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I9271

Sigma-Aldrich

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
Beilstein:
6543244
UNSPSC Code:
12171500
PubChem Substance ID:
329815467
NACRES:
NA.47

product name

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

Quality Level

200

Assay

≥90% (HPLC)

form

powder

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

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

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General description

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

Application

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

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
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
D Chhabra et al.
Biophysical journal, 89(3), 1902-1908 (2005-07-05)
Actin is the principal component of microfilaments. Its assembly/disassembly is essential for cell motility, cytokinesis, and a range of other functions. Recent evidence suggests that actin is present in the nucleus where it may be involved in the regulation of
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