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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

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About This Item

Empirical Formula (Hill Notation):
C16H8N2Na2O6S4 · xH2O
CAS Number:
207233-90-7
Molecular Weight:
498.48 (anhydrous basis)
Beilstein:
8179433
MDL number:
MFCD00009638
UNSPSC Code:
12352200
PubChem Substance ID:
24893761
NACRES:
NA.25
Assay:
≥80% (elemental analysis)
form:
powder
solubility:
0.1 M potassium bicarbonate: 50 mg/mL

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.

Biochem/physiol Actions

4,4′-Diisothiocyanatostilbene-2,2′-disulfonic acid is an anionic alkylating agent containing isothiocyanate residue.[1] It is a negatively charged homobifunctional cross-linking reagent.[2] 4,4′-Diisothiocyanatostilbene-2,2′-disulfonic acid is a specific inhibitor of cellular anion permeability used in cell transport studies.[3] 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.[1]In addition, it also inhibits calcium transport in vesicles.[4]
A specific inhibitor of cellular anion permeability used in cell transport studies.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H334,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN4279
MKCG5622
MKCD5234
MKBX6796V
MKBT1609V

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Nuclease activity of the MutS homologue MutS2 from Thermus thermophilus is confined to the Smr domain
Fukui K, et al.
Nucleic Acids Research, 35(3), 850-860 (2007)
Andrew A Kelso et al.
Molecular and biochemical parasitology, 210(1-2), 71-84 (2016-09-30)
The protozoan parasite responsible for human amoebiasis is Entamoeba histolytica. An important facet of the life cycle of E. histolytica involves the conversion of the mature trophozoite to a cyst. This transition is thought to involve homologous recombination (HR), which
Narongrit Thongon et al.
Pflugers Archiv : European journal of physiology, 468(11-12), 1809-1821 (2016-11-21)
Hypomagnesemia is the most concerned side effect of proton pump inhibitors (PPIs) in chronic users. However, the mechanism of PPIs-induced systemic Mg2+ deficit is currently unclear. The present study aimed to elucidate the direct effect of short-term and long-term PPIs
Michael Kittl et al.
International journal of molecular sciences, 20(14) (2019-07-18)
Many cell types express an acid-sensitive outwardly rectifying (ASOR) anion current of an unknown function. We characterized such a current in BV-2 microglial cells and then studied its interrelation with the volume-sensitive outwardly rectifying (VSOR) Cl- current and the effect
DIDS (4, 4'-Diisothiocyanatostilbene-2, 2'-disulfonate) directly inhibits caspase activity in HeLa cell lysates
Benitez-Rangel E, et al.
Cell death discovery, 1, 15037-15037 (2015)
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Questions

1–8 of 8 Questions  

  1. Are effects on membrane transport due to addition of 4,4´-Diisothiocyanatostilbene-2,2´-disulfonic acid disodium salt treatment reversible? i.e., can DIDS be 'washed out'?

    1 answer

    1. Unfortunately, this product has not been studied to determine reversibility. An older publication (see link #1) suggests that both reversible and irreversible binding occurs, while a more recent paper (see link #2) suggests that the process is irreversible. A further study of the literature would be recommended.

      Publication #1:
      https://link.springer.com/article/10.1007/BF01868957

      Publication #2:
      https://www.nature.com/articles/cddiscovery201537

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

  5. 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?

    1 answer

    1. 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).

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

  7. 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?

    1 answer

    1. 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).

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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