Near-infrared ratio type fluorescent molecular rotor, preparation method thereof and application of near-infrared ratio type fluorescent molecular rotor to detecting intracellular viscosity and protein denaturation
A fluorescent molecular and ratiometric technology, which is applied in fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, can solve the problems of sensitive response to viscosity and protein denaturation, and cannot meet the needs of practical applications, etc., to achieve the preparation method simple effect
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Embodiment 1
[0075] Synthesis and fluorescence properties of embodiment 1 compound I-1
[0076] Such as figure 1 Shown, the synthesis of compound I-1 comprises the following steps:
[0077] 1) Synthesis of Compound 1: Add 20mL of dichloromethane and 20mL of DMF into the bottle under ice bath and stir, then add 17.5mL of phosphorus oxychloride and stir at constant pressure, then add 5.3mL of cyclohexanone, heat to 80°C for 3 hours . After the reaction was complete, the product was poured into crushed ice to quench the reaction, and placed in the refrigerator overnight. The solvent was evaporated under vacuum to obtain the crude compound 1, which was directly used in the next reaction without further purification.
[0078] 2) Synthesis of compound 2: 5 g of 2,3,3-trimethyl-3H-benzindole and 6 g of iodoethane were added to 20 mL of acetonitrile. Heated to 110°C and refluxed for 24 hours. The solvent was evaporated under vacuum, and the resulting solid was washed 3 times with diethyl ethe...
Embodiment 2
[0082] The synthesis of embodiment 2 compound I-2 to I-15
[0083] Compounds I-2 to I-15 can be prepared in a similar manner to Example 1.
[0084] 1. Synthesis of compound I-2
[0085]
[0086] Compound 4 was used to replace compound 2 in Example 1, and the remaining reagents and preparation methods were the same as step 3) in Example 1 to prepare Compound 1-2, 1 H NMR (400MHz, CDCl3): δ (ppm): 8.18 (d, J = 8.0Hz, 1H), 7.96 (d, J = 7.6Hz, 1H), 7.62 (d, J = 7.2Hz, 1H), 7.56 (d,J=12.8Hz,1H),7.39(m,3H),7.30(t,J=7.6Hz,8.0Hz,1H),7.21(d,J=8.8Hz,1H),5.71(d,J =12.8Hz,1H),4.06(q,J=7.2Hz,2H),3.08(m,2H),2.74(m,2H),2.33(m,2H),1.86(s,3H),1.72(s , 3H), 1.61(s, 1H), 1.44(t, J=7.2Hz, 3H), 1.38(s, 3H).
[0087] 2. Synthesis of compound I-3
[0088]
[0089] Compound 5 was used to replace compound 2 in Example 1, and the remaining reagents and preparation methods were the same as step 3) in Example 1 to prepare Compound 1-3, 1 H NMR (400MHz, CDCl3): δ (ppm): 8.18 (d, J = 8.0Hz, 1H)...
Embodiment 3
[0128] The sensitivity of embodiment 3 compound 1-1 to viscosity in different viscosity solutions
[0129] Choose the mixed system of water and glycerin, and prepare solutions with different viscosities according to different mass ratios of water and glycerin. : glycerol = 8:2), 4.62cp (water: glycerin = 7:3), 8.72cp (water: glycerin = 6:4), 19.6cp (water: glycerol = 5:5), 32.8cp (water: glycerin =4:6), 62.5cp (water:glycerin=3:7), 160.1cp (water:glycerol=2:8), 401cp (water:glycerol=1:9), 1150cp (glycerol 100%).
[0130] Taking compound I-1 of the present invention and four cyanine compounds (cyanine) ICG, Cy7-4, Cy7-6, and Cy7-8 as examples, the above compounds were dissolved in DMSO (or organic solvents such as ethanol) Prepare a 2mM storage solution in the medium, and add a small amount of the storage solution into solutions with different viscosities to prepare a 10μM working solution. Take 2mL and add it into a quartz cuvette, and measure the ultraviolet absorption spec...
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