NHS Ester Labeling of Biomolecules Containing Primary Amino Groups
NHS (N-HydroxySuccinimide) esters and other activated esters (sulfo-NHS, sulfotetrafluorophenyl — STP) are reactive compounds suitable for the modification of amino groups. NHS is the most common type of activated esters.
Usual modifications are fluorescent labels, fluorescence quenchers, and other reporter groups. Alkyne and azido groups can be attached using activated esters to adapt biomolecules to click chemistry.
Especially common are modifications of proteins and peptides since they nearly always contain amino groups. Other examples are modifications of amino-oligonucleotides, amino-modified DNA, and amino-containing sugars.
The reaction of NHS esters with amino groups is strongly pH-dependent: at low pH, the amino group is protonated, and the modification does not occur. At higher-than-optimal pH, hydrolysis of NHS ester is quick, and the yield of modified molecule decreases. The optimal pH value for modification is 8.3-8.5.
Water is the most common solvent used to dissolve NHS esters for biomolecule labeling. If NHS ester is poorly soluble in aqueous solutions, it can be at first dissolved in dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) and then added to a solution of protein in a buffer with pH 8.3-8.5.
Important! Note that DMF can degrade into dimethylamine, which has a fishy smell and is able to react with activated esters. Therefore, to label biomolecules, it is important to use high-quality DMF that contains no dimethylamine and has no fishy odor.
We recommend using the following general protocol for the labeling of biomolecules with NHS esters produced by Lumiprobe:
- Calculate the required amount of NHS ester using the formula below or our protein labeling calculator: NHS_ester_weight [mg] = 8 × amino_compound_weight [mg] × NHS_ester_molar_weight [Da] / amino_compound_molar_weight [Da]. 8 is a molar excess of NHS ester. It is an empirical value for mono-labeling, suitable for many common proteins and peptides. However, in some cases using less or more NHS ester can increase the yield of the modified biomolecule. It depends on protein structure, reagent used for labeling, and its solubility. The molar weight of Lumiprobe products can be found on the corresponding product pages. For example, to label 3 mg of BSA (molar weight 66500 Dalton) with Cy5 NHS ester (molar weight 616 Dalton), and obtain maximum yield of mono-labeled product, one should use 8 × 3 mg × 616 Da / 66500 Da = 0.22 mg of Cy5 dye NHS ester.
- Calculate the volume of the reaction mixture. The optimal biomolecule concentration in labeling reaction is 1-10 mg per mL. The labeling can be performed on any scale, from nanomols to dozens of grams. If you label a low amount of biomolecule, keep the volume of the reaction mixture at a minimum (10-20 uL).
- Dissolve NHS ester in 1/10 reaction volume of water, DMF, or DMSO. Dimethylamine-free DMF or water are preferred solvents. NHS ester dissolved in DMF can be stored in solution for 1-2 months at −20ºC. The aqueous solution of NHS ester should be used immediately after preparation.
- Dissolve biomolecule in 9/10 reaction volume of buffer with pH 8.3-8.5. 0.1 M Sodium bicarbonate solution has appropriate pH. Another alternative is 0.1 M phosphate buffer. Note that pH is the most important factor for successfully labeling biomolecule with NHS ester. Avoid buffers containing amines (Tris-based buffers can sometimes be used but are not recommended. Tris contains amino group, but its affinity to activated esters is low). When doing large-scale labeling (using hundreds of milligrams of NHS ester), note that the mixture tends to acidify with time because of the hydrolysis of NHS ester. Monitor pH, or use a more concentrated buffer then.
- Add NHS ester solution to the solution of biomolecule, and vortex well. Keep on ice overnight, or at room temperature from 1 to 4 hours.
- Purify the conjugate using the appropriate method: gel-filtration for macromolecules is the most common. Chromatography is another alternative. For proteins and nucleic acids, ethanol or acetone precipitation can be used. Organic impurities (such as N-hydroxysuccinimide, NHS ester, and acid produced by hydrolysis) are almost always easily separated by these methods.
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DusQ® 1 NHS ester
Functionalized DusQ® 1 quencher derivative with quenching range from 480 - 580 nm for labeling of amine-containing molecules.
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| 21D20 | 5 mg |
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in stock | |
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DusQ® 21 NHS ester
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| 28D20 | 5 mg |
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in stock | |
| 48D20 | 25 mg |
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DusQ® 2 NHS ester
DusQ® 2 dark quencher with a quenching range from 560 - 670 nm with primary amine reactivity for synthesis of FRET probes. This NHS ester can be coupled to various molecules bearing amino groups.
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|---|---|---|---|---|
| 22D20 | 5 mg |
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5 days | |
| 42D20 | 25 mg |
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| 52D20 | 50 mg |
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DusQ® 3 NHS ester
Amino-reactive NHS ester for the labeling with far-red quencher DusQ® 3.
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|---|---|---|---|---|
| 23D20 | 5 mg |
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in stock | |
| 43D20 | 25 mg |
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| 53D20 | 50 mg |
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| 63D20 | 100 mg |
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DusQ® 9 NHS ester
Functionalized DusQ® 9 quencher derivative with quenching range from 500 - 600 nm for labeling amine-containing molecules.
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| 47D20 | 25 mg |
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exo-BCN-PNP
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| 2B220 | 5 mg |
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Hexynoic acid NHS ester
Hexynoic acid NHS ester for the labeling of biomolecules with alkyne group for copper-catalyzed click chemistry.
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| 41720 | 25 mg |
$95.00
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| 51720 | 50 mg |
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| 61720 | 100 mg |
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Hexynoic acid STP ester
Alkyne activated ester for the modification of amine groups. STP ester group is an excellent alternative to NHS ester functionality.
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| 569-25mg | 25 mg |
$179.90
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in stock | |
| 569-100mg | 100 mg |
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JOE NHS ester, 5-isomer
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An activated ester for the introduction of alkyne into peptides/proteins and click reaction.
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| 30720 | 10 mg |
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SiRhius® 650 NHS ester
A silicon-rhodamine fluorescent dye in the far-red range for covalent labeling of biomolecules containing primary amines, such as proteins, peptides, and antibodies.
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| 11S20 | 1 mg |
$280.00
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in stock | |
| 31S20 | 10 mg |
$1380.00
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in stock | |
| 51S20 | 50 mg |
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sulfo-Cyanine3.5 NHS ester
Amine-reactive activated ester of water-soluble, sulfonated sulfo-Cyanine3.5 dye.
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| 12320 | 1 mg |
$179.90
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in stock | |
| 22320 | 5 mg |
$469.90
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in stock | |
| 42320 | 25 mg |
$859.90
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in stock | |
| 52320 | 50 mg |
$1399.00
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in stock | |
| 62320 | 100 mg |
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in stock |
sulfo-Cyanine5 NHS ester
Water-soluble sulfo-Cyanine5 succinimidyl ester for labeling various amine-containing molecules in the aqueous phase.
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| Cat. # | Quantity | Price | Lead time | Buy this product |
|---|---|---|---|---|
| 13320 | 1 mg |
$99.00
|
in stock | |
| 23320 | 5 mg |
$159.90
|
in stock | |
| 43320 | 25 mg |
$489.90
|
in stock | |
| 53320 | 50 mg |
$809.90
|
in stock | |
| 63320 | 100 mg |
$1299.00
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in stock |
sulfo-Cyanine7 NHS ester
sulfo-Cyanine7 NHS ester is a water-soluble, near-infrared, amine-reactive dye.
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| Cat. # | Quantity | Price | Lead time | Buy this product |
|---|---|---|---|---|
| 15320 | 1 mg |
$119.90
|
in stock | |
| 25320 | 5 mg |
$209.90
|
in stock | |
| 45320 | 25 mg |
$599.90
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in stock | |
| 55320 | 50 mg |
$999.00
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in stock | |
| 65320 | 100 mg |
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in stock |
TAMRA NHS ester, 6-isomer
NHS-ester of TAMRA dye for proteins, peptides, and modified oligonucleotides labeling via reaction with amino groups. Pure 6-isomer.
Show pricing
| Cat. # | Quantity | Price | Lead time | Buy this product |
|---|---|---|---|---|
| 18120 | 1 mg |
$159.90
|
in stock | |
| 28120 | 5 mg |
$289.90
|
in stock | |
| 48120 | 25 mg |
$509.90
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in stock | |
| 58120 | 50 mg |
$719.90
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in stock | |
| 68120 | 100 mg |
$1150.00
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TCO-PEG4-NHS ester (axial isomer)
A heterobifunctional linker with trans-cyclooctene and NHS ester groups flanking PEG4 (tetraethylene glycol) for labeling of antibodies, proteins, and other primary amine-containing biomolecules.
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| Cat. # | Quantity | Price | Lead time | Buy this product |
|---|---|---|---|---|
| 3056-10mg | 10 mg |
$119.00
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in stock | |
| 3056-25mg | 25 mg |
$215.00
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in stock | |
| 3056-100mg | 100 mg |
$522.00
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in stock |
TR-X-NHS ester, 5-isomer
TR is a red-emitting fluorescent dye based on sulforhodamine scaffold, an amine-reactive NHS ester.
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| Cat. # | Quantity | Price | Lead time | Buy this product |
|---|---|---|---|---|
| 1V220 | 1 mg |
$125.00
|
in stock | |
| 2V220 | 5 mg |
$325.00
|
in stock | |
| 4V220 | 25 mg |
$510.00
|
in stock | |
| 5V220 | 50 mg |
$895.00
|
in stock | |
| 6V220 | 100 mg |
$1490.00
|
in stock |
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