A kind of multifunctional near-infrared fluorescent magnetic nanoparticle and its preparation and application

A magnetic nano, near-infrared technology, applied in the field of biomedicine, to achieve the effect of improving efficiency and accuracy, overcoming differences in biological distribution and selectivity

Inactive Publication Date: 2019-04-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, current diagnostic imaging methods have their own inherent advantages and disadvantages. If an imaging probe that combines the advantages of the two diagnostic methods can be provided, it will improve the efficiency and accuracy of diagnosis.

Method used

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  • A kind of multifunctional near-infrared fluorescent magnetic nanoparticle and its preparation and application
  • A kind of multifunctional near-infrared fluorescent magnetic nanoparticle and its preparation and application
  • A kind of multifunctional near-infrared fluorescent magnetic nanoparticle and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Synthesis of 10-methyl-10H-phenothiazine-3-carbaldehyde (ie compound 2, wherein R is H)

[0040] Weigh NaH (60% purity, 1.0 g, 25.1 mmol), slowly add DMF (10 mL) in a 50 mL round bottom flask in an ice-water bath, then add methyl iodide (1.3 g, 11.04 mmol) and compound Phenothiazine (2 g, 10.0 mmol), transferred to room temperature and stirred for 2 h, TLC monitored the reaction, added water, extracted with DCM (50 ml x 3), dried over magnesium sulfate and then concentrated to dryness, separated by silica gel column to obtain compound 1 (R is H), that is, 10-methyl-10H-phenothiazine (2.1 g), white solid, melting point: 96°C, yield 97%.

[0041] 1 H NMR (400MHz, (CD 3 ) 2 CO)δ7.21(td, J=8.0,1.5Hz,2H),7.21(d,J=2.0Hz,1H),7.14(d,J=1.5Hz,1H),6.96-6.93(m,4H) ,3.39(s,3H).

[0042] Slowly add phosphorus oxychloride (1.98 g, 1.18 mL, 12.9 mmol) dropwise into a 25 mL round bottom bottle with dry DMF (904 L, 11.73 mmol) in an ice-water bath at 0°C, and stir for 0.5...

Embodiment 2

[0044] Embodiment 2: Synthesis of 8-chloro-10-methyl-10H-phenothiazine-3-formaldehyde (ie compound 2, R is Cl)

[0045] Referring to the first step of the operation process in Example 1, the product compound 1 (R is Cl), namely 2-chloro-10-methyl-10H-phenothiazine, was isolated as a white solid with a melting point of 75°C and a yield of 97%.

[0046] 1 H NMR (400MHz, CDCl 3 )δ7.16(td, J=7.8,1.3Hz,1H),7.12(dd,J=7.8,1.3Hz,1H),6.99(d,J=8.5Hz,1H),6.94(t,J=7.5 Hz,1H),6.88(dd,J=8.5,2.0Hz,1H),6.78(d,J=8.5Hz,1H),6.73(d,J=2.0Hz,1H),3.29(s,3H).

[0047] Referring to the second step of the operation in Example 1, the product 8-chloro-10-methyl-10H-phenothiazine-3-carbaldehyde was isolated as a yellow solid with a melting point of 160° C. and a yield of 38%.

[0048] 1 H NMR (400MHz, CDCl 3 )δ7.16(td, J=7.8,1.4Hz,1H),7.11(dd,J=7.8,1.4Hz,1H),7.01(d,J=8.2Hz,1H),6.93(td,J=7.6 ,1.4Hz,1H),6.88(dd,J=8.2,2.0Hz,1H),6.8(d,J=8.2Hz,1H),6.75(d,J=2.0Hz,1H),3.35(s,3H ).

Embodiment 3

[0049] Example 3: Synthesis of (E)-3-(10-methyl-10H-phenothiazin-3-yl)acrolein (i.e. compound 3, R is H)

[0050] Saturated potassium carbonate solution (15 mL) was added to tris(3,6-dioxaheptyl)amine (TDA-1) (738 mg, 2.28 mmol, 1.1 equiv) in DCM (10 mL), Then (1,3-dioxolan-2-yl)methyltriphenylphosphine bromide (1.43 g, 3.32 mmol, 1.6 equiv) and compound 2 (500 mg, 2.07 mmol, 1 equiv ). The reaction system was heated to reflux and stirred for about 20 hours. After the reaction was monitored by TLC, it was first extracted with (DCM 2×25 ml), washed with saline, and the organic phase was dried with magnesium sulfate and concentrated to dryness. Added 20 ml of THF and 10% HCl (20 mL), stirred at room temperature for 1 h. The reaction system was adjusted to pH 7 with 10% NaOH in an ice-water bath at 0 degrees Celsius, then extracted with DCM (2x25 ml) and water, finally dried with saturated brine and magnesium sulfate, concentrated to dryness, and separated by silica gel column ...

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Abstract

The invention discloses multifunctional near infrared fluorescence magnetic nanoparticles as well as a preparation method and application thereof. The magnetic nanoparticles have a magnetic resonance imaging function and an optical imaging effect, is not only used for Alzheimer disease amyloid protein A beta plaque image, but also achieving an inhibiting effect on A beta-sample amyloid protein polymerization.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a magnetic nanoparticle with multifunctional near-infrared fluorescence and its preparation and application. Background technique [0002] Alzheimer's disease (AD) is a degenerative brain nervous system disease, which is one of the most common senile dementias. There are three main hypotheses for the pathological mechanism of AD: amyloid deposition, neurofibrillary tangles (neurofibrillary tangles), and cholinergic neuron degeneration. Among them, the "amyloid cascade hypothesis" is widely recognized. This hypothesis holds that in the early stage of AD, β-amyloid (Aβ, mainly Aβ40 and Aβ42) gradually aggregates and deposits to form amyloid plaques, triggering tau protein phosphorylation neurofibrillary tangles, eventually leading to neuronal loss, degeneration, and dementia. Due to the strong concealment of AD and the slow course of the disease, it is extremely critical for the early ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C09K11/06C09K11/02A61K31/5415A61P25/28A61K49/18A61K49/10A61K49/00
CPCA61K49/0002A61K49/0013A61K49/0017A61K49/0093A61K49/085A61K49/106A61K49/1818C07D417/06C09K11/025C09K11/06C09K2211/1007C09K2211/1033C09K2211/1037
Inventor 陈惠雄帕斯卡·道叶飞飞
Owner GUANGDONG UNIV OF TECH
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