Fluorescent probe for distinguishing detection of Cys/Hcy and GSH and preparation method of fluorescent probe
A technology of fluorescent probe and synthesis method, applied in the field of fluorescent probe, can solve the problem of different detection of thiols rarely reported, and achieve the effect of simple synthesis method, convenient operation and good metabolic pathway
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Embodiment 1
[0032] Preparation and characterization of NBD-O-1
[0033] (1) Preparation of Compound 1: In a 100ml round bottom flask, 4-diethylamino salicylaldehyde (1.93g, 10mmol), 6-hydroxyl-1-tetralone (1.62g, 10mmol) and high Chloric acid (3ml) was dissolved in 20mL of acetic acid, and the mixture was refluxed for 1.5 hours. After cooling to room temperature, the solution was poured into a mixture of ethyl acetate (15ml) and petroleum ether (15ml). The precipitate was filtered and washed with ethanol, then dried in vacuo to obtain pure dark purple solid compound 1 (2.88 g, yield: 90%). 1 HNMR (600MHz, DMSO-d 6 )δ11.11(s,1H),8.63(s,1H),8.16(d,J=8.6Hz,1H),7.91(d,J=9.3Hz,1H),7.41(d,J=9.3Hz, 1H), 7.27(s, 1H), 6.95(d, J=8.6Hz, 1H), 6.87(s, 1H), 3.67(q, J=6.9Hz, 4H), 3.01(s, 4H), 1.24( t,J=7.0Hz,6H). 13 C NMR (150MHz, DMSO-d 6 )δ164.73, 164.31, 158.24, 155.23, 148.36, 146.21, 132.03, 129.40, 120.70, 117.99, 117.67, 117.66, 116.16, 96.14, 45.71, 40.52, 26.98, 25.191.zI + calcd for 320...
Embodiment 2
[0036] (1) Prepare 2 mM NBD-O-1 fluorescent probe stock solution with dimethyl sulfoxide (DMSO); prepare 2 mM Cys / Hcy and GSH solutions with distilled water, respectively.
[0037] (2) 2mL CH 3 CN / PBS buffer solution (v / v=2 / 8, pH=7.4) and 10 μL of fluorescent probe stock solution were added to a fluorescent cuvette, and the fluorescence spectrum of the probe was measured on a fluorescence spectrophotometer, and then gradually added in different volumes Cys / Hcy and GSH solution, measured its fluorescence spectrum on a fluorescence spectrophotometer, after adding Cys / Hcy, the probe appeared two new fluorescence emission peaks at 550nm and 625nm, and the fluorescence intensity gradually increased with the addition of Cys / Hcy Until there is basically no change ( Figure 4 Middle (a), (b)); and after adding GSH, the probe only has a new fluorescence emission peak at 625nm ( Figure 4 Middle (c)), so distinguishing detection can be achieved.
[0038] (3) For Cys, take the Cys con...
Embodiment 3
[0040] In different fluorescent cuvettes, add 2mL CH 3 CN / PBS buffer (v / v=2 / 8, pH=7.4) and 10 μL fluorescent probe stock solution, then add Cys / Hcy and GSH respectively to make the final concentrations 50 μM and 20 μM, and 10 equivalents of other amino acids Aqueous solution, including Ala, Asp, Asn, Arg, Gly, Glu, Gln, His, IIe, Leu, Lys, Met, Phe, Pro, Ser, Tyr, Thr, Trp and Val, to make the final concentration of 100μM, and then in Measure the fluorescence spectrum on the fluorescence spectrophotometer, see the measurement results Figure 6 . Experiments have proved that these amino acids do not interfere with the differential detection of Cys / Hcy and GSH by the probe.
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