C<sub>60</sub> Fullerene with Tetraethylene Glycols as a Well-defined Soluble Building Block and Saccharide-conjugation Producing PDT Photosensitizer

Narumi, Atsushi; Nakazawa, Tatsufumi; Shinohara, Kosuke; Kato, Hirohisa; Iwaki, Yoshinori; Okimoto, Haruya; Kikuchi, Moriya; Kawaguchi, Seigou; Hino, Shodai; Ikeda, Atsushi; Shaykoon, Montaser Shaykoon Ahmed; Shen, Xiande; Duan, Qian; Kakuchi, Toyoji; Nomoto, Akihiro; Mikata, Yuji; Yano, Shigenobu

doi:10.1246/cl.190492

Cited by 6 publications

(3 citation statements)

References 37 publications

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“…The effect of fullerene glycosylation was also confirmed when Narumi et Al. [89] carried out a study showing that a glycoconjugated TEG-C60 (22, Figure 4, a fullerene conjugated with a malonamide chain bearing two glycosylated tetraethylene glycol, TEG) could be a promising approach to increase the photodynamic activity of C60. Moreover, it seems that it acts in aqueous medium forming micelles by hydrophobic interaction between C60 units that exposes on the surface the glycosylated TEG chains (the portion responsible of the tumour-targeting and the biocompatibility).…”

Section: Indirect Actionmentioning

confidence: 99%

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Synthesis and biological application of glyco- and peptide derivatives of fullerene C60

Tanzi

Terreni

Zhang

2022

European Journal of Medicinal Chemistry

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Section: Indirect Actionmentioning

confidence: 99%

“…In addition, the design of these derivative could be performed in order to induce the formation of stable micelles with a core of fullerene that expose the antigens on the surface [89].…”

Section: Immunological Propertiesmentioning

confidence: 99%

Synthesis and biological application of glyco- and peptide derivatives of fullerene C60

Tanzi

Terreni

Zhang

2022

European Journal of Medicinal Chemistry

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“…Sugar conjugation with C60 would allow the introduction of both hydrophilicity and tumor selectivity to a fullerene. PDT using sugar-conjugated C60 derivatives has been reported [ 70 , 71 , 72 , 73 ]. Sugar coating of C70 can be expected to lead to the development of useful PSs as well [ 74 ].…”

Section: Other Expected Photosensitizersmentioning

confidence: 99%

Potential of Photodynamic Therapy Based on Sugar-Conjugated Photosensitizers

Kataoka

Nishie

Tanaka

et al. 2021

JCM

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In 2015, the Japanese health insurance approved the use of a second-generation photodynamic therapy (PDT) using talaporfin sodium (TS); however, its cancer cell selectivity and antitumor effects of TS PDT are not comprehensive. The Warburg effect describes the elevated rate of glycolysis in cancer cells, despite the presence of sufficient oxygen. Because cancer cells absorb considerable amounts of glucose, they are visible using positron emission tomography (PET). We developed a third-generation PDT based on the Warburg effect by synthesizing novel photosensitizers (PSs) in the form of sugar-conjugated chlorins. Glucose-conjugated (tetrafluorophenyl) chlorin (G-chlorin) PDT revealed significantly stronger antitumor effects than TS PDT and induced immunogenic cell death (ICD). ICD induced by PDT enhances cancer immunity, and a combination therapy of PDT and immune checkpoint blockers is expected to synergize antitumor effects. Mannose-conjugated (tetrafluorophenyl) chlorin (M-chlorin) PDT, which targets cancer cells and tumor-associated macrophages (TAMs), also shows strong antitumor effects. Finally, we synthesized a glucose-conjugated chlorin e6 (SC-N003HP) that showed 10,000–50,000 times stronger antitumor effects than TS (IC50) in vitro, and it was rapidly metabolized and excreted. In this review, we discuss the potential and the future of next-generation cancer cell-selective PDT and describe three types of sugar-conjugated PSs expected to be clinically developed in the future.

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In-situ carbonizing of coal pitch on the surface of silica sphere as quasi-graphitized carbon stationary phase for liquid chromatography

Zhong

Wang

et al. 2023

Chinese Chemical Letters

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C₆₀ Fullerene with Tetraethylene Glycols as a Well-defined Soluble Building Block and Saccharide-conjugation Producing PDT Photosensitizer

Cited by 6 publications

References 37 publications

Synthesis and biological application of glyco- and peptide derivatives of fullerene C60

Synthesis and biological application of glyco- and peptide derivatives of fullerene C60

Potential of Photodynamic Therapy Based on Sugar-Conjugated Photosensitizers

In-situ carbonizing of coal pitch on the surface of silica sphere as quasi-graphitized carbon stationary phase for liquid chromatography

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C60 Fullerene with Tetraethylene Glycols as a Well-defined Soluble Building Block and Saccharide-conjugation Producing PDT Photosensitizer

Cited by 6 publications

References 37 publications

Synthesis and biological application of glyco- and peptide derivatives of fullerene C60

Synthesis and biological application of glyco- and peptide derivatives of fullerene C60

Potential of Photodynamic Therapy Based on Sugar-Conjugated Photosensitizers

In-situ carbonizing of coal pitch on the surface of silica sphere as quasi-graphitized carbon stationary phase for liquid chromatography

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C₆₀ Fullerene with Tetraethylene Glycols as a Well-defined Soluble Building Block and Saccharide-conjugation Producing PDT Photosensitizer