Acid response water-soluble near-infrared BODIPY light-sensitive agent and preparation method thereof

A water-soluble, near-infrared technology, applied in the field of material science, can solve the problems of poor water solubility, weak light absorption, cumbersome synthesis steps, etc., and achieve the effects of rapid synthesis, simple operation, and simple synthesis and purification

Active Publication Date: 2016-12-07
JIANGSU YAHONG MEDITECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Existing photosensitizers in photodynamic therapy have problems such as poor water solubility, weak light absorption in the near-infrared region, cumbersome synthesis steps, and difficult purification. The absorbing BODIPY photosensitizer has the advantages of good water solubility and strong absorption of light in the near-infrared region.

Method used

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  • Acid response water-soluble near-infrared BODIPY light-sensitive agent and preparation method thereof
  • Acid response water-soluble near-infrared BODIPY light-sensitive agent and preparation method thereof
  • Acid response water-soluble near-infrared BODIPY light-sensitive agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Syringaldehyde is hydrolyzed under acidic conditions to give 3,4,5-trihydroxybenzaldehyde

[0036] Weigh 2.0 g of syringaldehyde into a 250 mL two-necked flask, add about 100 mL of 1,2-dichloroethane, stir evenly, cool to 0°C, add 7.3 g of anhydrous aluminum trichloride, stir for 30 min, and use After 20 min, 8.7 g of pyridine was added using a constant pressure dropping funnel, and then refluxed at 90°C for 4 h. After cooling to 0°C, neutralize to neutral with 3 mol / L hydrochloric acid, extract with about 250 mL of ethyl acetate, wash with ice water 5 times, combine the organic layers, dry over anhydrous sodium sulfate, and distill under reduced pressure to obtain a brown solid. 0.83 g of product was obtained by 200-300 mesh silica gel column chromatography, and the yield was 49%. The obtained product was recrystallized from water to obtain a needle-shaped off-white solid. 1 H NMR (400 MHz, Acetone- d 6 ) δ 9.70 (s, 1H), 6.99 (s, 2H).

Embodiment 2

[0038] Same as Example 1, the difference is that the molar ratio of syringaldehyde to anhydrous aluminum trichloride and pyridine is 1.5:6.0:12.0, and the reaction yield is 40%.

Embodiment 3

[0040] Same as Example 1, the difference is that the molar ratio of syringaldehyde to anhydrous aluminum trichloride and pyridine is 1:8:16, and the reaction yield is 32%.

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Abstract

The invention relates to an acid response water-soluble near-infrared BODIPY light-sensitive agent and a preparation method thereof. The novel BODIPY light-sensitive agent is soluble in water, has absorption performance in a near-infrared area, and has the advantages of being good in water solubility and high in light absorption in the near-infrared area. Meanwhile, the invention further provides the preparation method of the BODIPY light-sensitive agent. Synthesis is quick, and purification is easy. According to the preparation method, by reasonably designing feeding equivalence ratio, the target product can be obtained only through extraction, washing and other simple processing in triglycol monomethyl ether and p-toluenesulfonic acid sulfonylation; by means of the ethyl alcohol re-crystallization method, high-purity BODIPY is obtained; target molecules are synthesized at a high yield through reasonable temperature control. The method has the advantages of being easy to operate, convenient and safe to use and the like. The prepared light-sensitive agent can be soluble in water, the maximum absorption peak is 655 nm, the maximum emission peak is 710 nm, and the light emitting intensity of the light-sensitive agent is gradually improved along with addition of trifluoroacetic acid.

Description

technical field [0001] The invention belongs to the technical field of material science and relates to a photosensitizer for photodynamic therapy, in particular to an acid-responsive water-soluble near-infrared BODIPY photosensitizer and a preparation method. Background technique [0002] Photodynamic therapy is an important method in the treatment of cancer. Photodynamic therapy requires three factors: light, oxygen, and photosensitizers. Photosensitizers play a pivotal role in photodynamic therapy. It is of great significance to quickly and conveniently synthesize photosensitizers with high efficiency by chemical methods. Due to (1) poor water solubility, (2) weak absorption of red light, traditional photosensitizers have limited penetration ability to tissues, (3) complex composition, (4) long residence time in the body, and relatively high skin phototoxicity. major reasons. These shortcomings greatly limit the therapeutic efficacy and wide application of photosensitize...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61K41/00A61P35/00
CPCA61K41/0057C07F5/022
Inventor 王晓军许加龙李秋艳
Owner JIANGSU YAHONG MEDITECH CO LTD
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