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Merck
CN

63175

4-Maleimidobutyric acid N-hydroxysuccinimide ester

≥98.0% (HPLC)

Synonym(s):

4-Maleimidobutyric acid N-succinimidyl ester, N-(γ-Maleimidobutyryloxy)succinimide, N-Succinimidyl 4-maleimidobutyrate, GMBS

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About This Item

Empirical Formula (Hill Notation):
C12H12N2O6
CAS Number:
80307-12-6
Molecular Weight:
280.23
UNSPSC Code:
12352106
NACRES:
NA.25
PubChem Substance ID:
329759802
MDL number:
MFCD00036817
Beilstein/REAXYS Number:
6427689

Key Documents

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Product Name

4-Maleimidobutyric acid N-hydroxysuccinimide ester, ≥98.0% (HPLC)

InChI

1S/C12H12N2O6/c15-8-3-4-9(16)13(8)7-1-2-12(19)20-14-10(17)5-6-11(14)18/h3-4H,1-2,5-7H2

SMILES string

O=C1N(CCCC(ON2C(CCC2=O)=O)=O)C(C=C1)=O

InChI key

PVGATNRYUYNBHO-UHFFFAOYSA-N

assay

≥98.0% (HPLC)

reaction suitability

reagent type: linker

mp

123-129 °C

functional group

NHS ester

storage temp.

2-8°C

Quality Level

100

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Application

A heterobifunctional cross-linking reagent with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5). Second coupling specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Provides a 7-atom linker.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0539
BCCM0407
BCBV0406
BCBV3389
SLBH6654

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Tae Hyun Kim et al.
Nature communications, 10(1), 1478-1478 (2019-04-02)
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Erdrin Azemi et al.
Acta biomaterialia, 4(5), 1208-1217 (2008-04-19)
Silicon-based implantable neural electrode arrays are known to experience failure during long-term recording, partially due to host tissue responses. Surface modification and immobilization of biomolecules may provide a means to improve their biocompatibility and integration within the host brain tissue.
Xiubo Zhao et al.
Journal of the Royal Society, Interface, 9(75), 2457-2467 (2012-05-04)
The specific recognition between monoclonal antibody (anti-human prostate-specific antigen, anti-hPSA) and its antigen (human prostate-specific antigen, hPSA) has promising applications in prostate cancer diagnostics and other biosensor applications. However, because of steric constraints associated with interfacial packing and molecular orientations
Yu Zhang et al.
Cancer biology & therapy, 17(11), 1177-1187 (2016-10-22)
Circulating tumor cells (CTCs) have been proposed to be an active source of metastasis or recurrence of hepatocellular carcinoma (HCC). The enumeration and characterization of CTCs has important clinical significance in recurrence prediction and treatment monitoring in HCC patients. We
Jae-Wan Jung et al.
Proteomics, 6(4), 1110-1120 (2006-01-13)
We modified gold arrays with a glutathione (GSH) surface, and investigated high-throughput protein interactions with a spectral surface plasmon resonance (SPR) biosensor. We fabricated the GSH exterior on gold surfaces by successive modification with aminoethanethiol, 4-maleimidobutyric acid N-hydroxysuccinimide ester and
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