Amphiphilic porphyrin-based photosensitizer and preparation and applications thereof

A porphyrin-based photosensitizer and amphiphilic technology, applied in the field of biomedicine, can solve the problems of poor biocompatibility and tumor targeting, and achieve the effect of good tumor cell uptake rate and efficient uptake

Active Publication Date: 2015-04-08
SOUTH CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the problems of poor biocompatibility and tumor targeting of existing clinical porphyrin photosensitizers, the primary purpose of the present invention is to provide an amphiphilic porphyrin photosensitizer

Method used

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  • Amphiphilic porphyrin-based photosensitizer and preparation and applications thereof
  • Amphiphilic porphyrin-based photosensitizer and preparation and applications thereof
  • Amphiphilic porphyrin-based photosensitizer and preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Under the protection of nitrogen, the porphyrin raw material 49.5mg (0.1mmol) P 1 -OH(5,15-bis(4-hydroxyphenyl)-21H,23H-porphyrin)( figure 2 shown in), 207.0mg (0.5mmol) diiodotriethylene glycol (I-PEG-I) ( figure 1 shown in ) and 138mg (1.0mmol) potassium carbonate (K 2 CO 3 ) was dissolved in 5mL of anhydrous DMF, the temperature was raised to 65°C, the reaction was terminated by TLC detection, and the solvent was removed to obtain a crude product, which was separated with a silica gel chromatographic column to obtain the purple porphyrin intermediate P 1 -I, structural formula such as image 3 As shown in , the yield was 88%.

[0038] Characterization data: 1 HNMR (CDCl 3 ):δ-3.15(s,2H),3.12(t,J=6.76Hz,4H),3.52(m,4H),3.58(m,8H),3.67(m,4H),3.75(dt,J= 5.24Hz, J=6.36Hz, 4H), 3.94(t, J=4.6Hz, 4H), 4.34(t, J=4.66Hz, 4H), 7.36(dd, J=1.64Hz, J=6.08Hz, 2H ),7.66(t,J=7.82Hz,2H),7.85(d,J=2.4Hz,3H),7.87(s,1H),9.10(d,J=4.56Hz,4H),9.37(d,J =4.60Hz, 4H), 10.30(s, 2H)...

Embodiment 2

[0044] (1) Under nitrogen protection, 56.0mg (0.05mmol) Porphyrin raw material 2 -OH(5,10,15-tris(4-(triethylene glycol monomethyl ether))-20-(4-hydroxyphenyl)-21H,23H-porphyrin)( figure 2 shown in), 103.5mg (0.25mmol) diiodotriethylene glycol (I-PEG-I) ( figure 1 shown in ) and 69mg (0.5mmol) of potassium carbonate (K 2 CO 3 ) was dissolved in 5mL of anhydrous DMF, the temperature was raised to 65°C, the reaction was terminated by TLC detection, and the solvent was removed to obtain a crude product, which was separated with a silica gel chromatographic column to obtain the purple porphyrin intermediate P 2 -I, structural formula such as image 3 As shown in , the yield was 81%.

[0045] Characterization data: 1 HNMR (CDCl 3 ):δ-2.76(s,2H),3.27(t,J=6.72Hz,2H),3.41(s,9H),3.60(m,8H),3.71(m,10H),3.81(m,10H) ,3.88(m,8H),4.09(t,J=4.98Hz,8H),4.42(m,8H),7.29(d,J=6.10Hz,8H),8.15(d,J=6.1Hz,8H) ,8.89(s,8H); MALDI-TOF MS:calcd.for[M + ]:1403.3936,found:1403.4206.

[0046] (2) ...

Embodiment 3

[0051] (1) Under nitrogen protection, 56.0mg (0.05mmol) Porphyrin raw material 3 -OH(5,10,15-tris(4-(triethylene glycol monomethyl ether))-20-(3-hydroxyphenyl)-21H,23H-porphyrin)( figure 2 shown in), 103.5mg (0.25mmol) diiodotriethylene glycol (I-PEG-I) ( figure 1 shown in ) and 69mg (0.5mmol) of potassium carbonate (K 2 CO 3 ) was dissolved in 5mL of anhydrous DMF, the temperature was raised to 65°C, the reaction was terminated by TLC detection, and the solvent was removed to obtain a crude product, which was separated with a silica gel chromatographic column to obtain the purple porphyrin intermediate P 3 -I, structural formula such as image 3 As shown in , the yield was 79%.

[0052] Characterization data: 1 HNMR (CDCl 3 ):δ-2.79(s,2H),3.13(t,J=6.76Hz,2H),3.43(s,9H),3.53(m,2H),3.60(m,10H),3.66(m,2H) ,3.73(m,8H),3.78(m,6H),3.87(m,6H),3.94(t,J=4.64Hz,2H),4.04(t,J=4.72Hz,6H),4.31(t, J=4.96Hz, 2H), 4.41(t, J=4.52Hz, 6H), 7.28(d, J=8.36Hz, 6H), 7.32(m, 1H), 7.61(t, J=7...

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Abstract

The invention discloses an amphiphilic porphyrin-based photosensitizer and preparation and applications thereof. The amphiphilic porphyrin-based photosensitizer disclosed by the invention is prepared through the steps that: Pn-OH and diiodo-tetraethylene glycol are reacted under the action of potassium carbonate, so that a porphyrin intermediate Pn-I is obtained; the intermediate acts with triphenylphosphine, so that a target metal-free amphiphilic porphyrin-based photosensitizer Pn-P is obtained; and the metal-free amphiphilic porphyrin-based photosensitizer Pn-P can act with metallicacetate, so that a target metal-bearing amphiphilic porphyrin-based photosensitizer PMn-P is obtained. Through spectroscopic analysis, a situation that the amphiphilic porphyrin-based photosensitizer has extremely strong red fluorescence, and also has an extremely high singlet oxygen quantum yield (41-57%) is measured. Finally, test results of cellular uptake rate in tumor cells HK-1 show that the product has extremely good tumor cell permeability, and can be efficiently taken in by tumor cells.

Description

technical field [0001] The invention belongs to the field of biomedicine, in particular to an amphiphilic porphyrin photosensitizer 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 clinical treatment. The molecular structure, energy band structure, e...

Claims

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Application Information

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