Cyclodextrin complexed [60]fullerene derivatives with high levels of photodynamic activity by long wavelength excitation

Atsushi Ikeda, Tatsuya Iizuka, Naotake Maekubo, Ryota Aono, Jun Ichi Kikuchi, Motofusa Akiyama, Toshifumi Konishi, Takuya Ogawa, Norihiro Ishida-Kitagawa, Hisashi Tatebe, Kazuhiro Shiozaki

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

We have evaluated the photodynamic activities of C60 derivative·γ-cyclodextrin (γ-CDx) complexes and demonstrated that they were significantly higher than those of the pristine C60 and C70·γ-CDx complexes under photoirradiation at long wavelengths (610-720 nm), which represent the optimal wavelengths for photodynamic therapy (PDT). In particular, the cationic C60 derivative·γ-CDx complex had the highest photodynamic ability because the complex possessed the ability to generate high levels of 1O2 and provided a higher level of intracellular uptake. The photodynamic activity of this complex was greater than that of photofrin, which is the most widely used of the known clinical photosensitizers. These findings therefore provide a significant level of information toward the optimization of molecular design strategies for the synthesis of fullerene derivatives for PDT.

Original languageEnglish (US)
Pages (from-to)752-756
Number of pages5
JournalACS Medicinal Chemistry Letters
Volume4
Issue number8
DOIs
StatePublished - Aug 8 2013
Externally publishedYes

Fingerprint

Photodynamic therapy
Photochemotherapy
Cyclodextrins
Dihematoporphyrin Ether
Fullerenes
Derivatives
Wavelength
Photosensitizing Agents
fullerene C60
pristine (C60)

Keywords

  • cyclodextrin
  • Fullerenes
  • photodynamic therapy
  • photosensitizers

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery
  • Biochemistry

Cite this

Cyclodextrin complexed [60]fullerene derivatives with high levels of photodynamic activity by long wavelength excitation. / Ikeda, Atsushi; Iizuka, Tatsuya; Maekubo, Naotake; Aono, Ryota; Kikuchi, Jun Ichi; Akiyama, Motofusa; Konishi, Toshifumi; Ogawa, Takuya; Ishida-Kitagawa, Norihiro; Tatebe, Hisashi; Shiozaki, Kazuhiro.

In: ACS Medicinal Chemistry Letters, Vol. 4, No. 8, 08.08.2013, p. 752-756.

Research output: Contribution to journalArticle

Ikeda, A, Iizuka, T, Maekubo, N, Aono, R, Kikuchi, JI, Akiyama, M, Konishi, T, Ogawa, T, Ishida-Kitagawa, N, Tatebe, H & Shiozaki, K 2013, 'Cyclodextrin complexed [60]fullerene derivatives with high levels of photodynamic activity by long wavelength excitation', ACS Medicinal Chemistry Letters, vol. 4, no. 8, pp. 752-756. https://doi.org/10.1021/ml4001535
Ikeda, Atsushi ; Iizuka, Tatsuya ; Maekubo, Naotake ; Aono, Ryota ; Kikuchi, Jun Ichi ; Akiyama, Motofusa ; Konishi, Toshifumi ; Ogawa, Takuya ; Ishida-Kitagawa, Norihiro ; Tatebe, Hisashi ; Shiozaki, Kazuhiro. / Cyclodextrin complexed [60]fullerene derivatives with high levels of photodynamic activity by long wavelength excitation. In: ACS Medicinal Chemistry Letters. 2013 ; Vol. 4, No. 8. pp. 752-756.
@article{d555e1359bb149639f7913a696743e1c,
title = "Cyclodextrin complexed [60]fullerene derivatives with high levels of photodynamic activity by long wavelength excitation",
abstract = "We have evaluated the photodynamic activities of C60 derivative·γ-cyclodextrin (γ-CDx) complexes and demonstrated that they were significantly higher than those of the pristine C60 and C70·γ-CDx complexes under photoirradiation at long wavelengths (610-720 nm), which represent the optimal wavelengths for photodynamic therapy (PDT). In particular, the cationic C60 derivative·γ-CDx complex had the highest photodynamic ability because the complex possessed the ability to generate high levels of 1O2 and provided a higher level of intracellular uptake. The photodynamic activity of this complex was greater than that of photofrin, which is the most widely used of the known clinical photosensitizers. These findings therefore provide a significant level of information toward the optimization of molecular design strategies for the synthesis of fullerene derivatives for PDT.",
keywords = "cyclodextrin, Fullerenes, photodynamic therapy, photosensitizers",
author = "Atsushi Ikeda and Tatsuya Iizuka and Naotake Maekubo and Ryota Aono and Kikuchi, {Jun Ichi} and Motofusa Akiyama and Toshifumi Konishi and Takuya Ogawa and Norihiro Ishida-Kitagawa and Hisashi Tatebe and Kazuhiro Shiozaki",
year = "2013",
month = "8",
day = "8",
doi = "10.1021/ml4001535",
language = "English (US)",
volume = "4",
pages = "752--756",
journal = "ACS Medicinal Chemistry Letters",
issn = "1948-5875",
publisher = "American Chemical Society",
number = "8",

}

TY - JOUR

T1 - Cyclodextrin complexed [60]fullerene derivatives with high levels of photodynamic activity by long wavelength excitation

AU - Ikeda, Atsushi

AU - Iizuka, Tatsuya

AU - Maekubo, Naotake

AU - Aono, Ryota

AU - Kikuchi, Jun Ichi

AU - Akiyama, Motofusa

AU - Konishi, Toshifumi

AU - Ogawa, Takuya

AU - Ishida-Kitagawa, Norihiro

AU - Tatebe, Hisashi

AU - Shiozaki, Kazuhiro

PY - 2013/8/8

Y1 - 2013/8/8

N2 - We have evaluated the photodynamic activities of C60 derivative·γ-cyclodextrin (γ-CDx) complexes and demonstrated that they were significantly higher than those of the pristine C60 and C70·γ-CDx complexes under photoirradiation at long wavelengths (610-720 nm), which represent the optimal wavelengths for photodynamic therapy (PDT). In particular, the cationic C60 derivative·γ-CDx complex had the highest photodynamic ability because the complex possessed the ability to generate high levels of 1O2 and provided a higher level of intracellular uptake. The photodynamic activity of this complex was greater than that of photofrin, which is the most widely used of the known clinical photosensitizers. These findings therefore provide a significant level of information toward the optimization of molecular design strategies for the synthesis of fullerene derivatives for PDT.

AB - We have evaluated the photodynamic activities of C60 derivative·γ-cyclodextrin (γ-CDx) complexes and demonstrated that they were significantly higher than those of the pristine C60 and C70·γ-CDx complexes under photoirradiation at long wavelengths (610-720 nm), which represent the optimal wavelengths for photodynamic therapy (PDT). In particular, the cationic C60 derivative·γ-CDx complex had the highest photodynamic ability because the complex possessed the ability to generate high levels of 1O2 and provided a higher level of intracellular uptake. The photodynamic activity of this complex was greater than that of photofrin, which is the most widely used of the known clinical photosensitizers. These findings therefore provide a significant level of information toward the optimization of molecular design strategies for the synthesis of fullerene derivatives for PDT.

KW - cyclodextrin

KW - Fullerenes

KW - photodynamic therapy

KW - photosensitizers

UR - http://www.scopus.com/inward/record.url?scp=84881414652&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84881414652&partnerID=8YFLogxK

U2 - 10.1021/ml4001535

DO - 10.1021/ml4001535

M3 - Article

AN - SCOPUS:84881414652

VL - 4

SP - 752

EP - 756

JO - ACS Medicinal Chemistry Letters

JF - ACS Medicinal Chemistry Letters

SN - 1948-5875

IS - 8

ER -