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Merck

M2786

3-Maleimidobenzoic acid N-hydroxysuccinimide ester

crystalline

Synonym(s):

MBS

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About This Item

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

Key Documents

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InChI key

LLXVXPPXELIDGQ-UHFFFAOYSA-N

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

form

crystalline

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

Quality Level

200

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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. 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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Notified Names

ishl_notified

M2786-500MG: + M2786-25MG:4548174006702 + M2786-VAR: + M2786-100MG-PW: + M2786-25MG-PW: + M2786-BULK: + M2786-100MG:4548174006696

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Certificates of Analysis (COA)

Lot/Batch Number
0000453968
0000453968
0000439812
0000439812
0000412263

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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
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)
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
Visualization of Actin Organization and Quantification in Fixed Arabidopsis Pollen Grains and Tubes
Qu X, et al.
Bio-protocol, 10(01), 204-211 (2020)
D A Barton et al.
Journal of microscopy, 237(1), 79-88 (2010-01-09)
Accurate preservation of microtubule and actin microfilament arrays is crucial for investigating their roles in plant cell development. Aldehyde fixatives such as paraformaldehyde or glutaraldehyde preserve cortical microtubule arrays but, unless actin microfilaments are stabilized with drugs such as m-maleimidobenzoyl
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