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Double-ratio type hemicyanine dye molecule as well as synthesis method and application thereof

A synthetic method and ratio-based technology, applied in the field of double-ratio semicyanine dye molecules and their synthesis, can solve the problems of inability to provide signals for distinguishing hypoxic levels, insufficient robustness of molecular imaging, false positives, etc.

Active Publication Date: 2021-08-20
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, most probes for monitoring tumor hypoxia are open-type, and molecular imaging of this single-on mode is often not robust enough to provide the signal needed to distinguish the site of hypoxia levels, leading to potential false-positive or false-negative diagnostic and therapeutic outcomes

Method used

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  • Double-ratio type hemicyanine dye molecule as well as synthesis method and application thereof
  • Double-ratio type hemicyanine dye molecule as well as synthesis method and application thereof
  • Double-ratio type hemicyanine dye molecule as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Synthesis and Characterization of Dye Molecule AS-Cy-1

[0054] Dissolve 255.5mg (0.5mmol) of raw material 1b in N,N-dimethylformamide (DMF), add 63.1mg (0.5mmol) of resorcinol and 12mg of hydrogenated sodium in a round-bottomed flask, under nitrogen protection and Stirring at 40°C for 8 hours;

[0055] After the reaction was completed, the reaction solution was poured into ice water and mixed, and 0.5ml of perchloric acid was added to allow the solid to be precipitated, and the crude product was obtained by suction filtration;

[0056] The obtained crude product was purified with a silica gel (200-300 mesh) chromatographic column with a volume ratio of 50:1 of dichloromethane and methanol as an eluent to obtain 106.3 mg of a blue solid (yield rate: 51.3 %).

[0057] refer to figure 1 , 1 H NMR (500MHz, DMSO-d 6 )δ8.26(d, J=14.4Hz, 1H), 7.77(dd, J=39.7, 7.7Hz, 2H), 7.58–7.53(m, 2H), 7.49(t, J=7.4Hz, 1H), 7.37(s,1H),7.11(d,J=2.3Hz,1H),6.94(dd,J=8.5,2.3Hz,1H),6.70(d,J...

Embodiment 2

[0061] Dye molecule BS-Cy-NO 2 Synthesis and characterization of

[0062] Dissolve 282.1mg (0.5mmol) of BS-Cy-1 in N,N-dimethylformamide (DMF) and add 108mg (0.5mmol) of brominated p-nitrotoluene and 17.3mg of potassium carbonate in a round bottom flask , stirred and reacted for 4 hours under nitrogen protection and 60°C;

[0063] After the reaction was completed, the reaction solution was poured into ice water and mixed, and 0.5ml of perchloric acid was added to allow the solid to be precipitated, and the crude product was obtained by suction filtration;

[0064] The obtained crude product was purified with a silica gel (200-300 mesh) chromatographic column with a volume ratio of 60:1 of dichloromethane and methanol as an eluent to obtain 227.6 mg of a blue solid (yield rate: 65.1 %).

[0065] refer to image 3 , 1 H NMR (600MHz, DMSO-d 6 ))δ8.38(t, J=11.8Hz, 1H), 8.32(d, J=8.6Hz, 1H), 8.26(d, J=8.9Hz, 1H), 8.19(d, J=8.2Hz, 1H ), 8.02(d, J=8.9Hz, 1H), 7.77(d, J=8.6Hz, ...

Embodiment 3

[0069] Dye molecule BS-Cy-NO 2 Spectrum in response to nitroreductase:

[0070] The dye molecule BS-Cy-NO prepared in configuration embodiment 2 2 DMSO mother solution with a concentration of 10mM; then add 1998μL liquid (PBS:methanol=8:2) and 2μL probe mother solution to the UV and fluorescent dishes respectively, add nitroreductase and NADH to the dish, and the ultraviolet spectrum can be observed The peak falls at 670nm and rises at 750nm, and the peak of the fluorescence spectrum falls at 760nm and rises at 800nm, showing a double ratio change, such as Figure 5 , Image 6 shown.

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Abstract

The invention discloses a double-ratio type hemicyanine dye molecule as well as a synthesis method and application thereof. According to the double-ratio near-infrared fluorescence and photoacoustic diagnosis and treatment dye molecule provided by the invention, the nitroreductase level directly related to the tumor treatment effect is visualized, quantified and evaluated, and the tumor hypoxia level is noninvasively monitored in real time through ratio near-infrared fluorescence and photoacoustic imaging so as to carry out prognosis and treatment evaluation; and the dye molecule BS-Cy-NO2 has a good photo-thermal effect and can be used for photo-thermal therapy of tumors. The dye molecule is simple in synthesis step, convenient to purify and excellent in imaging, and has a wide application prospect as a molecular diagnosis and treatment agent for double-ratio near-infrared fluorescence and photoacoustic imaging. The molecular structural formula of the dye is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of small organic molecule dyes, and specifically relates to a double-ratio type semicyanine dye molecule and its synthesis method and application. Background technique [0002] Malignant tumors exhibit different hypoxia levels of mild, moderate, and severe hypoxia during their growth and proliferation. Hypoxia levels are closely related to the efficacy of cancer treatments such as radiotherapy and chemotherapy, and even lead to tumor invasion, mutation, metastasis and drug resistance. Therefore, an accurate description of the distribution and degree of hypoxia in solid tumors will help to obtain accurate information about the degree of malignancy and migration of tumors, and the development of non-invasive imaging techniques for quantitative detection of tumor hypoxia levels in vivo is effective for cancer prognosis and diagnosis. Sex matters. Optical imaging that enables non-invasive and real-time visuali...

Claims

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Application Information

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IPC IPC(8): C09B23/10C07D417/06C07D409/06C09K11/06C12Q1/26G01N21/64G01N21/33A61K49/00A61K49/22A61K41/00A61P35/00
CPCC09B23/105C07D417/06C07D409/06C09K11/06C12Q1/26G01N21/6428G01N21/33A61K49/0032A61K49/22A61K41/0052A61P35/00G01N2333/90694C09K2211/1037C09K2211/1092C09K2211/1029
Inventor 陈华张淑平沈星灿秦雪
Owner GUANGXI NORMAL UNIV
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