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Here's a concise summary of N-Succinimidyl maleimidoacetate (≤100 words):
Chemical Identity:
Heterobifunctional crosslinker (C₁₀H₈N₂O₆) combining:
NHS ester: Reacts with primary amines (-NH₂, e.g., lysine)
Maleimide: Binds thiols (-SH, e.g., cysteine) via Michael addition.
Key Features:
Spacer arm: Acetate bridge (spacing: ~7.7 Å).
Orthogonal reactivity: Enables controlled two-step bioconjugation.
Water-sensitive: NHS ester hydrolyzes rapidly (use anhydrous solvents).
Primary Use:
Creating stable conjugates:
Antibody-drug conjugates (ADCs)
Protein-protein/peptide complexes
Surface functionalization.
Handling: Store dry at -20°C; use immediately after dissolving in DMSO/DMF.
Avoid aqueous buffers during reaction!
N-Succinimidyl maleimidoacetate (CAS 55750-62-4) is a heterobifunctional crosslinker widely used in bioconjugation chemistry. Here's a concise chemical breakdown:
Molecular Formula: C₁₀H₈N₂O₆
Molecular Weight: 252.18 g/mol
Structure: Combines two key functional groups:
N-Hydroxysuccinimide (NHS) ester: Reacts with primary amines (-NH₂) to form stable amide bonds.
Maleimide group: Bonds specifically with thiols (-SH) via Michael addition.
Structure:
O O
║ ║
O=C-N-CH₂-C-O- Succinimide
|
Maleimide (C₄H₂O₂)
2. Key Properties
| Property | Description |
|---|---|
| Solubility | Soluble in DMSO, DMF, acetonitrile; insoluble in water (hydrolyzes rapidly). |
| Reactivity | NHS ester: Fast reaction with amines (pH 7-9). Maleimide: Selective for thiols (pH 6.5-7.5). |
| Spacer Arm | Acetate linker (‑CH₂C(O)‑) provides ~7.7 Å spacing between conjugated molecules. |
Antibody-Drug Conjugates (ADCs): Links antibodies (via amine groups) to cytotoxic drugs (via thiols).
Protein-Protein Crosslinking: Creates stable complexes for structural studies.
Surface Immobilization: Functionalizes amine-coated surfaces (e.g., biosensors) with thiolated probes.
Peptide Modification: Introduces maleimide handles for site-specific labeling.
Storage: -20°C (desiccated); moisture-sensitive → NHS ester hydrolyzes in water.
In-Use Protocol: Dissolve in anhydrous DMF/DMSO immediately before reaction.
Half-Life: NHS ester hydrolyzes in buffer (t₁/₂ ~15 min at pH 7.4).
5. Comparison to Similar Reagents
| Reagent | Spacer Length | Key Advantage |
|---|---|---|
| N-Succinimidyl maleimidoacetate | 7.7 Å | Short spacer minimizes steric interference |
| SMCC (Succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate) | 11.6 Å | Longer spacer for bulky molecules |
Safety: Irritant (wear gloves/eye protection); avoid inhalation.
Supplier Examples:
Thermo Fisher Scientific (Cat. No. 38427)
Sigma-Aldrich (Cat. No. 857188)
Why It Matters: Enables precise, two-step conjugation of biomolecules with orthogonal reactivity—critical for developing targeted therapeutics and diagnostic tools.
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