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Photoacoustic ratiometric nanoprobe for detection of hydrogen sulfide in vivo, preparation method and application thereof

A technology of living body detection and nano-probe, applied in the field of tumor marker detection and imaging

Inactive Publication Date: 2019-10-22
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the most commonly used methods for detection and imaging of hydrogen sulfide are the methylene blue method and the sulfur ion selective electrode detection method. Their disadvantages are that both are destructive and require homogenization of samples. For the study of more detailed physiological functions of hydrogen sulfide , new detection methods are needed With the rapid development of non-destructive detection technologies such as fluorescent imaging fluorescent probes, many novel detection methods have emerged [a) Li, H.D.; Yao, Q.C.; Fan, J.L.; Jiang, N. ; Wang, J.Y.; Xia, J.; Peng, X.J.Chem.Commun.2015, 51, 16225-16228.b) C.Liu, J.Pan, S.Li, Y.Zhao, L.Y.Wu, C.E.Berkman, A.R. Whorton and M.Xian, Angew.Chem., IntEd., 2011, 50, 10327–10329c) H.Peng, Y.Cheng, C.Dai, A.L.King, B.L.Predmore, D.J.Lefer and B.Wang, Angew.Chem ., Int. Ed., 2011, 50, 9672–9675d) K. Sasakura, K. Hanaoka, N. Shibuya, Y. Mikami, Y. Kimura, T. Komatsu, T. Ueno, T. Terai, H. Kimura and T. Nagano, J. Am. Chem. Soc. 2011, 133, 18003–18005]
[0004] The main disadvantage of this type of method is that in live detection, the scattering of ultrasonic signals by biological tissues to physiological tissues of the human body is 3 to 4 orders of magnitude lower than that of general optical signals, which means that photoacoustic imaging can provide deeper imaging depth and higher imaging resolution

Method used

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  • Photoacoustic ratiometric nanoprobe for detection of hydrogen sulfide in vivo, preparation method and application thereof
  • Photoacoustic ratiometric nanoprobe for detection of hydrogen sulfide in vivo, preparation method and application thereof
  • Photoacoustic ratiometric nanoprobe for detection of hydrogen sulfide in vivo, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Example 1: Preparation of a photoacoustic ratiometric probe for in vivo detection of hydrogen sulfide in tumors.

[0094] 1. The specific synthesis steps of a photoacoustic ratio probe for in vivo detection of hydrogen sulfide in tumors provided by the present invention are as follows: figure 1 shown, as follows:

[0095] (1) Preparation of ① I precursor: m-aminophenol (436 mg, 4 mmol) was dissolved in 13 ml of absolute ethanol, tert-butyl dicarbonate (1.3 g, 6 mmol) was dissolved in 5 ml of absolute ethanol, added dropwise, stirred for 5 minutes, refluxed at 80 °C for 5 h, and the solution was concentrated in vacuo to give A as a white solid.

[0096] ② The white solid A (81.9 mg, 0.39 mmol) and sodium hydride (9.36 mg, 0.39 mmol) were added to a round-bottomed flask containing 2 ml of DMF (N,N-dimethylformamide), and the mixture was stirred at room temperature under nitrogen protection For 10 min, Cy7-Cl (100 mg, 0.156 mmol) was dissolved in 1 ml of DMF and added to...

Embodiment 2

[0117] Example 2: Absorption and fluorescence spectra before and after the reaction of probe I with sodium hydrosulfide.

[0118] The probe I solution and the sodium hydrosulfide aqueous solution obtained in Example 1 were prepared, and then the probe I solution was mixed with the sodium hydrosulfide aqueous solution for five minutes to measure its absorption; wherein, the concentration of probe I in the reaction system was 10 μM, The concentration of sodium hydrosulfide was 50 μM. absorption spectrum as Image 6 As shown, the fluorescence spectrum is as Figure 7 It can be seen from the figure that the probe has a fluorescence response before and after the reaction with sodium hydrosulfide.

Embodiment 3

[0119] Example 3: Photoacoustic imaging and ratio imaging after the reaction of probe I with different concentrations of sodium hydrosulfide.

[0120] A total of 6 groups of probe I solutions with a concentration of 20 μM, and aqueous solutions of sodium hydrosulfide with concentrations of 0, 20, 40, 60, 80, and 100 μM were prepared, and then the probe I solution was mixed with the aqueous sodium hydrosulfide solution and reacted (probe I). The consumption of solution I was 40 μl, and the consumption of sodium hydrosulfide aqueous solution was 1, 2, 3, 4, and 5 μl respectively). and the photoacoustic 2D map ( Figure 8 ). It can be seen from the figure that the photoacoustic signal intensity of 532nm gradually weakened with the increase of concentration, and the photoacoustic signal intensity of 700nm gradually increased. The needle can serve as a ratiometric photoacoustic probe for hydrogen sulfide detection.

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Abstract

The invention discloses a nanoprobe for photoacoustic rate bioassay of hydrogen sulfide, and a manufacture method and application thereof. The structural formula of the nanoprobe is shown as the formula I. The manufacture method of the nanoprobe mainly includes subjecting a raw material, Cy7-Cl, to nucleophilic substitution, knoevenagel condensation and amino azide reaction to obtain the nanoprobe. The problems of scattering and tissue absorption of fluorescence signals of fluorescence probes in bioassay are solved; the prepared nanoprobe has the advantages of high photoacoustic-signal penetration depth, imaging of deep tissues, high response speed, high specificity and high rate detection accuracy, and can be applied to bioassay of the hydrogen sulfide, or detection of the hydrogen sulfide in water and food. The formula I is shown in the specification.

Description

technical field [0001] The invention belongs to the field of tumor marker detection and imaging, and in particular relates to a photoacoustic ratio nanoprobe for detecting hydrogen sulfide in a living body, a preparation method and application thereof. Background technique [0002] Hydrogen sulfide is a toxic gas with the smell of rotten eggs. Hydrogen sulfide is the third biosynthetic gas transmitter after nitric oxide and carbon monoxide. Hydrogen sulfide plays an important role in many biological processes, such as blood vessels Relaxation of smooth muscle, regulation of neurotransmission, regulation of insulin signaling, inhibition of inflammation, sensing of oxygen, etc.; it also has a protective effect on the heart and nerves in the human body, and is an effective neuromodulatory substance, H 2 Physiologically relevant concentrations of S range from nanomolar to millimolar levels. At physiological concentrations, H 2 S is involved in a series of physiological regulat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/17
Inventor 张涛邢达马腾
Owner SOUTH CHINA NORMAL UNIVERSITY
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