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Merck

I9271

5-(Iodoacetamido)fluorescein

≥90% purity (HPLC), powder

Synonym(s):

5-IAF

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About This Item

Empirical Formula (Hill Notation):
C22H14INO6
CAS Number:
63368-54-7
Molecular Weight:
515.25
UNSPSC Code:
12171500
PubChem Substance ID:
329815467
NACRES:
NA.47
Beilstein/REAXYS Number:
6543244

Product Name

5-(Iodoacetamido)fluorescein, ≥90% (HPLC)

SMILES string

Oc1ccc2c(Oc3cc(O)ccc3C24OC(=O)c5cc(NC(=O)CI)ccc45)c1

InChI

1S/C22H14INO6/c23-10-20(27)24-11-1-4-15-14(7-11)21(28)30-22(15)16-5-2-12(25)8-18(16)29-19-9-13(26)3-6-17(19)22/h1-9,25-26H,10H2,(H,24,27)

InChI key

UATCLPJEZJKNHE-UHFFFAOYSA-N

assay

≥90% (HPLC)

form

powder

technique(s)

titration: suitable

color

yellow to orange

solubility

DMSO: 5 mg/mL

fluorescence

λex 492 nm; λem 515 nm (Mercaptoethanol adduct)
λex 493 nm; λem 522 nm (pH 9.2)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

−20°C

Quality Level

200

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Application

5-(Iodoacetamido)fluorescein is used for the synthesis of fluorescently labeled organelles (nuclei and nuclear matrices), proteins and peptides that include enzymes.

General description

5-(Iodoacetamido)fluorescein is a thiol reactive fluorescein derivative.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ5131
MKCW3411
MKCV1777
MKCT9233
MKCV3491

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Identification of the 5-iodoacetamidofluorescein reporter site on the Na,K-ATPase.
Tyson PA
The Journal of Biological Chemistry, 264, 726-726 (1989)
Multisite phosphorylation of the Saccharomyces cerevisiae filamentous growth regulator Tec1 is required for its recognition by the E3 ubiquitin ligase adaptor Cdc4 and its subsequent destruction in vivo.
Bao MZ
Eukaryotic Cell, 9, 31-31 (2010)
Lisa M Landino et al.
The Journal of biological chemistry, 279(33), 35101-35105 (2004-06-09)
Alterations in the redox status of proteins have been implicated in the pathology of several neurodegenerative conditions including Alzheimer and Parkinson diseases. We report that peroxynitrite- and hydrogen peroxide-induced disulfides in the neuron-specific microtubule-associated proteins tau and microtubule-associated protein-2 are
Lisa M Landino et al.
Free radical biology & medicine, 36(4), 497-506 (2004-02-21)
Cumulative oxidative damage to proteins coupled with a decrease in repair has been implicated in the pathology of several neurodegenerative diseases. Herein we report that peroxynitrite-induced disulfides in porcine brain tubulin are repaired by the thioredoxin reductase system composed of
Chris Chumsae et al.
Analytical chemistry, 81(15), 6449-6457 (2009-07-04)
Each human IgG1 antibody contains a total of thirty-two cysteine residues. In theory, all of them are involved in disulfide bonds, and no free sulfhydryl should be detected. However, literature has suggested that the presence of low levels of free
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