A kind of selenocysteine near-infrared fluorescent probe and its preparation method and application
A technology of selenocysteine and fluorescent probe, which is applied in the field of fluorescent probe for detecting selenocysteine in vivo and its preparation, can solve problems such as lack of detection, and achieve fast response, good selectivity and fluorescent signal stable effect
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[0072] 1. Materials and instruments
[0073] GIBCO DMEM high glucose medium (life technologies, USA); GIBCO fetal bovine serum (life technologies, USA); Penicillin Streptomycin Solution (100) ×) (Shanghai biyuntian Biotechnology Co., Ltd.); Phosphate buffer (PBS) (Beijing Zhongshan Jinqiao Biotechnology Co., Ltd.); Anhydrous sodium selenite (NA) 2 SeO 3 )(sanen Chemical Technology (Shanghai) Co., Ltd.); N - (4-formylphenyl) acetamide (Shanghai bide Pharmaceutical Technology Co., Ltd.); 2,4-dinitrobenzenesulfonyl (Shanghai TITAN Technology Co., Ltd.); Other reagents are domestic analytical pure.
[0074] Cells:
[0075] (1) Species and strain: human breast cancer MCF-7. Source: Cell Bank of Chinese Academy of Sciences.
[0076] Laboratory animals:
[0077] (2) Species and strains: healthy male Kunming mice, weighing 20-25g. Source: experimental animal center of Xuzhou Medical University.
[0078] (3) Species and strains: healthy female BALB / C nude (SPF grade), 5-6 weeks old. Source...
Embodiment 1
[0118] Preparation of compound II: freshly distilled cyclohexanone (508) μ 50. 4.9 mmol) dropwise added to concentrated H 2 SO 4 (6.7ml, 125.0mmol) and cooled to 0 ℃, then 4 - (diethylamino) - 2-hydroxybenzaldehyde (500mg, 2.6mmol) was added and stirred vigorously at 90 ℃ for 1.5h. After the reaction, cool and pour into ice water. Then add perchloric acid (620 μ 50. 10.8mmol) until red precipitates are precipitated, and cold water (40ml) is used × 3) Wash and dry. 600mg red solid was obtained with a yield of 65%. TLC(silica,DCM:MeOH,20:1v / v):R f =0.55.
Embodiment 2
[0120] NIR-MNH 2 Preparation: compound II (100mg, 0.28mmol) and N - (4-formylphenyl) acetamide (91.3mg, 0.56mmol) were dissolved in ethanol (20ml), and then piperidine (2.8) was added μ L,0.03mmol)。 The reaction mixture was heated to 85 ℃ for 12h. After the reaction, the solvent was removed by vacuum distillation. Reflux in the mixed solution of ethanol and hydrochloric acid (15ml, 2:1v / V) for 2h, and remove ethanol and Na under reduced pressure 2 CO 3 Adjust pH to neutral and precipitate dark green solid. The crude product was purified by silica gel column chromatography (silica, DCM: MeOH, 100:1v / V) to obtain 40 mg of blue-green solid with a yield of 40%. TLC(silica,DCM:MeOH,20:1v / v):R f =0.45; 1 H NMR(400MHz,DMSO-d 6 ): δ 8.36(s,1H),8.07(s,1H),7.82(d,J=9.6Hz,1H),7.56(d,J=8.8Hz,2H),7.33(dd,J=9.2,2.4Hz,1H),7.22(d,J=2.0Hz,1H),6.71(d,J=8.8Hz,2H),6.51(s,2H),3.64-3.69(m,4H),2.93(t,J=5.6Hz,2H),2.84(t,J=5.6Hz,2H),1.87(t,J=6.0Hz,2H),1.25(t,J=6.8Hz,6H); HRMS(ESI + ):(M) + calcd. forC...
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