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An amphiphilic anticancer photosensitizer with a large two-photon absorption cross-section and its preparation and application

A two-photon absorption and amphiphilic technology, applied in the field of biomedicine, can solve the problems of low two-photon absorption efficiency, poor biocompatibility and tumor targeting, and achieve good tumor cell permeability and good two-photon cell imaging Effect, the effect of strong lethality

Active Publication Date: 2016-06-01
SOUTH CHINA NORMAL UNIVERSITY
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Problems solved by technology

[0006] In order to overcome the problems of low two-photon absorption efficiency, poor biocompatibility and tumor targeting of existing clinical porphyrin photosensitizers, the primary purpose of the present invention is to provide an amphiphilic anticancer drug with a large two-photon absorption cross-section Photosensitizer

Method used

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  • An amphiphilic anticancer photosensitizer with a large two-photon absorption cross-section and its preparation and application
  • An amphiphilic anticancer photosensitizer with a large two-photon absorption cross-section and its preparation and application
  • An amphiphilic anticancer photosensitizer with a large two-photon absorption cross-section and its preparation and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Under nitrogen protection, combine 499.1mg (0.5mmol) ZnP, 102.0mg (0.25mmol) BD, 55.0mg (0.25mmol) 4-iodophenol and catalyst 28.9mg (0.025mmol) tetrakis (triphenylphosphine) Palladium (Pd(PPh 3 ) 4 ), 9.5 mg (0.05 mmol) of cuprous iodide (CuI) were dissolved in 20 mL of a mixed solvent (volume ratio 1:1) of dry tetrahydrofuran and triethylamine, and the temperature was raised to 45° C., TLC detected that the reaction was terminated, and the solvent was removed to obtain The crude product was separated by silica gel chromatography to obtain the purple porphyrin intermediate BD-ZnP-OH with a yield of 46%.

[0042] Characterization data: 1 HNMR (CDCl 3 / 5%d 5 -Pyridine): δ3.31(s,6H),3.48(q,J=4.40Hz,4H),3.62(q,J=4.92Hz,4H),3.68(t,J=4.12Hz,4H),3.77 (t, J=3.28Hz, 4H), 3.95(t, J=4.48Hz, 4H), 4.34(t, J=4.44Hz, 4H), 6.61(dd, J=1.44Hz, J=2.60Hz, 2H ),7.08(m,4H),7.34(m,2H),7.61(m,2H),7.75(m,6H),7.89(d,J=6.48Hz,2H),8.15(d,J=8.20Hz ,2H),8.87(d,J=4.56Hz,2H),8.92(d,J=4.56Hz...

Embodiment 2

[0054] (1) Under nitrogen protection, combine 499.1mg (0.5mmol) ZnP, 102.0mg (0.25mmol) BD, 55.0mg (0.25mmol) 4-iodophenol and catalyst 57.8mg (0.05mmol) tetrakis (triphenylphosphine) Palladium (Pd(PPh 3 ) 4 ), 19.0mg (0.1mmol) of copper iodide (CuI) was dissolved in 20mL of a mixed solvent (volume ratio 1:1) of dry tetrahydrofuran and triethylamine, the temperature was raised to 45° C., TLC detected that the reaction was terminated, and the solvent was removed to obtain The crude product was separated by silica gel chromatography to obtain the purple porphyrin intermediate BD-ZnP-OH with a yield of 48%.

[0055] (2) Under nitrogen protection, 62.5 mg (0.05 mmol) of the purple porphyrin intermediate obtained in step (1) BD-ZnP-OH, 207.0 mg (0.5 mmol) of diiodotriethylene glycol (I-PEG -I)( figure 1 shown in ) and 138mg (1mmol) potassium carbonate (K 2 CO 3 ) was dissolved in 5 mL of anhydrous DMF, the temperature was raised to 65°C, the reaction was terminated by TLC dete...

Embodiment 3

[0058] (1) Under nitrogen protection, combine 499.1mg (0.5mmol) ZnP, 102.0mg (0.25mmol) BD, 55.0mg (0.25mmol) 4-iodophenol and catalyst 57.8mg (0.05mmol) tetrakis (triphenylphosphine) Palladium (Pd(PPh 3 ) 4 ), 19.0mg (0.1mmol) of copper iodide (CuI) was dissolved in 20mL of a mixed solvent (volume ratio 1:1) of dry tetrahydrofuran and triethylamine, the temperature was raised to 65°C, TLC detected that the reaction was terminated, and the solvent was removed to obtain The crude product was separated by silica gel chromatography to obtain the purple porphyrin intermediate BD-ZnP-OH with a yield of 42%.

[0059] (2) Under nitrogen protection, 62.5mg (0.05mmol) of the purple porphyrin intermediate obtained in step (1) BD-ZnP-OH, 103.5mg (0.25mmol) of diiodotriethylene glycol (I-PEG -I)( figure 1 shown in ) and 69mg (0.5mmol) of potassium carbonate (K 2 CO 3 ) was dissolved in 5 mL of anhydrous DMF, the temperature was raised to 85°C, the reaction was terminated by TLC detecti...

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Abstract

The invention discloses an amphiphilic anticancer photosensitizer with a big two-photon absorption section as well as preparation and application thereof. The preparation of the amphiphilic anticancer photosensitizer comprises the following steps: under the action of ZnP, BD, 4-iodophenol tetrakis (triphenylphosphine) palladium and CuI, preparing an intermediate BD-ZnP-OH; then enabling the intermediate to react with diiodo tetraethylene glycol under the action of potassium carbonate and preparing an intermediate BD-ZnP-I; finally preparing the amphiphilic anticancer photosensitizer BD-ZnP-P through the intermediate and the triphenylphosphine. Through spectroscopic analysis, the obtained very high singlet oxygen quantum yield of the photosensitizer is 49 percent; finally, as the photosensitizer has the very big two-photon absorption section, 1725 GM is reached; meanwhile, in-vitro photodynamic test results in HeLa, A549, MCF-17 and HK-1 tumor cells show that the amphiphilic anticancer photosensitizer has very good tumor cell permeability and tumor cell killing ability under photo-induction.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to an amphiphilic anticancer photosensitizer with a large two-photon absorption cross section and its preparation and application. Background technique [0002] Malignant tumor is the first killer that endangers human life and health. Photodynamic therapy (PDT) is a minimally invasive tumor therapy based on photosensitizers, excitation light and singlet oxygen. PDT has the advantages of minimally invasive, less toxic and side effects, and high targeting, and has made remarkable achievements in the treatment of malignant tumors. It has become an important means of treating tumors in my country, Europe, America, Japan and many other countries. Among them, photosensitizer is the core of photodynamic therapy. The photodynamic activity, light absorption characteristics and targeting characteristics of photosensitizer determine its practicability and scope of application in clinica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6561A61K41/00A61P35/00
Inventor 张涛邢达吴宝艳邹争志黄伟国黄嘉良
Owner SOUTH CHINA NORMAL UNIVERSITY
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