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A0554

Sigma-Aldrich

4-Acetamido-4′-isothiocyanato-2,2′-stilbenedisulfonic acid disodium salt hydrate

powder, ≥80%

Synonym(s):

Disodium 4-acetamido-4′-isothiocyanato-stilben-2,2′-disulfonate, SITS

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About This Item

Empirical Formula (Hill Notation):
C17H12N2Na2O7S3 · xH2O
CAS Number:
51023-76-8
Molecular Weight:
498.46 (anhydrous basis)
Beilstein/REAXYS Number:
9177451
EC Number:
256-919-4
MDL number:
MFCD00007485
UNSPSC Code:
12352202
PubChem Substance ID:
24890434
NACRES:
NA.77

product name

4-Acetamido-4′-isothiocyanato-2,2′-stilbenedisulfonic acid disodium salt hydrate, ≥80%

assay

≥80%

form

powder

storage temp.

−20°C

SMILES string

[Na+].[Na+].CC(=O)Nc1ccc(\C=C\c2ccc(cc2S([O-])(=O)=O)N=C=S)c(c1)S([O-])(=O)=O

InChI

1S/C17H14N2O7S3.2Na/c1-11(20)19-15-7-5-13(17(9-15)29(24,25)26)3-2-12-4-6-14(18-10-27)8-16(12)28(21,22)23;;/h2-9H,1H3,(H,19,20)(H,21,22,23)(H,24,25,26);;/q;2*+1/p-2/b3-2+;;

InChI key

NPAWAMRXPHRVQY-WTVBWJGASA-L

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Application

Fluorescent marker for membranes; inhibits anion permeability of membranes. Also inactivates Na,K-ATPase, by covalent modification of a specific Lys residue.

Other Notes

Predominantly trans-isomer

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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M Montana Quick et al.
Journal of the American Society for Mass Spectrometry, 28(7), 1462-1472 (2017-03-21)
N-terminal derivatization of peptides with the chromogenic reagent 4-acetamido-4-isothiocyanatostilbene-2,2-disulfonic acid (SITS) is demonstrated to enhance the efficiency of 266 nm ultraviolet photodissociation (UVPD). Attachment of the chromophore results in a mass shift of 454 Da and provides significant gains in the number
C H Pedemonte et al.
FEBS letters, 314(1), 97-100 (1992-12-07)
The sodium pump or Na,K-ATPase, maintains the Na+ and K+ gradients across eukaryotic cell membranes at the expense of ATP. Incubation of purified canine renal Na,K-ATPase with 4-acetamido-4'-isothiocyanatostilbene-2,2'-disulfonic acid (SITS) inhibited the ATPase activity. Both the labeling of the protein
Dennis Kolosov et al.
Insect biochemistry and molecular biology, 116, 103263-103263 (2019-11-05)
Malpighian tubules (MTs) and the hindgut together constitute the excretory system of insects. Larvae of lepidopterans (butterflies and moths) demonstrate the so-called cryptonephric arrangement, where the distal blind end of each MT is embedded into the rectal complex. The rest
Carmen Vale et al.
Toxicological sciences : an official journal of the Society of Toxicology, 113(1), 158-168 (2009-10-10)
Azaspiracids (AZAs) are a group of marine toxins recently described that currently includes 20 members. Not much is known about their mechanism of action, although the predominant analog in nature, AZA-1 targets several organs in vivo, including the central nervous
Xuan Zhang et al.
Molecular pharmacology, 81(5), 689-700 (2012-02-14)
Transient receptor potential vanilloid type 1 (TRPV1) is a nonselective cation channel activated by capsaicin, low pH, and noxious heat and plays a key role in nociception. Understanding mechanisms for functional modulation of TRPV1 has important implications. One characteristic of
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