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63175

Sigma-Aldrich

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
Beilstein:
6427689
MDL number:
MFCD00036817
UNSPSC Code:
12352106
PubChem Substance ID:
329759802
NACRES:
NA.25

Quality Level

100

Assay

≥98.0% (HPLC)

reaction suitability

reagent type: linker

mp

123-129 °C

functional group

NHS ester

storage temp.

2-8°C

SMILES string

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

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

InChI key

PVGATNRYUYNBHO-UHFFFAOYSA-N

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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 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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0407
BCCM0539
BCBV0406
BCBV3389
SLBH6654

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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
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Molecular pharmaceutics, 15(7), 2559-2569 (2018-05-17)
Photodynamic therapy, a procedure that uses a photosensitizer to enable light therapy selectively at diseased sites, remains underutilized in oncological clinic. To further improve its cancer selectivity, we developed a polymeric nanosystem by conjugating a photosensitizer IRDye 700DX (IR700) and
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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