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:
Molecular Weight:
314.25
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1505254
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
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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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Visualization of Actin Organization and Quantification in Fixed Arabidopsis Pollen Grains and Tubes
Qu X, et al.
Bio-protocol, 10(01), 204-211 (2020)
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
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
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