Photophysical Properties of Pheophorbide-a Derivatives and Their Photodynamic Therapeutic Effects on a Tumor Cell Line<i>In Vitro</i>

Wang, Kang Kyun; Li, Jing; Kim, Bong Jin; Lee, Jeong Hyun; Shin, Hee Won; Ko, Si Hwan; Lee, Won Young; Lee, Changhee; Jeong, Seok Hoon; Kim, Yong Rok

doi:10.1155/2014/793723

Cited by 9 publications

(6 citation statements)

References 31 publications

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“…The phosphorescence decay signals from PA and PFNs were fitted to a single exponential function, yielding similar singlet oxygen lifetimes of 22.7 and 22.1 μs, respectively. These measured singlet oxygen lifetimes are consistent with the reported value . These results indicate that the same amount of singlet oxygen was generated from PA and PFN and that the singlet oxygen generated from PFNs did not undergo self-quenching by the interface modified MNPs. , …”

Section: Results and Discussionsupporting

confidence: 91%

“…The most direct measurement method for singlet oxygen is the detection of phosphorescence from the deactivation of singlet oxygen molecules induced by photoexcited PA . As shown in Figure , singlet oxygen phosphorescence signals from low concentrations of PA (0.016 μM) and PFNs (2.5 μg/mL) were measured in THF solution at a detection wavelength of 1270 nm to avoid light scattering from the MNPs.…”

Section: Results and Discussionmentioning

confidence: 99%

“…This suggests that the photophysical properties of PA are not altered by bonding between PA and MNPs. 10 The most direct measurement method for singlet oxygen is the detection of phosphorescence from the deactivation of singlet oxygen molecules induced by photoexcited PA. 28 As shown in Figure 4, singlet oxygen phosphorescence signals from low concentrations of PA (0.016 μM) and PFNs (2.5 μg/ mL) were measured in THF solution at a detection wavelength of 1270 nm to avoid light scattering from the MNPs. The intensities of the singlet oxygen phosphorescence signal at the zero time point were nearly identical for PA and PFNs in THF solution.…”

Section: ■ Experimental Methodsmentioning

confidence: 99%

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Eradication of Plasmodium falciparum from Erythrocytes by Controlled Reactive Oxygen Species via Photodynamic Inactivation Coupled with Photofunctional Nanoparticles

Wang

Jang

Shin

et al. 2017

ACS Appl. Mater. Interfaces

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We investigated the antimalarial effect of photodynamic inactivation (PDI) coupled with magnetic nanoparticles (MNPs) as a potential strategy to combat the emergence of drug-resistant malaria and resurgence of malaria after treatment. Because the malarial parasite proliferates within erythrocytes, PDI agents need to be taken up by erythrocytes to eradicate the parasite. We used photofunctional MNPs as the PDI agent because nanosized particles were selectively taken up by Plasmodium-infected erythrocytes and remained within the intracellular space due to the enhanced permeability and retention effect. Also, the magnetism of FeO nanoparticles can easily be utilized for the collection of photofunctional nanoparticles (PFNs), and the uptaken PFNs infected the erythrocytes after photodynamic treatment with external magnetics. Photofunctionality was provided by a photosensitizer, namely, pheophorbide A, which generates reactive oxygen species (ROS) under irradiation. PAs were covalently bonded to the surface of the MNPs. The morphology and structural characteristics of the MNPs were investigated by scanning electron microscopy and X-ray diffraction (XRD), whereas the photophysical properties of the PFNs were studied with Fourier transform infrared, absorption, and emission spectroscopies. Generation of singlet oxygen, a major ROS, was directly confirmed with time-resolved phosphorescence spectroscopy. To evaluate the ability of PFNs to kill malarial parasites, the PDI effect of PFNs was evaluated within the infected erythrocytes. Furthermore, malarial parasites were completely eradicated from the erythrocytes after PDI treatment using PFNs on the basis of an 8 day erythrocyte culture test.

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Section: Results and Discussionsupporting

confidence: 91%

Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Methodsmentioning

confidence: 99%

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Eradication of Plasmodium falciparum from Erythrocytes by Controlled Reactive Oxygen Species via Photodynamic Inactivation Coupled with Photofunctional Nanoparticles

Wang

Jang

Shin

et al. 2017

ACS Appl. Mater. Interfaces

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“…Chlorophyll - a and its derivatives are one family containing a large π conjugation system of porphyrin structure, which provides strong absorption in the 300 - 700 nm region . Major disadvantages of chlorophyll - a derivatives and other porphyrins are their naturally high hydrophobicity and have poor tumor ' s selectivity 12, 13 . To tackle these problems, hydrophilic bioconjugated molecules, such as polymers, dendrimers, peptides or lipids are introduced to improve the hydrophilicity of those molecules 1, 7, 14.…”

Section: Introductionmentioning

confidence: 99%

Ultra-small Pyropheophorbide-a Nanodots for Near-infrared Fluorescence/Photoacoustic Imaging-guided Photodynamic Therapy

Siwawannapong¹,

Zhang²,

Lei³

et al. 2020

Theranostics

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Rationale: Nanoparticles (NPs) that are rapidly eliminated from the body offer great potential in clinical test. Renal excretion of small particles is preferable over other clearance pathways to minimize potential toxicity. Thus, there is a significant demand to prepare ultra-small theranostic agents with renal clearance behaviors.Method: In this work, we report a facile method to prepare NPs with ultra-small size that show renal clearable behavior for imaging-guided photodynamic therapy (PDT). Pyropheophorbide-a (Pa), a deep red photosensitizer was functionalized with polyethylene glycol (PEG) to obtain Pa-PEG. The prepared NPs formed ultra-small nanodots in aqueous solution and showed red-shifted absorbance that enabling efficient singlet oxygen generation upon light irradiation.Results: In vitro studies revealed good photodynamic therapy (PDT) effect of these Pa-PEG nanodots. Most of the cancer cells incubated with Pa-PEG nanodots were destroyed after being exposed to the irradiated light. Utilizing the optical properties of such Pa-PEG nanodots, in vivo photoacoustic (PA) and fluorescence (FL) imaging techniques were used to assess the optimal time for PDT treatment after intravenous (i.v.) injection of the nanodots. As monitored by the PA/FL dual-modal imaging, the nanodots could accumulate at the tumor site and reach the maximum concentration at 8 h post injection. Finally, the tumors on mice treated with Pa-PEG nanodots were effectively inhibited by PDT treatment. Moreover, Pa-PEG nanodots showed high PA/FL signals in kidneys implying these ultra-small nanodots could be excreted out of the body via renal clearance.Conclusion: We demonstrated the excellent properties of Pa-PEG nanodots that can be an in vivo imaging-guided PDT agent with renal clearable behavior for potential future clinical translation.

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“…N 2. P 129-142 doi: http://dx.doi.org/10.7124/bc.00099E selectively accumulates in the tumor cells that determines its widespread using as a photosensitizer for photodynamic therapy (PDT) of tumors [3][4][5][6]. One of the mechanisms of the Pheo-a action on tumor tissues is based on the ability of the dye to produce singlet oxygen in cells under red light irradiation [7].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic study of binding of a cationic Pheophorbide-a to an antiparallel quadruplex Tel22

et al. 2019

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To study the binding of a water-soluble cationic Pheophorbide-a derivative (CatPheo-a) ta a Na +-stabilized antiparallel quadruplex formed by 22-mer oligonucleotide d[AG3(T 2 AG 3) 3 ] of the human DNA telomeric sequence (Tel22, PDB ID: 143D). Methods. Absorption and polarized fluorescence spectroscopy were used to determine the properties of DNA-ligand complexes. Fluorescence titration was applied to evaluate the Tel22 dye binding affinity. Absorption melting was used to estimate the effect of CatPheo-a on thermodynamic parameters of the Tel22 quadruplex folding. IR spectroscopy was used to detect singlet oxygen generation. Results. CatPheo-a was found to bind effectively to the Tel22 quadruplex via two competitive binding modes, which are characterized by opposite changes in the dye fluorescence. The spectroscopic properties of CatPheo-a + Tel22 complexes were determined. Thermodynamic parameters of the Tel22 quadruplex folding with/without CatPheo-a were calculated. Conclusions. CatPheo-a destabilizes the quadruplex structure of Tel22 with a twofold decrease in the equilibrium quadruplex folding constant at 37°C. The efficiency of singlet oxygen generation by CatPheo-a is higher than that by the anionic Pheo-a.

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Photophysical Properties of Pheophorbide-a Derivatives and Their Photodynamic Therapeutic Effects on a Tumor Cell LineIn Vitro

Cited by 9 publications

References 31 publications

Eradication of Plasmodium falciparum from Erythrocytes by Controlled Reactive Oxygen Species via Photodynamic Inactivation Coupled with Photofunctional Nanoparticles

Eradication of Plasmodium falciparum from Erythrocytes by Controlled Reactive Oxygen Species via Photodynamic Inactivation Coupled with Photofunctional Nanoparticles

Ultra-small Pyropheophorbide-a Nanodots for Near-infrared Fluorescence/Photoacoustic Imaging-guided Photodynamic Therapy

Spectroscopic study of binding of a cationic Pheophorbide-a to an antiparallel quadruplex Tel22

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