| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g | |||
| Other Sizes |
| Targets |
This compound does not have a specific biological target. The maleimide moiety is a highly specific and efficient reactive handle for thiol-containing molecules, such as cysteine residues in antibodies and other proteins, via Michael addition reaction. The five-carbon hydroxypentyl spacer provides flexibility and spacing between the conjugated antibody and payload. The primary hydroxyl group can be further functionalized or used for conjugation to activated carboxyl groups (via esterification).
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| ln Vitro |
ADC is made up of an antibody and an ADC linker that binds an ADC cytotoxin to it [1].
N-(5-Hydroxypentyl)maleimide is not a bioactive compound but serves as a versatile ADC linker. It is used in the synthesis of antibody-drug conjugates, such as Gemcitabine-O-Si(di-iso)-O-Mc. It provides stable, non-cleavable covalent bonds between the antibody and drug molecule, allowing for targeted delivery of the therapeutic agent to specific cells or tissues. It can also be used as a monomer in photoinitiator-free photopolymerizations for hydrogel synthesis. |
| ln Vivo |
No specific in vivo activity data is available for this linker. Its effects are determined by the final ADC into which it is incorporated. The non-cleavable nature ensures that the drug remains attached to the antibody during circulation, preventing premature release and reducing off-target toxicity. In ADC applications, the linker influences the pharmacokinetics, efficacy, and safety profile of the final conjugate.
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| Enzyme Assay |
For conjugation to thiol-containing antibodies (e.g., antibody with reduced interchain disulfides): Dissolve the antibody in PBS buffer (pH 6.5-7.5) containing 1-5 mM EDTA. Add TCEP (tris(2-carboxyethyl)phosphine) at a 2-10 fold molar excess over antibody disulfide bonds. Incubate at 37degC for 1-2 hours to partially reduce interchain disulfides and generate free thiols. Remove excess TCEP by buffer exchange using a desalting column. Dissolve N-(5-Hydroxypentyl)maleimide (pre-activated with a cytotoxic payload such as a maytansinoid or auristatin) in DMSO. Add the linker-drug conjugate to the reduced antibody in a 10-20 fold molar excess. Incubate at room temperature for 1-2 hours. Quench unreacted maleimide with N-acetylcysteine or cysteine (10-20 fold excess). Purify the ADC by size exclusion chromatography or ultrafiltration. Characterize by SDS-PAGE, HIC-HPLC, and MS.
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| Cell Assay |
For thiol labeling of proteins without drug payload: Dissolve protein containing free cysteine residues in PBS buffer (pH 6.5-7.5). Dissolve N-(5-Hydroxypentyl)maleimide (or its functionalized derivative, e.g., with a biotin or fluorophore) in DMSO. Add to protein solution at 5-20 fold molar excess. Incubate at 4degC or room temperature for 1-2 hours. Quench with excess cysteine. Remove unreacted reagent by dialysis or size exclusion chromatography. For hydrogel synthesis: Use N-(5-Hydroxypentyl)maleimide as a monomer in donor/acceptor pair photopolymerizations with N-vinylpyrrolidinone.
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| Animal Protocol |
No in vivo protocol exists for the linker alone. For ADCs containing this linker, standard protocols apply: Administer ADC intravenously to tumor-bearing mice at doses determined by the payload. Monitor tumor growth and body weight. Collect blood and tissues for pharmacokinetic and toxicokinetic analysis. The non-cleavable linker provides stability in circulation, resulting in an extended half-life and reduced off-target toxicity.
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| ADME/Pharmacokinetics |
No specific pharmacokinetic data is available for the linker alone. The non-cleavable alkyl chain is stable in systemic circulation and is not susceptible to enzymatic cleavage. The maleimide-thiol conjugate is stable under physiological conditions (pH 7.4) but may undergo retro-Michael reaction or exchange with thiols in plasma over extended periods (days to weeks). The linker contributes to the overall ADC pharmacokinetics.
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| Toxicity/Toxicokinetics |
N-(5-Hydroxypentyl)maleimide is generally considered to have low toxicity. The maleimide group is reactive and may cause skin and eye irritation; avoid direct contact. The compound is not intended for human use. Standard laboratory safety practices should be followed, including the use of gloves, safety glasses, and lab coats. Work in a well-ventilated area.
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| References | |
| Additional Infomation |
N-(5-Hydroxypentyl)maleimide is a research-grade ADC linker for laboratory use only, not for human therapeutic or diagnostic use. It is a non-cleavable linker that provides stable and long-lasting covalent bonds between the antibody and drug molecules. The 5-carbon alkyl spacer provides a specific degree of flexibility and spacing. The maleimide moiety reacts with thiols via Michael addition. The compound should be stored at -20degC in a dry, dark environment, protected from light and moisture. It is soluble in DMSO (10 mM). No clinical trials or approved status exist.
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| Molecular Formula |
C9H13NO3
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|---|---|
| Molecular Weight |
183.204
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| Exact Mass |
183.089
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| CAS # |
180608-78-0
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| PubChem CID |
18368754
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| Appearance |
Colorless to light yellow ointment
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| LogP |
1
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
13
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| Complexity |
217
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=O)N(C1=O)CCCCCO
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| InChi Key |
YTIZONIKDWSRFR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H13NO3/c11-7-3-1-2-6-10-8(12)4-5-9(10)13/h4-5,11H,1-3,6-7H2
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| Chemical Name |
1-(5-hydroxypentyl)pyrrole-2,5-dione
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.4585 mL | 27.2926 mL | 54.5852 mL | |
| 5 mM | 1.0917 mL | 5.4585 mL | 10.9170 mL | |
| 10 mM | 0.5459 mL | 2.7293 mL | 5.4585 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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