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D3514

Sigma-Aldrich

4,4′-Diisothiocyanatostilbene-2,2′-disulfonic acid disodium salt hydrate

≥80% (elemental analysis), powder

Synonym(s):
DIDS, Disodium 4,4′-diisothiocyanatostilbene-2,2′-disulfonate
Empirical Formula (Hill Notation):
C16H8N2Na2O6S4 · xH2O
CAS Number:
Molecular Weight:
498.48 (anhydrous basis)
Beilstein:
8179433
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥80% (elemental analysis)

form

powder

reaction suitability

reagent type: cross-linking reagent

color

yellow

solubility

0.1 M potassium bicarbonate: 50 mg/mL

storage temp.

2-8°C

SMILES string

[Na+].[Na+].[O-]S(=O)(=O)c1cc(ccc1\C=C\c2ccc(cc2S([O-])(=O)=O)N=C=S)N=C=S

InChI

1S/C16H10N2O6S4.2Na/c19-27(20,21)15-7-13(17-9-25)5-3-11(15)1-2-12-4-6-14(18-10-26)8-16(12)28(22,23)24;;/h1-8H,(H,19,20,21)(H,22,23,24);;/q;2*+1/p-2/b2-1+;;

InChI key

GEPAYBXVXXBSKP-SEPHDYHBSA-L

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Application

4,4′-Diisothiocyanatostilbene-2,2′-disulfonic acid disodium salt hydrate has been used:
  • as band3 protein inhibitor in rabbits(19)
  • for the inhibition of bicarbonate transporters in brain slice tissue(20)
  • as HCO3-/Cl- exchanger (anion exchanger) in embryos(21)

A negatively charged homobifunctional cross-linking reagent. The isothiocyanate groups react with primary amines at pH 9.0-10.0.

Packaging

25 mg in glass insert
100, 250 mg in poly bottle
1 g in poly bottle

Biochem/physiol Actions

4,4′-Diisothiocyanatostilbene-2,2′-disulfonic acid is an anionic alkylating agent containing isothiocyanate residue. It is a negatively charged homobifunctional cross-linking reagent. 4,4′-Diisothiocyanatostilbene-2,2′-disulfonic acid is a specific inhibitor of cellular anion permeability used in cell transport studies. The isothiocyanate groups react with primary amines at pH 9.0-10.0. 4,4′-Diisothiocyanatostilbene-2,2′-disulfonic acid alkylates lysine residues and inhibits apoptosis indirectly by targeting membrane based anion transporters.In addition, it also inhibits calcium transport in vesicles.
A specific inhibitor of cellular anion permeability used in cell transport studies.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Product Information Sheet

More Documents

Quotes and Ordering

  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  6. What is the solubility of 4,4´-Diisothiocyanatostilbene-2,2´-disulfonic acid disodium salt (Product No. D3514)?

    Product No. D3514 is soluble in 0.1 M KHCO3 (50 mg/mL) yielding a hazy, yellow-green solution. This may require heat for complete solubilization. DIDS is also soluble in DMSO.

  7. What is the solution stability of 4,4´-Diisothiocyanatostilbene-2,2´-disulfonic acid disodium salt (Product No. D3514)?

    We have no specific solution stability data for Product No. D3514, however, isothiocyanates are unstable in water and should not be stored in aqueous solutions.

  8. What are the fluorescent properties of 4,4´-Diisothiocyanatostilbene-2,2´-disulfonic acid disodium salt (Product No. D3514)?

    Product No. D3514 has an excitation maximum at a wavelength of 342 nm, and an emission maximum at a wavelength of 418 nm, measured in water.

  9. Is there a reference for the use of 4,4´-Diisothiocyanatostilbene-2,2´-disulfonic acid disodium salt (Product No. D3514) as a cross-linking reagent?

    The spectral properties of Product No. D3514 are: ?max: 220 nm, 265 nmExtinction coefficient: EmM = 3000 (280 nm, water), EmM = 54 (342 nm, water).  This information is from J. Membrane Biol., 29, 147-177 (1976).  

  10. Is there a reference for the use of 4,4´-Diisothiocyanatostilbene-2,2´-disulfonic acid disodium salt (Product No. D3514) as a cross-linking reagent?

    Product No. D3514 binds covalently (irreversibly) to the outer surface of human erythrocyte membrane protein, functioning as an anion transport inhibitor. It also can be used to cross-link membrane anion transport sites.  A good cross-linking reference is J. Membrane Biol., 29, 147-177 (1976).

  11. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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