M2786
3-Maleimidobenzoic acid N-hydroxysuccinimide ester
crystalline
Sinónimos:
MBS
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Fórmula empírica (notación de Hill):
C15H10N2O6
Número CAS:
Peso molecular:
314.25
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1505254
Form:
crystalline
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Permítanos ayudarleInChI 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
Categorías relacionadas
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.
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Qu X, et al.
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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
Ilenia Papa et al.
Nature, 547(7663), 318-323 (2017-07-13)
Protective high-affinity antibody responses depend on competitive selection of B cells carrying somatically mutated B-cell receptors by follicular helper T (T
Jeong Hwan Seong et al.
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