Bactericidal Effect of Silica Gel-Supported Porphyrinatophosphorus(V) Catalysts on <i>Escherichia coli</i> under Visible-Light Irradiation

Fueda, Yoshiyuki; Suzuki, Hanako; Komiya, Yasuhiro; Asakura, Yuka; Shiragami, Tsutomu; Matsumoto, Jin; Yokoi, Haruhiko; Yasuda, Masahide

doi:10.1246/bcsj.79.1420

Cited by 21 publications

(13 citation statements)

References 19 publications

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“…15 On the other hand, 1 showed a distinguishable spectral change of >130 nm that occurred at below 30% of RH, which is comparable to 25 ± 5% of RH for color change of NeoBLUE ® . Moreover, 1 can be safely used, since 2 does not include carcinogenic chemicals; the lethal dose (LD50) of 2a was more than 2000 mg kg -1 , 10 and adsorbed strongly on SiO2. The localization of 2 on the surface area of SiO2 beads is favorable for a distinguishable color change and high humidity-sensitivity.…”

Section: Discussionmentioning

confidence: 99%

“…The 3a -3c were identified by comparisons with the reported spectral data. 10 Cationic 3 was soluble in a polar solvent, such as alcohols and CH3CN, while 2 was insoluble in polar solvents such as CH3OH and CH3CN, and was poorly soluble even in relatively non-polar solvents, such as 1,4-dioxane, ethyl acetate, and 1,2-dimethoxyethane. 11 Therefore, CHCl3 and 2-propanol were selected as solvents to solve 2 and 3, respectively.…”

Section: Methodsmentioning

confidence: 99%

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Quantitative Analysis for a Color-Change of Humidity Indicator by Microscopic Absorption Spectrometry

et al. 2011

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Quantitative Analysis for a Color-Change of Humidity Indicator by Microscopic Absorption Spectrometry

et al. 2011

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“…Moreover, the toxicity of M(tpp) is low. The lethal dose 50 (LD 50 ) of Sb(tpp) [9] and P(tpp) [10] was more than 2000 mg/kg. Therefore, M(tpp) can be safely used in living environmental fields.…”

Section: Porphyrin Chromophoresmentioning

confidence: 99%

“…Our first experiment for photoinactivation using Sb(tpp)/SiO 2 was reported in 2003 against E. coli [10]. Photoinactivation of E. coli was enacted as follows: E. coli k-12 (IFO3335) was cultured aerobically at 30°C for 8 h in a basal medium (pH 6.5) consisting of 1% bactotriptone, 0.5% yeast extract, and 1% NaCl.…”

Section: Photoinactivation Of E Coli By M(tpp)/sio 2 (M = P Sb)mentioning

confidence: 99%

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Yasuda¹,

Matsumoto²

2018

Visible-Light Photocatalysis of Carbon-Based Materials

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This chapter describes the photocatalysis action of (dihydroxo)tetraphenyl¬porphyrinato complexes of high valent P (V), Ge (IV), and Sb (V) (P(tpp), Ge(tpp), and Sb(tpp)). These chromophores were fixed onto silica gel (SiO2) through Coulombic forces and hydrogen bonding between axial hydroxo ligands and silanol groups to produce M(tpp)/SiO2 (M = P, Ge, and Sb) composites. M(tpp)/SiO2 were applied to the photo-inactivation of Escherichia coli and Legionella pneumophila. Moreover, M(tpp)/SiO2 was subjected to practical experiments for the photoinactivation of L. pneumophila naturally occurring in a cooling tower and a public fountain. It is noteworthy that 80 g of Sb(tpp)/SiO2 catalyst, containing 40 mg of Sb(tpp) maintained a concentration of Legionella species below 100 CFU/100 mL for 120 days in 13 m3 of water in a fountain under sunlight exposure. The photoinactivation proceeded through the liberation of M(tpp) from SiO2, adsorption of M(tpp) inside bacteria, and generation of reactive oxygen species, such as singlet oxygen, under visible light irradiation, thus resulting in bacteria apoptosis. Based on these results, we developed water-soluble porphyrins by modification of P and Sb porphyrin axial ligands to alkyloxo, alkylethylenedioxy, and alkylpyridinium groups. These water-soluble porphyrins were applied to the photodynamic inactivation of E. coli and Saccharomyces cerevisiae.

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“…The CHCl 3 extract was then evaporated to provide dihydroxide(tetraphenylporphyrinato)-phosphorus chloride (2b, [(HO) 2 P(tpp)]Cl) in 87% yield. 37 Preparation of Bis(5-bromo-3-oxapentan-1-olato)tetraphenylporphyrinatophosphorus(V) Chloride (2c).…”

mentioning

confidence: 99%

Spectroscopic Analysis of the Interaction of Human Serum Albumin with Tricationic Phosphorus Porphyrins Bearing Axial Pyridinio Groups

Matsumoto

Kubo

Shinbara

et al. 2013

Bulletin of the Chemical Society of Japan

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Much attention has been paid to water-soluble porphyrins and metalloporphyrins as potential sensitizers for photodynamic therapy (PDT). Thus, water-soluble tricationic phosphorus porphyrin complexes were prepared via the introduction of an N-alkylpyridinio group on the axial ligands of phosphorus porphyrins. The resulting tricationic phosphorus porphyrins readily dissolve in aqueous solutions without the formation of aggregates, even at high concentration. Moreover, the affinity of the porphyrins to human serum albumin (HSA) is a key factor in their application to PDT since HSA plays an important role in the transport of drug molecules to a target cell. Interactions between the tricationic phosphorus porphyrins and HSA were examined on the basis of changes in the Soret bands of the absorption and fluorescence spectra of phosphorus porphyrin solutions in the presence of HSA and the fluorescence quenching of HSA by the tricationic phosphorus porphyrins. Tricationic phosphorus porphyrins with moderately long alkyl chains on the pyridinio group were strongly adsorbed on the HSA at a position near the tryptophan residue of HSA. This result suggests that tricationic phosphorus porphyrins containing alkyl groups are good candidates as PDT reagents because of their high water solubility and high affinity for HSA.Much attention has been paid to porphyrins and metalloporphyrins because of their potential for use as sensitizers for photosterilization 1,2 and photodynamic therapy (PDT). 36 In general, photosensitizers used in clinical applications should meet the following requirements: i) sufficient solubility in water for handling in aqueous media, ii) strong absorption at longer wavelengths in the visible region, iii) the capability to generate active oxygen species, such as singlet oxygen, via energy transfer from the triplet state of the sensitizer and/or to directly oxidize tumor cells via photoinduced electron transfer, 7,8 and iv) adsorption on the plasma proteins, such as albumin, hemoglobin, and lipoproteins, which carry sensitizers to tumor cells.911 Among these proteins, we focused on human serum albumin (HSA), which is the most abundant plasma protein, since HSA has the ability to bind many kinds of drugs 12,13 and is applied to drug delivery systems.14 In general, water solubilization of porphyrins has been achieved through the introduction of ionic groups such as pyridinium, 7,1518 sulfonate, 1921 and phosphonium 18,22 in the porphyrin rings. However, despite the presence of such ionic groups, many types of water-soluble porphyrins tend to form face-to-face aggregates, resulting in low water solubility in buffer and saline solutions. 17,22,23 To prevent this face-to-face interaction, we have examined water solubilization via modification of the axial ligands of antimony-and phosphoruscontaining porphyrins. 2428 Recently, we prepared watersoluble phosphorus porphyrins bearing axial ligands, such as hydrophilic ethyleneoxy and/or hydrophobic alkoxy groups. 27,28 However, the presence of other components such...

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Bactericidal Effect of Silica Gel-Supported Porphyrinatophosphorus(V) Catalysts on Escherichia coli under Visible-Light Irradiation

Cited by 21 publications

References 19 publications

Quantitative Analysis for a Color-Change of Humidity Indicator by Microscopic Absorption Spectrometry

Quantitative Analysis for a Color-Change of Humidity Indicator by Microscopic Absorption Spectrometry

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Spectroscopic Analysis of the Interaction of Human Serum Albumin with Tricationic Phosphorus Porphyrins Bearing Axial Pyridinio Groups

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