Conjugated c (RGDfC) sulfur-nitrogen double-doped graphene quantum dot as well as preparation method and application thereof
A graphene quantum dot and double doping technology, applied in the field of quantum dots, can solve the problems of not being able to actively target tumor cells, not having tumor targeting, and not being able to overcome resistance, etc., achieving good biocompatibility, synthetic The method is simple and easy to operate
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[0072] (1) Preparation of polythiophene analog PT2:
[0073] The preparation route is as follows:
[0074]
[0075] 4-Bromobenzyl bromide (0.25 g, 1 mmol) was dissolved in 20 mL CH 2 Cl 2 / CH 3 OH (v / v=3 / 2) mixed solution, then added N,N-dimethyldodecylamine (0.4mL, 1.3mmol), stirred at room temperature for 12h. The reaction solution was concentrated to 5 mL, poured into 200 mL of anhydrous ether, filtered, washed and dried to obtain compound 1. Compound 1 (0.4g), Na 2 CO 3 (0.5g), Pd(PPh 3 ) 4 (200 mg) and thiophene-3-boronic acid (0.128 g) were dissolved in ethanol (20 mL), and 10 mL of double-distilled water was added under nitrogen protection, refluxed at 90° C. for 6 hours, and ethanol was removed under reduced pressure. CH 2 Cl 2 (3×20mL) extract the residue, collect the organic layer with anhydrous MgSO 4 After drying and column purification, compound 2 was obtained. Under nitrogen protection, 4 equivalents of FeCl 3 Dissolve in 30 mL anhydrous CHCl 3 i...
Embodiment 1
[0079] Embodiment 1, preparation of conjugated c(RGDfC) sulfur nitrogen double-doped graphene quantum dots of the present invention
[0080] (1) Take 50 μl concentration of 20 μM sulfur and nitrogen double-doped graphene quantum dot aqueous solution (prepared with double distilled water), place it in 750 μl double distilled water, then add 100 μl concentration of 40 mM EDC / NHS mixture aqueous solution (EDC and NHS The mass ratio is 2:1, prepared by double-distilled water) to react at 25°C for 20min.
[0081] (2) Add 100 μl of 1 mM c(RGDfC) aqueous solution (prepared with double distilled water) to the above reaction solution, keep at 4° C., and react for 2 h.
[0082] (3) Transfer the reactant to a 10kDa ultrafiltration tube, centrifuge at 4°C and 8000g centrifugal force for 6min, remove the filtrate, and obtain sulfur-nitrogen double-doped graphene quantum dots conjugated with c(RGDfC).
Embodiment 2
[0083] Embodiment 2, preparation of conjugated c(RGDfC) sulfur nitrogen double-doped graphene quantum dots of the present invention
[0084] (1) Take 50 μl concentration of 20 μM sulfur and nitrogen double-doped graphene quantum dot aqueous solution (prepared with double distilled water), place it in 750 μl double distilled water, then add 100 μl concentration of 40 mM EDC / NHS mixture aqueous solution (EDC and NHS The mass ratio is 2:1, prepared by double distilled water) to react at 25°C for 10min.
[0085] (2) Add 100 μl of 1 mM c(RGDfC) aqueous solution (prepared with double distilled water) to the above reaction solution, keep at 4° C., and react for 4 hours.
[0086] (3) Transfer the reactant to a 10kDa ultrafiltration tube, centrifuge at 4°C and 8000g centrifugal force for 6min, remove the filtrate, and obtain sulfur-nitrogen double-doped graphene quantum dots conjugated with c(RGDfC).
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