Fluorescent probe and preparation and application methods thereof
A technology of fluorescent probes and fluorescent dyes, which is applied in the fields of sulfonate preparation, fluorescence/phosphorescence, chemical instruments and methods, etc. It can solve the problems of low fluorescence quantum yield, the method cannot be used as a qualified fluorescent protein label, and the fluorescence brightness is not high.
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Embodiment 1
[0151] Using molecular rotors as viscosity-responsive fluorescent dyes to construct fluorescently activated covalently labeled probes suitable for HaloTag protein tags 1:
[0152]
[0153] Compound 1:
[0154] N-methyl-N-(2-hydroxyethyl)-4-aminobenzaldehyde (0.358g, 2mmol) and tert-butyl cyanoacetate (0.338g, 2.4mmol) were dissolved in 50ml of absolute ethanol, and the catalytic Measure anhydrous zinc chloride, heat in an oil bath for 5 hours under the protection of Ar, after the reaction is completed, cool to room temperature, remove part of the solvent by rotary evaporation, a large amount of solids are precipitated in the system, filter, wash the filter cake twice with cold ethanol, and dry in vacuum , to obtain yellow compound 1 (0.49 g, 81%). 1 H-NMR (400MHz, DMSO-d 6 ): δ=8.01(s, 1H), 7.97(d, 2H, J=9.2Hz), 6.85(d, 2H, J=9.2Hz), 4.79(bt, 1H), 3.59-3.55(m, 4H) , 3.08(s, 3H), 1.50(s, 9H).
[0155] Compound 2:
[0156] The synthetic method is synthesized with referen...
Embodiment 2
[0160] Using molecular rotors as viscosity-responsive fluorescent dyes to construct fluorescently activated covalently labeled probes suitable for HaloTag protein tags 2:
[0161]
[0162] Compound 3:
[0163] The synthesis method is synthesized by referring to the method disclosed in the document J. Das et. al. Bioorg. Med. Chem. Lett. 2005, 15, 337-343. 1 H-NMR (400MHz, CDCl 3 ): δ=7.74(d, 1H, J=4.0Hz), 7.55(d, 1H, J=4.0Hz), 7.36-7.42(m, 2H), 4.12(s, 2H).
[0164] Synthesis of compound 4:
[0165] Refer to the synthesis method of compound 1. 1 H-NMR (400MHz, DMSO-d 6 ): δ=8.11—8.07 (m, 2H), 8.01—7.97 (m, 3H), 7.70 (d, 1H, J=8.8Hz), 7.46—7.43 (m, 1H), 6.27 (dd, 1H, J =9.2, 1.6Hz), 6.02(s, 1H), 3.88(t, 2H, J=5.6Hz), 3.64(t, 2H, J=5.6Hz), 3.15(s, 3H).
[0166] Probe 2:
[0167] Referring to the synthesis method of probe 1, the yield was 75%. 1 H-NMR (400MHz, DMSO-d 6 ): δ=8.18(t, 1H), 8.11—8.07(m, 2H), 8.01—7.97(m, 2H), 7.70(d, 1H, J=8.8Hz), 7.46—7.43(m, 1H), 6.27(...
Embodiment 3
[0169] Using the molecular rotor as a viscosity-responsive fluorescent dye to construct a fluorescence-activated covalently labeled fluorescent probe suitable for HaloTag protein labeling3:
[0170]
[0171] Compound 5:
[0172] It was synthesized according to the synthetic method of compound 1, and the yield was 95%. 1 H-NMR (400MHz, CDCl 3 ): δ=8.09(s, 1H), 8.02(d, 1H, J=8.0Hz), 7.98(d, 2H, J=9.2Hz), 7.86(d, 1H, J=8.4Hz), 7.48(t , 1H, J=7.8Hz), 7.36(t, 1H, J=7.36Hz), 6.73(d, 2H, J=9.2Hz), 3.88(t, 2H, J=5.6Hz), 3.64(t, 2H , J=5.6Hz), 3.15 (s, 3H).
[0173] Probe 3:
[0174] It was synthesized according to the synthesis method of probe 1, and the yield was 65%. 1 H-NMR (400MHz, DMSO-d 6): δ=8.18(t, 1H), 8.02(d, 1H, J=8.0Hz), 7.98(d, 2H, J=9.2Hz), 7.86(d, 1H, J=8.4Hz), 7.48(t , 1H, J=7.8Hz), 7.36(t, 1H, J=7.36Hz), 6.73(d, 2H, J=9.2Hz), 3.88(t, 2H, J=5.6Hz), 3.69(t, J =4.9Hz, 2H), 3.64(t, 2H, J=5.6Hz), 3.63-3.60(m, 2H), 3.56-3.53(m, 2H), 3.52(t, J=6.6Hz, 2H), 3.44 (t...
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