| Size | Price | Stock | Qty |
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| 10g |
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| 25g |
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| Other Sizes |
| Targets |
4-Maleimidobenzoic acid targets thiol (-SH) groups on proteins and peptides through its maleimide functional group. The maleimide group undergoes a Michael addition reaction with thiols at pH 6.5-7.5 to form stable thioether bonds. The compound does not target a specific protein or enzyme but rather serves as a chemical crosslinker that can connect thiol-containing molecules to amine-containing molecules via its two reactive groups. The carboxylic acid group can be activated (e.g., with EDC/NHS) to react with primary amines, forming amide bonds. This dual reactivity makes 4-maleimidobenzoic acid a versatile tool for bioconjugation.
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| ln Vitro |
The in vitro activity of 4-maleimidobenzoic acid is its function as a heterobifunctional crosslinking agent. The maleimide group reacts selectively with thiols at pH 6.5-7.5 to form stable thioether bonds. The carboxylic acid group can be activated for amide bond formation with primary amines. This enables the creation of stable conjugates between proteins, peptides, and other biomolecules. The compound is used to synthesize maleimidobenzoyl spacers, which are valuable for creating defined linkages in bioconjugates. The crosslinking reaction is efficient and specific, making the compound widely used in protein chemistry and bioconjugation research.
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| ln Vivo |
4-Maleimidobenzoic acid is not used as a therapeutic agent. Its in vivo utility is limited to research applications involving the conjugation of biomolecules for studies of protein function, drug delivery, and diagnostic development. The compound is not intended for systemic therapeutic use.
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| Enzyme Assay |
In vitro crosslinking assays for 4-maleimidobenzoic acid involve activating the carboxylic acid group with a carbodiimide (such as EDC) and NHS to form an NHS ester. The activated compound is then incubated with amine-containing molecules to form an amide bond. The maleimide group is then reacted with thiol-containing molecules at pH 6.5-7.5 to form a stable thioether bond. The formation of the conjugate can be confirmed by SDS-PAGE, mass spectrometry, or other analytical methods.
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| Cell Assay |
For in vitro cellular experiments, 4-maleimidobenzoic acid is not typically used directly in cell-based assays. However, conjugates prepared using this crosslinker can be added to cell culture medium for incubation with target cells. For example, a protein conjugated to a drug or fluorescent label via 4-maleimidobenzoic acid could be used to study cellular uptake, localization, or function. The conjugates can be analyzed by fluorescence microscopy or flow cytometry.
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| Animal Protocol |
In vivo animal experiments with 4-maleimidobenzoic acid are not typically performed, as the compound is primarily used as a research tool for in vitro bioconjugation. However, conjugates prepared using this crosslinker could be administered to animal models for studying drug delivery, imaging, or protein function in vivo.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 4-maleimidobenzoic acid have not been characterized, as the compound is a research-use crosslinking reagent rather than a drug candidate. The compound has a molecular weight of 217.18 g/mol and should be stored under appropriate conditions.
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| Toxicity/Toxicokinetics |
The compound is intended for research use only and not for human therapeutic or diagnostic applications. Standard laboratory safety precautions should be observed when handling this chemical reagent.
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| References |
[1]. Lau A, et, al. Conjugation of doxorubicin to monoclonal anti-carcinoembryonic antigen antibody via novel thiol-directed cross-linking reagents. Bioorg Med Chem. 1995 Oct;3(10):1299-304.
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| Additional Infomation |
4-Maleimidobenzoic acid (CAS#: 17057-04-4) is a heterobifunctional crosslinking agent characterized by a maleimide group that selectively reacts with thiols and a carboxylic acid group that can be activated for amide bond formation. It is used as a protein crosslinker and to synthesize maleimidobenzoyl spacers. The compound has no clinical or therapeutic applications.
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| Molecular Formula |
C11H7NO4
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|---|---|
| Molecular Weight |
217.18
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| Exact Mass |
217.037
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| CAS # |
17057-04-4
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| PubChem CID |
86925
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
447.1±28.0 °C at 760 mmHg
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| Flash Point |
224.2±24.0 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.669
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| LogP |
0.77
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
16
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| Complexity |
348
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C([H])=C([H])C(N1C1C([H])=C([H])C(C(=O)O[H])=C([H])C=1[H])=O
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| InChi Key |
LKUOJDGRNKVVFF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H7NO4/c13-9-5-6-10(14)12(9)8-3-1-7(2-4-8)11(15)16/h1-6H,(H,15,16)
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| Chemical Name |
4-(2,5-dioxopyrrol-1-yl)benzoic 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 Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
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| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.6045 mL | 23.0224 mL | 46.0448 mL | |
| 5 mM | 0.9209 mL | 4.6045 mL | 9.2090 mL | |
| 10 mM | 0.4604 mL | 2.3022 mL | 4.6045 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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