Novel alpha-amylase inhibitor alcaftadine series compounds and application thereof

A technology of amylase inhibitor and alcatadine, which is applied to a new class of alpha-amylase inhibitor alcatadine series compounds and their application fields, can solve the problems of hydrolysis inactivation development and the like

Active Publication Date: 2008-08-06
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polypeptide α-amylase inhibitors are widely found in the seeds of food crops and microbial metabolites, but they are difficult to develop as effective drugs because they are easily hydrolyzed and inactivated by proteases in the human gastrointestinal tract

Method used

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  • Novel alpha-amylase inhibitor alcaftadine series compounds and application thereof
  • Novel alpha-amylase inhibitor alcaftadine series compounds and application thereof
  • Novel alpha-amylase inhibitor alcaftadine series compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: Separation and preparation of alcaftadine series compounds

[0035] Cultivate fermented seeds in a 500mL triangular flask, each bottle contains 100mL of liquid medium, which contains: oatmeal 2%, potassium nitrate 0.1%, sodium chloride 0.05%, dipotassium hydrogen phosphate 0.05%, magnesium sulfate 0.05%, ferrous sulfate 0.001 %. Adjust the pH to 7.2-7.5 with NaOH, sterilize with high-pressure steam at 121°C for 20 minutes, and inoculate the slant spores of the strain ZG0656 after cooling [that is, Streptomyces coelicoflavus var.nankaiensis ZG0656 (Streptomyces coelicoflavus var. Preservation Management Committee General Microbiology Center" (No. 13, Zhongguancun North Yiyi, Haidian District, Beijing, Institute of Microbiology, Chinese Academy of Sciences), its preservation number is CGMCC No.2097], cultivated in an air bath shaker at 200rpm 28°C for 48 hours as fermented seeds . Put 7.5L medium of the same composition into a 10L stainless steel mechanica...

Embodiment 2

[0037] Example 2: Chemical structures of alcaftadine monomers I03, II03, III03, IV03.

[0038] The physical and chemical properties of alcaftadine monomers I03, II03, III03, and IV03 are shown in Table 1. The molecular formula and molecular weight were analyzed by high-resolution mass spectrometry (+)ESI-FTMS. For the infrared spectrum of representative compound III03, see figure 2 .

[0039] Table 1. Physicochemical properties and molecular characteristics of alcaftadine

[0040] Alcatadine I03 Alcatadine II03 Alcatadine III03 Alcatadine IV03

[0041] Appearance White powder White powder White powder White powder

[0042] UV Spectrum End Absorption End Absorption End Absorption End Absorption

[0043] Infrared Spectrum 3385, 1029cm -1 3385, 1041cm -1 3416, 1044cm -1 3405, 1039cm -1

[0044] [α] 18 D +159° +165° +168° +153°

[0045] Molecular formula C 37 h 63 NO 28 C 56 h 94 N 2 o 40 C 75 h 125 N 3 o ...

Embodiment 3

[0062] Example 3: Alcaftadine inhibits α-amylase activity at the enzymatic level

[0063] With 0.05-2% soluble starch as the substrate, 450 μL of solutions containing different concentrations of substrates and different concentrations of α-amylase inhibitors were pre-incubated at 37°C for 10 minutes, and then 50 μL of 5 U / mL porcine pancreatic α-amylase ( Sigma company product) to start the reaction, sample 50 μL every 5 minutes, add 50 μL 3M NaOH to stop the reaction. The determination of reducing sugar is based on maltose, adding 75 μL of 1% 3,5-dinitrosalicylic acid to the sample, then bathing in boiling water for 5 minutes, and measuring the light absorption value at 490 nm after appropriate dilution. Taking time as the abscissa and reducing sugar production as the ordinate, the slope of the obtained straight line is the initial reaction velocity.

[0064] The double reciprocal curve and the Dixon curve plot showed that the inhibitory effects of the four monomers on porci...

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Abstract

A new quasi-oligosaccharide alpha-amylase inhibitor as alcaftadine compound is represented as the formula (I) at right, wherein m is integer of 0-7, n is integer of 1-4 and q is integer of 0-3, The mixture and monomer of the alcaftadine compound are white amorphous powder which dissolves in water and DMSO easily, dissolves in methanol, alcohol and acetone slightly and not dissolves in other organic solvents. The alcaftadine compound contains different amounts of acarviosine-amylaceum structural units and reducing glucose terminals, particularly the compound with high repeated times and significant different structure with prior quasi-oligosaccharide alpha-amylase inhibitor. Therefore, the compound is a new quasi-oligosaccharide alpha-amylase inhibitor with the application for preparing the drug of diabetes and adiposis or the like.

Description

【Technical field】 [0001] The present invention relates to a new class of α-amylase inhibitors, that is, alcaftadine series compounds, and the application of the series of compounds in medicines for treating diseases such as diabetes. 【Background technique】 [0002] Diabetes mellitus is a group of metabolic diseases characterized by hyperglycemia caused by insufficient insulin secretion and / or impaired insulin action. It is manifested by an abnormal increase in the concentration of glucose in the blood and urine. When the blood sugar and urine sugar are too high, the typical symptoms of "three more and one less" will appear, that is, polydipsia, polyuria, polyphagia and weight loss, accompanied by fatigue powerless. Diabetes is generally divided into type 1 diabetes, type 2 diabetes and gestational diabetes and other types. Type 2 diabetes can not only cause microvascular complications, such as peripheral neuropathy, eye disease, diabetic nephropathy, etc., but also can cau...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/22C07H5/06C08B37/00A61K31/7028A61P3/10
Inventor 白钢耿鹏朱元元张奇
Owner NANKAI UNIV
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