Fullerene water soluble

There are, indeed, many biological implications that have been triggered by the advent of fullerenes. They range from potential inhibition of HIV-1 protease, synthesis of dmgs for photodynamic therapy and free radical scavenging (antioxidants), to participation in photo-induced DNA scission processes [156, 157, 158, 159, 160, 161, 162 and 163]. These examples unequivocally demonstrate the particular importance of water-soluble fullerenes and are summarized in a few excellent reviews [141, 1751. 

Guldi D M, Hungerbuhler H and Asmus K-D 1997 Radiolytio reduotion of a water-soluble fullerene oluster J. Phys. Chem. A 101 1783-6... 

Andersson T, Nilsson K, Sundahl M, Westman G and Wennerstrom O 1992 Cgg embedded in y-oyolodextrin a water-soluble fullerene J. Chem. Soc., Chem. Common. 604-6... 

Guldi D M 1997 Capped fullerenes stabilization of water-soluble fullerene monomers as studied by flash photolysis and pulse radiolysis J. Phys. Chem. A 101 3895-900... 

Irie K, Nakamura Y, Ohigashi H, Tokuyama H, Yamago S and Nakamura E 1996 Photooytotoxioity of water-soluble fullerene derivatives Biosci. Biotech. Biochem. 60 1359-61... 

Braun, T. (1997) Water soluble fullerene-cyclodextrin suframolecular assemblies preparation, structure, properties (an annotated bibliography). Fullerene Sci. Technol. 5, 615-626. 

Samal, S., and Gcckclcr, K.E. (2000) Cyclodextrin-fullerenes a new class of water-soluble fullerenes. /. Cbem. Soc. Cbem. Comm., 1101-1102. 

Beuerle F, Witte P, Hartnagel U, Lebovitz R, Parng C, Hirsch A (2007) Cytoprotective activities of water-soluble fullerenes in zebrafish models. J. Exp. Nanosci. 2 147-170. 

Da Ros T, Prato M, Novello F, Maggini M, Banfi E (1996) Easy access to water soluble fullerene derivatives via 1,3-dipolar cycloadditions of azomethine ylides to C60. J. Org. Chem. 61 9070-9072. 

Nakamura E, Tokuyama H, Yamago S, Shiraki T, Sugiura Y (1996) Biological activity of water-Soluble fullerenes. Structural dependence of DNA cleavage, cytotoxicity, and enzyme inhibitory activities including HIV-Protease inhibition. Bull. Chem. Soc. Jpn. 69 2143-2151. 

Niwa Y, Iwai N (2006) Genotoxicity in cell lines induced by chronic exposure to water-soluble fullerenes using micronucleus test. Environ. Health Prev. Med. 11 292-297. 

Xiao L, Takada H, Maeda K, Haramoto M, Miwa N (2005) Antioxidant effects of water-soluble fullerene derivatives against ultraviolet ray or peroxylipid through their action of scavenging the reactive oxygen species in human skin keratinocytes. Biomed. Pharmacother. 59 351-358. 

Xiao L, Takada H, Gan XH, Miwa N (2006) The water-soluble fullerene derivative Radical Sponge exerts cytoprotective action against UVA irradiation but not visible-light-catalyzed cytotoxicity in human skin keratinocytes. Bioorg. Med. Chem. Lett. 16 1590-1595. 

Yamawaki H, Iwai N (2006) Cytotoxicity of water-soluble fullerene in vascular endothelial cells. Am. J. Physiol. Cell Physiol. 290 1495-1502. 

Antioxidant Properties of Water-Soluble Fullerene Derivatives... 

In this contribution we want to provide a short overview addressing the current state-of-the-art of water-soluble fullerene derivatives and their potential applications as antioxidant or neuroprotective drug candidates. After summarizing the most prominent concepts of designing water-soluble fullerenes in the first chapter we will present some more recent achievements with respect to biological activities of antioxidant fullerenes, with emphasis on our own results. 

The two most commonly used derivatization methods for exohedral functionalization are the nucleophilic cyclopropanation with malonates (Bingel, 1993) and the formation of fulleropyrrolidines (Maggini et al., 1993). Both of these protocols have been used extensively to produce water-soluble fullerenes for biomedical applications. Other stable water-soluble fullerene adducts have also been reported (Hirsch and Brettreich, 2005). Sections 3.2.2-3.2.5 will give a short overview on the state-of-the-art of water-soluble fullerene derivatives and outline some general trends for designing such molecular structures. 

Beside fulleropyrrolidines and malonate adducts, a variety of other water-soluble fullerene derivatives with entirely different addition patterns have been synthesized within the past years (Fig. 3.6). These investigations have enhanced the available... 

Fig. 3.7 Water-soluble fullerene sugar derivative containing a 60 electron 7t-system...

In order to test whether water-soluble fullerenes could be potential agents against the treatment of Parkinson s disease and other CNS degenerative diseases related to neuronal apoptosis, the protective effects of water-soluble fullerene derivatives 1 and 6-8 on 6-hydroxydopamine-induced apoptosis of CNS dopaminergic neurons (Silva et al., 2005) in developing zebrafish were investigated. It was demonstrated that 1,6 and 7 were able to protect 42%, 47% and 23%, respectively of total CNS neurons, whereas 1,6 and 8 blocked each with 60%, 100% and 60% of specific dopaminergic neuronal death in the diencephalon as it is exemplarily shown for 8 in Fig. 3.8. 

Figure 3.10 shows the protection of zebrafish embryo hair cells by various water-soluble fullerene derivatives. The data for both gentamicin- and cisplatinum-induced apoptotic cell death are summarized in Table 3.3. Comparing the data for... 

Foley S, Crowley C, Smaihi M, Bonfils C, Erlanger BF, Seta P, Larroque C (2002) Cellular localisation of a water-soluble fullerene derivative. Biochem. Biophys. Res. Commun. 294 116-119. 

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