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Merck

M2786

Sigma-Aldrich

3-Maleimidobenzoic acid N-hydroxysuccinimide ester

crystalline

Sinónimos:

MBS

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About This Item

Fórmula empírica (notación de Hill):
C15H10N2O6
Número de CAS:
Peso molecular:
314.25
Beilstein/REAXYS Number:
1505254
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

form

crystalline

Quality Level

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. 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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Visualization of Actin Organization and Quantification in Fixed Arabidopsis Pollen Grains and Tubes
Qu X, et al.
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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)
Ilenia Papa et al.
Nature, 547(7663), 318-323 (2017-07-13)
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Genes, 9(7) (2018-07-04)
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