Synthesis Of C₆₀ Amino-acid Derivatives And Study Of Their Biological Performance

Fullerene is the third allotropic form of carbon besides diamond and graphite, C60 is the representative in the fullerenes. Because of the special structure and properties of C60, it shown great potential of prospective applications in fields of biology, chemistry, materials and nanoscience. According to the molecular design principle, three kinds of the biocompatible fullerene amino-acid derivatives were synthesized by the nucleophilic addition for the first time. They also characterized by FT-IR, 1HNMR, 13C-NMR RF. Meanwhile, by studying the water-solubility of these products, we found these products could easily solve in H2O. We studied their antioxidative and radical scavenging properties, and their protective effects on culturing cells. The studies may provide basic data for finding better antioxidative C60 derivatives. Meanwhile, we also discussed and analyzed influencing factors of these biological properties and structure-activity relationships in order to obtain basic information for designing and synthesizing biologically compatible C60 derivatives.1. C60-L-Phenylalanine Derivatives(FLPD), C60- L-Methionine Derivatives(FLMD) and C60- L-Methionine Derivatives(FLVD) were synthesized by the nucleophilic addition of C60 with amino-acids in toluene/ethanol.. They also characterized by FT-IR, 1HNMR, 13C-NMR, RF.2. The luminol chemiluminescent system for measuring O2-? radical and the o-phenathroline chemiluminescent system for measuring ?OH radical were useed. The biocompatible C60 amino-acid derivatives have obvious scavenging activity against superoxide O2-? generated in chemiluminescence systems and hydroxyl radicals ?OH generated in chemiluminescence systems. The experimentation also showed that the scavenging O2-? and ?OH activity of the biocompatible C60 amino-acid derivatives were with the following sequence: FLPD> FLMD> FLVD. The results showed that the scavenging activity against ROS of biocompatible C60 amino-acid derivatives were associated primarily with the number ofπbond of C60, the steric effect, electronic effect and the scavenging activity of the addition group of the biocompatible C60 amino-acid derivatives.3. The fluorescent probe 2, 7-Dichlorofluorescein diacetate (DCF-DA) was used to monitor the scavenging activity of FLPD,FLMD,FLVD against intracellular ROS by flow cytometry. The protective effect of FLPD,FLMD,FLVD against apoptosis were assessed by MTT, PI stained flow cytometric method and so on. We also used the method of single-cell gel electrophoresis to detection the DNA damage because of H2O2-induced.The results showed that the biocompatible amino acid C60 derivatives had excellent protective effect on PC12 cells injury caused by the accumulation of ROS and the protective effect on PC12 were with the following sequence: FLPD> FLMD> FLVD.