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PDT compound and preparation method and application thereof

A compound and complex 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. Injury, effect of large tissue penetration depth

Active Publication Date: 2021-12-03
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 preparation method and application thereof
  • PDT compound and preparation method and application thereof
  • PDT compound and preparation method and application thereof

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preparation example Construction

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

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

[0073] Step two:

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

[0075] Wherein, in step 1, it is preferred that the acetylacetonate salt of the ion ligand M is a sodium salt or a potassium salt, and its molar weight is 1 to 2 times that of the porphyrin molar weight; The reaction was completed in tric...

Embodiment 1

[0106] The synthesis of embodiment 1 compound Lu-1

[0107]

[0108] Step 1: Add Lu(acac)·6H to the Schlenk tube 2 O (lutetium acetylacetonate hexahydrate) 0.10mmol, porphyrin a (0.05mmol) and 8mL solvent trichlorobenzene, degassed, filled with nitrogen, sealed tube at 240°C for 1-3h. After monitoring the reaction system until there was no porphyrin fluorescence, it was cooled to room temperature. Separated by silica gel column chromatography, eluting with petroleum ether, dichloromethane, and dichloromethane / methanol=5 / 1 respectively, the rare earth porphyrins were collected. Rare earth porphyrin and Ligand tris (dimethyl phosphite) sodium cyclopentadienyl cobalt (Ⅲ) acid (NaL OMe ) (0.05mmol) dissolved in 10mL CHCl 3 / MeOH=1 / 1, react at 60°C for 2h, 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: Dissolve Lu-a in anhydrous an...

Embodiment 2

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

[0116]

[0117] Reaction process is substantially similar to embodiment 1, difference is:

[0118] After getting Lu-1, further use BF 3 ·Et 2 O catalyzed etherification in methanol solvent to give 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 a preparation method and application thereof. A stable complex is formed by an axial ligand, an ion ligand and a structure-adjusted porphyrin compound, so that red shift of an absorption spectrum of the compound is realized, the PDT compound with strong phototoxicity, large tissue penetration depth and good biocompatibility is obtained, and the PDT compound also has photothermal effect and fluorescence property, the treatment effect can be improved, and the damage of photodynamic therapy to an organism can be reduced.

Description

technical field [0001] The invention relates to the field of photodynamic therapy (PDT), in particular to a photosensitive compound and its preparation method and application. 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). Photosensitizing compounds are compounds that play a decisive role in photodynamic therapy. [0003] PDT has the advantages of high selectivity, non-invasive or minimally invasive, repeatable treatment, and low toxicity, and it is increasingly playing an important role in the comprehensive treatment of tumors. 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 photosensitiz...

Claims

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Application Information

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Patent Type & Authority Applications(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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