12 research outputs found

    Synthesis of hydroazafullerene C59HN, the parent hydroheterofuIlerene

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    The electronic and geometric properties of C60 can be perturbed by replacing one or more carbon atoms of the fullerene skeleton with an atom of a different element. Exchange of one carbon atom with nitrogen, a trivalent atom with a lone pair of electrons, produces the azafullerene radical C59N·, which is isoelectronic with the C60 radical anion. The process is slightly similar to doping silicon with phosphorus. We have previously described the synthesis of the azafullerene dimer; here we report the bulk preparation of the simplest azafullerene, C59HN. The electronic, vibrational and 13C NMR spectroscopic features of C59HN are similar to those of the dimer, except for the signature of the sp3 (C-H) carbon. C59HN should open the door to a new chemistry of heterofullerenes.

    Anti-Human Immunodeficiency Virus, Toxicity in Cell Culture, and Tolerance in Mammals of a Water-Soluble Fullerene

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    The bis(monosuccinimide) derivative of p,p'-bis(2-aminoethyl)diphenyl C60, 1, had substantial activity against HIV-1 and HIV-2 in acutely or chronically infected human lymphocytes, and activity against AZT-resistant HIV-1 in vitro (EC50 ~ 3-7 µM). This activity was primarily associated with virucidal and anti-protease properties of 1. The fullerene had very low cytotoxicity (IC50 > 100 µM in PBMC, H9, Vero, and CEM cells) in various cells. Compound 1 did not interact with the CD4+ receptor on human lymphocytes even at 100 µM. Similarly, no anti-fusion activity was noted at that concentration. No toxicity in mice was apparent when 1 was administered intraperitoneally at 50 mg/kg per day for 6 days.
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