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pdt compound and its preparation method and use

A compound and drug technology, applied in the field of photosensitizing compounds and their preparation, can solve the problems of inability to realize diagnosis and treatment at the same time, complex composition of clinical photosensitizers, limited tissue penetration depth, etc., so as to achieve fluorescence imaging and reduce damage to the body. , the effect of large tissue penetration depth

Active Publication Date: 2022-06-03
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, PDT also has some disadvantages: In PDT, photosensitizers generally need to be used together with nanoparticles with luminescent properties to determine the aggregation of photosensitizers in the body, which makes the composition of clinical photosensitizers complicated; The half-life of the compound (or photosensitizer) in the body roughly judges the clearance rate of the photosensitive compound in normal tissues to determine the timing of phototherapy, which also leads to low therapeutic selectivity and strong side effects of photosensitivity throughout the body
At present, porphyrin compounds are the research hotspots of PDT compounds, but most of them are only suitable for diagnosis or only for photodynamic therapy, which cannot realize diagnosis and treatment at the same time, and the tissue penetration depth is also very limited

Method used

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  • pdt compound and its preparation method and use
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  • pdt compound and its preparation method and use

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preparation example Construction

[0071] The present invention also provides the preparation method of the above-mentioned PDT compound, comprising:

[0072] Step 1: Under anaerobic conditions, porphyrin and the acetylacetonate of ionic ligand M are reacted at 200-240 ° C for 1-3 h to obtain intermediate I; the sodium salt of intermediate I and axial ligand L is dissolved in chloroform / Reaction in the mixed solvent of methanol=1 / 1 to obtain intermediate product I;

[0073] Step 2:

[0074] Under an inert gas atmosphere, the intermediate product I is dissolved in the organic solvent I, a reducing agent is added dropwise at -100 to -60° C., and the reaction is completed in the dark after returning to room temperature to obtain a PDT compound.

[0075] Wherein, in step 1, preferably the acetylacetonate of described ionic ligand M is sodium salt or potassium salt, and its molar weight is 1~2 times of porphyrin molar weight; The acetylacetonate of porphyrin and ionic ligand M is The reaction was completed in tri...

Embodiment 1

[0106] Example 1 Synthesis of compound Lu-1

[0107]

[0108] Step 1: Add Lu(acac) 6H to the Schlenk tube 2 O (lutetium acetylacetonate hexahydrate) 0.10 mmol, porphyrin a (0.05 mmol) and 8 mL of solvent trichlorobenzene, degassed, filled with nitrogen, and sealed at 240° C. to react for 1 to 3 h. After monitoring the reaction system until there was no porphyrin fluorescence, it was cooled to room temperature. Separated by silica gel column chromatography, eluted with petroleum ether, dichloromethane, dichloromethane / methanol=5 / 1, and collected rare earth porphyrin. Rare earth porphyrin and Ligand tris(dimethyl phosphite) Sodium cyclopentadienyl cobalt(Ⅲ) (NaL OMe ) (0.05mmol) dissolved in 10mL CHCl 3 / MeOH=1 / 1, react at 60°C for 2 h, remove the solvent by rotary evaporation, separate the solid by silica gel column chromatography, and recrystallize from dichloromethane / n-hexane (1~10:10) to obtain Lu-a.

[0109] Step 2: Under a nitrogen atmosphere, Lu-a was dissolve...

Embodiment 2

[0115] The synthesis of embodiment 2 compound Lu-2

[0116]

[0117] The reaction process is basically similar to Example 1, and the difference is:

[0118] After obtaining Lu-1, further use BF 3 ·Et 2 O catalyzed, etherified in methanol solvent to obtain Lu-2.

[0119] Structural Characterization Data:

[0120] UV / Vis(CH 2 Cl 2 ,25℃):λ max (nm)(logε): 345(4.99), 397(5.15), 509(3.98), 545(4.50), 690(4.16), 749(5.10).

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Abstract

The invention provides a PDT compound and its preparation method and application. Stable complexes are formed by axial ligands, ionic ligands, and structurally adjusted porphyrin compounds, so that the absorption spectrum of the compound is red-shifted, and a compound with strong phototoxicity, large tissue penetration depth, and good biocompatibility is obtained. PDT compounds also have both photothermal effect and fluorescence properties, which help to improve the therapeutic effect and reduce the damage of photodynamic therapy to the body.

Description

technical field [0001] The present invention relates to the field of photodynamic therapy (PDT), in particular to a photosensitive compound and its preparation method and use. Background technique [0002] After the photosensitive compound is enriched in the diseased tissue, the photosensitive compound is activated by light, and the excited photosensitive compound kills the lesion to achieve the purpose of treating the disease. This method is called photodynamic therapy (PDT). Photosensitive compounds are compounds that play a decisive role in photodynamic therapy. [0003] PDT has the advantages of high selectivity, non-invasive or minimal trauma, reproducible treatment, and low toxicity, and has increasingly shown an important role in the comprehensive treatment of tumors. However, PDT also has some disadvantages: in PDT, photosensitizing compounds generally need to be used together with nanoparticles with luminescent properties to determine the aggregation of photosensit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C07F15/06C09K11/06A61K41/00A61K49/00A61K49/22A61P35/00G01N21/33G01N21/3577G01N21/359G01N21/64
CPCC07F15/06C09K11/06C07F5/022A61K41/0076A61K41/0052A61P35/00A61K49/0036A61K49/22G01N21/6428G01N21/6456G01N21/33G01N21/359G01N21/3577C09K2211/187C09K2211/1077C09K2211/1044G01N2021/6417A61K2300/00
Inventor 张俊龙杨字舒王炳武张洪
Owner PEKING UNIV
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