Efficient singlet oxygen generation from sugar pendant C60 derivatives for photodynamic therapy.

The amidation reaction between C60 with an activated ester group (1) and acetylated Glc (AcGlc) with an amino group (2) was performed to yield the target AcGlc-pendant C60 compound (3). The water soluble deacetylated compound, Glc-pendant C60 compound (4), exhibited high photocytotoxicity against HeLa cells due to the more efficient singlet oxygen generation as compared with that of Glc-pendant azafulleroids.

[1]  Michael R Hamblin,et al.  T-cell mediated anti-tumor immunity after photodynamic therapy: why does it not always work and how can we improve it? , 2015, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[2]  Chengzhong Yu,et al.  Preparation of fluorescent mesoporous hollow silica-fullerene nanoparticles via selective etching for combined chemotherapy and photodynamic therapy. , 2015, Nanoscale.

[3]  Chen-Ho Tung,et al.  Biological Applications of Supramolecular Assemblies Designed for Excitation Energy Transfer. , 2015, Chemical reviews.

[4]  K. Ohkubo,et al.  Singlet oxygen generation from Li⁺@C⁺₆₀ nano-aggregates dispersed by laser irradiation in aqueous solution. , 2015, Chemical communications.

[5]  R. Pandey,et al.  Porphyrin-based photosensitizers and the corresponding multifunctional nanoplatforms for cancer-imaging and phototherapy , 2015 .

[6]  R. Peng,et al.  Facile access to novel [60]fullerenyl diethers and [60]fullerene-sugar conjugates via annulation of diol moieties. , 2015, Organic letters.

[7]  Jiechao Ge,et al.  Amphiphilic trismethylpyridylporphyrin-fullerene (C70) dyad: an efficient photosensitizer under hypoxia conditions. , 2015, Journal of materials chemistry. B.

[8]  Liang Cheng,et al.  Functional nanomaterials for phototherapies of cancer. , 2014, Chemical reviews.

[9]  G. Diao,et al.  Water-soluble inclusion complex of fullerene with γ-cyclodextrin polymer for photodynamic therapy. , 2014, Journal of materials chemistry. B.

[10]  Jun Gao,et al.  A fullerene-based multi-functional nanoplatform for cancer theranostic applications. , 2014, Biomaterials.

[11]  J. Nierengarten,et al.  Fullerene sugar balls: a new class of biologically active fullerene derivatives. , 2014, Chemistry, an Asian journal.

[12]  C. Ortiz Mellet,et al.  Fullerene-sp2-iminosugar balls as multimodal ligands for lectins and glycosidases: a mechanistic hypothesis for the inhibitory multivalent effect. , 2013, Chemistry.

[13]  R. Roy,et al.  Multivalent glycoconjugate syntheses and applications using aromatic scaffolds. , 2013, Chemical Society reviews.

[14]  M. Tzirakis,et al.  Radical reactions of fullerenes: from synthetic organic chemistry to materials science and biology. , 2013, Chemical reviews.

[15]  J. Kikuchi,et al.  Location of [60]fullerene incorporation in lipid membranes. , 2011, Chemical communications.

[16]  Y. Hagiya,et al.  Current states and future views in photodynamic therapy , 2011 .

[17]  A. Morita,et al.  Effect and Mechanism of a New Photodynamic Therapy with Glycoconjugated Fullerene , 2010, Photochemistry and photobiology.

[18]  M. Sánchez‐Navarro,et al.  Fullerene sugar balls. , 2010, Chemical communications.

[19]  H Abrahamse,et al.  Photodynamic therapy (PDT): a short review on cellular mechanisms and cancer research applications for PDT. , 2009, Journal of photochemistry and photobiology. B, Biology.

[20]  T. Takeya,et al.  Intracellular uptake and photodynamic activity of water-soluble [60]- and [70]fullerenes incorporated in liposomes. , 2008, Chemistry.

[21]  Qian Peng,et al.  Milestones in the development of photodynamic therapy and fluorescence diagnosis , 2007, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[22]  A. Oseroff,et al.  Photophysical, electrochemical characteristics and cross-linking of STAT-3 protein by an efficient bifunctional agent for fluorescence image-guided photodynamic therapy , 2007, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[23]  Michael R Hamblin,et al.  Photodynamic therapy with fullerenes , 2007, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[24]  J. Kikuchi,et al.  An extremely effective DNA photocleavage utilizing functionalized liposomes with a fullerene-enriched lipid bilayer. , 2007, Journal of the American Chemical Society.

[25]  Y. Ishida,et al.  Synthesis and reactions of 2,2-[60]fullerenoalkanoyl chlorides. , 2006, The Journal of organic chemistry.

[26]  A. Tomé,et al.  Synthesis and solvent dependence of the photophysical properties of [60]fullerene-sugar conjugates , 2005 .

[27]  Thomas Kocher,et al.  Photodynamic therapy for periodontal diseases: state of the art. , 2005, Journal of photochemistry and photobiology. B, Biology.

[28]  K. Ohkubo,et al.  Production of an ultra-long-lived charge-separated state in a zinc chlorin-C60 dyad by one-step photoinduced electron transfer. , 2004, Angewandte Chemie.

[29]  M. Prato,et al.  Fullerene derivatives: an attractive tool for biological applications. , 2003, European journal of medicinal chemistry.

[30]  E. Nakamura,et al.  Functionalized fullerenes in water. The first 10 years of their chemistry, biology, and nanoscience. , 2003, Accounts of chemical research.

[31]  M. Tanihara,et al.  Detection of 1270 nm emission from singlet oxygen and photocytotoxic property of sugar-pendant 60 fullerenes. , 2003, Bioorganic & medicinal chemistry letters.

[32]  M. D. Rooij,et al.  Electrochemical Methods: Fundamentals and Applications , 2003 .

[33]  R. Schibli,et al.  Derivatization of glucose and 2-deoxyglucose for transition metal complexation: substitution reactions with organometallic 99mTc and Re precursors and fundamental NMR investigations. , 2001, Chemistry.

[34]  S. Fukuzumi,et al.  Effects of Lowering Symmetry on the ESR Spectra of Radical Anions of Fullerene Derivatives and the Reduction Potentials , 2000 .

[35]  F. Diederich,et al.  Fullerene Sugars: Preparation of Enantiomerically Pure, Spiro‐Linked C‐Glycosides of C60 , 1992 .

[36]  Manivannan Ethirajan,et al.  The role of porphyrin chemistry in tumor imaging and photodynamic therapy. , 2011, Chemical Society reviews.

[37]  Allen J. Bard,et al.  Electrochemical Methods: Fundamentals and Applications , 1980 .