| Size | Price | |
|---|---|---|
| 100mg | ||
| Other Sizes |
| Targets |
Its primary biological targets are thiol groups (-SH) in proteins and peptides. It acts as a functional group for bioconjugation, targeting cysteine residues for the site-specific attachment of drugs, labels, or polymers.
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|---|---|
| ln Vitro |
Maleimide exhibits fluorescence quenching ability and can be used for the specific detection of thiol analytes as fluorogenic probes. It is a key component in the production of antibody-drug conjugates (ADCs), which are used in cancer research. Its derivatives have been shown to inhibit enzymes like prostaglandin endoperoxide synthases and topoisomerase II through covalent modification.
|
| ln Vivo |
Specific in vivo activity is not a primary focus, as Maleimide is a chemical reagent. However, its utility in creating ADCs has significant in vivo implications for targeted cancer therapy. The maleimide linker enables the stable attachment of a cytotoxic drug to an antibody, which then delivers the drug specifically to tumor cells in vivo.
|
| Enzyme Assay |
To assess thiol reactivity, a typical protocol involves incubating the maleimide-containing compound with a thiol-containing molecule (e.g., cysteine or a model peptide) in a suitable buffer (e.g., PBS, pH 6.5-7.5). The reaction progress is monitored by HPLC or mass spectrometry to determine the rate and efficiency of conjugation.
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| Cell Assay |
Maleimide is used in the preparation of antibody-drug conjugates (ADCs). The process involves the partial reduction of antibodies to generate free thiol groups, followed by reaction with a maleimide-containing drug-linker. The conjugation efficiency and the drug-to-antibody ratio (DAR) are then characterized using techniques like hydrophobic interaction chromatography (HIC) or mass spectrometry.
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| Animal Protocol |
Animal studies are not conducted with Maleimide itself. Instead, the ADCs or conjugates prepared using Maleimide are evaluated in vivo. These studies typically involve xenograft mouse models, where the ADC's efficacy, pharmacokinetics, and toxicity are assessed following intravenous administration.
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| ADME/Pharmacokinetics |
As a small molecule (MW 97.07 g/mol), Maleimide is not typically developed as a drug itself. Its pharmacokinetic properties are not a primary focus. However, its use as a linker in ADCs influences the overall PK of the conjugate. It is soluble in DMSO, water, and ethanol, which aids in its use for bioconjugation.
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| Toxicity/Toxicokinetics |
Maleimide is an irritant and is toxic if ingested. It can cause severe skin burns and eye damage. Specific toxicological data are available in its Safety Data Sheet (SDS). It should be handled with appropriate personal protective equipment in a well-ventilated fume hood. It is classified as a hazardous substance.
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| References | |
| Additional Infomation |
Maleimide is a cyclic dicarboxyimide in which the two carboxyl groups on the nitrogen atom, together with the nitrogen atom itself, form a 1H-pyrrole-2,5-diketone structure. It is an EC 5.99.1.3 inhibitor of DNA topoisomerase (ATP hydrolysis). It belongs to the dicarboxyimide class of compounds and is a member of the maleimide family. Its function is similar to that of maleic acid. It is derived from the hydride of 1H-pyrrole.
Maleimide is a cornerstone reagent in bioconjugation chemistry. Its selective reactivity with thiols under mild conditions makes it a popular choice for creating stable and defined conjugates. This includes the formation of ADCs, which are a major class of anticancer therapeutics, as well as the development of fluorescent probes for thiol-containing biomolecules and the functionalization of surfaces for biological applications. |
| Molecular Formula |
C4H3NO2
|
|---|---|
| Molecular Weight |
97.07
|
| Exact Mass |
97.016
|
| CAS # |
541-59-3
|
| Related CAS # |
25721-74-8;42867-30-1 (silver(+1) salt);67859-67-0 (potassium-silver(+1)[2:1:1:] salt)
|
| PubChem CID |
10935
|
| Appearance |
White to off-white solid
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
264.4±23.0 °C at 760 mmHg
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| Melting Point |
91-93 °C(lit.)
|
| Flash Point |
113.7±22.6 °C
|
| Vapour Pressure |
0.0±1.2 mmHg at 25°C
|
| Index of Refraction |
1.606
|
| LogP |
-0.69
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
7
|
| Complexity |
132
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C1C([H])=C([H])C(N1[H])=O
|
| InChi Key |
PEEHTFAAVSWFBL-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
|
| Chemical Name |
pyrrole-2,5-dione
|
| Synonyms |
Maleimide
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| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO: ≥ 100 mg/mL (1030.18 mM)
H2O: 50 mg/mL (515.09 mM） |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (25.75 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 (25.75 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 (25.75 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 60 mg/mL (618.11 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 10.3018 mL | 51.5092 mL | 103.0184 mL | |
| 5 mM | 2.0604 mL | 10.3018 mL | 20.6037 mL | |
| 10 mM | 1.0302 mL | 5.1509 mL | 10.3018 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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