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Asymmetric near-infrared cyanine dye and preparing method and application thereof

An infrared cyanine, asymmetric technology, used in the field of biomedical materials, can solve problems such as non-degradability, and achieve the effects of large conjugated system, good tumor inhibition effect, and good photothermal conversion efficiency.

Active Publication Date: 2016-05-18
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The currently reported photothermal therapeutic agents are mainly inorganic materials such as gold nanoparticles, graphene, carbon nanotubes, etc., as well as some organic polymers, but they all have the problem that they cannot be degraded in vivo.

Method used

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  • Asymmetric near-infrared cyanine dye and preparing method and application thereof
  • Asymmetric near-infrared cyanine dye and preparing method and application thereof
  • Asymmetric near-infrared cyanine dye and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The synthesis of the intermediate shown in embodiment 1, formula II

[0062]

[0063] In 20mL of dry DMF, slowly add 18.5mL (200mmol) phosphorus oxychloride, heat to 50°C, slowly add 5g (51mmol) cyclohexanone after 30min, then raise the temperature to 60°C, and react for 8h. After the reaction, cool to room temperature with ice water, and then pour into 100 g of crushed ice four times. Stir at room temperature and stand overnight to obtain a yellow solid, which is filtered and recrystallized from dichloromethane to obtain the intermediate represented by formula II as needle-shaped yellow crystals.

[0064] 1 HNMR (600MHz, DMSO-D6) δ10.06(s, 1H), 4.06(s, 1H), 3.25(t, 4H), 2.63(m, 2H).

[0065] Confirmed that the structure is correct.

Embodiment 2

[0066] The synthesis of the intermediate shown in embodiment 2, formula III

[0067]

[0068] Add 2.0g (20mmol) cyclohexanone into 10mL concentrated sulfuric acid with stirring and cool to 0°C, weigh 3.13g (10mmol) 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid and add to the above reaction solution, stirred and heated at 90°C for 2 h, after the reaction was completed and cooled to room temperature, poured into 200 g of crushed ice, added 4 mL of perchloric acid, filtered, washed with cold water, and dried in vacuum to obtain the intermediate shown in formula III, which was directly purified without purification for the next reaction.

[0069] 1 HNMR (600MHz, DMSO-D6) δ8.17(d, J=7.9Hz, 1H), 7.83(t, J=7.5Hz, 1H), 7.74(t, J=7.7Hz, 1H), 7.29(t, J=9.2Hz, 2H), 7.17(d, J=16.1Hz, 1H), 7.00(d, J=9.6Hz, 1H), 3.63(d, J=6.9Hz, 4H), 3.18–2.98(m, 2H), 2.44(d, J=26.4Hz, 2H), 2.12(dt, J=16.4, 13.3Hz, 2H), 1.84(s, 2H), 1.67(ddd, J=26.1, 12.8, 6.9Hz, 2H ),1.17(t,J=6.7Hz,6H),0.98(t,J=7....

Embodiment 3

[0071] The synthesis of the intermediate shown in embodiment 3, formula IV

[0072]

[0073] Under the protection of nitrogen, the raw material 2,3,3-trimethyl-4,5-benzo-3H-indole (4.0g, 19.1mmol) was dissolved in dry acetonitrile, and ethyl iodide (14.9g, 95.5 mmol), heated and stirred at 85°C for 10 h. After the reaction solution was cooled to room temperature, the purple solid intermediate represented by formula IV was obtained by filtration, washed with acetone, dried under vacuum, and directly used in the next reaction without further purification.

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Abstract

The invention discloses an asymmetric near-infrared cyanine dye and a preparing method and application thereof. The structural formula of the asymmetric near-infrared cyanine dye is shown as the formula I. The preparing method of the asymmetric near-infrared cyanine dye includes the following steps that 1, a compound shown as the formula II and a compound shown as the formula III are subjected to a condensation reaction to obtain a compound shown as the formula V; 2, the compound shown as the formula V and a compound shown as the formula IV are subjected to a condensation reaction to obtain the asymmetric near-infrared cyanine dye shown as the formula I. According to the asymmetric near-infrared cyanine dye, the conjugated system is large, high near-infrared absorption is achieved, the fluorescence quantum yield is low, the probability of nonradiative jumping is large, and therefore good photo-thermal conversion efficiency is achieved; the asymmetric near-infrared cyanine dye is further wrapped with BSA with good biocompatibility, the water solubility of the dye is improved, the retention time in the body is prolonged, and the asymmetric near-infrared cyanine dye can serve as a photo-thermal therapeutic agent for photo-thermal treatment and has the very important effect in the tumor treating aspect.

Description

technical field [0001] The invention relates to an asymmetric near-infrared cyanine dye and its preparation method and application, belonging to the technical field of biomedical materials. Background technique [0002] Photothermal therapy is a minimally invasive tumor treatment technology developed in recent years. This treatment method uses a special photothermal therapeutic agent to absorb near-infrared light, and converts the absorbed light energy into heat to increase the temperature of the tumor site. High, thereby inducing apoptosis or a treatment method that has a direct lethal effect on cells. Compared with traditional surgical treatment, systemic toxicity is greatly reduced, and it is regarded as one of the very potential tumor treatment techniques. Compared with traditional techniques, this technique also has potential advantages such as simple procedure, quicker recovery, fewer complications, and shorter hospital stay. The core of photothermal therapy is the m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/00C07D405/12A61K41/00A61K9/51A61P35/00
CPCA61K9/5169A61K41/0052C07D405/12
Inventor 梁琼麟周炳江
Owner TSINGHUA UNIV
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