Anti-aggregation-caused-quenching functional heptamethine cyanine dye based on click activation large steric hindrance as well as preparation method and application thereof
An alkyl and aryl technology, applied in biomedical imaging, anti-aggregation and quenching heptamethasone functional cyanine dye and its preparation field, can solve the problem of low background signal-to-noise ratio, improve detection sensitivity, Fast and sensitive response ability, increase the effect of fluorescent signal
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Embodiment 1
[0068] The synthetic route of diethylene glycol bromoethyl methyl ether parent dye CyBI7P:
[0069]
[0070] 1.1 Synthesis of diethylene glycol bromoethyl methyl ether benzindole quaternary ammonium salt:
[0071] Dissolve 0.611g of 1,1,2-trimethyl 1[H]benzindole, 0.917g of diethylene glycol-2-bromoethyl methyl ether in 10ml of acetonitrile, and react the mixture in a reaction kettle at 80°C for 36 hours , standing to cool, then poured into ether for washing, filtered, and recrystallized from methanol to obtain 0.96 g of diethylene glycol bromoethyl methyl ether benzindole bromide quaternary ammonium salt, with a yield of 80%.
[0072] 1.2 Synthesis of condensing agent 2-chloro-1-formyl-3-hydroxymethinecyclohexene:
[0073] 18ml POCl 3 Add 17ml of dry dichloromethane solution and mix for later use. Add 40ml of dry dichloromethane and 40ml of dry DMF in turn to a 250mL round bottom flask and mix well. Under ice bath conditions, the mixed POCl 3 The dichloromethane solut...
Embodiment 2
[0077] Synthesis of CyP-Tz, a functionalized Anti-ACQ heptamethine cyanine dye with click activation:
[0078]
[0079] The parent dye CyBI7P prepared in Example 1 was pre-dried in a vacuum oven at 40° C. overnight. Add dry 0.5g CyBI7P and 0.51g Tz in turn to a 100ml round bottom flask, add 15ml anhydrous DMF to dissolve. After stirring for 1.5 h at 80°C under the protection of nitrogen, the reaction solution was quenched by pouring into ice water, and a blue solid was precipitated by filtration, separated by column chromatography (methanol:dichloromethane=1:50v / v), and concentrated with petroleum ether to precipitate a solid , vacuum dried overnight to obtain the blue dye CyP-Tz 0.3g, yield 50.92%. The product structure is identified by high resolution. Calculated value: 1012.5701, Tested value: 1012.5843. Mass spectrometry results such as figure 1 Shown in (b).
Embodiment 3
[0081] The spectral characteristics of the click-activated mid-position-substituted functionalized Anti-ACQ heptamethine cyanine dye CyP-Tz, the parent dye CyBI7P, and the commercial heptamethine cyanine dye ICG (CAS: 3599-32-4):
[0082] Accurately weigh 5 mg of CyP-Tz solid with a balance, dissolve it in 1 ml of dimethyl sulfoxide (DMSO) to prepare a mother solution with a concentration of 4.58 mM; then take the mother solution and dilute it in methanol to obtain a test solution. The absorption intensity and fluorescence emission intensity of CyP-Tz were measured by UV spectrophotometer and Edinburgh 1000 fluorescence spectrometer. The molar absorptivity of the compounds was calculated using the Lambert-Beer law. The calculation formula is A=εcb, where A represents the absorption intensity, ε represents the molar extinction coefficient, c is the concentration of the compound (in mol / L), and b is the thickness of the quartz cell (in cm). The test result shows that the UV abs...
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