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Merck
CN

M8759

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
EC Number:
261-368-8
UNSPSC Code:
47101511
PubChem Substance ID:
24897286
Beilstein/REAXYS Number:
1505254
MDL number:
MFCD00005514

Key Documents

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InChI key

LLXVXPPXELIDGQ-UHFFFAOYSA-N

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

SMILES string

O=C1CCC(N1OC(C2=CC=CC(N3C(C=CC3=O)=O)=C2)=O)=O

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

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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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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D A Barton et al.
Journal of microscopy, 237(1), 79-88 (2010-01-09)
Accurate preservation of microtubule and actin microfilament arrays is crucial for investigating their roles in plant cell development. Aldehyde fixatives such as paraformaldehyde or glutaraldehyde preserve cortical microtubule arrays but, unless actin microfilaments are stabilized with drugs such as m-maleimidobenzoyl
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
Tatsuya Maruhashi et al.
Hypertension research : official journal of the Japanese Society of Hypertension, 38(7), 485-490 (2015-03-06)
The RhoA/Rho-associated kinase (ROCK) pathway has a key physiological role in the pathogenesis of atherosclerosis. Increased ROCK activity is associated with cardiovascular diseases. Endogenous nitric oxide (NO) has an anti-atherosclerotic effect, whereas the exogenous NO-mediated cardiovascular effect still remains controversial.
N Sattayasai et al.
Journal of interferon research, 11(1), 41-48 (1991-02-01)
Antibodies to three conserved regions of all human interferon (IFN)-alpha 1 subtypes were raised by immunizing rabbits with short synthetic peptides coupled to a carrier. These peptides correspond to amino acid residues 29-36, 31-36, 126-131, 139-151, and 142-151 of the
H H Keah et al.
The journal of peptide research : official journal of the American Peptide Society, 57(1), 1-10 (2001-02-13)
The synthesis of peptides containing 0, 1 and 2 cysteine residues related to the human sperm tail protein, tpx-1, is described. These synthetic peptides, following conjugation to keyhole limpet hemocyanin modified with maleimidobenzoic acid N-hydroxysuccinimide ester, were used as immunogens
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