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M2786

Sigma-Aldrich

3-Maleimidobenzoic acid N-hydroxysuccinimide ester

crystalline

Synonym(s):

MBS

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25 MG
$65.50
100 MG
$176.00

About This Item

Empirical Formula (Hill Notation):
C15H10N2O6
CAS Number:
58626-38-3
Molecular Weight:
314.25
Beilstein/REAXYS Number:
1505254
MDL number:
MFCD00005514
UNSPSC Code:
12352108
PubChem Substance ID:
24896768
NACRES:
NA.22

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form

crystalline

Quality Level

200

reaction suitability

reagent type: cross-linking reagent

mp

175-177 °C (lit.)

solubility

DMSO: ≤20 mg/mL

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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General description

may require addition of solvent to coupling buffer to at least 5% to maintain solubility

Application

3-Maleimidobenzoic acid N-hydroxysuccinimide ester (MBS) has been used as a protein cross-linker.[1] It has been used for the stabilization of actin filaments in plant tissue samples.[2]
3-Maleimidobenzoic acid N-hydroxysuccinimide ester has been used:
  • in the fixation of pollen in Arabidopis[3]
  • as a component of Murashige and Skoog (MS) medium to stabilize F-actin in Eucalyptus root hairs[4]
  • in the fixation of F-actin labelled pollen tubes of Lilium davidii[5]

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.[5]

Other Notes

The aryl maleimide is less stable than alkyl maleimide linkers.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000312704
0000350703
0000350702
0000340550
0000312704

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Visualization of Actin Organization and Quantification in Fixed Arabidopsis Pollen Grains and Tubes
Qu X, et al.
Bio-protocol, 10(01), 204-211 (2020)
Jeong Hwan Seong et al.
Genes, 9(7) (2018-07-04)
The 14-3-3 family of proteins performs key regulatory functions in phosphorylation-dependent signaling pathways including cell survival and proliferation, apoptosis, regulation of chromatin structure and autophagy. In this study, the zeta isoform of 14-3-3 proteins (designated as Tm14-3-3ζ) was identified from
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)
Andrii Slonchak et al.
BMC genomics, 20(1), 474-474 (2019-06-12)
Extracellular vesicles (EVs) are small membrane vesicles secreted by the cells that mediate intercellular transfer of molecules and contribute to transduction of various signals. Viral infection and action of pro-inflammatory cytokines has been shown to alter molecular composition of EV
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
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