Iron complex for photoacoustic imaging and photothermal therapy and preparation method and application of iron complex

A technology of iron complexes and photothermal therapy, applied in echo/ultrasonic imaging agents, medical preparations containing active ingredients, pharmaceutical formulas, etc., can solve the problems of poor repeatability, poor stability of small organic molecules and difficult to be modified, etc. Achieve the effect of low cost, improved biocompatibility and water solubility, and easy availability of raw materials

Active Publication Date: 2020-04-21
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reproducibility of nanomaterials is poor, and the stability of small organic molecules is poor and difficult to be modified.

Method used

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  • Iron complex for photoacoustic imaging and photothermal therapy and preparation method and application of iron complex
  • Iron complex for photoacoustic imaging and photothermal therapy and preparation method and application of iron complex
  • Iron complex for photoacoustic imaging and photothermal therapy and preparation method and application of iron complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of intermediate S

[0030] Wrap a layer of crushed ice around a 100mL three-necked flask, and dissolve triphenylamine formaldehyde (4.09g, 0.015mol) in 20mL of purified anhydrous CH 2 Cl 2 Added to the three-necked flask, stirred for 15min. Slowly add chlorosulfonic acid (14.00 g, 0.120 mol, 30 mL of refined anhydrous CH 2 Cl 2 dilution), after the dropwise addition, the reaction was continued for 2h under this condition. Slowly add an appropriate amount of water dropwise to quench the reaction, and raise the temperature to 40°C for 2 h. Cool to room temperature, and then adjust the pH to 7-8 with 4mol / L NaOH aqueous solution. Add ethanol and spin dry with a rotary evaporator to remove water, recrystallize with ethanol, filter with suction, and dry in vacuum for 24 hours to obtain 5.86 g of a yellow solid with a yield of 81.9%. 1 H NMR (400MHz, DMSO-d6) δppm: 9.80(s, 1H), 7.76(d, J=8.7Hz, 2H), 7.62(d, J=8.5Hz, 4H), 7.10(d, J=8.5Hz ,4H)...

Embodiment 2

[0031] Embodiment 2: the synthesis of ligand L

[0032] Add NaOH (2.40g, 0.068mol) aqueous solution and 2-acetylpyridine (3.03g, 0.025mol) to a 250mL three-necked flask, heat up to 80°C, and stir for 30min. S (4.33g, 0.010mol) was dissolved in an appropriate amount of ethanol, added to the above reaction system, and stirred for 30min. Add appropriate amount of NH to the constant pressure dropping funnel 3·H 2 O, continue to react for 6h, let stand overnight. Suction filtration, rinse with ethanol three times, recrystallize the solid with ethanol, and dry the obtained solid in a vacuum oven for 24 hours to obtain 4.12 g of a yellow solid with a yield of 60.1%. 1 H NMR (400MHz,D 2 O)δppm: 8.22–8.08(m,2H),7.72–7.60(m,2H),7.52–7.34(m,8H),7.10–6.98(m,2H),6.83–6.74(m,2H),6.73 –6.60(m,4H),6.41–6.29(m,2H).ESI-MS m / z: calcd for:(M-2Na) / 2:317.05,found:317.04.Anal.Calc.for C 33 h 22 N 4 Na 2 o 6 S 2 : C, 58.23; H, 3.26; N, 8.23%; Found: C, 57.98; H, 3.46; N, 8.01%.N, 8.01%.

Embodiment 3

[0033] Embodiment 3: the synthesis of target product

[0034] Pour ligand L (0.6542g, 0.0010mol) into a 250mL round-bottomed flask, add an appropriate amount of refined acetonitrile to dissolve it completely, and add ferric chloride (0.0811g, 0.0005mol) dropwise at 80°C ) in acetonitrile (10mL) solution, a solid precipitated out slowly. After stirring for 2 h, it was cooled to room temperature. A purple solid was obtained by suction filtration, and then the solid was recrystallized with ethanol, filtered by suction, and dried in a vacuum oven for 24 hours to obtain 0.4712 g of a purple solid product with a yield of 68%. 1 HNMR (400MHz, d6-DMSO) δ9.52 (4H, s), 8.95 (4H, d, J 7.9), 8.38 (4H, d, J 8.4), 7.96 (4H, t, J7.7), 7.61 ( 8H,d,J 8.5),7.29(4H,d,J 8.5),7.21(4H,d,J 5.3),7.17–6.74(12H,m).ESI-MS m / z:calcd for:(M- 2Na) / 2:662.06,found:662.06.Anal.Calc.for C 66 h 44 FeN 8 o 12 S 4 : C, 46.44; H, 2.60; N, 6.56%; Found: C, 46.39; H, 2.61; N, 6.56%.

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Abstract

The invention discloses an iron complex for photoacoustic imaging and photothermal therapy and a preparation method and application of the iron complex. The iron complex is a complex FeL2 synthesizedby coordination of a sulfonic triphenylamine terpyridyl functional ligand and Fe. By introducing sulfonic triphenylamine to a terpyridyl ligand, the biocompatibility and water solubility of the complex are improved, the intramolecular electron donating capacity is enhanced, a conjugated system is increased, intramolecular charge transfer is facilitated, and the optical property is optimized. Research results show that the complex has an excellent photoacoustic imaging effect and relatively high photothermal conversion efficiency and is a photoacoustic imaging contrast agent which can be used for photothermal therapy.

Description

technical field [0001] The present invention relates to an iron complex that can be used for photoacoustic imaging and photothermal therapy and its preparation method and application, specifically a complex of terpyridine triphenylamine sulfonate iron that can be used for photoacoustic imaging and photothermal therapy and its synthesis method. Background technique [0002] Photoacoustic imaging (PAI), which combines the advantages of high resolution of optical imaging and deep tissue penetration of acoustic imaging, has attracted extensive attention in recent years. Excellent photoacoustic imaging contrast agents should have the characteristics of low quantum yield, high molar extinction coefficient, excellent photostability and biocompatibility. Materials that can be used as photoacoustic imaging (PAI) have been greatly developed in recent years. For example, metal nanomaterials, carbon-based nanomaterials, and small organic molecules have been widely used in photoacousti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38A61K41/00A61K49/22A61P43/00
CPCC07D213/38A61K49/22A61K41/0052A61P43/00
Inventor 田肖和项攀沈玉张琼李胜利马文周虹屏吴杰颖田玉鹏
Owner ANHUI UNIVERSITY
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