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A molecularly targeted anticancer photosensitizer tamoxifen-phthalocyanine conjugate and preparation method thereof

A tamoxifen, molecular targeting technology, applied in the field of organic and metal coordination compound synthesis, to achieve the effect of definite composition, favorable for industrial production, and single structure

Active Publication Date: 2016-01-27
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports on the coupling of molecular target drugs and photosensitizers

Method used

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  • A molecularly targeted anticancer photosensitizer tamoxifen-phthalocyanine conjugate and preparation method thereof
  • A molecularly targeted anticancer photosensitizer tamoxifen-phthalocyanine conjugate and preparation method thereof
  • A molecularly targeted anticancer photosensitizer tamoxifen-phthalocyanine conjugate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 (M=Zn (II), n=3, α-position monosubstituted)

[0041] 1) Add 0.57g (1.90mmol) of the compound in sequence to a 50mL reaction bottle equipped with a magnetic stirring device, an airway device and a reflux condensing device 2 , 0.5g (1.30mmol) compound 1 and 30 mL of acetonitrile, stirred until completely dissolved, under the protection of nitrogen, 0.48 g (3.44 mmol) of anhydrous potassium carbonate was added to the reaction flask, and the reaction was carried out at 85°C for 12 hours. After the reaction was over, the acetonitrile was removed by rotation under reduced pressure, and the 2 Cl 2 Extracted three times, dried over anhydrous magnesium sulfate, evaporated under reduced pressure to remove CH 2 Cl 2 , to CH 2 Cl 2 :CH 3 A mixed solution of OH=30:1 (V / V) was used as an eluent, and passed through a silica gel column to obtain about 0.35 g of a viscous light yellow liquid (ie compound 3), with a yield of about 51.81%. 1 HNMR (400MHz, CDCl 3 ): δ...

Embodiment 2

[0044] Example 2 (M=Zn (II), n=3, β-position monosubstituted)

[0045] 1) Add 2.34g (7.80mmol) of the compound in sequence to a 50mL reaction bottle equipped with a magnetic stirring device, an airway device and a reflux condensing device 2 , 1.0g (2.6mmol) compound 1 and 50mL of acetonitrile, stirred until completely dissolved, under nitrogen protection, 0.96g (6.88mmol) of anhydrous potassium carbonate was added to the reaction flask, and reacted at 85°C for 20 hours. After the reaction was over, the acetonitrile was removed by rotation under reduced pressure, and the 2 Cl 2 Extracted three times, dried over anhydrous magnesium sulfate, evaporated under reduced pressure to remove CH 2 Cl 2 , to CH 2 Cl 2 :CH 3 The mixed solution of OH=30:1 (V / V) was used as the eluent and passed through a silica gel column to obtain about 0.8 g of a viscous light yellow liquid (namely compound 3), with a yield of about 59.20%. 1 HNMR (400MHz, CDCl 3 ): δ 0.92(m,3H,CH 3 ),2.38(s,3...

Embodiment 3

[0048] Example 3 (M=Al, n=3, α single substitution)

[0049] 1) Add 1.0g (3.33mmol) of the compound in sequence to a 50mL reaction bottle equipped with a magnetic stirring device, an airway device and a reflux condensing device 2 , 0.5g (1.30mmol) compound 1 and 40mL of acetonitrile, stirred until completely dissolved, under the protection of nitrogen, 0.48g (3.44mmol) of anhydrous potassium carbonate was added to the reaction flask, and the reaction was carried out at 85°C for 8 hours. After the reaction was over, the acetonitrile was removed by rotation under reduced pressure, and the 2 Cl 2 Extracted three times, dried over anhydrous magnesium sulfate, evaporated under reduced pressure to remove CH 2 Cl 2 , to CH 2 Cl 2 :CH 3 A mixed solution of OH=30:1 (V / V) was used as an eluent, and passed through a silica gel column to obtain about 0.48 g of a viscous light yellow liquid (namely compound 3), with a yield of about 68.10%. 1 HNMR (400MHz, CDCl 3 ): δ 0.92(m,3H,...

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Abstract

The invention discloses a molecular target anticancer photosensitizer tamoxifen-phthalocyanine conjugate and its preparation method and application. The molecular target drug tamoxifen is introduced around the metal phthalocyanine macrocycle to increase the concentration of phthalocyanine. Targeting of cyanine, and linking the phthalocyanine core and tamoxifen with polyethylene glycol chains to enhance its amphiphilicity and biocompatibility. The compound is expected to improve the targeting of photosensitizers in photodynamic therapy, and at the same time may realize the dual efficacy of photodynamic therapy and molecular target therapy. The conjugate has a single structure and a definite composition. The synthesis method of the invention is simple, the raw materials are easy to obtain, the cost is low, and it is beneficial to industrialized production.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, and relates to a tamoxifen-phthalocyanine conjugate of a molecularly targeted anticancer photosensitizer and a preparation method and application thereof. Background technique [0002] Photodynamic therapy is the use of photosensitive drugs (also known as photosensitizers) to produce photodynamic effects under the excitation of light of a certain wavelength to diagnose and treat diseases. The action process is that the photosensitizer enters the human body, and after a certain period of time, the photosensitizer is selectively enriched in the diseased tissue, and then the diseased tissue is irradiated with light of a certain wavelength, and the photosensitizer undergoes a series of photophysical and photochemical reactions under the excitation of light. Generate active oxygen to kill diseased cells and achieve the purpose of treating diseases. At present, ther...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00A61K31/138
CPCA61K31/138A61K41/0071A61K47/60C07D487/22
Inventor 薛金萍张凤玲周晓琴张明俊
Owner FUZHOU UNIV
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