Amino fullerene material for inhibiting tumor metastasis
A technology of aminofullerene and tumor metastasis, applied in the field of aminofullerene materials, can solve the problems of no aminated fullerene derivatives, difficult detection and determination of modified hydroxyl groups, etc., and achieve stable and controllable preparation and excellent water solubility , Molecular biology target clear effect
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Embodiment 1
[0100] Embodiment 1: Preparation of aminofullerene molecules
[0101] Synthesis method: 5g C 60 Dissolve in 625mL chlorobenzene, add 13g 4-(tert-butoxycarbonylamino)piperidine and 5mL cumene hydroperoxide (80%), stir at room temperature (600rpm) for 48h, dilute the reaction solution 10 times and perform HPLC detection , the reaction was complete, the reaction was stopped, the reaction solution was washed with 300mL saturated ammonium chloride solution and 300mL saturated sodium bicarbonate solution successively, the organic layer was dried over anhydrous sodium sulfate, concentrated and evaporated to dryness at 60°C to obtain a reddish-brown solid.
[0102] After the reaction product was dissolved in toluene, it was separated by column chromatography, and the eluent was ethyl acetate / toluene 10%, 12%, 15%, 20%. Tri-addition and tetra-addition aminofullerene samples protected by tert-butoxycarbonyl were isolated.
[0103] Add 375mL TFA / CHCl to 1g of the separated aminofullere...
Embodiment 2
[0106] Embodiment 2: Preparation of aminofullerene mixture C 70 -EDA
[0107] Synthesis method: Ammonia molecules can undergo nucleophilic addition reaction with fullerene carbon cage through its amino group. This reaction is an endothermic process, and the reaction temperature is a key factor affecting the reaction product. 100mL C 70 O-xylene solution (2mg / mL) was added dropwise to EDA (100mL), under N 2 Stir under protection at different temperatures (including 50°C, 100°C and 130°C). Until the solution turns reddish brown, excess EDA and solvent are removed by rotary evaporation. The crude product was then further reacted with EDA (100 mL) at room temperature under nitrogen for 12 hours; the EDA was removed and the final product was dissolved with hydrochloric acid (1 mM) and purified by dialysis against ultrapure water for two days. Various EDA-modified C 70 Hydrochloride (abbreviated as C 70 -EDA) freeze-dried into powder. Characterization of C by elemental analys...
Embodiment 3
[0112] Embodiment 3: Preparation of other aminofullerene derivatives
[0113] 1. by C 60 Preparation of Aminofullerene Derivatives from Fullerene
[0114] 5g C 60 Dissolved in chlorobenzene, add 10 times in C 60 A molar amount of tert-butoxycarbonyl-protected amines (add 5mL cumene hydroperoxide (80%)), anilines or bromoanilines, stir at room temperature for 48h, take the reaction solution and dilute it by 10 times and carry out HPLC detection, the reaction After completion, the reaction solution was washed successively with saturated ammonium chloride solution and saturated sodium bicarbonate solution, the organic layer was dried over anhydrous sodium sulfate, concentrated and evaporated to dryness at 60°C to obtain the reaction product.
[0115] After the reaction product was dissolved in toluene, it was separated by column chromatography, and the eluent was ethyl acetate / toluene solution in different proportions. Aminofullerenes with different addition numbers protected...
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