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Chlorin galactoside compounds as well as preparation method and application thereof

A technology of galactoside and chlorin, which is applied in the field of chemical medicine, can solve the problems of small absorption coefficient, complex method, poor tumor cell selectivity, etc., and achieves the effects of easy control of conditions, simple synthesis method and favorable production.

Inactive Publication Date: 2018-02-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the first-generation and second-generation photosensitizers have been used, there are still many defects: the absorption coefficient at the maximum absorption wavelength of the red light treatment area is small, so that the 630nm laser does not kill the tumor deeply enough; the selectivity to tumor cells is poor, Moreover, it has disadvantages such as limited enrichment capacity and residence time.
Chen Gaojian et al. (a complex porphyrin sugar-containing photosensitizer and its preparation method, 2013, announcement number: CN103285403B) reported that a sugar-containing polymer complexed porphyrin can be used as a photosensitizer, but since the product is a polymer, Non-single product, which brings great difficulties to further drug development, and the maximum absorption wavelength of artificially synthesized porphyrin is relatively short; Mikhail A.Grin et al. Grin, etal, Journal of Porphyrins and Phthalocyanines, 2009, 13:336–345) use click chemistry to glycosylate the porphine skeleton, but this method is complicated and requires the protection of the coordination center in advance

Method used

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  • Chlorin galactoside compounds as well as preparation method and application thereof
  • Chlorin galactoside compounds as well as preparation method and application thereof
  • Chlorin galactoside compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of compound 3b

[0049] Compound 1 (CHC) (100.0 mg) was dissolved in DMF (1.7 ml). N 2 Protected and stirred in an ice bath. EDCI (38.5 mg) was added, stirring continued in the ice bath, and the ice bath was removed. After stirring at room temperature for 2.5h, 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-galactopyranose hydrochloride (83.3 mg) was dissolved in DMF ( 1ml), add 40μl of triethylamine and mix thoroughly. Add it into the reaction solution, stir at room temperature, and monitor the reaction termination by TLC. The reaction solution was diluted with 50 ml of dichloromethane, and extracted with aqueous citric acid (25 mL×3). The organic phase was dried, filtered and the filtrate was concentrated. Separation by column chromatography, the elution condition was (dichloromethane / methanol=9:1), and the intermediate product 2b (57.8mg) was obtained; the compound 2b was dissolved in DMF (0.6ml), added iodomethane (31 μl), carbonic acid Potassium (15...

Embodiment 2

[0053] Synthesis of compound 6b

[0054] Dissolve methylated chlorophyllin a (100.0 mg) in CHCl 3 (1.8ml), N 2 Protected and stirred in an ice bath. EDCI (38.5 mg) was added, stirring continued in the ice bath, and the ice bath was removed. After stirring at room temperature for 2.5h, 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-galactopyranose hydrochloride (83.1 mg) was dissolved in DMF ( 1ml), add 40μl of triethylamine and mix thoroughly. Add it into the reaction solution, stir at room temperature, and monitor the reaction termination by TLC. The reaction solution was diluted with 50 ml of dichloromethane, and extracted with aqueous citric acid (25 mL×3). The organic phase was dried, filtered and the filtrate was concentrated. Separation by column chromatography, the elution condition was (dichloromethane / methanol=9:1), and the intermediate product 5b (55.1mg) was obtained; the compound 5b was dissolved in methanol (0.6ml), and 1 times the amount (molar ratio) of met...

Embodiment 3

[0058] Synthesis of Compound 11

[0059]

[0060] Compound 1 (100 mg) was dissolved in 5% H 2 SO4 / MeOH solution (2ml), N 2 Protection, stirring at room temperature, TLC monitoring reaction termination. Rotary evaporator concentrated to remove methanol. The reaction solution was diluted with dichloromethane (25ml), washed with deionized water, aqueous sodium bicarbonate solution, and saturated NaCl solution once (25ml). The organic phase was dried, filtered and the filtrate was concentrated. After separation by column chromatography, the elution condition was (dichloromethane / methanol=19:1), and 96.2 mg was obtained with a yield of 97%. Compound 8: 1 H NMR (400MHz, CDCl3) δ9.64(1H, s, 10-H), 9.50(1H, s, 5-H), 8.72(1H, s, 20-H), 8.01(1H, dd, J= 17.6, 11.6Hz, 3 1 -H),6.32(1H,dd,J=17.6Hz,1.2Hz,3 2a -H),6.12(1H,dd,J=11.6,1.2Hz,3 2b -H),5.51(1H,d,J=18Hz,15 1a -H),5.26(1H,d,J=18Hz,15 1b -H),4.46(1H,q,J=7.6Hz,18-H),4.12(1H,d,J=7.2Hz,17-H),3.82(3H,s,12 1 -H),3.74(2H,dd,J...

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Abstract

The invention discloses chlorin galactoside compounds as well as a preparation method and application thereof, and belongs to the technical fields of chemistry and medicines. The chlorin galactoside compounds provided by the invention improve targeting effects on tumor cells by a photosensitizer and a sound sensitizer through selectively combining with galectin. The in-vitro antitumor activity evaluation shows that the chlorin galactoside compounds provided by the invention have higher photoactivity and sound activity on human hepatocellular carcinoma cell Hep G2 compared with that of a chlorin e 6 which is used as a control group; the compounds provided by the invention can be used for preparation of the photosensitizer and the sound sensitizer used in photodynamic therapy and sonodynamictherapy methods of tumor therapy; and the preparation process of the compounds is simple, the reaction conditions are easy to control, and the compounds are beneficial for production.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and relates to a class of chlorin-galactoside compounds and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT) is a new tumor treatment technology. It uses a photosensitizer to produce singlet oxygen ( 1 o 2 ) and superoxide free radicals, they can efficiently kill tumor cells. Photodynamic therapy has very obvious advantages in the treatment of tumors with large areas and deep growth sites. [1,2] . Its outstanding features are mainly manifested in: 1) Good tissue selectivity, can specifically kill tumor cells; 2) Low toxicity and side effects, photosensitizers will not undergo photosensitization without light exposure; 3) Applicable to a variety of tumors, such as skin Cancer, oral cancer, esophageal cancer, lung cancer, bladder cancer, and genital tumors; 4) The treatment cycle is short, and the curative effect generally ap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/06C07H13/04C07H5/06C07H1/00A61P35/00
CPCC07H1/00C07H5/06C07H13/04C07H13/06
Inventor 郭修晗王世盛蔡蕊赵伟杰李悦青李广哲田诗德
Owner DALIAN UNIV OF TECH
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