One kind of magnetic resonance imaging developers and two-photon imaging developers and preparation method thereof

A magnetic resonance imaging and two-photon imaging technology, which is applied in peptide preparation methods, chemical instruments and methods, organic chemistry, etc., can solve the problems of low cell uptake rate, high preparation difficulty, and difficult targeting

Active Publication Date: 2013-07-10
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to propose a class of magnetic resonance imaging imaging agent and two-photon imaging imaging agent and preparation method thereof, so as to obtain a nano-imaging agent capable of real-time controllable self-assembly, and overcome the difficulty of preparing traditional nano-imaging agents. Disadvantages such as low cellular uptake rate and difficult targeting

Method used

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  • One kind of magnetic resonance imaging developers and two-photon imaging developers and preparation method thereof
  • One kind of magnetic resonance imaging developers and two-photon imaging developers and preparation method thereof
  • One kind of magnetic resonance imaging developers and two-photon imaging developers and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0042] The final product A of the first compound in this embodiment 1 The synthetic route of is as follows:

[0043]

[0044] First, the lysine-cysteine-arginine-arginine-valine-arginine peptide is synthesized, and the specific steps are as follows: 0.33 mmol of 2-chlorotrityl chloride resin in 2 After eight minutes of swelling in mL of N,N-dimethylformamide, 0.66 mmol of the first amino acid N-fluorenylmethoxycarbonyl-N'-tert-butoxycarbonyl-L-lysine was added to the reactor Add 0.66 mmol N,N-diisopropylethylamine, react for two hours, react with 30 microliters of methanol for 20 minutes, cut off the first amino acid protecting group, Kaiser test shows blue, add activated 0.55 Millimoles of the second amino acid cysteine ​​was reacted for two hours, and the Caesar test showed yellow, and the protective group was cut off, and the Caesar test was blue, and 0.55 mmol of activated third amino acid arginine was added to react for three hours, Caesar The test shows yellow, the ...

Embodiment 2

[0083] Example 2: Final product A of the first compound 1 In vitro verification experiment of condensation reaction

[0084] What adopted in this embodiment in vitro experiment is the final product A of the first compound 1 At a concentration of 100 μmol / L, in a concentration of 100 mmol / L 4-hydroxyethylpiperazineethanesulfonic acid buffer, 1 mmol / L trichloroethyl phosphate, 1 mmol / L calcium chloride, and 5 μL of furin, the total volume was In 100 μL of the solution, incubate at 30°C for 17 hours to condense into dimers and self-assemble into nanoparticles.

[0085] Figure 5 The final product A of the first compound in this example is given 1 Transmission electron microscopy characterization of in vitro condensation-formed nanoparticles; Image 6 Be the final product A of the first compound in embodiment 2 1 UV absorption at 500-700nm before and after in vitro digestion.

[0086] in Figure 5 It is a transmission electron microscope (TEM) characterization of the nanopa...

Embodiment 3

[0087] Example 3: Verifying the occurrence of condensation reactions at the cellular level

[0088] Firstly, human malignant breast cancer cell line MDA-MB-468 was cultured, and the specific operation was as follows: the malignant breast cancer cell line MDA-MB-468 was cultured in DMEM high-glucose medium containing 10% bovine serum albumin by volume, and the cells were cultured in The concentration is 5% CO 2 Cultured in a 37°C incubator in an air environment, and the medium was changed once a day.

[0089] Observe the slices of cells and compounds cultured by transmission electron microscope photos, the specific operation is as follows: the malignant breast cancer cell line MDA-MB-468 cells are planted in two 6 cm culture dishes, about 6 million cells, on the top The stated volume concentration is 5% CO 2 After culturing in a constant temperature incubator at 37°C in an air environment for 12 hours, add the final product A of the first compound to the two plates of cells r...

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Abstract

The invention discloses a preparation method of one kind of magnetic resonance imaging developers and two-photon imaging developers. The preparation method is characterized by comprising the steps of: firstly, synthesizing a lysine-cysteine-arginine-arginine-valine-arginine peptide fragment and a valine-arginine-cysteine-arginine-lysine-arginine peptide fragment, connecting the fragments with 2-amino-6-cyanobenzothiazole and then connecting a macrocyclic compound, and reacting with metal ions in a buffer solution to obtain five compounds, wherein the final product A1 of a first compound, the final product A2 of a second compound and the final product A5 of a fifth compound are magnetic resonance imaging developers, and the final product A3 of a third compound and the final product A4 of afourth compound are two-photon imaging developers. Because of being micromolecules, the magnetic resonance imaging developers and two-photon imaging developers have the advantages of good hydrophilia, easiness of preparation and high absorption; and the final product A1 of the first compound and the final product of the third compound have peptide fragments with specific enzyme specificity recognition, and have the advantage of high targeting.

Description

technical field [0001] The invention belongs to the technical field of imaging agents, and in particular relates to an imaging agent for magnetic resonance imaging, an imaging agent for two-photon imaging and a preparation method thereof. Background technique [0002] In recent years, nanomaterials have been widely reported and applied as imaging probes. A sub-journal of the American Chemical Society (J.Am.Chem.Soc., 2007, Vol.129, P.3848) reported a quantum dot imaging agent for both magnetic resonance imaging and optical imaging. Although this imaging agent has a good imaging effect, it is relatively difficult to prepare the imaging agent because the core of the CdSe nanoparticle must first be synthesized, and then not only the outer shell of the nanoparticle must be synthesized, but also the water-soluble organic compound must be modified. Difficulty; and because the nanoparticle synthesized in vitro has the disadvantages of low cell uptake rate and no specific targeting...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/16C07K1/06C07K1/04
CPCY02P20/55
Inventor 梁高林曹春艳
Owner UNIV OF SCI & TECH OF CHINA
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