Adsorption of tetrakis(4-sulfophenyl)porphyrin onto liposomal surfaces composed of neutral diacylphosphatidylcholine and release by cyclodextrin

Tsuchiya, Yoichi; Nakaya, Toshimi; Kakigi, Tomoyuki; Sugikawa, Kouta; Ikeda, Atsushi

doi:10.1039/c8ra01411f

Cited by 3 publications

(3 citation statements)

References 27 publications

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“…However, it is known that anionic DNA and nanoparticles could adsorb onto neutral liposomal surfaces comprising diacylphosphatidylcholine. Although the details of the interactions were unclear, multipoint interactions might have occurred between the negative charges of nanoparticles or materials and the positive charge of ammonium groups or the phosphorus‐nitrogen dipole of the diacylphosphatidylcholine of cells [38–40] . The intracellular uptakes of the negatively charged CGN‐ 1 and CGN‐ 2 complexes by HeLa cells may have also been caused by the same reason.…”

Section: Resultsmentioning

confidence: 99%

Selective Photodynamic Activity of Tetrakis(4‐aminophenyl)porphyrins with and without Acetyl Protecting Groups on Cancer and Normal Cells

Okuno

Yamana

Kawamura

et al. 2023

Chemistry A European J

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Tetrakis(4‐aminophenyl)porphyrin (1) and tetrakis(4‐acetamidophenyl)porphyrin (2) were dissolved in water with the incorporation of a polysaccharide (λ‐carrageenan (CGN)) as a water‐solubilizing agent. Although the photodynamic activity of the CGN‐2 complex was considerably lower than that of the CGN‐1 complex, the selectivity index (SI; IC50 in a normal cell/IC50 in a cancer cell) of the CGN‐2 complex was considerably higher than that of the CGN‐1 complex. This is because the photodynamic activity of the CGN‐2 complex was significantly affected by the intracellular uptakes by the normal and cancer cells. During in vivo experiments, the CGN‐2 complex inhibited tumor growth under light irradiation with high blood retention compared with the CGN‐1 complex and Photofrin, which exhibited lower blood retention. This study showed that the photodynamic activity and SI are influenced by substituent groups of arene in the meso‐positions of porphyrin analogs.

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Section: Resultsmentioning

confidence: 99%

Selective Photodynamic Activity of Tetrakis(4‐aminophenyl)porphyrins with and without Acetyl Protecting Groups on Cancer and Normal Cells

Okuno

Yamana

Kawamura

et al. 2023

Chemistry A European J

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“…Anionic 26 was adsorbed onto liposomal surfaces composed of neutral lipid 1,2-dipalmitoyl-sn-glycero-phosphatidylcholine (DPPC) at high lipid concentrations. [77] Although the details of the interactions remain unclear, multipoint interactions might exist between the negative charges of 26 and the positive charge N + of the phosphorus-nitrogen dipole of DPPC. [78,79] By adding TMe-β-CDx, 26 was released from the liposomal surface and formed a complex with two TMe-β-CDx units.…”

Section: Transfer Of Porphyrin Derivative From Liposomal Surface To C...mentioning

confidence: 99%

“…Conversely, tetrakis(4‐sulfophenyl)porphyrin 26 is transferred from the surface of lipid membranes to TMe‐β‐CDx cavities. Anionic 26 was adsorbed onto liposomal surfaces composed of neutral lipid 1,2‐dipalmitoyl‐ sn ‐glycero‐phosphatidylcholine (DPPC) at high lipid concentrations [77] . Although the details of the interactions remain unclear, multipoint interactions might exist between the negative charges of 26 and the positive charge N + of the phosphorus‐nitrogen dipole of DPPC [78,79] .…”

Section: Transfer Of Porphyrin Derivative From Liposomal Surface To C...mentioning

confidence: 99%

“On‐Off” Switching of Functional Guest Molecules via Exchange of Natural Product Solubilizing Agents

Kawasaki

Ikeda

2023

ChemBioChem

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For the development of delivery systems, the solubilization of hydrophobic guest molecules in water is an important yet challenging task. This can be achieved by preparing stable aqueous solutions with a high concentration of guest molecules using a natural product as a solubilizing agent and a mechanochemical high‐speed vibration milling apparatus as a solubilizing method. Various solubilizing agent‐guest molecule complexes can be obtained via the exchange between solubilizing agents, which enables the “on‐off” switching of the properties of functional guest molecules, such as fluorescence intensity, and photodynamic activity. In the exchange method, guest molecules can transfer into cell membranes such as lysosomes and exosomes. Therefore, the exchange method of the solubilizing agents not only creates novel solubilizing agent‐guest molecule complexes but also is applied to drug delivery systems.

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High photodynamic activities of water-soluble inclusion complexes of 5,15-diazaporphyrins in cyclodextrin

et al. 2019

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Adsorption of tetrakis(4-sulfophenyl)porphyrin onto liposomal surfaces composed of neutral diacylphosphatidylcholine and release by cyclodextrin

Abstract: Interactions between tetrakis(4-sulfophenyl)porphyrin and liposomal surfaces with neutral diacylphosphatidylcholine occurred and can be controlled by the addition of cyclodextrin.

Cited by 3 publications

References 27 publications

Selective Photodynamic Activity of Tetrakis(4‐aminophenyl)porphyrins with and without Acetyl Protecting Groups on Cancer and Normal Cells

Selective Photodynamic Activity of Tetrakis(4‐aminophenyl)porphyrins with and without Acetyl Protecting Groups on Cancer and Normal Cells

“On‐Off” Switching of Functional Guest Molecules via Exchange of Natural Product Solubilizing Agents

High photodynamic activities of water-soluble inclusion complexes of 5,15-diazaporphyrins in cyclodextrin

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