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Merck
CN

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

Key Documents

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Product Name

3-Maleimidobenzoic acid N-hydroxysuccinimide ester, crystalline

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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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.

General description

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000453968
0000453968
0000439812
0000439812
0000412263

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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)
Opioids Binding Mu and Delta Receptors Exhibit Diverse Efficacy in the Activation of Gi2and Gx/z Transducer Proteins in Mouse Periaqueductal Gray Matter.
Garzon J
Journal of Pharmacology and Experimental Therapeutics, 281, 549-557 (1997)
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
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)
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)
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