| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
2-Nitro-5-thiocyanatobenzoic acid targets cysteine residues in proteins. It reacts with the thiol group of cysteine to form a cyanylated derivative, which then undergoes a rearrangement and cleavage reaction that specifically breaks the peptide bond on the amino-terminal side of the cysteine residue. This property makes it a valuable tool for protein sequencing and structural studies.
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| ln Vitro |
2-Nitro-5-thiocyanatobenzoic acid (NTCB) is an extremely reactive reagent that quickly attaches cyano groups to thiolates that are nucleophilic. It quickly cyanolines protein cysteine when given to a protein to make S-cyanocysteine, which then reversibly adds itself intramolecularly to the cysteine N-amide to produce 1-acyl-2-Iminothiazolidine, an intermediate substitution that can be nucleophilically acylated [1].
In vitro, 2-nitro-5-thiocyanatobenzoic acid is used to cyanylate proteins and specifically cleave the amino-terminal peptide bond of cysteine residues. This reaction is widely employed in protein chemistry for peptide mapping, generating defined peptide fragments for analysis by mass spectrometry or Edman degradation. It is also used to introduce cyano groups into proteins for various biochemical applications. |
| ln Vivo |
There are no in vivo applications for 2-nitro-5-thiocyanatobenzoic acid as it is a chemical reagent for in vitro protein chemistry. It is not a therapeutic agent and is not administered to animals.
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| Enzyme Assay |
The in vitro protein cleavage protocol involves reacting the protein with 2-nitro-5-thiocyanatobenzoic acid under mild conditions. The reagent selectively cyanylates cysteine thiol groups. Upon treatment with base, the cyanylated cysteine undergoes a rearrangement that leads to cleavage of the peptide bond on the amino-terminal side of the cysteine residue. The resulting peptide fragments can be analyzed by SDS-PAGE or mass spectrometry. The compound is soluble in DMF (25 mg/ml), DMSO (11 mg/ml), ethanol (25 mg/ml), and PBS (pH 7.2, 0.3 mg/ml).
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| Cell Assay |
There are no standard in vitro cell-based assays for 2-nitro-5-thiocyanatobenzoic acid as it is not a cell-permeant probe or drug. Its use is limited to biochemical applications with purified proteins or cell lysates.
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| Animal Protocol |
There are no in vivo animal experimental protocols for 2-nitro-5-thiocyanatobenzoic acid as it is not a drug or in vivo probe.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 2-nitro-5-thiocyanatobenzoic acid are not characterized as it is not a drug. It is a chemical reagent for research use. It should be stored at -20°C.
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| Toxicity/Toxicokinetics |
No toxicity data for 2-nitro-5-thiocyanatobenzoic acid are available. As a research chemical, it should be handled with standard laboratory safety precautions. It is not for human or veterinary use.
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| References |
[1]. Qiao Y, et al. Site-Specific Conversion of Cysteine in a Protein to Dehydroalanine Using 2-Nitro-5-thiocyanatobenzoic Acid. Molecules. 2021;26(9):2619. Published 2021 Apr 29.
[2]. Price NC. Alternative products in the reaction of 2-nitro-5-thiocyanatobenzoic acid with thiol groups. Biochem J. 1976;159(1):177-180. |
| Additional Infomation |
2-Nitro-5-thiocyanatobenzoic acid (NTCB) is a protein chemistry reagent used to cyanylate proteins and specifically cleave the amino-terminal peptide bond of cysteine residues. It is a crystalline solid with CAS number 30211-77-9. It is for research use only and not for human or veterinary use.
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| Molecular Formula |
C8H4N2O4S
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|---|---|
| Molecular Weight |
224.1934
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| Exact Mass |
223.989
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| CAS # |
30211-77-9
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| PubChem CID |
92266
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| Appearance |
White to light yellow solid powder
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| Density |
1.63g/cm3
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| Boiling Point |
449ºC at 760mmHg
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| Melting Point |
156-157ºC(lit.)
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| Flash Point |
225.4ºC
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| Index of Refraction |
1.5690 (estimate)
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| LogP |
2.389
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
15
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| Complexity |
318
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S(C#N)C1C([H])=C([H])C(=C(C(=O)O[H])C=1[H])[N+](=O)[O-]
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| InChi Key |
NQUNIMFHIWQQGJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H4N2O4S/c9-4-15-5-1-2-7(10(13)14)6(3-5)8(11)12/h1-3H,(H,11,12)
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| Chemical Name |
2-nitro-5-thiocyanatobenzoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~446.05 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (11.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4605 mL | 22.3025 mL | 44.6050 mL | |
| 5 mM | 0.8921 mL | 4.4605 mL | 8.9210 mL | |
| 10 mM | 0.4461 mL | 2.2303 mL | 4.4605 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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