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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

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

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Vishakha Dastidar et al.
Journal of bacteriology, 189(15), 5550-5558 (2007-05-29)
In gram-negative bacteria, transporters belonging to the resistance-nodulation-cell division (RND) superfamily of proteins are responsible for intrinsic multidrug resistance. Haemophilus influenzae, a gram-negative pathogen causing respiratory diseases in humans and animals, constitutively produces the multidrug efflux transporter AcrB (AcrB(HI)). Similar
Linda Ojemyr et al.
Biochemistry, 48(10), 2173-2179 (2009-01-27)
Proton transport across biological membranes is a key step of the energy conservation machinery in living organisms, and it has been proposed that the membrane itself plays an important role in this process. In the present study we have investigated
Yumiko Takatsuka et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(15), 6559-6565 (2010-03-10)
The AcrB trimeric multidrug efflux transporter of Escherichia coli pumps out a very wide spectrum of compounds. Although minocycline and doxorubicin have been cocrystallized within the large binding pocket in the periplasmic domain of the binding protomer, nothing is known
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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