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Preparation and application of boron dipyrromethene-gadolinium conjugate nano diagnosis and treatment reagent

A nano-assembly and nano-assembly technology, applied in the field of chemical biology, can solve the problems of application limitations, poor water solubility, etc., and achieve the effect of enhancing magnetic resonance imaging, increasing stability, and enhancing the effect of magnetic resonance imaging

Inactive Publication Date: 2021-01-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to its poor water solubility, its application in living organisms is often limited.

Method used

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  • Preparation and application of boron dipyrromethene-gadolinium conjugate nano diagnosis and treatment reagent
  • Preparation and application of boron dipyrromethene-gadolinium conjugate nano diagnosis and treatment reagent
  • Preparation and application of boron dipyrromethene-gadolinium conjugate nano diagnosis and treatment reagent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of amphiphilic BD-Gd molecules, see the synthetic route image 3 : Synthesis of compound BD-Gd. Compound BD-Az (186.9 mg, 0.2 mmol) and alk -DOTA-Gd (59.6 mg, 0.1 mmol), sodium ascorbate (19.8 mg, 0.1 mmol) and anhydrous copper sulfate (8.0 mg, 0.05 mmol) were dissolved in 10 ml of THF / water (4 mL / 1 mL) solution. Under the protection of nitrogen, the reaction was stirred at room temperature for 48 h. After the reaction was completed, the solvent was removed by filtration and rotary evaporation, and the residue was purified by HPLC to obtain a black solid product BD-Gd (23.1 mg) with a yield of 15.1%. HRMS (ESI): Calculated for C 66 h 81 BC l2 f 2 GdN 10 o 15 + [M+H] + m / z 1530.4557; found 1530.4547.

Embodiment 2

[0027] Example 2. Preparation method of BD-Gd / P nanoassembly: take 0.5 ml of BD-Gd molecular DMF solution (1 mg / mL), slowly drop into 9.5 ml (1 mg / ml) P aqueous solution, and stir overnight at 900 RPM. Heated at 95 °C for 10 min, cooled naturally to 20 °C, transferred to an ultrafiltration tube (10 K), centrifuged at 2000 RPM for 1 h, discarded the lower aqueous solution, added water to the upper layer and redispersed the assembly , centrifuge again. After repeated operations three times, the assembly was filtered with a 0.22 μM filter membrane and stored at 4 °C for later use. (concentration 19.0 g / L P; 0.653 mM BD-Gd). The absorption spectra of the assembly BD-Gd / P in water and DMF are as follows Figure 4 shown.

Embodiment 3

[0028] Example 3. Research on the photothermal conversion performance of BD-Gd / P nanoassemblies: Take the prepared BD-Gd / P (5 μM BD-Gd) nanoassemblies and irradiate the samples with 808 nm laser (1 W / cm 2, 10 min), let it cool down naturally, as a cycle, irradiate the sample five times repeatedly, and test the photothermal stability of the sample. Such as Figure 7 As shown, the BD-Gd / P nanoassembly is stable in photothermal conversion and has good resistance to photodrifting.

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Abstract

The invention relates to preparation and application of a boron dipyrromethene-gadolinium (BD-GD) conjugate nano diagnosis and treatment reagent. The diagnosis and treatment reagent is composed of BD-Gd and a polymer PEG113-b-PCL8 (P). The preparation method comprises the following steps: firstly, covalently linking a boron dipyrromethene molecule with a water-soluble magnetic resonance imaging (MRI) contrast agent alk-DOTA-Gd to obtain a BD-Gd conjugate; and then, co-assembling the polymer P and BD-Gd to form a nano assembly which is stable in water and controllable in particle size. Comparedwith a BD-Gd single molecule, the prepared nano assembly absorbs red shift by 138 nanometers, the molar extinction coefficient is increased by nearly 2 times, the photothermal conversion efficiency reaches 71.5%, and the nano assembly can be used for near-infrared photoacoustic imaging and photothermal therapy. Meanwhile, compared with alk-DOTA-Gd, the MRI signal of the nano assembly is enhancedby 1.4 times, and the enhanced MRI effect is achieved. The prepared nano diagnosis and treatment reagent is applied to living tumor imaging and treatment, enhanced photoacoustic and magnetic resonancebimodal imaging and a good photothermal treatment effect are achieved.

Description

technical field [0001] The invention belongs to the field of chemical biology, and the research content is based on the covalently modified boron dipyrrole (BODIPY) dye molecule of the magnetic resonance imaging agent, which forms a nanostructure through co-assembly with a high molecular polymer, and is used for multimodal imaging of tumors with photothermal therapy. Background technique [0002] Multimodal imaging has important potential for clinical application. It can combine the advantages of different imaging methods, and can obtain multiple imaging information at the same time, thereby improving the accuracy of clinical judgment. As the most commonly used technique for clinical diagnosis, magnetic resonance (MR) imaging has excellent tissue penetration depth, high soft tissue contrast and spatial and temporal resolution. However, MR imaging has its own disadvantages, such as relatively low sensitivity and long detection time. Photoacoustic (PA) imaging has the advant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/10A61K49/12A61K49/00A61K49/22A61K49/18B82Y5/00B82Y15/00A61K41/00A61P35/00
CPCA61K49/108A61K49/126A61K49/0002A61K49/225A61K49/186A61K49/1857B82Y5/00B82Y15/00A61K41/0052A61P35/00
Inventor 李昌华闫潇洒苏美慧
Owner NANKAI UNIV
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