Fluorescent probe for anticancer platinum prodrug reduction activation as well as preparation method and application thereof
A fluorescent probe and prodrug technology, applied in the field of biochemistry, can solve the problems of different cisplatin and changing the uptake characteristics of pharmacophore
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Embodiment 1
[0035] A preparation method of a fluorescent probe capable of detecting platinum (II) (cisplatin), the synthetic route is as follows figure 1 As shown, it specifically includes the following steps:
[0036] (1) In a two-necked round-bottomed flask equipped with magnets, add rhodamine 6G 0.480 g, 1.0 mmol, hydroxylamine hydrochloride 0.140 g, 2.0 mmol, potassium carbonate 0.276 g, 2.0 mmol and DMF 3.0 mL. 25 o C for 12 h. The reaction mixture was poured into saturated brine, the solid was collected by filtration, and dried to obtain the crude rhodamine 6G hydroxamic acid, which was then separated by column chromatography, methanol / ethyl acetate=1:4, v / v, R f =0.6, rhodamine 6G hydroxamic acid was obtained, and the productive rate was 95.0%.
[0037] (2) Dissolve 220 mg, 0.48 mmol of rhodamine 6G hydroxamic acid in 2 mL of DMF, and add 671 μL, 4.81 mmol of triethylamine and 829 μL, 9.62 mmol of 1,2-dibromoethane. The reaction mixture was heated at 60 o C under reflux for 4 ...
Embodiment 2
[0040] A method for preparing a fluorescent probe capable of detecting platinum (II) (cisplatin), using DMSO as a solvent to synthesize a fluorescent molecular probe (1), comprising the following steps:
[0041] (1) In a two-necked round-bottomed flask equipped with magnets, add rhodamine 6G 0.480 g, 1.0 mmol, hydroxylamine hydrochloride 0.140 g, 2.0 mmol, potassium carbonate 0.276 g, 2.0 mmol, and DMSO 3.0 mL. 25 o C was reacted for 11 h. The reaction mixture was poured into saturated brine, the solid was collected by filtration, and dried to obtain the crude rhodamine 6G hydroxamic acid, which was then separated by column chromatography, methanol / ethyl acetate=1:4, v / v, R f =0.6, rhodamine 6G hydroxamic acid was obtained, and the yield was 94.5%.
[0042] (2) Dissolve 220 mg, 0.48 mmol of rhodamine 6G hydroxamic acid in 2 mL of DMSO, and add 1004 μL of triethylamine, 7.20 mmol and 1034 μL, 12 mmol of 1,2-dibromoethane. The reaction mixture was heated at 80 o C under refl...
Embodiment 3
[0045] A method for preparing a fluorescent probe capable of detecting platinum (II) (cisplatin), using DMA as a solvent to synthesize a fluorescent molecular probe (1), comprising the following steps:
[0046] (1) In a two-necked round-bottomed flask equipped with magnets, add rhodamine 6G 0.480 g, 1.0 mmol, hydroxylamine hydrochloride 0.140 g, 2.0 mmol, potassium carbonate 0.276 g, 2.0 mmol, and DMA 3.0 mL. 25 o C for 10 h. The reaction mixture was poured into saturated brine, the solid was collected by filtration, and dried to obtain the crude rhodamine 6G hydroxamic acid, which was then separated by column chromatography, methanol / ethyl acetate=1:4, v / v, R f =0.6, rhodamine 6G hydroxamic acid was obtained, and the yield was 93.7%.
[0047] (2) Dissolve 220 mg, 0.48 mmol of rhodamine 6G hydroxamic acid in DMA 2 mL, and add 468 μL, 3.36 mmol of triethylamine and 620 μL, 7.20 mmol of 1,2-dibromoethane. The reaction mixture was heated at 70 o C under reflux for 5 h. The s...
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