論文 - 松本 仁
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Non-Cytotoxic Photodynamic Therapy with Talaporfin Sodium Reduces the Expression of CXCR4 and Enhances Chemotherapeutic Efficacy in Undifferentiated Gastric Cancer Cell Line HGC27 査読あり
Kai K, Ishizuka T, Matsumoto J, Shimamawari K, Mori R, Fidya, Lkham-Erdene B, Kubota T, Ikenoue M, Higuchi K, Nanashima A, Hishikawa Y
Acta Histochem. Cytochem 58 ( 2 ) 2025年4月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Jin Matsumoto , Yuna Sugita , Kana Sato , Kazuya Tanimura , Ami Fujino , Tsutomu Shiragami
Tetrahedron Letters 142 155100 2024年6月
担当区分：筆頭著者, 責任著者 記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Tetrahedron Letters
We report the synthesis of nonmetal high-valent phosphorus(V) hydroporphyrin complexes: PV-isobacteriochlorin, PV-chlorin, and two isomers of PV-phlorin, via simple hydrogenation of di(methoxo)tetraphenylporphyrin phosphorus(V) with a hydrogen source and Pd/C catalyst. These PV-hydroporphyrin complexes exhibit long-wavelength absorption bands in the biological optical window. PV-isobacteriochlorin and PV-chlorin complexes are stable against auto-oxidation and exhibit the photoproduction of singlet oxygen under red light irradiation.
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Kurogi K., Sakakibara Y., Hashiguchi T., Kakuta Y., Kanekiyo M., Teramoto T., Fukushima T., Bamba T., Matsumoto J., Fukusaki E., Kataoka H., Suiko M.
PNAS Nexus 3 ( 3 ) 2024年3月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：PNAS Nexus
Cytosolic sulfotransferases (SULTs) are cytosolic enzymes that catalyze the transfer of sulfonate group to key endogenous compounds, altering the physiological functions of their substrates. SULT enzymes catalyze the O-sulfonation of hydroxy groups or N-sulfonation of amino groups of substrate compounds. In this study, we report the discovery of C-sulfonation of α,β-unsaturated carbonyl groups mediated by a new SULT enzyme, SULT7A1, and human SULT1C4. Enzymatic assays revealed that SULT7A1 is capable of transferring the sulfonate group from 3′-phosphoadenosine 5′-phosphosulfate to the α-carbon of α,β-unsaturated carbonyl-containing compounds, including cyclopentenone prostaglandins as representative endogenous substrates. Structural analyses of SULT7A1 suggest that the C-sulfonation reaction is catalyzed by a novel mechanism mediated by His and Cys residues in the active site. Ligand-activity assays demonstrated that sulfonated 15-deoxy prostaglandin J2 exhibits antagonist activity against the prostaglandin receptor EP2 and the prostacyclin receptor IP. Modification of α,β-unsaturated carbonyl groups via the new prostaglandin-sulfonating enzyme, SULT7A1, may regulate the physiological function of prostaglandins in the gut. Discovery of C-sulfonation of α,β-unsaturated carbonyl groups will broaden the spectrum of potential substrates and physiological functions of SULTs.
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Synthesis of Germacyclic Compounds by Cyclization and Annulation Reactions Utilizing In Situ Generated Germyl Cations 査読あり
H. Arii, Y. Iwanami, D. Nakane, H. Masuda, J. Matsumoto, T. Shiragami, K. Mochida, T. Kawashima
Organometallics 2021, 40, 1363−1370 40 ( 9 ) 1363 - 1370 2021年4月
掲載種別：研究論文（学術雑誌）
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N. N. H. Mai, Y. Yamaguchi, N. Choijookhuu, J. Matsumoto, A. Nanashima, H. Takagi, K. Sato, L. Q. Tuan, Y. Hishikawa
Acta Histochemica et Cytochemica 53 ( 4 ) 61 - 72 2020年7月
記述言語：英語 掲載種別：研究論文（学術雑誌）
Photodynamic therapy (PDT) uses photosensitizer activation by light of a specific wavelength, and is a promising treatment for various cancers; however, the detailed mechanism of PDT remains unclear. Therefore, we investigated the anticancer effect of PDT using a novel phosphorus tetraphenylporphyrin (Ptpp) in combination with light emitting diodes (Ptpp-PDT) in the NOZ human biliary cancer cell line. Cell viability and apoptosis were examined by MTT assay, flow cytometry and TUNEL assay for 24 hr after Ptpp-PDT. MitoTracker and JC-1 were used as markers of mitochondrial localization and membrane potential. The levels of mitochondrial oxidative phosphorylation (OXPHOS) complexes, Bcl-2 family proteins, cytochrome c and cleaved caspase-3 were examined by western blotting and immunohistochemistry. The results revealed that Ptpp localized to mitochondria, and that Ptpp-PDT efficiently decreased cell viability in a dose- and time-dependent manner. JC-1 and OXPHOS complexes decreased, but apoptotic cells increased from 6 to 24 hr after Ptpp-PDT. A decrease in Bcl-xL and increases in Bax, cytochrome c and cleaved caspase-3 were also found from 6 to 24 hr after Ptpp-PDT. Based on these results, we conclude that Ptpp-PDT induces anticancer effects via the mitochondrial apoptotic pathway by altering the Bax/Bcl-xL ratio, and could be an effective treatment for human biliary cancer.
DOI： 10.1267/ahc.20-00002
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Jin Matsumoto, Kyosuke Takemori, Jun Ishikawa, Yu Nabetani, Mamoru Fujitsuka, Tetsuro Majima, Masahide Yasuda
Medicinal Chemistry Research 27 ( 11-12 ) 2530 - 2537 2018年12月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Medicinal Chemistry Research
Tetraphenylporphyrinatophosphorus(V) complexes (1) comprising two axially linked benzylidene imidazolone (Biz) moieties, which are chromophores of the green fluorescent protein, were prepared. In medical applications such as photodynamic therapy, the P-porphyrin part (Ptp) is expected to sensitize to generate singlet oxygen, whereas the Biz units act as fluorescent probes. The fluorescence spectra of 1 were analyzed under the excitations of Biz at 370 nm. Fluorescence stemming from the excited states of Biz and Ptp was observed at 460 and 610 nm, respectively. The intramolecular quenching of Biz in the excited singlet state by Ptp occurred, resulting in weak fluorescence from Biz. The introduction of a cyano group in the Biz units of 1 enhanced their fluorescence quantum yield up to 7.7 × 10−4. The fluorescence spectra of 1 under the excitations of Ptp at 550 nm were extremely similar to that of a reference compound of P-porphyrin without the Biz chromophore, dimethoxy(tetraphenylporphyrinato)phosphorus chloride. The physicochemical parameters of Ptp remained unaltered following the introduction of Biz on the axial positions of P-porphyrin.
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Jin Matsumoto, Masahide Yasuda
Medicinal Chemistry Research 27 ( 5 ) 1478 - 1484 2018年3月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Medicinal Chemistry Research
Alkylpyridinium (Apy)-bonded porphyrins have received considerable attention as singlet-oxygen (1O2) sensitizers for photodynamic inactivation (PDI). It is expected that the introduction of Apy makes porphyrins water-soluble and enhances the affinity of porphyrins to DNA. Here, we focused on Apy-bonded P-porphyrins that were prepared through the modification of axial ligands of meso-tetraphenylporphyrinatophosphorus by the Apy’s group and linkers. These water-soluble porphyrins (1) were applied to sensitize the inactivation of Escherichia coli under visible-light irradiation, since there are only few 1O2 sensitizers that can efficiently inactivate E. coli at low concentrations. The PDI activities were evaluated using the half-life (T1/2 in min) of E. coli and the minimum effective concentrations ([P]) of the porphyrin sensitizers. It was found that the PDI activity towards E. coli depends on the alkyl chain length of Apy. The [P] value for E. coli was optimized to be 0.25 μM of bis[5-(3- ethyl-1-pyridinio)-3-oxapentyloxo]tetraphenylporphyrinatophosphorus dibromide chloride (1b). Since the previous results on the optimized [P] value for S. cerevisiae was 50 nM for 1b, it was found that the [P] value for E. coli was larger than that for S. cerevisiae.
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Hiramure Y., Suga K., Umakoshi H., Matsumoto J., Shiomori K.
Solvent Extraction Research and Development 25 ( 1 ) 37 - 46 2018年
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Solvent Extraction Research and Development
© 2018 Japan Association of Solvent Extraction. All rights reserved. Poly-N-isopropylacrylamide (PNIPA) cryogels containing liposomes were prepared by polymerization under freezing conditions at sub-zero temperature. The cryogel had a highly porous structure with 20–30 μm pore size. The wall thickness of the cryogel containing liposomes was larger than that without liposomes. The structural change and aggregation of the liposomes in the cryogel were observed. The immobilization of the phospholipid and the dynamic property of the lipid membrane in the cryogel were confirmed. The cryogel containing liposomes showed chiral recognition ability toward L-Trp. The selective adsorption of L-Trp was achieved with the PNIPA cryogel containing liposome.
DOI： 10.15261/serdj.25.37
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Non-aggregated porphyrins: An approach to develop high-performance PDT sensitizers
Matsumoto J., Yasuda M.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 76 ( 6 ) 566 - 574 2018年
掲載種別：研究論文（学術雑誌） 出版者・発行元：Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Photodynamic inactivation (PDI) has received considerable attention as a methodology leading to the medical applications such as photodynamic therapy (PDT) for tumor cells. Porphyrin derivatives are attractive singlet-oxygen sensitizers for PDT because of their strong absorption band in the visible-light region. In general, free-base porphyrins comprise four Q-bands regions near 515, 550, 590, and 645 nm; these band regions have wider and longer wavelengths in comparison with that of the Q-bands of metalloporphyrins (560-610 nm). Therefore, most sensitizers for PDT are based on free-base porphyrins or chlorins (i.e. photofrin and laserphyrin). We have been interested in the use of phosphorus porphyrins (P-porphyrins) as photosensitizer. It is advantageous in P-porphyrins that water - solubilization is easily achieved through the modification of the axial ligands and the presence of these axial ligands also prevents the formation of porphyrin-ring aggregates. The aggregation may lower the water solubility of the porphyrins and retard the incorporation of the porphyrins into the target cell. This review is focused on the phosphorus porphyrin (1 and 2) modified by axial ligands such as -(CH2CH2O)m(CH2)nH and alkylpyridinium (APy) group, respectively. The PDI activities of 1 and 2 for Saccharomyces cerevisiae, Escherichia coli, and a human biliary cancer cell line (NOZ) have been evaluated using the half-life (T1/2 in min) of bacteria and the minimum effective concentrations ([P]) of the sensitizers. As the results, the [P] values for the PDI of S. cerevisiae was optimized to be 5 nM for 1 e (m = 2, n = 6) and 1 f (m = 1, n = 6). In the case of the PDI of NOZ cell, the IC50 for 1e was determined to be 37.6 nM which were one hundredth the IC50 (7.57 μM) for mono-L-aspartyl chlorin e6 (laserphyrin). The [P] values for S. cerevisiae were optimized to be 40 nM at 2h (alkyl=hexyl).In the case of the PDI of E. coli using 2, the PDI activity depends on the alkyl chain length of Apy. The(P] value for E. coli was optimized to be 250 nM (2b, alkyl=ethyl). Thus the P-porphyrins are applicable to the PDI of bacteria and cancer cells in low concentrations.
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Matsumoto J., Suzuki K., Yasuda M., Yamaguchi Y., Hishikawa Y., Imamura N., Nanashima A.
Bioorganic and Medicinal Chemistry 25 ( 24 ) 6536 - 6541 2017年12月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Bioorganic and Medicinal Chemistry
© 2017 Elsevier Ltd A series of phosphorus porphyrin complexes ([(RO) 2 P(tpp)]Cl, tpp = tetraphenylporphyrinato group, R = −(CH 2 CH 2 O) m (CH 2 ) n H; 1a: m = 2, n = 2; 1b: m = 2, n = 4; 1c: m = 2, n = 6; 1d: m = 3, n = 6) were used for the photodynamic therapy (PDT) of human biliary cancer cell line (NOZ) when exposed to the irradiation of light emitting diodes (LEDs). A Dulbecco's modified Eagle's medium (DMEM) containing NOZ cells (2000 cell well −1 ) and 1 (0–100 nM) was introduced into a 96-well microplate and incubated for 24 h to accumulate 1 into the NOZ cells and to multiply the NOZ cells until the cell number reached 10 4 cells well −1 . After replacing the DMEM medium containing 1 with a fresh DMEM medium without 1, the plates were irradiated for 30 min at 610 nm. After incubation was performed for 24 h in dark conditions, the cell viability of the NOZ cells was determined using the MTT assay. The half maximum inhibitory concentrations 50 (IC 50 ) of 1a–1d were found to be in the range of 33.7–58.7 nM for NOZ. These IC 50 values for the NOZ were one hundredth the IC 50 value (7.57 μM) for mono-L-aspartyl chlorin e6 (laserphyrin®). Thus, it was found that the PDT activity of 1a–1d was much higher than the mono-L-aspartyl chlorin e6. Similarly, IC 50 vales of 1a–1d for HeLa cells were found to be 27.8–52.5 nM. This showed that 1a–1d had high photodynamic activity in cancer cells. At the same time, it was speculated that an LED is a useful light source for deactivating the cancer cells because it can excite the sensitizers with peak width in their absorption spectra using the light of the specified wave length with band width of 10–20 nm; LEDs provide a homogeneous light distribution for the target cells.
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Matsumoto J., Suzuki K., Uezono H., Watanabe K., Yasuda M.
Bioorganic and Medicinal Chemistry Letters 27 ( 23 ) 5258 - 5261 2017年12月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Bioorganic and Medicinal Chemistry Letters
© 2017 Elsevier Ltd Polycationic porphyrins have received substantial attention in developing singlet oxygen-sensitizers for biological use such as in the photoinactivation of bacteria and photodynamic therapy (PDT) of tumor cells because they have strong binding affinities for DNA and proteins. However, these strong cellular interactions can retard elimination of the drug after PDT. Therefore, the studies on the interactions of porphyrins with other molecules present much interest, in order to modulate the sensitizers’ activity or even remove them from the human body after PDT. Here, we studied the additive effect of heparin on the photoinactivation by polycationic porphyrins using Escherichia coli as a model cell. Tricationic P-porphyrin sensitizers substituted with an N-alkylpyridinium group (alkyl = pentyl (1a), hexyl (1b), and heptyl (1c)) or N-hexylammonium (1d) as the axial ligand were used. Additionally, dicationic Sb-porphyrin substituted with an N-hexylpyridinium group (1e) was prepared. We studied the additive effect of heparin on the photoinactivation of E. coli by 1a–1e. The bactericidal activities were evaluated using the half-life (T 1/2 in min) of E. coli and the minimum effective concentrations ([P]) of the porphyrin sensitizers. In the absence of heparin, the [P] values were determined to be 0.4–0.5 μM for 1a−1c and 2.0 μM for 1d−1e. The bactericidal activity of 1a−1c was completely retarded by the addition of heparin (1.0 μM). However, the addition of heparin (1.0 μM) could not completely retard the bactericidal activity of 1d−1e whose [P] values were relatively large. It is suggested that tricationic 1a−1c adsorbed onto the anionic heparin through electrostatic interactions. The adsorption of 1 on heparin disturbs the uptake of 1 into E. coli cells. Thus, the addition of heparin was found to be a useful method for retarding photoinactivation.
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Matsumoto J., Suemoto Y., Kanemaru H., Takemori K., Shigehara M., Miyamoto A., Yokoi H., Yasuda M.
Journal of Photochemistry and Photobiology B: Biology 168 124 - 131 2017年3月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Journal of Photochemistry and Photobiology B: Biology
� 2017 Elsevier B.V. Activity of singlet oxygen sensitizers for photoinactivation of bacteria and photodynamic therapy of tumor cells has been evaluated using nonpathogenic model cells, such as Escherichia coli, Saccharomyces cerevisiae, and HeLa cells. Among them, E. coli, gram-negative bacterium, has complex membrane structures in the cell wall, resulting in an impermeable barrier to antimicrobial agents. Therefore, few singlet oxygen sensitizers have photoinactivation activities toward E. coli at low concentrations. Recently polycationic porphyrins have received much attention as a new type of singlet oxygen sensitizers because they have strong binding affinities for DNA and proteins. Here, we prepared 13 types of di- and tricationic P- and Sb-porphyrin sensitizers substituted with the N-alkylpyridinium (APy) group at the axial ligand or the meso position to examine their bactericidal activity toward E. coli under visible-light irradiation. Photobactericidal activities were evaluated using half-life (T 1/2 in min) of E. coli and minimum effective concentrations of the porphyrin sensitizers. Di-cationic P-porphyrins containing the Apy group at meso position exhibited bactericidal activity under dark conditions. Tricationic porphyrins showed a higher bactericidal activity than monocationic porphyrins. It was found that the bactericidal activity depended on the alkyl chain length of APy. Tricationic porphyrin with N-heptylpyridinium in two axial ligands was the most reactive for the photoinactivation of E. coli.
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紫外線吸収剤の担持によるポルフィリン型湿度検出剤の耐光化 査読あり
Matsumoto T., Fukuda K., Sugano K., Matsumoto J., Yasuda M., Fueda Y., Shiomori K.
Kagaku Kogaku Ronbunshu 43 ( 2 ) 123 - 128 2017年
記述言語：日本語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Kagaku Kogaku Ronbunshu
© 2017 The Society of Chemical Engineers, Japan. A cobalt-free humidity indicator (HDI) for silica gel was developed using tetraphenylporphyrin (Tpp), which showed a distinguishable color change depending on pH. The HDI was prepared by mixing dichloro (tetraphenylporphyrinato)- phosphorus chloride (PTpp) and MgCl 2 with SiO 2 and drying at 130°C for 24 h. During the preparation, the PTpp was decomposed into the protonated Tpp (H2Tpp 2+ ). The pH change arose from proton release by the reaction of MgCl 2 with silanol of the SiO 2 under dry conditions and neutralization under humid conditions. The HDI showed green color due to H2Tpp 2+ under dry conditions and orange color due to Tpp under humid conditions. However, the HDI underwent partial decoloration on extended exposure to sunlight. Here, to prevent this decoloration, UV-absorbents coumarin and dibenzosuberenone were loaded onto the HDI. The HDIs with coumarin and without coumarin were irradiated at 352 nm and their microscopic absorption spectra were measured on a confocal laser scanning microscope. The absorbance at 650 nm and 515 nm of the HDI were monitored under dry and wet conditions, respectively. The light-protecting ability of UV-absorbent was analyzed by assuming that the decomposition process obeyed first-order kinetics. It was concluded that the additions of 0.125 wt% of coumarin and 0.050 wt% of dibenzosuberenone were effective to prevent decoloration of green color of H2Tpp 2+ as well as orange color of Tpp.
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Solid-Phase Aromatic Nitration with Mg(NO3)2 on Silica Gel 査読あり
Tomoko Matsumoto, Ayaka Yamauchi, Jun Ishikawa, Guan-Hong Jin, Jin Matsumoto, Yoshiyuki Fueda, Masahide Yasuda
Int. J. Org. Chem 7 1 - 11 2016年12月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Matsumoto J., Kai Y., Yokoi H., Okazaki S., Yasuda M.
Journal of Photochemistry and Photobiology B: Biology 161 279 - 283 2016年8月
記述言語：英語 掲載種別：研究論文（学術雑誌） 出版者・発行元：Journal of Photochemistry and Photobiology B: Biology
� 2016 Elsevier B.V. As singlet-oxygen ( 1 O 2 ) sensitizer, water-soluble P-porphyrins (1) were prepared by the modification of axial ligands of tetraphenylporphyrinatophosphorus by N-alkyl-pyridinium group to give bis[3-(1-alkyl-4-pyridinio)propoxo]tetraphenylporphyrinatophosphorus(V) (alkyl�=�hexyl (1a) and butyl (1b)) and bis[5-(3-alkyl-1-pyridinio)-3-oxapentyloxo] tetraphenylporphyrinatophosphorus(V) (alkyl�=�hexyl (1c), butyl (1d), and ethyl (1e)). The quantum yields (Φ Δ ) for the formation of 1 O 2 were extremely high (e.g. Φ Δ ï¿½=�0.88 (1a) and 0.87 (1c)). The 1 could bind human serum albumin (HSA) with high binding constants to produce a complex of HSA with 1 (1/HSA). Here, inactivation of Saccharomyces cerevisiae (yeast) was examined using the complex of HSA (400�nM) with 1 (20–50�nM) under visible-light irradiation. The bactericidal activity of 1 was evaluated by half-life (T 1/2 in min) which was time required to be reduced to one-half initial concentration of yeasts. Under irradiation in the presence of HSA, minimum concentrations ([P]) of 1 were adjusted as T 1/2 became the values among 0–120�min. The [P] values were determined to be 20�nM for 1a, 30�nM for 1b, and 50�nM for 1c–1e. The 1/HSA sterilized yeast with 12–36�min of T 1/2 when the concentration of 1 was set to [P]. In the photo-activation in the absence of HSA at the concentration of [P] of 1, however, the T 1/2 values of 1a, 1b, 1d, and 1e were > �120�min and T 1/2 of 1c was 44�min. Thus, the complexation of 1 with HSA apparently enhanced the bactericidal activity of 1. This is the first finding on the assistance of HSA to the photo-inactivation of yeast cell by porphyrins.
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Two-electron oxidation of water to form hydrogen peroxide sensitized by di(hydroxo)porphyrin GeIV complex under visible-light irradiation 査読あり
T. Shiragami, H. Ozawa, K. Kajihara, J. Matsumoto, M. Yasuda
J. Photochem. Photobiol. A: Chem. 313 131 - 136 2015年12月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Synthesis of di(glucosyloxo)phosphorus tetraphenylporphyrin complex with affinity to glucose recognizing Concanavalin A 査読あり
T. Shiragami, Y. Nakamura, J. Matsumoto, M. Otsuki, M. Yasuda
Dyes and Pigments 120 147 - 154 2015年9月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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ESI-FTMSによる多価カチオンポルフィリン錯体の質量スペクトル測定 査読あり
T. Shiragami, A. Kuroki, J. Matsumoto, M. Yasuda
分析化学 64 ( 7 ) 551 - 556 2015年8月
記述言語：日本語 掲載種別：研究論文（学術雑誌）
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Visible-light-driven Fuel Cell Constructed by Germanium(IV) Porphyrin/TiO2 Electrode Using Alcohols as an Electron Donor 査読あり
T. Shiragami, H. Ozawa, K. Kajihara, J. Matsumoto, M. Yasuda
Chemistry Letters 44 ( 3 ) 265 - 267 2015年3月
記述言語：英語 掲載種別：研究論文（学術雑誌）
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Concentration-dependent luminescence of ionic liquids consisting of trialkyl(pentafluorocyclo? triphosphazenyl)ammonium moiety 査読あり
T. Shiragami, Y. Nakamura, J. Matsumoto, M. Otsuki, M. Yasuda
Physical Chemistry Chemical Physics 16 ( 40 ) 22046 - 22051 2014年10月
記述言語：英語 掲載種別：研究論文（学術雑誌）