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Sigma-Aldrich

5-Maleimido-eosin

for fluorescence, ≥93% (HPLC)

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Synonym(s):
EMA, Eosin-5-maleimide
Empirical Formula (Hill Notation):
C24H9Br4NO7
CAS Number:
150322-02-4
Molecular Weight:
742.95
MDL number:
MFCD07437936
PubChem Substance ID:
329759808
NACRES:
NA.32

grade

for fluorescence

Quality Level

100

Assay

≥93% (HPLC)

fluorescence

λex 524 nm; λem 545 nm (after derivatization with 2-mercaptoethanol)

storage temp.

2-8°C

SMILES string

Oc1c(Br)cc2c(Oc3c(Br)c(O)c(Br)cc3C24OC(=O)c5cc(ccc45)N6C(=O)C=CC6=O)c1Br

InChI

1S/C24H9Br4NO7/c25-13-6-11-21(17(27)19(13)32)35-22-12(7-14(26)20(33)18(22)28)24(11)10-2-1-8(5-9(10)23(34)36-24)29-15(30)3-4-16(29)31/h1-7,32-33H

InChI key

YRCLWXRIEYQTAV-UHFFFAOYSA-N

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General description

5-Maleimido-eosin, also known as EMA or Eosin-5-maleimide, is a fluorescent binding agent. The 5-Maleimido-eosin binding test measures the EMA-labeled cells reduced mean channel fluorescence (MCF) reading.

Application

Eosin-5-maleimide has been used as a fluorescent probe for the human erythrocyte band 3 protein. It is widely used as a diagnostic probe for the laboratory detection of hereditary spherocytosis (HS) by flow cytometry. The eosin-5-maleimide binding test was done to analyze the effect of alectinib (first line of treatment) for anaplastic lymphoma kinase (ALK).

Other Notes

Triplet probe. Measurement of rotational diffusion of protein in solution and in membranes, including myosin and pyruvate dehydrogenase

related product

Product No.
Description
Pricing

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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A J Visser et al.
European journal of biochemistry, 121(1), 233-235 (1981-12-01)
The enzymatically reduced lipoyl residues of the transacetylase component of the pyruvate dehydrogenase complex from Escherichia coli were labeled with eosin maleimide. Using eosin as triplet probe, triplet-triplet absorption dichroism measurements were performed to obtain rotational correlation times of the
Delay in the measurement of eosin-5'-maleimide (EMA) binding does not affect the test result for the diagnosis of hereditary spherocytosis.
Ciepiela O, Kotula I, Gorska E, et al.
Clinical Chemistry and Laboratory Medicine, 0, 1-7 (2012)
P A Knauf et al.
The American journal of physiology, 264(5 Pt 1), C1144-C1154 (1993-05-11)
Eosin-5-maleimide (EM) has been used as a fluorescent probe for the external-facing transport site of the human erythrocyte band 3 protein. Changes in chloride concentration at both sides of the membrane have no significant effect on the inhibitory potency of
Paola Bianchi et al.
Haematologica, 97(4), 516-523 (2011-11-08)
The laboratory diagnosis of hereditary spherocytosis commonly relies on NaCl-based or glycerol-based red cell osmotic fragility tests; more recently, an assay directly targeting the hereditary spherocytosis molecular defect (eosin-5'-maleimide-binding test) has been proposed. None of the available tests identifies all
S Ishiwata et al.
The Journal of biological chemistry, 262(17), 8314-8317 (1987-06-15)
We studied the rotational Brownian motions of myosin heads, of which the sulfhydryl group was selectively labeled with the triplet probe 5-eosinylmaleimide, in myofibril by using flash-induced phosphorescence anisotropy decay measurements. The anisotropy decay curve under relaxing conditions consisted of
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