M2786

3-Maleimidobenzoic acid N-hydroxysuccinimide ester

crystalline

• Synonym(s): MBS
• Empirical Formula (Hill Notation): C₁₅H₁₀N₂O₆
• CAS Number: 58626-38-3
• Molecular Weight: 314.25
• Beilstein: 1505254
• MDL number: MFCD00005514
• UNSPSC Code: 12352108
• PubChem Substance ID: 24896768

Properties

• form: crystalline
• Quality Level: 200
• reaction suitability: reagent type: cross-linking reagent
• mp: 175-177 °C (lit.)
• solubility: DMSO: ≤20 mg/mL (may require addition of solvent to coupling buffer to at least 5% to maintain solubility)
• functional group: NHS ester; maleimide
• storage temp.: −20°C
• SMILES string: O=C1CCC(N1OC(C2=CC=CC(N3C(C=CC3=O)=O)=C2)=O)=O
• InChI: 1S/C15H10N2O6/c18-11-4-5-12(19)16(11)10-3-1-2-9(8-10)15(22)23-17-13(20)6-7-14(17)21/h1-5,8H,6-7H2
• InChI key: LLXVXPPXELIDGQ-UHFFFAOYSA-N

Description

Application

3-Maleimidobenzoic acid N-hydroxysuccinimide ester (MBS) has been used as a protein cross-linker. It has been used for the stabilization of actin filaments in plant tissue samples.

3-Maleimidobenzoic acid N-hydroxysuccinimide ester has been used:

• in the fixation of pollen in Arabidopis
• as a component of Murashige and Skoog (MS) medium to stabilize F-actin in Eucalyptus root hairs
• in the fixation of F-actin labelled pollen tubes of Lilium davidii

Heterobifunctional crosslinking reagent reactive toward primary amine and sulfhydryl. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.0, followed by coupling to compounds containing sulfhydryl by thioether at same pH. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates.

Biochem/physiol Actions

3-Maleimidobenzoic acid N-hydroxysuccinimide is used as a fixative for the preservation of pollen tube F-actin distribution. It imposes less damage when used on pollen tubes.

Other Notes

The aryl maleimide is less stable than alkyl maleimide linkers.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable