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Merck
CN

M8759

Sigma-Aldrich

3-Maleimidobenzoic acid N-hydroxysuccinimide ester

Synonym(s):

MBS

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About This Item

Empirical Formula (Hill Notation):
C15H10N2O6
CAS Number:
58626-38-3
Molecular Weight:
314.25
Beilstein:
1505254
EC Number:
261-368-8
MDL number:
MFCD00005514
UNSPSC Code:
47101511
PubChem Substance ID:
24897286

Key Documents

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mp

175-177 °C (lit.)

solubility

ethyl acetate or DMF: ≤20 mg/mL (may require addition of solvent to coupling buffer to at least 5% to maintain solubility)

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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Application

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.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
105K1067
088H1336
069H0919
047H0168
040H0643

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T Arata
Journal of biochemistry, 109(2), 335-340 (1991-02-01)
Polymerization of G-actin in the presence of salt and phalloidin was blocked by treatment of G-actin with m-maleimidobenzoic acid N-hydroxysuccinimide ester (MBS) (designated as m-actin). The actin dimer produced by chemical crosslinking of F-actin with N,N'-p-phenylenedimaleimide did not polymerize and
H R Mortensen et al.
Dysphagia, 30(3), 304-314 (2015-02-19)
Many head and neck cancer (HNC) survivors experience reduced quality of life due to radiotherapy (RT)-related dysphagia. The aim of this prospective randomized trial was to evaluate the impact of prophylactic swallowing exercises on swallowing-related outcomes in HNC patients treated
D A Collings et al.
Planta, 212(3), 392-403 (2001-04-06)
The distribution of actin filaments within the gravity-sensing columella cells of plant roots remains poorly understood, with studies over numerous years providing inconsistent descriptions of actin organization in these cells. This uncertainty in actin organization, and thus in actin's role
T Arata
Journal of structural biology, 123(1), 8-16 (1998-10-17)
Attachment of G-actin to a myosin head was for the first time visualized by electron microscopy of heavy meromyosin (HMM) molecules decorated using a chemical crosslinker with G-actin, which is made resistant to salt- and myosin-induced polymerization by treatment with
C J Chen et al.
Bioconjugate chemistry, 5(6), 557-564 (1994-11-01)
Antibodies conjugated to oligomeric carboranyl compounds have a high potential as target species for boron neutron capture therapy (BNCT) of solid tumors. As a first step toward developing conjugates with BNCT capabilities, an oligomeric nido-carboranyl phosphate diester (Kane, R. R.
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