An Extremely Effective DNA Photocleavage Utilizing Functionalized Liposomes with a Fullerene-Enriched Lipid Bilayer

Ikeda, Atsushi; Doi, Yuki; Hashizume, Makoto; Kikuchi, Jun; Konishi, Toshifumi

doi:10.1021/ja070243s

Cited by 112 publications

(97 citation statements)

References 25 publications

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“…51 Liu and coworkers 52 used a water soluble conjugate between anthrylcyclodextrin and C 60 to carry out photocleavage of pGEX5x2 DNA. Ikeda et al 53 used functionalized liposomes encorporating both C 60 and C 70 fullerenes into the lipid bilayer to carry out photocleavage of ColE1 supercoiled plasmid DNA using λ > 350 nm light. Interestingly C 70 was significantly better (3.5 times) than C 60 in photocleaving DNA.…”

Section: Dna Cleavage and Mutagenicitymentioning

confidence: 99%

Photodynamic therapy with fullerenes

Mróz

Tegos

Gali

et al. 2007

Photochem Photobiol Sci

274

209

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Fullerenes are a class of closed-cage nanomaterials made exclusively from carbon atoms. A great deal of attention has been focused on developing medical uses of these unique molecules especially when they are derivatized with functional groups to make them soluble and therefore able to interact with biological systems. Due to their extended π-conjugation they absorb visible light, have a high triplet yield and can generate reactive oxygen species upon illumination, suggesting a possible role of fullerenes in photodynamic therapy. Depending on the functional groups introduced into the molecule, fullerenes can effectively photoinactivate either or both pathogenic microbial cells and malignant cancer cells. The mechanism appears to involve superoxide anion as well as singlet oxygen, and under the right conditions fullerenes may have advantages over clinically applied photosensitizers for mediating photodynamic therapy of certain diseases.

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Section: Dna Cleavage and Mutagenicitymentioning

confidence: 99%

Photodynamic therapy with fullerenes

Mróz

Tegos

Gali

et al. 2007

Photochem Photobiol Sci

274

209

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“…Light-harvesting liposomes of LMIC 60 -DiD were prepared via fullerene exchange from the γ-cyclodextrin (γ-CDx) cavity to DiD contained liposomes (liposome-DiD) following a previously reported method. [10][11][12][13] Due to the efficient intracellular uptake of liposomes by tumor cells in our previously reports, liposomes with cationic surfaces were used for the preparation of LMIC 60 -DiD. 10,11 The structures of DiD and lipids are shown in Figure S1 in the Supporting Information.…”

mentioning

confidence: 99%

“…1,2 Due to the formation of a long-lived triplet state and the high photoproduction ability of ROS, fullerenes have attracted significant attention as PS of PDT. [3][4][5][6][7][8][9][10][11][12][13] We have previously reported that liposomal lipid membrane can be used for solubilization of unmodified [60]fullerenes (C 60 ) to overcome their poor water solubility. The produced cationic lipid membrane incorporating C 60 (LMIC 60 ) showed high cytotoxicity under light irradiation between 350-500 nm.…”

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confidence: 99%

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Photodynamic Activity of Liposomal Photosensitizers via Energy Transfer from Antenna Molecules to [60]Fullerene

Ikeda

Akiyama

Ogawa

et al. 2010

ACS Med. Chem. Lett.

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Photodynamic therapy (PDT) is an emerging approach for the treatment of tumor diseases that has received growing interest in the past few years. In this study, we constructed liposomal photosensitizers (PS) for PDT by shoehorning as light-harvesting "antenna" molecules and dense [60]fullerene (C 60 ) into lipid membrane bilayers. The liposomal PS showed improved photodynamic activity toward human cancer cells via the photoenergy transfer from photoactivated antenna molecules to C 60 .KEYWORDS Energy transfer, fullerenes, photodynamic therapy, photosensitizers, liposomes P hotodynamic therapy (PDT) is a next-generation cancer treatment based on cytotoxic reactive oxygen species (ROS) producing photochemical reactions between photoexcited photosensitizers (PS) and molecular oxygen. 1,2 Due to the formation of a long-lived triplet state and the high photoproduction ability of ROS, fullerenes have attracted significant attention as PS of PDT. [3][4][5][6][7][8][9][10][11][12][13] We have previously reported that liposomal lipid membrane can be used for solubilization of unmodified [60]fullerenes (C 60 ) to overcome their poor water solubility. The produced cationic lipid membrane incorporating C 60 (LMIC 60 ) showed high cytotoxicity under light irradiation between 350-500 nm.10-13 However, from a practical application standpoint, the poor absorption of C 60 between 600 and 700 nm, which is the optimal wavelength range for PDT, remains problematic.In photosynthesis, solar energy is efficiently converted into chemical potential energy by highly organized multiprotein assemblies in the thylakoid membrane architecture of chloroplasts. In this process, photon energy is absorbed by the pigment antenna molecules and transferred to the reaction centers. The energy transfer model which occurs between pigment antenna molecules and the reaction centers represents an attractive approach to overcome the poor absorption of C 60 at long wavelengths. In this study, thylakoid membrane architecture mimetic liposomal PS of PDT were constructed by shoehorning light-harvesting "antenna" molecules and dense C 60 into lipid membrane bilayers (Figure 1). In this PS, photoenergy was absorbed by antenna molecules and transferred to C 60 to generate the ROS. To construct the liposomal PS, LMIC 60 is a convenient platform for placing antenna molecules and C 60 in close proximity because the antenna molecule-introduced liposome can be easily prepared through liposome staining using a lipid membrane probe. By employing liposomes, a direct covalent link between the antenna molecules and C 60 can be avoided, resulting in the efficient generation of ROS because unmodified fullerenes generate ROS more efficiently than other chemically modified C 60 derivatives. 14 1,1 0 -Dioctadecyl-3,3,3 0 ,3 0 -tetramethylindodicarbocyanine (DiD) molecules, dialkylated carbocyanine lipid membrane probes, were used as light-harvesting antenna molecules because dialkylated carbocyanine lipid membrane probes have no appreciable cytotoxicity, 15,16 and DiD m...

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“…121 Outros estudos com derivados fulerênicos, visando a aplicação na TFD, foram realizados. 119,[124][125][126][127][128][129][130] Observa-se claramente que o ponto central destes trabalhos é a busca por compostos mais hidrossolúveis. Neste contexto, podemos destacar os derivados fulerênicos contendo sacarídeos sintetizados por Mikata et al 130 (Figura 15).…”

Section: Uso Em Terapia Fotodinâmicaunclassified

Fulereno[C60]: química e aplicações

Santos¹,

Rocha²,

Alves³

et al. 2010

Quím. Nova

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Recebido em 7/5/09; aceito em 22/9/09; publicado na web em 25/2/10 FULLERENE C 60 : CHEMISTRY AND APPLICATIONS. Fullerene chemistry has become a very active research field in the two last decades, largely because of the exceptional properties of the C 60 molecule and the variety of fullerene derivatives that appear to be possible. In this review, a general analysis of fullerene C 60 reactivity is performed. The principal methods for the covalent modification of this fascinating carbon cage are presented. The prospects of using fullerene derivatives as medicinal drugs and photoactive materials in light converting devices are demonstrated.Keywords: fullerene C 60 ; nanomaterials; carbon allotropes. Este artigo de revisão teve o objetivo de sistematizar as principais informações relacionadas à reatividade singular desta forma de carbono e aos principais métodos até então desenvolvidos para a funcionalização química do fulereno [C 60 ] bem como exemplificar a grande e versátil gama de aplicações encontradas até hoje para esta nanomolécula e seus derivados quimicamente modificados. INTRODUÇÃO HISTÓRICO, MÉTODOS DE OBTENÇÃO E PURIFICAÇÃOEmbora desde 1966 cálculos teóricos demonstrassem a possibilidade da existência de "gaiolas" estáveis formadas exclusivamente por átomos de carbono, 2 somente em 1985 um experimento realizado por Kroto et al. comprovou experimentalmente a existência de tais compostos. 3 Nesse experimento, uma placa de grafite foi submetida a um laser pulsado de alta frequência e os agregados gerados no plasma foram analisados por espectrometria de massas. O experimento mostrou a formação de moléculas grandes constituídas exclusivamente por átomos de carbono, com fórmula C n onde n= 30-190, sendo C 60 e C 70 os mais abundantes. Sob condições específicas para a formação destes agregados, o espectro de massas apresentou o pico do C 60 como principal. Esta molécula, excepcionalmente estável e simétrica, foi chamada pelos pesquisadores de fullerene em homenagem ao arquiteto americano B. Fuller, responsável pela invenção dos domos geodési-cos, forma arquitetônica que segue o mesmo princípio de simetria e estabilidade. Sir H. W. Kroto, R. F. Curl e R. E. Smalley procuravam, neste experimento, mimetizar condições interestelares para comprovar a existência de grandes e excepcionais cadeias de carbono no espaço e não suspeitavam que, graças a sua descoberta, seriam agraciados com o Nobel de Química alguns anos mais tarde, em 1996.A descoberta destas espécies moleculares de carbono excitou profundamente a comunidade científica. Entretanto, somente em 1990, R. Taylor, um especialista em cromatografia, foi capaz de obter pela primeira vez 4 amostras puras de C 60 e C 70 em quantidades mínimas, mas suficiente para começar a exploração de suas propriedades químicas e espectroscópicas. No mesmo ano, o desenvolvimento por Krätschmer et al. 5 de um método para a síntese de C 60 em quantidades "macroscópicas" representou uma etapa decisiva para a área que se tornou, nos últimos 20 anos, um tema maior da química contempo...

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An Extremely Effective DNA Photocleavage Utilizing Functionalized Liposomes with a Fullerene-Enriched Lipid Bilayer

Abstract: A surface-functionalized liposome with a high C70 concentration (LMIC70) was synthesized by exchange reaction from an unstable fullerene complex, C70·γ-CDx. The DNA photocleavage ability of LMIC70 is extremely higher than that of LMIC60 or C60·γ-CDx.

Cited by 112 publications

References 25 publications

Photodynamic therapy with fullerenes

Photodynamic therapy with fullerenes

Photodynamic Activity of Liposomal Photosensitizers via Energy Transfer from Antenna Molecules to [60]Fullerene

Fulereno[C60]: química e aplicações

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