One-class bi-benzyl pentaMethyl cyanine fluorescent dye as well as preparation method and application thereof
A bisbenzylpentamethine and fluorescent dye technology, applied in the field of bisbenzylpentamethine fluorescent dyes
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Embodiment 1
[0037] The synthesis of embodiment 1. dyestuff I-1:
[0038]
[0039] Accurately weigh 524mg (2mmol) of intermediate II-1, 258mg (1mmol) of condensing agent malondialdehyde aniline hydrochloride (III-1) and mix them into a 10ml single-necked flask. Add 164 mg (2 mmol) of sodium acetate, dissolve in 5 ml of acetic anhydride, heat and stir, and stop heating after reflux for 40 min. After cooling, pour it into a saturated aqueous solution of NaCl, stir and precipitate blue particles. Filter, wash with ether, dry and weigh to obtain 520mg of blue solid, the reaction crude yield is 74%. The product was purified by normal phase silica gel column chromatography (petroleum ether: ethyl acetate = 1:10). The NMR and high-resolution mass spectrometry data of dye I-1 are as follows:
[0040] 1 H NMR(400MHz,DMSO)δ8.35(t,2H,CH=CH),7.66(d,J=7.4Hz,2H,Ar-H),7.56(d,J=7.9Hz,2H,Ar-H ),7.42-7.20(m,12H,Ar-H),7.01(t,J=7.4Hz,2H,Ar-H),6.38(d,J=13.6Hz,3H,CH=CH),5.39(s ,4H,N-CH 2 ),1.73(s,12H,...
Embodiment 2
[0041] Embodiment 2. The synthesis of dyestuff 1-2:
[0042]
[0043] Accurately weigh 524mg (2mmol) of intermediate II-2, 258mg (1mmol) of condensing agent malondialdehyde aniline hydrobromide (III-2) and mix them into a 10ml single-necked flask. Add 164 mg (2 mmol) of sodium acetate, dissolve in 5 ml of acetic anhydride, heat and stir, and stop heating after reflux for 40 min. After cooling, pour it into a saturated aqueous solution of NaCl, stir and precipitate blue particles. Filtered, washed with ether, dried and weighed to obtain 430 mg of blue solid, the reaction crude yield was 70%. The product was purified by normal phase silica gel column chromatography (petroleum ether: ethyl acetate = 1:10). The NMR and high-resolution mass spectrometry data of dye I-1 are as follows:
[0044] 1 H NMR(400MHz,DMSO)δ8.35(t,2H,CH=CH),7.66(d,J=7.4Hz,2H,Ar-H),7.56(d,J=7.9Hz,2H,Ar-H ),7.42-7.20(m,12H,Ar-H),7.01(t,J=7.4Hz,2H,Ar-H),6.38(d,J=13.6Hz,3H,CH=CH),5.39(s ,4H,N-CH 2 ),1....
Embodiment 3
[0045] Example 3. Absorption and emission spectra of dye 1-1 in DMSO and water
[0046] The dye I-1 was dissolved in DMSO and water respectively, and a solution with a final concentration of 5 μM was prepared.
[0047] The test results are attached figure 1 As shown, the maximum absorption of dye I-1 in DMSO is at 654 / 662nm, and the maximum emission spectrum is at 672nm; the maximum absorption and maximum emission spectrum in water are respectively at 647nm and 662nm. The maximum absorption and emission spectra of the visible dye I-1 are both in the near-infrared region. From figure 1 It can also be seen that the absorption and emission intensities of the probe in a hydrophobic environment are greater than those in a water environment, so when the probe interacts with mitochondrial lipids, it will show stronger fluorescence.
[0048] The instruments used are ultraviolet-visible spectrophotometer, model: Hp8453; fluorescence spectrophotometer, model: FP-6500.
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