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Preparation and application of a water-soluble porphyrin complex

A porphyrin complex, water-soluble technology, applied in the field of preparation of water-soluble porphyrin complex, can solve the problems of limited PDT treatment application, long residence time, limited depth of light penetration tissue, etc., and achieve good biocompatibility , simple chemical structure, deep tissue penetration depth

Active Publication Date: 2020-03-17
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, most of the drugs that have been approved by the drug regulatory departments of many countries for clinical application are mixtures, which have a long residence time in the body and need to be protected from light for more than 4 weeks.
In addition, some porphyrin complexes have limited light penetration tissue depth (below 0.5 cm) due to red blood cells and light scattering in vivo, limiting the therapeutic application of PDT on larger tumors.

Method used

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  • Preparation and application of a water-soluble porphyrin complex
  • Preparation and application of a water-soluble porphyrin complex
  • Preparation and application of a water-soluble porphyrin complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of polyfluorene

[0025]

[0026] Preparation of Compound 2: Add 1 (3.0 mmol), 1,6-dibromohexane (27.0 mmol), and tetrabutylammonium bromide (0.3 mmol) into a reaction flask, vacuumize, and add 200 mL KOH saturated solution. Stir at 75°C for 1 h, cool down to room temperature, extract with dichloromethane, distill off 1,6-dibromohexane under reduced pressure, load the sample by dry method, and purify by column chromatography to obtain 2. Yield: 83%. 1 HNMR (400MHz, CDCl 3 )δ7.54(s,1H),7.52(s,1H),7.47(d,J=1.7Hz,1H),7.45(d,J=1.7Hz,1H),7.43(d,J=1.6Hz, 2H),5.30(s,2H),3.30(t,J=6.8Hz,4H),1.98–1.86(m,4H),1.74–1.61(m,4H),1.28–1.02(m,10H),0.65 –0.52(m,4H).

[0027] Preparation of Compound 4: Add 3 (3.0 mmol), 1,6-dibromohexane (27.0 mmol), and tetrabutylammonium bromide (0.3 mmol) into a reaction flask, vacuumize, and add 200 mL KOH saturated solution. Stir at 75°C for 1 h, cool down to room temperature, extract with dichloromethane, distill...

Embodiment 2

[0034] Embodiment 2: the preparation of water-soluble porphyrin complex

[0035]

[0036] Preparation of compound 12: Add 11 (2.5mmol) into the reaction flask, vacuumize, add dichloromethane (250mL), blow nitrogen for 20min, add pyrrole (2.5mmol), boron trifluoride diethyl ether (0.8mmol), normal temperature Stir for 3h, then add DDQ (2.0mmol), continue the reaction for 1h, filter with suction, spin off the DCM in the filtrate under reduced pressure, and purify by column chromatography to obtain 12. Yield 15%. 1 H NMR (400MHz, CDCl 3 )δ8.82(s,8H),8.21(q,J=7.9Hz,8H),7.52(s,4H),6.98(d,J=14.8Hz,2H),5.30(s,2H),1.53( d, J=21.4Hz, 48H), -2.82(s, 2H).

[0037] The preparation of compound 13: 12 (1mmol), 10 (3mmol), Pd[P(Ph) 3 ] 4 (0.01mmol) into the reaction flask, vacuumize, add toluene (150mL), ethanol (20mL), potassium carbonate solution (40mL, 2mol / L), stir at 85°C for 2h, cool down to room temperature, extract with dichloromethane, Dry loading and column chromatography ...

Embodiment 3

[0040] Embodiment 3: Absorption and emission spectrum test of porphyrin complex

[0041] The spectrum test concentration adopted in the present invention is 10 μM, the test solvent is PBS solution mixed with 1% DMSO, and when the emission spectrum is measured, the excitation wavelength is 520 nm. The absorption and emission spectra of porphyrin as figure 1 shown. The complex exhibits strong absorption at 320-450nm in the ultraviolet region and 500-550nm in the visible light region. In particular, the complex can be excited by visible light, which greatly reduces the damage to cells caused by the excitation light source in cell imaging experiments. Its emission is wide, and the emission peak is located at 710nm. Red light emission increases the penetration depth of biological tissue, making it more suitable for biological imaging. figure 2 It is the emission spectrum of porphyrin under different oxygen concentrations, which shows that the emission decreases gradually with th...

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Abstract

The invention discloses preparation and application of a water-soluble porphyrin complex. The complex is prepared from a porphyrin center and a novel fluorene trimer unit. Luminous intensity of the complex can be reduced with increase of oxygen concentration, and emission lifetime of the complex can be shortened with increase of the oxygen concentration; the complex has relatively high singlet oxygen quantum yield; state change of cells before and after culture can be detected with confocal imaging and lifetime imaging technologies, and therefore, it is verified that the complex has better photodynamics therapy effect. The complex has broad application prospect in the aspects of bioimaging and photodynamics therapy.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to a preparation method of a class of water-soluble porphyrin complex and its application research in the fields of cell imaging and photodynamic therapy. Background technique [0002] Photodynamic therapy is a new disease treatment method based on the interaction of light, photosensitizers and oxygen. The research on photosensitizers (photodynamic therapy drugs) is the key to affecting the prospects of photodynamic therapy. A photosensitizer is a special chemical substance whose basic function is to transfer energy. It can absorb photons and be excited, and then quickly transfer the absorbed light energy to another component of the molecule, so that it is excited and the photosensitizer itself returns to energy. to the ground state. As the first photosensitizer, Porfimer Sodium, was approved for marketing in the United States, Canada, the Europea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/31G01N21/33G01N21/64A61K41/00A61P35/00
CPCA61K41/0076C07D487/22C09K11/06C09K2211/1416C09K2211/185G01N21/314G01N21/33G01N21/64G01N21/6408G01N2021/3155
Inventor 赵强刘淑娟宋如箱吕壮黄维涂真珍彭佳丽
Owner NANJING UNIV OF POSTS & TELECOMM
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