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Surface self-assembly gold nanoprobe with free radical capture performance and preparing method and application thereof

A technology that captures free radicals and free radicals. It is used in medical preparations containing active ingredients, organic active ingredients, and drug combinations. It can solve the problems of limited capture performance, slow speed, and cell apoptosis, and achieve efficient and rapid capture and acceleration. Reaction speed, effect of enhancing chemical reactivity

Inactive Publication Date: 2009-09-09
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of the Spin trapping-ESR method in vivo is limited by the free radical trapping performance of the existing nitrone probes (that is, the addition reaction with short-lived free radicals to generate more stable paramagnetic nitroxide free radicals spin addition). The limitations of the reactivity of the compound)
This is mainly manifested in: 1. Since the reaction speed of GSH (glutathione) and free radicals is much faster than that of nitrone free radical probes and free radicals, GSH greatly interferes with the formation of stable accelerators between probes and free radicals. reaction of compounds (R.P.Mason.Free.Radic.Biol.Med.2004,36,1214-1223); 2. Because the reaction speed of nitrone probes and free radicals is very slow, it usually reacts to free radicals in biological systems Detection requires a fairly high concentration (> 10mM) of nitrone probes, but high concentrations of nitrone probes are prone to cause cell apoptosis (S.Pou, D.J.Hassett, B.E.et.al.Anal.Biochem.1989 , 177, 1-6)

Method used

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  • Surface self-assembly gold nanoprobe with free radical capture performance and preparing method and application thereof
  • Surface self-assembly gold nanoprobe with free radical capture performance and preparing method and application thereof
  • Surface self-assembly gold nanoprobe with free radical capture performance and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1. Method 1 Preparation of surface self-assembled gold nanoprobe B with high-efficiency free radical capture performance, R=NH, n=2.

[0071] Preparation of compound 5 (CMPO)

[0072]

[0073] Preparation of compound 1

[0074] N 2 Under protection, 7.5 mL of ethanol, 7.6 mL of pyridine, and 50 mL of chloroform were added to the single-necked flask. Under an ice-water bath, 15 mL of chloroform and 9.9 mL of 2-bromopropionyl bromide were slowly added dropwise. React overnight at room temperature to obtain a light yellow solution. After the reaction is complete, respectively, with 10% H 2 SO 4 solution, saturated NaHCO 3 Solution washing, anhydrous MgSO 4 dry. After filtration, the chloroform was removed by rotary evaporation to obtain 14 g of the product, and 8 g of the product were obtained after vacuum distillation (b.p=43-45° C. 0.05 mmHg). Yield 49%.

[0075] Preparation of compound 2

[0076] Add 10.8g NaNO to the single-necked bottle 2 , 12.8...

Embodiment 2

[0091] Example 2. Preparation of surface self-assembled gold nanoprobe B (R=0, n=11) with high-efficiency free radical capture performance

[0092] 1. The preparation process of tetraoctylammonium bromide-protected gold nanoparticles is as in Example 1.

[0093] 2. Take 10 mg of tetraoctyl ammonium bromide-protected gold nanoparticles and 8.6 mg of ω-hydroxyundecyl mercaptan dissolved in an appropriate amount of solvent, and stir at room temperature for 6-24 hours. After the reaction was completed, the solvent was distilled off, and the obtained residue was dissolved in methanol, and purified by Sephadex LH-20 to obtain purified gold nanoparticles C (R=O, n=11). The characteristic absorption peak of its infrared spectrogram has a hydroxyl absorption peak at 3358; XPS results show that the ratio of gold atoms to sulfur atoms in gold nanoparticles C (R=O, n=11) is 4.5: 1; TEM results show that the average particle size The diameter is 4.5±0.5nm.

[0094] 3. Take 20 mg of gold ...

Embodiment 3

[0096] Example 3. Preparation of surface self-assembled gold nanoprobe B (R=O, n=4) with high-efficiency free radical capture performance

[0097] 1. The preparation process of tetraoctylammonium bromide-protected gold nanoparticles is as in Example 1.

[0098] 2. Take 55mg (2.4×10 -4 mol) ω-aminobutyl disulfide hydrochloride, 72mg (5×10 -4 mol) CMPO, 73.7mg (6.0×10 -4 mol) DMAP, 81.6mg (6.0×10 -4 mol)HOBt, 267.2mg (6.0×10 -4 mol) BOP, 400-800μl (2.0-4.0×10 -3 mol) NMM, dissolved in an appropriate amount of solvent, reacted at room temperature for 12-24 hours, after removing the solvent, with an appropriate amount of CH 2 Cl 2 After dissolution, respectively, with HCl solution, saturated NaHCO 3 solution, washed with saturated NaCl solution, anhydrous Na 2 SO 4 dry. Column separation yielded 60 mg of the product. 1 H-NMR (400MHz, CHCl 3 )δ: 1.33(s, 6H), 1.40-1.56(m, 16H), 2.56(t, 4H), 3.20(t, 4H), 7.35(t, 2H), 8.10(m, 2H).

[0099] 3. Dissolve 10 mg of tetraoctyla...

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Abstract

The invention discloses a surface self-assembly gold nanoprobe with the free radical capture performance and a preparing method and the application thereof. The surface self-assembly gold nanoprobe with the high free radical capture performance is prepared by the following steps: the surface of a gold nano-particle is connected with nitrone free radical probe ligand with the structure of formula II by a connexon of the structure of formula I. The nitrone free radical probe ligand is connected with R3 radical group end. The gold nano-particle is connected with sulfhydryl end of the connexon. In formula Ia and formula Ib, R3 is -OH, -NH2 or -COOH, n is equal to 2-11, and n1 is equal to 1-4. In formula IIc, R1 is -P(O)(OC2H5)2, and R2 is OH, COOH or CH2OH. The surface self-assembly gold nanoprobe with the high free radical capture performance can capture free radicals under low concentration and can be applied as an antioxidant.

Description

technical field [0001] The invention relates to a surface self-assembled gold nanoprobe with free radical capture performance, a preparation method and application thereof. Background technique [0002] Nanoparticles have been widely used in the fields of biology and medicine due to their unique physical and chemical properties, such as: bioluminescence labeling (P.Hazarika, F.Kukolka, C.M.Niemeyer.Angew.Chem.Int.Ed.2006,45,6827 -6830.), DNA structure detection (H.Otsuka, Y.Nagasaki, K.Kataoka.Adv.Drug.Deliver.Rev.2003, 55, 403-419), drug delivery and cell imaging (J.Chen.et .al.Nano.Lett.2005, 5, 473-477) and so on. As a short-lived active intermediate produced in oxygen metabolism organisms, oxygen free radicals have physiological and pathological effects that cannot be ignored in biological systems, especially superoxide free radicals (O 2 · - ) and many reactive oxygen species (ROS) that are subsequently generated with superoxide radicals. ROS bear or participate in ...

Claims

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Application Information

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IPC IPC(8): C07F1/12A61K31/40A61K31/683A61P39/06G01N24/10
Inventor 杜立波刘扬田秋
Owner INST OF CHEM CHINESE ACAD OF SCI
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