materials as nano‐photosensitizers (NPSs) for photodynamic therapy (PDT). Compared to previously reported nanomaterials that have been used as either carriers to load organic PSs or energy donors to excite the attached organic PSs through a Foster resonance energy transfer process, these NPSs possess intrinsic 1O2 generation capacity with extremely high 1O2 quantum yield (e.g., 1.56, 1.3, 1.26, and 1.09) than any classical organic PS reported to date, and thus are facilitating to make a revolution in PDT. In this review, the recent advances in the development of various inorganic nanomaterials as NPSs, including metal‐based (gold, silver, and tungsten), metal oxide‐based (titanium dioxide, tungsten oxide, and bismuth oxyhalide), metal sulfide‐based (copper and molybdenum sulfide), carbon‐based (graphene, fullerene, and graphitic carbon nitride), phosphorus‐based, and others (hybrids and MXenes‐based NPSs) are summarized, with an emphasis on the design principle and 1O2 generation mechanism, and the photodynamic therapeutic performance against different types of cancers. Finally, the current challenges and an outlook of future research are also discussed. This review may provide a comprehensive account capable of explaining recent progress as well as future research of this emerging paradigm.

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Boron‐Fluorine Photosensitizers for Photodynamic Therapy

Cited by 22 publications

References 59 publications

Properties of halogenated and sulfonated porphyrins relevant for the selection of photosensitizers in anticancer and antimicrobial therapies

Properties of halogenated and sulfonated porphyrins relevant for the selection of photosensitizers in anticancer and antimicrobial therapies

Visible-to-Near-Infrared Light-Driven Photocatalytic Hydrogen Production Using Dibenzo-BODIPY and Phenothiazine Conjugate as Organic Photosensitizer

Inorganic Nanomaterials with Intrinsic Singlet Oxygen Generation for Photodynamic Therapy

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