Synthetic method of acridinium ester DMAE-NHS
In chemiluminescence, the traditional acridine ester AE-NHS can already be used to label biological macromolecules such as antigens, antibodies, special proteins, DNA, etc., so as to realize the chemiluminescence analysis of biomolecules, but the stability, reagent compatibility and other issues are slightly obvious. Inadequate, after the modification of functional groups, the newly developed DMAE-NHS has better chemiluminescence performance.
Advantages of acridine ester DMAE-NHS:
Compared with traditional acridine esters, DMAE-NHS has higher luminous efficiency, better thermal stability, and stronger hydrophilicity. The chemiluminescence reagent has high photon yield and low background. It is compatible with proteins, antigens, and antibodies. After coupling, the luminous efficiency is almost unaffected, making it an excellent chemiluminescence immunoassay labeling reagent.
Synthetic route of acridine ester DMAE-NHS:
1. Synthesis of 1-((4-hydroxy-3,5-dimethylbenzoyl)oxy)-2,5-pyrrolidinedione by combining 4-hydroxy-3,5-dimethylbenzoic acid with N-Hydroxysuccinimide is dissolved in N,N-dimethylformamide (DMF) and reacted under the action of a condensing agent to obtain a crude product, which is recrystallized to obtain a pure product;
2. Synthesis of 2',6'-dimethyl-4'-(N-succinimidyl) phenyl-acridine-9-carboxylate, the product obtained from 1 is 1-((4-hydroxy-3, 5-Dimethylbenzoyl)oxy)-2,5-pyrrolidinedione and acridine-9-carbonyl chloride are dissolved in anhydrous pyridine and heated under the action of a catalyst to obtain a crude product. Column chromatography Separation and purification.
3. Synthesize acridinium ester DMAE·NHS, dissolve the product of 2 and dimethyl sulfate in anhydrous toluene to react, filter the resulting mixture; wash the filter residue and then recrystallize to obtain the
target product acridinium ester chemiluminescent substrate DMAE·NHS.
For the synthesis of acridinium ester DMAE·NHS, compared with other synthesis methods of acridinium ester chemiluminescent substrates, the steps are simple, no protecting group strategy is required, the reaction conditions are mild, the product yield and purity are higher, and no expensive chemistry is required Reagents and solvents, and solvents can be recycled, can meet the needs of mass production, and have broad application prospects by reducing the cost of production and analysis and testing.
In addition to the acridine ester DMAE·NHS, Desheng has also synthesized 5 other acridine esters, such as acridine sulfonamide NSP-SA, acridinium ester NSP-DMAE-NHS, etc. The products are favored by many domestic and foreign partners.
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