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A kind of erlotinib-phthalocyanine conjugate and preparation method thereof

The technology of a conjugate and phthalocyanine is applied in the field of targeted anti-cancer molecule erlotinib phthalocyanine conjugate and its preparation, which can solve the problem of unsatisfactory tumor tissue targeting, difficulty in separation, difficulty in synthesis, etc. The problem is to achieve the effect of low cost, easy availability of raw materials and simple synthesis method.

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

However, most of the existing substituted phthalocyanine metal complexes have problems such as difficult synthesis, many side reactions, and difficult separation.
At the same time, there is an important problem that the targeting of phthalocyanine to tumor tissue is not ideal, so the research on the targeting of photosensitizers has become a hot research topic now.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1 (M=Zn, m=3, R 1 =R 2 =-OCH 2 CH 2 OCH 3 , α single substitution)

[0034] 1) Add compound 10.5g (1.27mmol) and compound 20.68g (1.95mmol) into N,N-dimethylformamide (DMF), after both are dissolved, add K 2 CO 3 0.7g (5.07mmol), reacted at 50°C for 6h under the protection of nitrogen. After the reaction was finished, the DMF was spin-dried, and then the crude product was extracted with dichloromethane, followed by separation on a silica gel column with a dichloromethane-methanol volume ratio of 30:1 as the eluent to obtain 30.4 g of the compound. The yield was 55%. 1 HNMR (500MHz, CDCl 3 ): δ 8.41(s,1H,ArH),7.84(s,1H,ArH),7.45(s,1H,ArH),7.16(t, J =8.0Hz,1H,ArH),6.89(d, J =8.0Hz,1H,ArH),6.59(s,1H,ArH),6.41(d, J =8.0Hz,1H,ArH),4.49-4.45(m,4H,CH 2 ),4.40-4.38(m,4H,CH 2 ),3.80(t, J =4.5Hz,2H,CH 2 ),3.73(t, J =4.5Hz,4H,CH 2 ),3.67(t, J =4.5Hz,2H,CH 2 ),3.66-3.63(m,4H,CH 2 ),3.39-3.37(m,4H,CH 2 ),3.31(s,6H,CH 3 ),3.12(s,1H,CH),2.3(brs,1H,OH)...

Embodiment 2

[0037] Embodiment 2 (M=Al, m=6, R 1 =R 2 =-OCH 2 CH 2 OCH 3 , β single substitution)

[0038] 1) Add compound 10.5g (1.27mmol) and compound 20.68g (1.95mmol) into N,N-dimethylformamide (DMF), after both are dissolved, add K 2 CO 3 0.7g (5.07mmol), reacted at 50°C for 6h under the protection of nitrogen. After the reaction was finished, the DMF was spin-dried, and then the crude product was extracted with dichloromethane, followed by separation on a silica gel column with a dichloromethane-methanol volume ratio of 30:1 as the eluent to obtain 30.4 g of the compound. The yield was 55%. 1 HNMR (500MHz, CDCl 3 ): δ 8.36(s,1H,ArH),7.41(s,1H,ArH),7.24(s,1H,ArH),7.01(t, J =8.0Hz,1H,ArH),6.74(d, J =8.0Hz,1H,ArH),6.59(s,1H,ArH),6.41(d, J =8.0Hz,1H,ArH),4.32-4.29(m,4H,CH 2 ),4.26-4.22(m,4H,CH 2 ),3.70(t, J =4.5Hz,2H,CH 2 ),3.60(t, J=4.5Hz,4H,CH 2 ),3.56(t, J =4.5Hz,2H,CH 2 ),3.54-3.52(m,4H,CH 2 ),3.50-3.48(m,4H,CH 2 ),3.46-3.43(m,4H,CH 2 ),3.40-3.38(m,4H,CH 2 ),3...

Embodiment 3

[0041] Embodiment 3 (M=Si, m=8, R 1 =R 2 = H, α monosubstituted)

[0042] 1) Add compound 10.5g (1.27mmol) and compound 20.68g (1.95mmol) into N,N-dimethylformamide (DMF), after both are dissolved, add K 2 CO 3 0.7g (5.07mmol), reacted at 50°C for 6h under the protection of nitrogen. After the reaction was completed, the DMF was spin-dried, and then the crude product was extracted with dichloromethane, and then the volume ratio of dichloromethane-methanol was 30:1 as the eluent, and the compound 3 (0.4 g) was obtained by separation on a silica gel column. 1 HNMR (500MHz, CDCl 3 ): δ 8.49(s,1H,ArH),7.62(s,1H,ArH),7.36(s,1H,ArH),7.28(t, J =8.0Hz,1H,ArH),7.19(t, J =8.0Hz,1H,ArH),7.01(t, J =8.0Hz,1H,ArH),6.88(d, J =8.0Hz,1H,ArH),6.75(s,1H,ArH),6.55(d, J =8.0Hz,1H,ArH),4.89-4.86(m,4H,CH 2 ),4.78-4.75(m,4H,CH 2 ),3.92(t, J =4.5Hz,2H,CH 2 ),3.77(t, J =4.5Hz,4H,CH 2 ),3.64(t, J =4.5Hz,2H,CH 2 ),3.55-3.53(m,2H,CH 2 ),3.49-3.47(m,4H,CH 2 ),3.43-3.40(m,4H,CH 2 ),3.30...

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Abstract

The invention discloses an erlotinib-phthalocyanine conjugate which targets anti-cancer molecules, and a preparation method as well as an application of the erlotinib-phthalocyanine conjugate. Through introducing erlotinib with a long alcoxyl chain into the periphery of the metal phthalocyanine large ring, the amphipathy, the biocompatibility and the targeting of photo-sensitizer can be increased. The phthalocyanine conjugate is not easy to aggregate, which is beneficial for improving cell uptake rate; meanwhile, the compound is simple in structure and is free from isomer, and the product is easy to purify accordingly. By adopting the compound, the targeting of the photo-sensitizer in photo-dynamics therapy is helpful to be enhanced, and the activity of the photo-sensitizer in photo-dynamics therapy can be enhanced at the same time. As the synthetic method provided by the invention is simple, the side reaction is small, the yield is relatively high, the raw material is easily available and the cost is low, and the preparation method is beneficial for industrial production.

Description

technical field [0001] The invention belongs to the field of synthesis of organic and metal coordination compounds, and relates to a targeted anti-cancer molecule erlotinib phthalocyanine conjugate and its preparation method and application. Background technique [0002] Phthalocyanine is a class of macrocyclic compounds with good photophysical and photochemical properties. It is used in high-tech fields, including semiconductor devices, photovoltaic and solar cells, electrophotography, rectifiers, and photosensitizers for LB film photodynamic therapy. Photosensitizers have great development prospects. [0003] The diversity and structural "tailorability" of phthalocyanine compounds provide the possibility for people to rationally design the required phthalocyanine compounds. Linking phthalocyanine with other functional groups to form new functional materials with complementary functions is one of the important development directions of phthalocyanine compounds. However, m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61K47/48A61K31/517A61P35/00
Inventor 薛金萍刘见永李俊张凤玲黄琪
Owner FUZHOU UNIV
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