Synthesis and Photophysical Properties of <i>S</i>-Mannosylated Chlorins and Their Effect on Photocytotoxicity in HeLa Cells

Moriwaki, Kazumasa; Sawada, Takuya; Akiyama, Motofusa; Ikeda, Atsushi; Kikuchi, Jun‐ichi; Matsumura, Takeko; Yano, Shigenobu; Kataoka, Hiromi; Inoue, Masahiro; Akashi, Hidetoshi

doi:10.1246/bcsj.20170271

Cited by 14 publications

(7 citation statements)

References 40 publications

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“…Chlorin is a dihydroporphyrin that promises to have better photodynamic activity as a PS than compound 3 . This is based on its high ROS generation efficiency and strong absorption of light at long wavelengths that penetrate tissues more deeply. − Although a supramolecular approach with water-soluble host molecules simplifies the preparation of water-soluble chlorins compared with further covalent modification of chlorins, the noncovalent functionalization of chlorins by their incorporation in the water-soluble host molecules is very limited because the preparation of water-soluble chlorin complexes with high concentrations is considerably difficult. Herein, stable water-soluble chlorin complexes were successfully obtained with TMeβCD and λ-carrageenan using a mechanochemical HSVM technique.…”

Section: Introductionmentioning

confidence: 99%

Solubilization of Tetrahydroxyphenylchlorin in Water and Improved Photodynamic Activity after Complexation with Cyclic Oligo- and Polysaccharides

Yamana

Kawasaki

Sugikawa

et al. 2020

ACS Appl. Bio Mater.

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Chlorins with phenol units were dissolved in water via complexation with the solubilizing agents trimethyl-β-cyclodextrin and λ-carrageenan using a high-speed vibration milling technique. The photodynamic activities of the trimethyl-β-cyclodextrin (TMeβCD) and λ-carrageenan complexes were similar to that of Photofrin. However, the λ-carrageenan chlorin complexes were more stable in aqueous solutions than the TMeβCD–chlorin complexes. Thus, λ-carrageenan-complexed chlorin would be more suitable as a photosensitizer.

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Section: Introductionmentioning

confidence: 99%

Solubilization of Tetrahydroxyphenylchlorin in Water and Improved Photodynamic Activity after Complexation with Cyclic Oligo- and Polysaccharides

Yamana

Kawasaki

Sugikawa

et al. 2020

ACS Appl. Bio Mater.

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“…Production of reactive oxygen species such as singlet oxygen ( 1 O 2 ) is essential for the application to PDT as photosensitizers. The ability to generate singlet oxygen was investigated using 1,3‐diphenylbenzofuran (DPBF) similar to the literature procedure [27] . Figure 6a shows the spectral change when the DMF solution of bacteriochlorin 2 in the presence of excess DPBF was irradiated with light at>600 nm.…”

Section: Resultsmentioning

confidence: 99%

“…Because far‐red to near‐infrared light with a wavelength of more than 700 nm is quite useful for PDT, bacteriochlorins 1 – 4 are regarded to be attractive candidates for utilization as photosensitizers [13] . Since C17‐propionate residue of the BChl‐ a derivatives can be easily modified to other ester chains, introduction of tumor targeting ligand such as carbohydrates, [27,33] peptides, [34] or folic acid [35] would lead to the development of new BChl‐based sensitizers with specific accumulation properties to cancer cells. Besides this, properties of 1 – 4 as electron‐donating components in BHJ‐OSCs combined with PC 71 BM were investigated.…”

Section: Resultsmentioning

confidence: 99%

“…The ability to generate singlet oxygen was investigated using 1,3-diphenylbenzofuran (DPBF) similar to the literature procedure. [27] Figure 6a shows the spectral change when the DMF solution of bacteriochlorin 2 in the presence of excess DPBF was irradiated with light at > 600 nm. Absorption of singlet oxygen quencher DPBF around 400 nm gradually decreased, while the Q y peak of 2 at 710 nm did not change under the conditions.…”

Section: Photodynamic Activities Of Far-red Light Absorbing Bacteriocmentioning

confidence: 99%

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Synthesis of C3/C13‐Substituted Semi‐Synthetic Bacteriochlorophyll‐a Derivatives and Their Properties as Functional Dyes

et al. 2020

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Natural bacteriochlorophyll-a was converted to chemically stable free-base derivatives with different substituents along the y-axis. Compared to the natural type compound methyl pyrobacteriopheophorbide-a possessing the C3-acetyl and C13keto-carbonyl groups, its deoxo-bacteriochlorin lacking the C3and C13-carbonyl groups showed a blue-shift of the Q y peak. On the other hand, introduction of the dicyanomethylene group(s) at the 3 1-and/or 13 1-position(s) caused an opposite effect due to its electron-withdrawing ability as well as the expansion of the π-conjugation system along the y-axis, and the Q y peak maxima were red-shifted to around 780 nm. These semi-synthetic bacteriochlorins in an aerated solvent could generate singlet oxygen upon illumination with far-red light, which was evaluated by mouse B16 melanoma cells to be applicable as photosensitizers. Besides this, it was demonstrated that they could be utilized as electron-donating materials combined with fullerene derivatives to fabricate bulk-heterojunction organic solar cells.

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“…These disadvantages presented by first-generation photosensitizers (porphyrin-based PS) created the necessity to investigate new compounds and initiated the development of second-generation photosensitizers ( Chatterjee et al, 2008 ; Zhang et al, 2017 ). Thus, second-generation PS includes compounds such as porphyrins (with defined chemical structures and rapid clearance), chlorins, bacteriochlorins, pheophorbides, and phthalocyanines ( Yoon et al, 2013 ; Moriwaki et al, 2018 ). Second-generation PS is characterized by chemical purity, higher singlet oxygen generation, and better penetration deeply into tissues due to their maximum absorption in the wavelength range of 650–800 nm.…”

Section: Photosensitizersmentioning

confidence: 99%

Upconversion rare Earths nanomaterials applied to photodynamic therapy and bioimaging

et al. 2022

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Light-based therapies and diagnoses including photodynamic therapy (PDT) have been used in many fields of medicine, including the treatment of non-oncological diseases and many types of cancer. PDT require a light source and a light-sensitive compound, called photosensitizer (PS), to detect and destroy cancer cells. After absorption of the photon, PS molecule gets excited from its singlet ground state to a higher electronically excited state which, among several photophysical processes, can emit light (fluorescence) and/or generate reactive oxygen species (ROS). Moreover, the biological responses are activated only in specific areas of the tissue that have been submitted to exposure to light. The success of the PDT depends on many parameters, such as deep light penetration on tissue, higher PS uptake by undesired cells as well as its photophysical and photochemical characteristics. One of the challenges of PDT is the depth of penetration of light into biological tissues. Because photon absorption and scattering occur simultaneously, these processes depend directly on the light wavelength. Using PS that absorbs photons on “optical transparency windows” of biological tissues promises deeper penetration and less attenuation during the irradiation process. The traditional PS normally is excited by a higher energy photon (UV-Vis light) which has become the Achilles’ heel in photodiagnosis and phototreatment of deep-seated tumors below the skin. Thus, the need to have an effective upconverter sensitizer agent is the property in which it absorbs light in the near-infrared (NIR) region and emits in the visible and NIR spectral regions. The red emission can contribute to the therapy and the green and NIR emission to obtain the image, for example. The absorption of NIR light by the material is very interesting because it allows greater penetration depth for in vivo bioimaging and can efficiently suppress autofluorescence and light scattering. Consequently, the penetration of NIR radiation is greater, activating the biophotoluminescent material within the cell. Thus, materials containing Rare Earth (RE) elements have a great advantage for these applications due to their attractive optical and physicochemical properties, such as several possibilities of excitation wavelengths – from UV to NIR, strong photoluminescence emissions, relatively long luminescence decay lifetimes (µs to ms), and high sensitivity and easy preparation. In resume, the relentless search for new systems continues. The contribution and understanding of the mechanisms of the various physicochemical properties presented by this system is critical to finding a suitable system for cancer treatment via PDT.

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Synthesis and Photophysical Properties of S-Mannosylated Chlorins and Their Effect on Photocytotoxicity in HeLa Cells

Cited by 14 publications

References 40 publications

Solubilization of Tetrahydroxyphenylchlorin in Water and Improved Photodynamic Activity after Complexation with Cyclic Oligo- and Polysaccharides

Solubilization of Tetrahydroxyphenylchlorin in Water and Improved Photodynamic Activity after Complexation with Cyclic Oligo- and Polysaccharides

Synthesis of C3/C13‐Substituted Semi‐Synthetic Bacteriochlorophyll‐a Derivatives and Their Properties as Functional Dyes

Upconversion rare Earths nanomaterials applied to photodynamic therapy and bioimaging

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