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5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid sodium salt (CAS 160369-85-7)

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Alternate Names:
X-NeuNAc
CAS Number:
160369-85-7
Purity:
≥98%
Molecular Weight:
559.72
Molecular Formula:
C19H21BrClN2O9Na
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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5-Bromo-4-chloro-3-indolyl alpha-D-N-acetylneuraminic acid sodium salt is a chromogenic substrate for neuraminidases. These are enzymes that cleave glycosidic linkages of neuraminic acids. Upon hydrolysis by neuraminidase, halogenated indol-3-ol is released and undergoes rapid aerobic oxidation to the dark blue pigment 5,5′-dibromo-4-4′-dichloroindigo, which can be used to quantify neuraminidase activity. This product can be used to facilitate the screening of bacterial colonies or plaques for the detection of either natural or mutant neuraminidase activity. Preliminary kinetic studies indicate that this compound is a good substrate for neuraminidase and is quite stable under identical conditions in the absence of enzyme. These results suggest that 5-Bromo-4-chloro-3-indolyl alpha-D-N-acetylneuraminic acid sodium salt can be useful to screen for bacterially-encoded enzyme production directly on agar plates.


5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid sodium salt (CAS 160369-85-7) References

  1. Fluorescent cytochemical detection of sialidase activity using 5-bromo-4-chloroindol-3-yl-alpha- D- N-acetylneuraminic acid as the substrate.  |  Saito, M., et al. 2002. Histochem Cell Biol. 117: 453-8. PMID: 12029493
  2. Age-dependent reduction in sialidase activity of nuclear membranes from mouse brain.  |  Saito, M., et al. 2002. Exp Gerontol. 37: 937-41. PMID: 12086703
  3. NAN fusions: a synthetic sialidase reporter gene as a sensitive and versatile partner for GUS.  |  Kirby, J. and Kavanagh, TA. 2002. Plant J. 32: 391-400. PMID: 12410816
  4. Comparison of L-selectin and E-selectin ligand specificities: the L-selectin can bind the E-selectin ligands sialyl Le(x) and sialyl Le(a).  |  Berg, EL., et al. 1992. Biochem Biophys Res Commun. 184: 1048-55. PMID: 1374233
  5. Lewis X-containing glycans are specific and potent competitive inhibitors of the binding of ZP3 to complementary sites on capacitated, acrosome-intact mouse sperm.  |  Kerr, CL., et al. 2004. Biol Reprod. 71: 770-7. PMID: 15128590
  6. Imaging of sialidase activity in rat brain sections by a highly sensitive fluorescent histochemical method.  |  Minami, A., et al. 2011. Neuroimage. 58: 34-40. PMID: 21703353
  7. Development of a point-of-care diagnostic for influenza detection with antiviral treatment effectiveness indication.  |  Murdock, RC., et al. 2017. Lab Chip. 17: 332-340. PMID: 27966711
  8. Persistent reduction in sialylation of cerebral glycoproteins following postnatal inflammatory exposure.  |  Demina, EP., et al. 2018. J Neuroinflammation. 15: 336. PMID: 30518374
  9. Rapid screening of neuraminidase inhibitors with the benzoic acid skeleton from Paeonia suffruticosa Andrews by solid-phase extraction with an enzyme activity switch combined with mass spectrometry analysis.  |  Chen, M., et al. 2022. J Chromatogr A. 1676: 463213. PMID: 35717865
  10. An affinity interaction guided two-dimensional separation system for the screening of neuraminidase inhibitors from Reynoutria japonica Houtt. roots.  |  Chen, M., et al. 2022. J Chromatogr A. 1678: 463338. PMID: 35901666
  11. A single amino acid residue can determine the ligand specificity of E-selectin.  |  Kogan, TP., et al. 1995. J Biol Chem. 270: 14047-55. PMID: 7539797
  12. Sulfated glycolipids are ligands for a lymphocyte homing receptor, L-selectin (LECAM-1), Binding epitope in sulfated sugar chain.  |  Suzuki, Y., et al. 1993. Biochem Biophys Res Commun. 190: 426-34. PMID: 7678958
  13. X-Neu5Ac: a novel substrate for chromogenic assay of neuraminidase activity in bacterial expression systems.  |  Fujii, I., et al. 1993. Bioorg Med Chem. 1: 147-9. PMID: 8081844

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid sodium salt, 10 mg

sc-217158
10 mg
$256.00

5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid sodium salt, 50 mg

sc-217158A
50 mg
$549.00

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. 5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid sodium salt, sc-217158, is a white to off-white solid.
Answered by: Chemical Support 4
Date published: 2017-06-02
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Rated 5 out of 5 by from Great substrateI brought several times of this substrate to detect the sialidase activity. The product is easy to use and the price also reasonable.
Date published: 2017-06-12
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5-Bromo-4-chloro-3-indolyl α-D-N-acetylneuraminic acid sodium salt is rated 5.0 out of 5 by 1.
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