An internal standard for the quantification of indoxyl sulfate
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Unlabeled Version(s)
16926Indoxyl Sulfate (potassium salt)
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Indoxyl Sulfate-d5 (potassium salt)

Item No. 34511

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1H-indol-3-yl-2,4,5,6,7-d5 sulfate, potassium salt
CAS Number
1644451-34-2
Molecular Formula
C8HD5NO4S • K
Formula Weight
256.3
Purity
≥99% deuterated forms (d1-d5)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: slightly solubleMethanol: slightly soluble
SMILES
[O-]S(OC1=C([2H])NC2=C([2H])C([2H])=C([2H])C([2H])=C21)(=O)=O.[K+]
InChi Code
InChI=1S/C8H7NO4S.K/c10-14(11,12)13-8-5-9-7-4-2-1-3-6(7)8;/h1-5,9H,(H,10,11,12);/q;+1/p-1/i1D,2D,3D,4D,5D;
InChi Key
MDAWATNFDJIBBD-GWVWGMRQSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    Product Description

    Indoxyl sulfate-d5 is intended for use as an internal standard for the quantification of indoxyl sulfate (Item No. 16926) by GC- or LC-MS. Indoxyl sulfate is a uremic toxin and a metabolite of tryptophan (Item No. 29600).1 It is formed via sulfation of indoxyl, an intermediate generated from tryptophan by intestinal bacteria, by the sulfotransferase (SULT) isoform 1A1 variant 2 (SULT1A1*2) in the liver.2,1 Indoxyl sulfate activates the aryl hydrocarbon receptor (AhR) in HepG2 40/6 hepatoma cells (EC50 = 12.1 nM in a reporter assay).3 It also inhibits the organic anion transporter (OAT) isoforms OAT1 and OAT3 (Kis = 34.2 and 74.4 µM, respectively for the rat transporters) in S2 proximal tubule cells.4 Indoxyl sulfate (0.2 and 1 mM) increases superoxide anion and nitric oxide levels in isolated human mononuclear blood cells.5 It increases serum creatinine and blood urea nitrogen (BUN) levels in the 5/6 nephrectomized rat model of chronic renal failure when administered at a dose of 50 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Niwa, T. Uremic toxicity of indoxyl sulfate. Nagoya J. Med. Sci. 72(1-2), 1-11 (2010).

    2. Banoglu, E., and King, R.S. Sulfation of indoxyl by human and rat aryl (phenol) sulfotransferases to form indoxyl sulfate. Eur. J. Drug Metab. Pharmacokinet. 27(2), 135-140 (2002).

    3. Schroeder, J.C., Dinatale, B.C., Murray, I.A., et al. The uremic toxin 3-indoxyl sulfate is a potent endogenous agonist for the human aryl hydrocarbon receptor. Biochemistry 49(2), 393-400 (2010).

    4. Enomoto, A., Takeda, M., Tojo, A., et al. Role of organic anion transporters in the tubular transport of indoxyl sulfate and the induction of its nephrotoxicity. J. AM. Soc. Nephrol. 13(7), 1711-1720 (2002).

    5. Pieniazek, A., Gwozdzinski, L., Hikisz, P., et al. Indoxyl sulfate generates free radicals, decreases antioxidant defense, and leads to damage to mononuclear blood cells. Chem. Res. Toxicol. 31(9), 869-875 (2018).