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
Form:
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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Comparison of F-actin fluorescent labeling methods in pollen tubes of Lilium davidii
Wang L, et al.
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