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Mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate as well as preparation method and application thereof

A technology of Mycobacterium tuberculosis and a conjugate is applied in the field of tuberculosis vaccine development to achieve the effects of solving the problem of low immune protection, avoiding the problem of bacterial drug resistance and improving the immune effect

Active Publication Date: 2017-02-15
CANSINO BIOLOGICS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The glycosyl part of Mycobacterium tuberculosis PGL-tb1 is used as a hapten and coupled with a carrier to prepare an oligosaccharide conjugate vaccine, but there is no related report

Method used

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  • Mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate as well as preparation method and application thereof
  • Mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate as well as preparation method and application thereof
  • Mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate as well as preparation method and application thereof

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Experimental program
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preparation example Construction

[0058] The general synthesis method of the above-mentioned Mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate, the steps are as follows:

[0059] ⑴Reaction between oligosaccharides and linkers

[0060] Dissolve triphenylphosphine (0.07 equivalents), cuprous iodide (0.14 equivalents) and bistriphenylphosphorus palladium dichloride (0.07 equivalents) in triethylamine, and stir the reaction at 40°C for 15 Minutes, configured as a catalyst, ready for use. The prepared oligosaccharide substrate and 6-chlorohexyne (10 equivalents) were dissolved in triethylamine, and then the prepared catalyst was added. The reaction was stirred at 40°C for 2 hours. TLC detection showed that the reaction was complete, and ethyl acetate was added to the reaction solution, extracted with 2mol / L hydrochloric acid solution, then, the organic phase was further extracted with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the s...

Embodiment 1

[0069] (2,3,4-Tri-O-methyl-α-L-fucosyl)-(1→3)-α-L-rhamnosyl-(1→3)-(1-(6 -(4-Hydroxyphenyl)-hexylamino)-2-O-methyl-α-L-rhamnose)-CRM 197 Synthesis of the conjugate (PGL-tb1-CRM 197 )Synthesis

[0070] ⑴2,3,4-tri-O-methyl-α-L-fucosyl-(1→3)-2,4-di-O-benzyl-α-L-rhamnosyl-(1 → 3)-1-(1-chloro-6-(4-hydroxyphenyl)-5-hexyne)-2-O-methyl-4-benzyl-α-L-rhamnose (A1) synthesis

[0071]

[0072] Weigh 9.9 mg triphenylphosphine (39 μmol), 14.4 mg cuprous iodide (75 μmol) and 26.4 mg bistriphenylphosphine palladium dichloride (39 μmol) and dissolve them in redistilled triethylamine (18 mL). Stir the reaction at 40°C for 15 minutes, configure it as a catalyst, and set aside. With 2,3,4-tri-O-methyl-α-L-fucosyl-(1→3)-2,4-di-O-benzyl-α-L-rhamnosyl-( 1→3)-1-p-iodophenyl-2-O-methyl-4-benzyl-α-L-rhamnose (1.5g, 0.51mmol, refer to Angew.Chem.Int.Ed.2012,51 : the synthesis method of 11774) and 0.6mL (5.08mmol) of 6-chlorohexyne were dissolved in 6.09mL triethylamine, then, adding catalyst 12...

Embodiment 3

[0084] 2,3,4-Tri-O-methyl-α-L-fucosyl-(1→3)-α-L-rhamnosyl-(1→3)-1-p-phenylhexylamino- Synthesis of 2-O-methyl-α-L-rhamnose-BSA glycoconjugate

[0085]

[0086] Take A3 (5mg), BSA (20mg) and synthesize A3-BSA conjugate (23mg) according to the method of step (4) of the general synthesis method. Mass Spectrum: MALDI-TOF-MS (m / z) 66415

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Abstract

The invention relates to a mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate as well as a preparation method and an application thereof. In the mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate provided by the invention, oligosaccharide, which is clear and simple in chemical structure, instead of a mixture, can be massively synthesized by virtue of a chemical method, and by coupling a designed linker to a vector, an antigen can be prepared; the problem of low and unstable BCG (Bacillus Calmette Guerin) vaccine immune protection force can be solved; and the mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate, for some special people low in immunity, can also achieve a relatively immune effect.

Description

technical field [0001] The invention relates to a mycobacterium tuberculosis PGL-tb1 oligosaccharide conjugate and a preparation method and application thereof, belonging to the technical field of tuberculosis vaccine development. Background technique [0002] Tuberculosis is a chronic infectious disease caused by Mycobacterium tuberculosis (Mtb) infection. About 1 / 3 of the people in the world are infected with MTB, and 5% to 10% of the infected people develop into TB patients, and about 2 million tuberculosis patients die every year. Tuberculosis chemotherapy is a relatively complete and effective method for the treatment and control of tuberculosis. However, with the increase of primary and acquired multidrug-resistant tuberculosis and extensively drug-resistant tuberculosis, current chemotherapy for tuberculosis is facing various challenges. Although chemotherapy can improve the patient's condition and prolong life, it brings disadvantages such as great pain, strong sid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K39/385A61K39/04A61P31/06
CPCA61K39/04A61K39/385A61K2039/60A61K2039/6037A61K2039/6081
Inventor 孟欣朱涛郁彭姬传明潘国军陈鹤苏超沈棣
Owner CANSINO BIOLOGICS INC
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