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Comparison of several acridinium esters produced by Desheng

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Comparison of several acridinium esters produced by Desheng

Acridine ester is a chemical substance that can be used as a chemiluminescent label. Acridine salts and related compounds have been widely proven to be very useful chemiluminescent labels. Its stability, labeling specificity and detection sensitivity surpass that of radioisotopes. . Under alkaline conditions, NHS is substituted as a leaving group, and the protein forms a stable amide bond with the acridine ester. However, acridinium ester is only a general term for acridinium salt. If subdivided, Desheng can provide 7 different acridinium esters (see the table below) for you to choose from, so what are these 7 acridinium esters? What are the similarities and differences? Let us continue to look down.

 

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Magnetic particle chemiluminescence method using acridinium ester

1. Desheng acridine ester types:

1.1 Acridinium Ester No. 0-Acridinium Ester (AE-NHS)
【CAS】None
【Appearance】Yellow solid or powder
【Purity】≥98%
【Molecular Weight】N/A
【Storage conditions】-20℃, avoid light
[Transportation Conditions] It can be transported at room temperature (20-25°C) within 48 hours, and it needs to be transported at -20°C for more than 48 hours.


1.2 Acridinium Ester No. 1-Acridinium Ester (DMAE-NHS)
【English name】2',6'-dimethyl-4'-(N-succinimidyloxycarbonyl)phenyl-10-methyl-acridinium-9-carboxylate methosulfate
[Chinese name] 9-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-2,6-dimethylphenoxy]carbonyl]-10-methyl
Acridine Methyl Sulfate
【CAS】115853-74-2
【Appearance】Yellow solid or powder
【Purity】≥98%
【Molecular Weight】594.13, C29H26N2O10S
【Storage conditions】-20℃, avoid light
[Transportation Conditions] It can be transported at room temperature (20-25°C) within 48 hours, and it needs to be transported at -20°C for more than 48 hours.

 

1.3 Acridinium Ester No. 2-Acridinium Ester (Me-DMAE-NHS)
【English name】2',6'-Dimethylcarbonylphenyl 10-Methyl-9-acridinecarboxylate 4'-NHS Ester Triflate
[Chinese name] 2',6'-Dimethylcarbonylphenyl 10-methyl-9-acridine carboxylate 4'-NHS ester trifluoromethanesulfonate
【CAS】None (115853-74-2, DMAE-NHS analogue)
【Appearance】Yellow solid or powder
【Purity】≥98%
【Molecular Weight】632.56, C29H23F3N2O9S
【Storage conditions】-20℃, avoid light
[Transportation Conditions] It can be transported at room temperature (20-25°C) within 48 hours, and it needs to be transported at -20°C for more than 48 hours.

 

1.4 Acridinium Ester No. 3-Acridinium Ester (NSP-DMAE-NHS)
【English name】2',6'-DiMethylcarbonylphenyl-10-sulfopropylacridinium-9-carboxylate 4'- NHS Ester
[Chinese name] 9-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]-2,6-dimethylphenoxy]carbonyl]-10-( 3-
Sulfopropyl)-acridine inner salt
【CAS】194357-64-7
【Appearance】Yellow solid or powder
【Purity】≥98%
【Molecular Weight】590.6, C30H26N2O9S
【Storage conditions】-20℃, avoid light
[Transportation Conditions] It can be transported at room temperature (20-25°C) within 48 hours, and it needs to be transported at -20°C for more than 48 hours.

 

1.5 Acridine ester No. 4-acridine salt (NSP-SA)
[English name] 3-[9-(((3-(carboxypropyl)[4-methxylphenyl]sulfonyl)amine)carboxyl]-10-acridiniumyl)-1-propanesulfonateinner salt
[Chinese name] Acridine salt (NSP-SA)
【CAS】211106-69-0
【Appearance】Yellow solid or powder
【Purity】≥98%
【Molecular Weight】584.66, C28H28N2O8S2
【Storage conditions】-20℃, avoid light
[Transportation Conditions] It can be transported at room temperature (20-25°C) within 48 hours, and it needs to be transported at -20°C for more than 48 hours.

 

1.6 Acridine ester No. 5-acridine salt (NSP-SA-NHS)
[English name] 3-[9-(((3-(N-succinimidyloxycarboxypropyl)[4-methxylphenyl]sulfonyl)amine)carboxyl]-10-acridiniumyl)-1-propanesulfonateinner salt
[Chinese name] Acridine salt (NSP-SA-NHS)
【CAS】199293-83-9
【Appearance】Yellow solid or powder
【Purity】≥98%
【Molecular Weight】681.73, C32H31N3O10S2
【Storage conditions】-20℃, avoid light
[Transportation Conditions] It can be transported at room temperature (20-25°C) within 48 hours, and it needs to be transported at -20°C for more than 48 hours.

 

1.7 Acridine ester No. 6-acridinium hydrazide (NSP-SA-ADH)
【CAS】None
【Appearance】Yellow solid or powder
【Purity】≥98%
【Molecular weight】740.85, C34H40N6O9S2
【Storage conditions】-20℃, avoid light
[Transportation Conditions] It can be transported at room temperature (20-25°C) within 48 hours, and it needs to be transported at -20°C for more than 48 hours.

two. The structural difference of acridine esters


Six kinds of acridine esters, of which Nos. 1 to 3 are acridine esters; Nos. 4 to 6 are acridine sulfonamide lactates; Nos. 1 to 4 are NHS active esters; No. 5 is acridine carboxylic acid with carboxyl group; 6 The number is acridine hydrazide, which contains free amino groups.

 

three. Hydrolysis resistance and stability
Traditional acridinium ester No. 0 (AE-NHS) and No. 1 to 3 have been modified in their structure to increase steric hindrance and enhance hydrolysis resistance. No. 0 is only stable in acidic solutions. When the pH value is greater than 6.3, it is easy to hydrolyze, while No. 1 to 3 are not. For example, at room temperature, it is very good in PB buffer with pH 7.0.
It is stable. After 16 days, the luminescence activity is only reduced by 3.6%.
No. 4 to No. 6 is the introduction of sulfonamide groups, and its stability is higher than that of acridine esters (No. 0 to No. 3). The reason is that the C-N bond and C-O bond are more stable.
The bond level is different, the C-N bond is larger than the C-O bond. Acridine amide compounds (No. 4~6) have stronger resistance to hydrolysis than acridine esters (No. 0~3).
Things. No. 4 to No. 6 are stable in acidic solution (pH<4.8), and the protein conjugate is stored at room temperature for 4 weeks, and its photon yield does not decrease. The freeze-dried product
It can be stored for more than one year at -20°C.

 

four. Hydrophilicity
Nos. 3 to 6 are modified in hydrophilicity on the basis of Nos. 1 to 2. The introduction of propanesulfonic acid internal salt increases its water solubility and makes it compatible with antibodies,
The markers formed by nucleic acids are water-soluble, and subsequent luminescence detection can be performed in water.

Fives. The difference in marking
Since the essence of the antibody is a protein, it contains an amine group and can directly react with No. 1 to No. 4 (NHS active ester) for coupling.
No. 5 is acridine carboxylic acid, which requires the addition of condensing agent EDCI, etc., in order to have a coupling reaction with amine-containing proteins.


SIX. is acridine hydrazide, which contains free amino groups. The end of acridine hydrazide is suitable for direct coupling to polysaccharides, nucleic acids or proteins containing aldehyde groups.

six. Comparison of luminous performance
As acridines No. 1 to No. 6 have the same luminescence matrix and mechanism, their luminescence performance should not be much different.

Pub Time : 2021-07-06 15:04:25 >> News list
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