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Sigma-Aldrich

N-(5-Fluoresceinyl)maleimide

≥90% (HPLC), BioReagent, suitable for fluorescence

Synonym(s):

5-Maleimido-fluorescein

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About This Item

Empirical Formula (Hill Notation):
C24H13NO7
CAS Number:
75350-46-8
Molecular Weight:
427.36
MDL number:
MFCD00077345
UNSPSC Code:
12352111
PubChem Substance ID:
329755743
NACRES:
NA.32

product line

BioReagent

Quality Level

100

Assay

≥90% (HPLC)

fluorescence

λex 490 nm; λem 518 nm in 0.1 M Tris pH 8.0

suitability

corresponds for coupling to thiols
suitable for fluorescence

storage temp.

2-8°C

SMILES string

Oc1ccc2c(Oc3cc(O)ccc3C24OC(=O)c5cc(ccc45)N6C(=O)C=CC6=O)c1

InChI

1S/C24H13NO7/c26-13-2-5-17-19(10-13)31-20-11-14(27)3-6-18(20)24(17)16-4-1-12(9-15(16)23(30)32-24)25-21(28)7-8-22(25)29/h1-11,26-27H

InChI key

AYDAHOIUHVUJHQ-UHFFFAOYSA-N

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General description

N-(5-Fluoresceinyl) maleimide, also known as fluorescein-5-maleimide (FM), is a fluorescent derivatization reagent. The pH during the derivatization reaction plays a critical role.

Application

N-(5-Fluoresceinyl) maleimide or fluorescein-5-maleimide is used as a fluorescent biosensor to detect nanoparticles.

N-(5-Fluoresceinyl) maleimide (5-FM) is used to fluorescence label molecules such as proteins and peptides via their thiol groups.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

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

Certificates of Analysis (COA)

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Oluyemi Akinloye et al.
Analytical and bioanalytical chemistry, 409(4), 903-915 (2016-12-03)
The ability to detect and quantify nanoparticles is essential but there is currently no simple, sensitive, and rapid method for the detection of nanomaterials. We have developed a novel peptide-based fluorescence-based biosensor for detection and measurement of negatively charged engineered
Nicola Giangregorio et al.
Biochimica et biophysica acta, 1767(11), 1331-1339 (2007-10-27)
During substrate translocation mitochondrial carriers cycle between the cytoplasmic-state (c-state) with substrate-binding site open to the intermembrane space and matrix-state (m-state) with the binding site open to the mitochondrial matrix. Here, the accessibility of Cys-58, Cys-136 and Cys-155 of the
Michael Raba et al.
Journal of molecular biology, 382(4), 884-893 (2008-08-12)
Selected residues of transmembrane domain (TM) IX were previously shown to play key roles in ligand binding and transport in members of the Na(+)/solute symporter family. Using the Na(+)/proline transporter PutP as a model, a complete Cys scanning mutagenesis of
Robert E Dempski et al.
The Journal of biological chemistry, 281(47), 36338-36346 (2006-09-19)
The Na+/K+-ATPase maintains the physiological Na+ and K+ gradients across the plasma membrane in most animal cells. The functional unit of the ion pump is comprised of two mandatory subunits including the alpha-subunit, which mediates ATP hydrolysis and ion translocation
Chuck R Smallwood et al.
Molecular microbiology, 72(5), 1171-1180 (2009-05-13)
We studied the reactivity of 35 genetically engineered Cys sulphydryl groups at different locations in Escherichia coli FepA. Modification of surface loop residues by fluorescein maleimide (FM) was strongly temperature-dependent in vivo, whereas reactivity at other sites was much less
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