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Application of mitochondrial targeting contrast media molecule as T2 contrast media

A contrast agent and mitochondrial technology, applied in the field of medical imaging, can solve the problems that the duration of the signal enhancement effect cannot meet the long-term observation, and the survival and migration status of labeled cells cannot be clearly determined.

Active Publication Date: 2017-06-27
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This contrast agent acts as a T 1 When contrast agents are applied to live images of cell transplants, the survival and migration of labeled cells in vivo cannot be clearly determined, and the duration of the signal enhancement effect cannot meet the needs of long-term observation.

Method used

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  • Application of mitochondrial targeting contrast media molecule as T2 contrast media
  • Application of mitochondrial targeting contrast media molecule as T2 contrast media
  • Application of mitochondrial targeting contrast media molecule as T2 contrast media

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1: Synthesis of the contrast agent molecule Gd-DOTA-TPP targeting mitochondria ( Image 6 )

[0072] 1. Bu t 3 Synthesis of DOTA (1,4,7-tris(tert-butoxycarbonylmethyl)-10-(acetic acid)-1,4,7,10-tetraazacyclododecane). Synthesize starting from 1,4,7,10-tetraazacyclododecane (Cyclen) as follows:

[0073] a) Weigh 10.0g Cyclen and 29.3g NaHCO 3 Place in a 1L three-necked flask, and add 50mL of acetonitrile. Weigh 37.4g of tert-butyl bromoacetate in a fume hood, add 20mL of acetonitrile, mix well, and put it into the dropping funnel. in an ice bath and N 2 Under protection, the acetonitrile solution of tert-butyl bromoacetate was slowly added dropwise to the reaction mixture in the three-neck flask. After the dropwise addition was completed, stirring was continued at room temperature for 30 hours. The solid was filtered off, acetonitrile was removed by rotary evaporation, and recrystallized twice with toluene to obtain 16 g of white solid Bu t 3 DO3A (1,4,...

Embodiment 2

[0083] Embodiment 2: (Gd-DOTA) 4 Synthesis of -TPP-targeted mitochondrial contrast agent molecules ( Figure 7 )

[0084] 1, synthesize Bu according to embodiment 1 t 3 DOTA and Ph 3 P(Br)(CH 2 ) 4 COOH.

[0085] 2. Synthesize DOTA by solid phase synthesis 4 -TPP: The steps are briefly described as follows: Synthesize on a solid-phase synthesizer according to the traditional Fmoc method, press Figure 7 In the structure shown, amino acids are sequentially coupled from the C-terminal to the N-terminal. First solid phase carrier 2-chlorotrityl resin 1g, add 2.0g Fmoc-Lys(Mtt)-OH successively, 1.77gPh 3 P(Br)(CH 2 ) 4 COOH is condensed, and the conditions for the condensation of carboxyl and amino groups in each step are 50mL of DMF as a solvent, adding 0.96g of TBTU, 0.41g of HOBt condensing agent and 2.5mL of base DIPEA, and reacting at 25°C for about 24 hours. Ketone color development shall prevail to determine whether the condensation of carboxyl and amino groups ...

Embodiment 3

[0090] Embodiment 3: (Gd-DOTA) 4 -linker-TPP synthesis of contrast agent molecules targeting mitochondria (the spacer here is Acp) ( Figure 8 , dendrimers)

[0091] 1. Synthesize Bu according to the method of Example 1 t 3 DOTA and Ph 3 P(Br)(CH 2 ) 4 COOH.

[0092] 2. Synthesize DOTA by solid phase synthesis 4 -linker-TPP:

[0093] The steps are briefly described as follows: synthesize on a solid-phase synthesizer by the traditional Fmoc method, press Figure 8 In the structure shown, amino acids are sequentially coupled from the C-terminal to the N-terminal. First, solid phase carrier 2-chlorotrityl resin 1g, add 2.0g Fmoc-Lys(Mtt)-OH, 1.77g Ph 3 P(Br)(CH 2 ) 4 COOH is condensed, and the conditions for the condensation of carboxyl and amino groups in each step are 50mL of DMF as a solvent, adding 0.96g of TBTU, 0.41g of HOBt condensing agent and 2.5mL of base DIPEA, and reacting at 25°C for about 24 hours. Ketone color development shall prevail to determine whe...

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Abstract

The invention discloses an application of a mitochondrial targeting contrast media molecule as a T2 contrast media. The mitochondrial targeting contrast media molecule includes a phosphonium cation, which is combined with cell mitochondria and has a structure general formula like <->P<+>(X1)(X2)(X3), and a superpara-magnetic metal complex used as a radiography unit for enhancing contrast ratio of magnetic resonance imaging. The invention also discloses the mitochondrial targeting contrast media molecule and a preparation method thereof, wherein one or more <->P<+>(X1)(X2)(X3) cations are combined with 1-8 superpara magnetic metal complex molecules through dendritic or linear molecules, meanwhile, a connexon and a spacer are employed for improving the spatial structures between the <->P<+>(X1)(X2)(X3) cations and the dendritic or linear molecules and between the dendritic or linear molecules and the superpara magnetic metal complex. The invention further discloses magnetically labeled cells labeled by the mitochondrial targeting contrast media molecule, a combination of the magnetically labeled cells and a scaffold material, and a method of performing magnetic resonance image in-vivo tracing therewith.

Description

technical field [0001] The invention relates to the field of medical imaging, in particular to a contrast agent molecule targeting mitochondria as a magnetic resonance T 2 The purposes of contrast agent, the present invention also relates to a kind of contrast agent molecule targeting mitochondria, the magnetic labeling cell of its mark, and the combination body of magnetic labeling cell and support material, and use them to carry out magnetic resonance imaging (Magnetic Resonance Imaging, MRI) live tracking method. Background technique [0002] Stem cell regenerative medicine is an emerging biomedical field. Its basic idea is to achieve the regeneration and repair of damaged tissues and organs by inducing the directional differentiation of stem cells in the transplanted body. In the process of stem cell regenerative medicine, it is necessary to track in real time the physiological behaviors such as survival, migration, homing, and directional differentiation of stem cells ...

Claims

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Application Information

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IPC IPC(8): A61K49/10A61K49/12C12N5/0775C12N5/0797C12N5/074C12N5/0735
CPCA61K49/10A61K49/124A61K49/146C12N5/0606C12N5/0623C12N5/0657C12N5/0662A61K49/06A61K51/04
Inventor 邓宗武谭波张艳辉张宏岩张海禄
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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