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Zinc ion proportion photoacoustic probes with mitochondrion-targeting function and application of probes

A proportional, anionic technology, applied in the field of biosensing, can solve problems such as increased memory and thinking skills, backward brain development and maturation, incomplete development of gender characteristics, etc., to achieve good biocompatibility, deep tissue penetration depth, Simple preparation method

Active Publication Date: 2020-02-18
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Numerous studies have shown that Zn in vivo 2+ The deficiency will lead to a series of diseases: Zn 2+ Promote the growth and tissue regeneration of the body, Zn in male adolescents 2+ Deletion will lead to short stature and incomplete development of sex characteristics; in addition, Zn 2+ Has important physiological effects on brain development and function. Zinc is involved in the process of sending signals to the central nervous system, increasing memory and thinking skills. Zinc deficiency can lead to delayed brain development and maturation

Method used

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  • Zinc ion proportion photoacoustic probes with mitochondrion-targeting function and application of probes
  • Zinc ion proportion photoacoustic probes with mitochondrion-targeting function and application of probes
  • Zinc ion proportion photoacoustic probes with mitochondrion-targeting function and application of probes

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the preparation of compound 1

[0033]

[0034] 2, 4-dihydroxybenzaldehyde (10mmol), lutidine amine (10mmol) and sodium triacetoxyborohydride (20mmol) were dissolved in 100mL dichloroethane (DCE), ice bath and Ar atmosphere conditions After 24 hours of reaction, add 100mLNaHCO 3 Quench the reaction, extract 3 times with dichloromethane, use 50mL each time, collect the organic phase, Na 2 SO 4 Drying, spinning the solvent to obtain a yellow solid, carrying out column chromatography, methanol: dichloromethane (CH 2 Cl 2 )=50:1(v / v), after passing the crude product, use CH 2 Cl 2 Recrystallized with methanol, the final white product compound 1, yield: 31%. 1 H NMR (400 MHz, DMSO-d 6 )δ10.38(s,1H),9.13(s,1H),8.51(ddd,J=4.9,1.8,0.9Hz,2H),7.85–7.70(m, 2H),7.42(dt,J=7.9, 1.1Hz, 2H), 7.26(ddd, J=7.6, 4.8, 1.1Hz, 2H), 6.94(d, J=8.1Hz, 1H), 6.21(d, J=2.4Hz, 1H), 6.19-6.14( m,J=8.1Hz,1H),3.75(s,4H),3.57(s,2H). 13 C NMR (101 MHz, DMSO-d 6 )δ 159.00, 158....

Embodiment 2

[0035] Example 2: Preparation of photoacoustic probe HD-Zn

[0036] In a dry round bottom flask, add compound 1 (1 mmol), K 2 CO 3 (1mmol) and anhydrous DMF (3ml), the mixture was stirred at room temperature under nitrogen protection for 30min, and then the starting material compound 2 (0.5 mmol dissolved in 5ml anhydrous DMF) was injected by syringe. The reaction mixture was heated to 70° C. for 3 hours under nitrogen protection, the solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (CH 2 Cl 2 / methanol=50:1, v / v) separation to obtain the blue-green target product HD-Zn with a yield of 52.6%. 1 HNMR (400MHz, Methanol-d 4 )δ8.61(d, J=14.7Hz, 1H), 8.40(d, J=4.8Hz, 2H), 7.67(td, J=7.7, 1.7Hz, 2H), 7.55(d, J=7.3Hz, 1H),7.48–7.28(m,7H),7.19 (dd,J=7.4,5.0Hz,2H),6.78(s,1H),6.34(d,J=14.7Hz,1H),4.20(t,J =7.3Hz, 2H), 3.80(d, J =18.7Hz, 6H), 2.72-2.55(m, 2H), 1.83(t, J=7.1Hz, 4H), 1.71(s, 6H), 0.98(t ,J=7.3Hz, 3H). 1...

Embodiment 3

[0037] Embodiment 3: the emission spectrum test of HD-Zn

[0038] The spectral test concentration that the present invention adopts is 5 μ M, and test solvent is the HEPES solution (50 mM, 100 mM KNO) mixed with 1% DMSO 3 , pH7.4), when measuring the emission spectrum, the excitation wavelength is 633nm. Zn 2+ The solution is ZnCl 2 Soluble in water preparation.

[0039] The emission spectrum of HD-Zn is as figure 1 shown. When adding 1 equivalent of Zn 2+ After that, the fluorescence is enhanced by about 1 / 3 times, and the wavelength is also blue-shifted; it shows that the probe HD-Zn has a positive effect on Zn in the fluorescence spectrum. 2+ The response is not obvious.

[0040] Embodiment 3: Absorption spectrum test and detection limit calculation of HD-Zn

[0041] The absorption spectrum test concentration that the present invention adopts is 5 μ M, and test solvent is the HEPES solution (50mM, 50mM KNO) that is mixed with 1%DMSO 3 ,pH7.4), such as figure 2 As...

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Abstract

The invention discloses zinc ion proportion photoacoustic probes with a mitochondrion-targeting function. The probes have a structural formula shown in the description, or the probes provided by the invention can be excited by visible light, have red light emission, can reduce the damage of a biological sample by an excitation light source, and have a deeper tissue penetration depth. In-vitro andin-vivo photoacoustic imaging experiments show that the probes provided by the invention have good photoacoustic imaging performance for Zn<2+>, can be applied to biological imaging, mitochondrial labeling and Zn<2+> photoacoustic imaging, have a simple chemical mechanism and good biocompatibility, and have good application prospects.

Description

technical field [0001] The invention belongs to the technical field of biosensing. It specifically relates to a class of xanthene derivatives that can be used as Zn with mitochondrial targeting function 2+ Ratiometric photoacoustic probes are used in the fields of cell imaging, mitochondrial labeling, and photoacoustic imaging. Background technique [0002] In recent years, photoacoustic imaging, as a new imaging modality, has attracted more and more attention. Photoacoustic imaging combines the advantages of optical imaging and ultrasound imaging. On the one hand, it penetrates deeper than pure optical imaging (can break through laser confocal microscopy (LCSM), two-photon excitation microscopy (TPEF), optical weak coherence High-resolution optical imaging such as tomography (OCT) has a "soft" limit (~1mm); on the other hand, it has a higher resolution than traditional MRI and PET imaging; its image resolution can reach submicron, micron order of magnitude, which can ach...

Claims

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Application Information

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IPC IPC(8): C07D405/14C09K11/06G01N21/64A61K49/22
CPCC07D405/14C09K11/06G01N21/6428A61K49/22C09K2211/1029C09K2211/1088
Inventor 何卫江郭子建方红宝
Owner NANJING UNIV
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