Product of Maillard reaction of tryptophan and glucose and its preparation method and application

A technology of Maillard reaction and glucose, applied in the field of medicine, can solve the problem of no tumor inhibitory effect and other problems

Active Publication Date: 2012-06-27
HARBIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there is no information about the inhibitory effect of Maillard products on tumors.

Method used

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  • Product of Maillard reaction of tryptophan and glucose and its preparation method and application
  • Product of Maillard reaction of tryptophan and glucose and its preparation method and application
  • Product of Maillard reaction of tryptophan and glucose and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of the Maillard product of embodiment 1 tryptophan and glucose

[0021] Raw materials: L-tryptophan was purchased from SIGMA; D-glucose was purchased from Tianjin Fengchuan Chemical Reagent Technology Co., Ltd.

[0022] Synthesis of Maillard products of tryptophan and glucose: as figure 1 As shown, take 5 g of L-tryptophan and 40 g of D-glucose and add it to 600 ml of anhydrous methanol, heat and reflux for 5 hours, and evaporate to dryness under reduced pressure at 40 degrees Celsius to 50 ml, add 8 ml of water, and add the resulting solution to the cellulose ( Whatman company, in the 44 * 550mm chromatographic column that CF-11 cellulose) fills, use the n-butanol solution saturated with water to carry out elution, obtain 20ml eluate, vacuum freeze-dry, obtain target product-brown yellow solid 2- 5g.

Embodiment 2

[0023] Synthesis of the Maillard product of embodiment 2 tryptophan and glucose

[0024] Raw materials: L-tryptophan was purchased from SIGMA; D-glucose was purchased from Tianjin Fengchuan Chemical Reagent Technology Co., Ltd.

[0025] Dissolve 0.58g of potassium hydroxide in 12ml of methanol, then add 3g of L-tryptophan, stir to completely dissolve the tryptophan, then add 15ml of methanol solution containing 1.5g of D-glucose. The above solution was stirred and heated to reflux at 70° C. for 2 h. After the reaction, the solution was cooled to room temperature, and the solution was concentrated to 10 ml using a vacuum rotary evaporator, filtered with suction to remove excess amino acids, and the solution was cooled to 0°C. Add acetone dropwise to the solution until no precipitation occurs, and filter with suction to obtain an amorphous yellow powder. The yellow powder was redissolved in methanol, acetone was added dropwise to make it precipitate, and it was suction filtere...

Embodiment 3

[0026] Synthesis of the Maillard product of embodiment 3 tryptophan and glucose

[0027] Raw materials: L-tryptophan was purchased from SIGMA; D-glucose was purchased from Tianjin Fengchuan Chemical Reagent Technology Co., Ltd.

[0028] Materials: Dowex 50W-X8H+ column (10*2cm) was purchased from Dow Company, USA.

[0029] Add 1g of L-tryptophan and 9g of D-glucose into 150ml of chromatographically pure methanol and heat to reflux for 5h. The mixture is concentrated under reduced pressure, dissolved in 50ml of double distilled water, and the sample is added to a Dowex 50W-X8H+ column (10*2cm), Use 200ml of water as the mobile phase for elution (to elute excess glucose). The product was eluted with 150 ml of 1 mol / L ammonia water, and the eluent was rotary evaporated to obtain a crude product. RP-HPLC was used for separation, and the mobile phase was methanol:water=65:35, which contained 0.1% TFA. The product-containing eluate was dried under reduced pressure. The obtained ...

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Abstract

The invention discloses a product of the Maillard reaction of tryptophan and glucose and its preparation method and application. The invention also discloses a pharmaceutical composition for treating tumors. The pharmaceutical composition for treating tumors contains an effective dose of the product of the Maillard reaction of tryptophan and glucose and pharmaceutically acceptable carriers. A result of the research shows that the product of the Maillard reaction of tryptophan and glucose has strong cell targeted killing effects on a human cervical carcinoma cell line, a human colon cancer cell line, a human mucoepidermoid carcinoma cell line, an adenoid cystic carcinoma cell line, a lymphoma cell line, a breast cancer cell line and a lung cancer cell line, and does not produce apoptosis induction effects on common cells. The pharmaceutical composition which is utilized for treating tumors and is prepared from tryptophan has low toxicity, high efficiency and an important meaning in the filed of antitumor drug development.

Description

technical field [0001] The invention relates to a Maillard reaction product of tryptophan and glucose, a preparation method thereof and an application of the obtained product in preparing medicine for treating tumor diseases. The invention belongs to the field of medicine. Background technique [0002] Malignant tumors are a serious threat to human health and life. Although there are many anticancer drugs on the market, they have serious side effects, which bring heavy mental burden and unrelieved grief to patients and their families. At the same time, it also causes a great economic burden to the patient's family and the society. At present, the number of deaths due to tumors in the world reaches more than 5 million every year, and its mortality rate accounts for the first place among various causes of death in many countries. Although the existing methods of drug therapy, chemotherapy, and radiotherapy have certain effects, they also have serious side effects. Therefore,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A61K31/405A61P35/00
Inventor 张志仁马和平杨宝峰初文峰刘小燕赵丹王秋石
Owner HARBIN MEDICAL UNIVERSITY
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