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I9271

5-(Iodoacetamido)fluorescein

Name: 5-(Iodoacetamido)fluorescein
Brand: SIGMA

≥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

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Properties

Product Name

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

Quality Level

200

assay

≥90% (HPLC)

form

powder

technique(s)

titration: suitable

color

yellow to orange

solubility

DMSO: 5 mg/mL

fluorescence

λ_ex 492 nm; λ_em 515 nm (Mercaptoethanol adduct), λ_ex 493 nm; λ_em 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

Description

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.

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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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)

Cysteine oxidation of tau and microtubule-associated protein-2 by peroxynitrite: modulation of microtubule assembly kinetics by the thioredoxin reductase system.

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

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