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
Beilstein:
1505254
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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