Water-soluble fullerenes have attracted attention as promising compounds that have been used to forge new paths in the field of photo-biochemistry. To prepare water-soluble fullerenes, we employed lipid-membrane-incorporated fullerenes (LMICx; x=60 or 70) by using the fullerene exchange method from a gamma-cyclodextrin (gamma-CD) cavity to vesicles. LMIC60 have low toxicity in the dark and engender cell death by photoirradiation (lambda>350 nm). Furthermore, the photodynamic activity of LMIC70 is 4.7-fold that of LMIC60 for the same photon flux (lambda>400 nm). One of the reasons for the higher phototoxicity of LMIC70 is the higher generation of singlet oxygen (1O2) in LMIC70 than in LMIC60. The difference between LMIC60 and LMIC70 is considered to be simply derived from the amount of light absorption in the 400-700 nm region that is suitable for photodynamic therapy (PDT). To the best of our knowledge, this is the first case in which biological activity of C70 and its derivatives toward HeLa cells has been assayed.
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.
Intracellular uptake of a lipid-membrane-incorporated C(60) with a cationic surface into HeLa cells was found to induce cell death under visible light irradiation in high efficiency.
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