Synthesis and Transfection Capability of Multi-Functionalized Fullerene Polyamine

A new fullerene transfection reagent bearing multiple-functional groups has been synthesized by diastereoselective double cycloaddition reaction. The highly oxygenated reagent transfers extra-cellular DNA into mammalian cells with the efficiency comparable to that of a nor-analogue.

[1]  E. Nakamura,et al.  Fullerene–Oligonucleotide Conjugates: Photoinduced Sequence‐Specific DNA Cleavage , 1995 .

[2]  Eiichi Nakamura,et al.  Functionalized Fullerene as an Artificial Vector for Transfection. , 2000, Angewandte Chemie.

[3]  F. Diederich,et al.  Configurational Description of Chiral Fullerenes and Fullerene Derivatives with a Chiral Functionalization Pattern , 1997 .

[4]  H. Ohigashi,et al.  Photocytotoxicity of water-soluble fullerene derivatives. , 1996, Bioscience, biotechnology, and biochemistry.

[5]  J. Tour,et al.  Assembly of DNA/Fullerene Hybrid Materials. , 1998, Angewandte Chemie.

[6]  H. Isobe,et al.  Optical Resolution of Chirally Functionalized [60]Fullerene Through Formation of Diastereomeric Methoxyphenylacetic Acid Esters , 1999 .

[7]  E. Nakamura,et al.  One-Step Multiple Addition of Amine to [60]Fullerene. Synthesis of Tetra(amino)fullerene Epoxide under Photochemical Aerobic Conditions , 2000 .

[8]  F. Diederich,et al.  Absolute configuration of chiral fullerenes and covalent derivatives from their calculated circular dichroism spectra , 1998 .

[9]  E. Nakamura,et al.  General synthesis of cyclopropenones and their acetals , 1992 .

[10]  C. Burger,et al.  Spherical bilayer vesicles of fullerene-based surfactants in water: a laser light scattering study. , 2001, Science.

[11]  E. Nakamura,et al.  In vivo biological behavior of a water-miscible fullerene: 14C labeling, absorption, distribution, excretion and acute toxicity. , 1995, Chemistry & biology.

[12]  F. Diederich,et al.  Optically Active Macrocycliccis-3 Bis-Adducts of C60: Regio- and Stereoselective Synthesis, Exciton Chirality Coupling, and Determination of the Absolute Configuration, and First Observation of Exciton Coupling between Fullerene Chromophores in a Chiral Environment , 2000 .

[13]  E. Nakamura,et al.  Regio- and diastereo-controlled double cycloaddition to [60] fullerene: one-step synthesis of Cs and C2 chiral organofullerenes with new tris-annulating reagents , 1996 .

[14]  Y. Ikada,et al.  Photodynamic Effect of Polyethylene Glycol–modified Fullerene on Tumor , 1997, Japanese journal of cancer research : Gann.

[15]  E. Nakamura,et al.  Biological Activity of Water-Soluble Fullerenes. Structural Dependence of DNA Cleavage, Cytotoxicity, and Enzyme Inhibitory Activities Including HIV-Protease Inhibition , 1996 .

[16]  C. Greck,et al.  Synthesis of Diepoxides and Diaziridines, Precursors of Enantiomerically Pure a-Hydroxy and a-Amino Aldehydes or Acids, from D-Mannitol , 1987 .

[17]  W. Denny,et al.  Potenial antitumor agents. 28. Deoxyribonucleic acid polyintercalating agents. , 1978, Journal of medicinal chemistry.

[18]  SawamuraMasaya,et al.  Pentaorgano[60]fullerene R5C60−. A Water Soluble Hydrocarbon Anion , 2000 .

[19]  Eiichi Nakamura,et al.  Photoinduced biochemical activity of fullerene carboxylic acid , 1993 .

[20]  Shuichi Nakamura,et al.  Enantioselective Reactions of Configurationally Unstable α‐Thiobenzyllithium Compounds , 2000 .

[21]  R. Bernstein,et al.  On the Mechanism of DNA Cleavage by Fullerenes Investigated in Model Systems: Electron Transfer from Guanosine and 8-Oxo-Guanosine Derivatives to C60 , 1999 .

[22]  N. Miyata,et al.  •OH and O2•- Generation in Aqueous C60 and C70 Solutions by Photoirradiation: An EPR Study , 1998 .

[23]  E. Nakamura,et al.  Synthetic and Computational Studies on Symmetry-Defined Double Cycloaddition of a New Tris-Annulating Reagent to C60 , 1997 .

[24]  K. Fukui,et al.  Atomic Force Microscope Studies on Condensation of Plasmid DNA with Functionalized Fullerenes , 2001 .