Intraperitoneal photodynamic therapy mediated by a fullerene in a mouse model of abdominal dissemination of colon adenocarcinoma

Mróz, Paweł; Xia, Yumin; Asanuma, Daisuke; Konopko, Aaron M.; Zhiyentayev, Timur; Huang, Ying‐Ying; Sharma, Sunil; Khan, Usman; Wharton, Tim; Hamblin, Michael R.

doi:10.1016/j.pdpdt.2011.03.278

Cited by 11 publications

(13 citation statements)

References 28 publications

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“…injection of C 60 derivatives and found that necrotic cell death was dominant compared with apoptosis, which was determined using the TUNEL assay. 42 The reduction potential of electronically excited TFPP was estimated as approximately +1.15 V vs SCE. [43][44][45] The value is comparable to that of the electronically excited 3 C 60 and much higher than that of the electronically excited state of 5,10,15,20-tetraphenyporphyrin estimated as approximately +0.65 V vs SCE.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Photophysical Properties, and Biological Evaluation of trans-Bisthioglycosylated Tetrakis(fluorophenyl)chlorin for Photodynamic Therapy

et al. 2015

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trans-Bisthioglycosylated tetrakis(fluorophenyl)chlorin (7) was designed as a powerful photodynamic therapy (PDT) photosensitizer based on the findings of our systematic studies. We show here that the trans-bisthioglycosylated structure of 7 enhanced its uptake by HeLa cells and that the chlorin ring of 7 increased the efficiency of reactive oxygen species generation under the standard condition of our photocytotoxicity test. The versatility of 7 in PDT treatment was established using weakly metastatic B16F1 melanoma cells, metastatic 4T1 breast cancer cells, the RGK-1 gastric carcinoma mucosal cell line, and three human glioblastoma cell lines (U87, U251, and T98G). The pharmacokinetics of 7 in mice bearing 4T1 breast cancer cells showed a high tumor-to-skin concentration ratio (approximately 60) at 24 h after intraperitoneal injection. The PDT efficacy of 7 in vivo was approximately 250-times higher than that of mono-l-aspartyl chlorin e6 (9) in mice bearing 4T1 breast cancer cells.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Photophysical Properties, and Biological Evaluation of trans-Bisthioglycosylated Tetrakis(fluorophenyl)chlorin for Photodynamic Therapy

et al. 2015

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“…By contrast Yamakoshi et al 44 found that in polar solvents, especially those containing reducing agents (such as NADH at concentrations found in cells), illumination of various fullerenes will generate different ROS produced by Type 1 mechanism such as superoxide anion and hydroxyl radical. Mroz et al 45, 46 showed that photoactivation of a mono‐cationic fullerene BB4 (a mono‐substituted version of the tris‐cationic BB6) produced ROS from Type I mechanism as well as Type II. Despite much theoretical discussion it is still not clear what physical or chemical factors influence the Type I/Type II balance amongst different PS 47.…”

Section: Discussionmentioning

confidence: 99%

Type I and Type II mechanisms of antimicrobial photodynamic therapy: An in vitro study on gram‐negative and gram‐positive bacteria

et al. 2012

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Background and Objectives Antimicrobial photodynamic therapy (APDT) employs a nontoxic photosensitizer (PS) and visible light, which in the presence of oxygen produce reactive oxygen species (ROS), such as singlet oxygen (1O2, produced via Type II mechanism) and hydroxyl radical (HO•, produced via Type I mechanism). This study examined the relative contributions of 1O2 and HO• to APDT killing of Gram-positive and Gram-negative bacteria. Study Design/Materials and Methods Fluorescence probes, 3'-(p-hydroxyphenyl)-fluorescein (HPF) and singlet oxygen sensor green reagent (SOSG) were used to determine HO• and 1O2 produced by illumination of two PS: tris-cationic-buckminsterfullerene (BB6) and a conjugate between polyethylenimine and chlorin(e6) (PEI–ce6). Dimethylthiourea is a HO• scavenger, while sodium azide (NaN3) is a quencher of 1O2. Both APDT and killing by Fenton reaction (chemical generation of HO•) were carried out on Gram-positive bacteria (Staphylococcus aureus and Enteroccoccus fecalis) and Gram-negative bacteria (Escherichia coli, Proteus mirabilis and Pseudomonas aeruginosa. Results Conjugate PEI-ce6 mainly produced 1O2 (quenched by NaN3), while BB6 produced HO• in addition to 1O2 when NaN3 potentiated probe activation. NaN3 also potentiated HPF activation by Fenton reagent. All bacteria were killed by Fenton reagent but Gram-positive bacteria needed a higher concentration than Gram-negatives. NaN3 potentiated Fenton-mediated killing of all bacteria. The ratio of APDT killing between Gram-positive and Gram-negative bacteria was 2 or 4:1 for BB6 and 25:1 for conjugate PEI-ce6. There was a NaN3 dose dependent inhibition of APDT killing using both PEI-ce6 and BB6 against Gram-negative bacteria while NaN3 almost failed to inhibit killing of Gram-positive bacteria. Conclusion Azidyl radicals may be formed from NaN3 and HO•. It may be that Gram-negative bacteria are more susceptible to HO• while Gram-positive bacteria are more susceptible to 1O2. The differences in NaN3 inhibition may reflect differences in the extent of PS binding to bacteria (microenvironment) or differences in penetration of NaN3 into cell walls of bacteria.

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“…However, 3 PS* also leads to the efficient generation of a radical anion of PS (PS • − ) especially in polar solvents containing reducing agents such as NADH. Electron transfer from PS • − to oxygen results the generation of the superoxide radical (O 2 • − ), which can further react with H + , Fe 2+ , or PS • − forming the hydroxyl radical (OH • ) and releasing O 2 (Equations –7) . The latter pathway is known as the type I photochemical pathway, frequently discussed with regard to PDT.

{PS}^{• -} + O_{2} \to PS + {O_{2}}^{•}^{-}

2 {O_{2}}^{•}^{-} + 2 H^{+} \to O_{2} + H_{2} O_{2}

{HO}_{2}^{•} + {HO}_{2}^{•} \to H_{2} O_{2 +} O_{2}

{HO}_{2}^{•} + {O_{2}}^{•}^{-} + H^{+} \to H_{2} O_{2 +} O_{2}

H_{2} O_{2} + {Fe}^{2 +} \to {OH}^{•} + {OH}^{-} + {Fe}^{3 +}

{Fe}^{3 +} + {O_{2}}^{•}^{-} \to {Fe}^{2 +} + O_{2}

{PS}^{• -} ...

…”

Section: Need To Enhance the Type I Photochemical Pathwaymentioning

confidence: 99%

Enhancing Type I Photochemistry in Photodynamic Therapy Under Near Infrared Light by Using Antennae–Fullerene Complexes

Huang

Liu

et al. 2018

Cytometry Pt A

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Photodynamic therapy (PDT) has been developed as salvage or palliative treatment for a wide range of tumors. The principle underlying this therapy is the generation of reactive oxygen species through two types of photochemical pathways. As compared with the type II pathway, the type I pathway offers a higher oxidizing ability for photosensitive residues such as tryptophan, lower oxygen dependency, and deeper tissue penetration ability. In this review, we focus on the enhancement of the type I pathway in the near infrared (NIR) optical therapeutic window of wavelength 700-1,100 nm by using antennae-fullerene complexes. When photo-induced electron transfer occurs from antennas to fullerene, the pathway switches from type II to type I. Enhancing the type I pathway leads to less oxygen dependency and stronger capacity for tryptophan oxidation. Then, antennae that transfer long-wavelength light (e.g., NIR light) energy to fullerene via photo-induced energy and/or electron transfer have the ability to affect deep-seated tumors. On the basis of theories on photo-induced energy/electron transfer in other fields such as solar cells, here, we summarize the mechanism by which the switch from the type II to type I pathway occurs in antenna-fullerene-based PDT.

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Intraperitoneal photodynamic therapy mediated by a fullerene in a mouse model of abdominal dissemination of colon adenocarcinoma

Cited by 11 publications

References 28 publications

Synthesis, Photophysical Properties, and Biological Evaluation of trans-Bisthioglycosylated Tetrakis(fluorophenyl)chlorin for Photodynamic Therapy

Synthesis, Photophysical Properties, and Biological Evaluation of trans-Bisthioglycosylated Tetrakis(fluorophenyl)chlorin for Photodynamic Therapy

Type I and Type II mechanisms of antimicrobial photodynamic therapy: An in vitro study on gram‐negative and gram‐positive bacteria

Enhancing Type I Photochemistry in Photodynamic Therapy Under Near Infrared Light by Using Antennae–Fullerene Complexes

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