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M2786

Sigma-Aldrich

3-Maleimidobenzoic acid N-hydroxysuccinimide ester

crystalline

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

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

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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The role of actin in root hair morphogenesis: studies with lipochito-oligosaccharide as a growth stimulator and cytochalasin as an actin perturbing drug.
Miller DD
The Plant Journal, 17, 141-141 (1999)
Comparison of F-actin fluorescent labeling methods in pollen tubes of Lilium davidii
Wang L, et al.
Plant Cell Reports, 24(5), 266-270 (2005)
A Dauphin et al.
Plant biology (Stuttgart, Germany), 8(2), 204-211 (2006-03-21)
The fungus Pisolithus microcarpus establishes an ectomycorrhiza with Eucalyptus globulus. This symbiosis involves a fungal synthesis and secretion of hypaphorine, an indolic compound. Previous studies have shown that hypaphorine induces an alteration in the actin cytoskeleton of elongating root hairs
Actin organization during Eucalyptus root hair development and its response to fungal hypaphorine
Dauphin A, et al.
Plant Biology (Stuttgart, Germany), 8(02), 204-211 (2006)
Ilenia Papa et al.
Nature, 547(7663), 318-323 (2017-07-13)
Protective high-affinity antibody responses depend on competitive selection of B cells carrying somatically mutated B-cell receptors by follicular helper T (T
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