Hypochlorous acid fluorescence ratio probe and application thereof

A fluorescent ratio probe and fluorescent probe technology, applied in the field of organic small molecule fluorescent probes, can solve the problems of hypochlorous acid fluorescent ratio probe blank and other problems, and achieve the effect of broad application prospects.

Inactive Publication Date: 2015-11-04
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although there are many reports on the ratiometric probes of hypochlorous acid, the fluorescent ratio probes of hypochlorous acid based on the mechanism of TBET are still blank so far.

Method used

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  • Hypochlorous acid fluorescence ratio probe and application thereof
  • Hypochlorous acid fluorescence ratio probe and application thereof
  • Hypochlorous acid fluorescence ratio probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Dissolve 6-dimethylamino-2-naphthoyl chloride (0.25mmol) and rhodamine B thiohydrazide (0.25mmol) in 5ml of dry pyridine, under nitrogen protection, stir at room temperature for 2h, then stir under reflux 6 hours. The reaction solvent was distilled off under reduced pressure, and the crude product was purified by column chromatography to obtain a light yellow solid, 50.6 mg, yield: 30.2%.

[0025] structure confirmation spectral data, 1 H NMR(300MHz,DMSO)δ10.60(s,1H),8.09(s,1H),8.01(d,J=6.6Hz,1H),7.74(d,J=9.1Hz,1H),7.68–7.48 (m,4H),7.24(dd,J=9.1,2.3Hz,1H),7.13(d,J=6.5Hz,1H),6.91(d,J=1.9Hz,1H),6.49(d,J= 8.7Hz, 2H), 6.34(m, 4H), 3.33(s, 8H), 3.03(s, 6H), 1.07(t, J=6.9Hz, 12H). 13 C NMR(75MHz,DMSO)δ164.53,153.15,149.51,148.55,136.31,135.86,132.92,129.73,129.65,128.74,128.20,125.34,125.11,124.74,124.35,123.74,116.50,107.60,104.81,103.33,96.99,63.45 ,59.71,43.60,12.40.HRMS:m / z[M+H] + calcd for C 41 h 44 N 5 o 2 S:670.3216,found:670.3261; m / z[M+2H] 2+ calcd for C 4...

Embodiment 2

[0029] Add 10 equivalents of t-BuOOH, t-BuOO, H 2 o 2 ,HO·,NO,NOOO - , 1 o 2 , - o 2 , and 1 equivalent of HOCl. Fluorescence test was performed after 1 h of action.

[0030] The results showed that the probe had a better response only to HOCl and a higher selectivity to hypochlorous acid than other reactive oxygen species. See figure 2 , 3.

Embodiment 3

[0032] Intracellular fluorescence imaging test:

[0033] After the RAW264.7 cells were transferred to a small glass bottle and incubated for 24 hours, one group was incubated with 10 μM of the probe for 4 hours, and then washed three times with PBS for confocal cell imaging detection. The other group used 1 μg mL -1The LPS was incubated for 12h, then washed three times with PBS, then incubated with 10μM of the probe for 4h, then washed three times with PBS for confocal cell imaging detection. The excitation wavelength used is 405nm, the collection wavelength of the blue channel is 405-550nm, and the collection wavelength of the red channel is 550-650nm. See Figure 4 .

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Abstract

The present invention discloses a TBET mechanism based hypochlorous acid fluorescence ratio probe, and the hypochlorous acid fluorescence ratio probe is a mono-thio bi-hydrazide core structure organic small molecule compound which is formed by connection of Rhodamine B thio-hydrazide and 6-dimethylamino-2-naphthoyl, and has the chemical structural formula of formula (I). The TBET mechanism based hypochlorous acid fluorescence ratio probe can selectively effect with hypochlorous acid, with increasing of concentration of the hypochlorous acid, the fluorescence emission intensity at 585nm gradually increases, and gradually weakens at 440nm; and the relation of the ratio (I585 / I440) and hypochlorous acid concentration in a certain range is linear. Intracellular ratio imaging can be achieved, and the TBET mechanism based hypochlorous acid fluorescence ratio probe is expected to play a role in industrial production and clinical medicine, and has broad application prospects.

Description

technical field [0001] The invention relates to a fluorescent ratio probe and its application, in particular to a hypochlorous acid fluorescent ratio probe based on a TBET (through bond energy transfer) mechanism and its application; it belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Hypochlorous acid is one of the most important reactive oxygen species in living organisms. It is catalyzed by hydrogen peroxide and chloride ions in living organisms through myeloperoxidase [A. Hammer et al, Lab. Invest., 2001, 81, 543]. On the one hand, hypochlorous acid as an endogenous bactericide plays an important role in resisting bacterial invasion [Z.M.Prokopowicz et al, Immunol., 2010, 184, 824]; on the other hand, the uncontrolled production of hypochlorous acid is associated with certain diseases Related, such as: arthritis, kidney disease, lung injury, arteriosclerosis, and tumors [R.Rao et al, Front. Biosci., 2008, 13, 7210; D.I. Pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1011C09K2211/1029C09K2211/1088G01N21/6428G01N21/6486
Inventor 赵宝祥苗俊英张延如孟宁
Owner SHANDONG UNIV
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