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Near-infrared iodo-bodipy photosensitizer and preparation method thereof

A fluoroboron dipyrrole photosensitizer and a technology for fluoroboron dipyrrole, which are applied in the field of near-infrared iodo fluoroboron dipyrrole photosensitizers and the preparation thereof, can solve the problems of many synthesis steps, poor solubility, limited application and the like, and achieve The effect of low cell damage, easy modification and high molar absorptivity

Inactive Publication Date: 2017-06-30
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most near-infrared fluoroboron-dipyrrole dyes have many steps to synthesize, are difficult, and have poor solubility, which limits their further application in the fields of biology, environment, and medicine.

Method used

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  • Near-infrared iodo-bodipy photosensitizer and preparation method thereof
  • Near-infrared iodo-bodipy photosensitizer and preparation method thereof
  • Near-infrared iodo-bodipy photosensitizer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Equipped with a water separator in the round bottom flask, 2,6-diiodo BODIPY (123.6mg, 0.20mmol), 2-formyl-6,10-dibromotripolyindene (0.138g, 0.2mmol) and p- Toluenesulfonic acid (40mg) was dissolved in 25mL toluene and 2mL piperidine, the mixture was heated to reflux at 140°C, and the solvent was collected until evaporated to dryness. The reactant was concentrated and subjected to silica gel column chromatography, the eluent was (petroleum ether: CH 2 Cl 2 =1:1), a green solid A (113.7 mg, 28.79%) was obtained. Esi-MS: calcd for C 102 h 99 BBr 4 f 2 I 2 N 2 1975.1597, found: 1974.27598 (M - ); 1 H NMR: (600MHz, CDCl 3 )δ8.36(t, J=7.80Hz, 3H), 8.33(s, 1H), 8.19(t, J=9.00Hz, 4H), 7.92(s, 1H), 7.89(s, 1H), 7.79( d, J=7.20Hz, 2H), 7.69(s, 2H), 7.59(d, J=1.80Hz, 2H), 7.53-7.50(m, 4H), 7.37-7.35(m, 2H), 703(s , 2H), 3.02-2.92(m, 12H), 2.40(s, 3H), 2.29-2.26(m, 4H), 2.15-2.06(m, 14H), 1.53(s, 6H), 0.30-0.21(m , 36H); UV-vis: 315nm, 357nm, 409nm, 682nm ( figure 1...

Embodiment 2

[0030] Equipped with a water trap in the round bottom flask, 2,6-diiodo BODIPY (185.4mg, 0.30mmol), 2-formyl-6,10-diiodotripolyindene (237.7mg, 0.30mmol) and p Toluenesulfonic acid (50 mg) was dissolved in 25 mL of toluene and 2 mL of piperidine, the mixture was heated to reflux at 140°C, and the solvent was collected until evaporated to dryness. The reactant was concentrated and subjected to silica gel column chromatography, and the eluent was (petroleum ether / CH 2 Cl 2 =7:3), to obtain green solid B (89.7mg, 13.82%). Esi-MS: calcd for C 102 h 99 BF 2 I 6 N 2 2163.16, found: 2163.15 (M + ); 1 H NMR: (600MHz, CDCl 3 )δ8.36(t, J=9.00Hz, 4H), 8.07(t, J=9.00Hz, 4H), 7.91(s, 1H), 7.88(s, 1H), 7.80-7.77(m, 4H), 7.73-7.69(m, 6H), 7.56(d, J=8.40Hz, 2H), 7.03(s, 2H), 3.01-2.90(m, 12H), 2.40(s, 3H), 2.28-2.25(m, 4H), 2.15-2.05(m, 14H), 1.53(s, 6H), 0.29-0.21(m, 36H); UV-vis: 319nm, 358nm, 407nm, 683nm( image 3 ); Emission Wavelength: 710nm ( Figure 4 ).

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PUM

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Abstract

The invention relates to a kind of near-infrared iodofluoroboron dipyrrole photosensitizer and a preparation method thereof. It is synthesized by Knoevenagel condensation reaction under the catalysis of p-toluenesulfonic acid and piperidine by using terindaldehyde and iodo-BODIPY derivatives. Both the absorption and emission wavelengths are above 680nm, and can penetrate deeply into biological tissues under the irradiation of near-infrared light. It can be used as a superior near-infrared photosensitizer for photodynamic therapy of tumors and cancers. In addition, this type of compound has excellent photophysical properties such as high molar extinction coefficient and good photostability, and has potential application value in laser dyes, biomedicine and other fields.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a near-infrared iodofluoroboron dipyrrole photosensitizer and a preparation method thereof. Background technique [0002] In recent years, photodynamic therapy (PDT) has attracted increasing attention due to its non-invasive treatment for various cancers. Photodynamic therapy relies on photosensitizers combined with specific light radiation to generate singlet oxygen, a cytotoxic agent capable of eradicating tumors through cell damage, vasculature damage, or immune system response. Fluoroboron dipyrrole (BODIPY) derivatives, as a new class of fluorescent dyes, exhibit superior photophysical properties compared to other dyes, and their flexible and easy-to-modify structures help to better adjust their optical properties. However, since BODIPY is a strong fluorescent dye, it is difficult for effective intersystem crossing to occur, and it is usually ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06A61K41/00A61P35/00
CPCC07F5/022A61K41/0057C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1096
Inventor 徐海军孙丹倪百宁郭颖昕朱阳明
Owner NANJING FORESTRY UNIV
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