Resorufin β-D-glucuronide sodium salt
| Name | Resorufin-Glc Sodium Salt |
| Synonyms | Resorufin-β-D-glucuronide sodium salt |
| CAS Number | 12540-91-7 |
| Molecular Formula | C18H14NNaO9 |
| Molecular Weight | 431.30 g/mol |
| Specifications & Purity | ≥95% (Vacuum foil packaging) |
Resorufin β-D-glucuronide sodium salt (CAS 125440-91-7), a water-soluble fluorogenic substrate for β-glucuronidase (GUS/β-Gluc) enzymes, undergoes rapid hydrolysis to release intensely fluorescent resorufin (Ex/Em 571/585 nm, ε=56,000 M⁻¹cm⁻¹), providing >500-fold signal amplification for ultrasensitive detection in real-time assays. With formula C18H14NNaO9 (MW 411.29 g/mol), this orange conjugate links resorufin via β1-O-glycosidic bond to D-glucuronic acid (uronic acid of glucose), stable at neutral pH but cleaved by bacterial (E. coli GusA) or eukaryotic β-glucuronidases (EC 3.2.1.31) with kcat/Km ~10^6 M⁻¹s⁻¹, ideal for no-wash kinetic monitoring. Employed in plant molecular biology as GUS reporter gene substrate (replacing X-Gluc for fluorescence over chromogenesis), microbial GUS detection in microbiome studies, HTS for glucuronidase inhibitors (e.g., irinotecan toxics), and diagnostics of Crigler-Najjar/Gilbert syndromes via UGT1A1 activity. Superior to FDGlu for live imaging due to cytoplasmic retention, cell-permeability (10-100 μM loading), and multiplexing with GFP/CFP, it quantifies phase II drug metabolism (glucuronidation), lysosomal storage disorders, and xenobiotic detox in single cells via droplet microfluidics or flow cytometry.
Appearance
- Orange to orange-red crystalline powder.
- Non-fluorescent until enzymatic hydrolysis.
Source
- Enzymatic synthesis using bovine/plant β-glucuronidase on resorufin.
- Commercial: Sigma-Aldrich (≥90%), BOC Sciences.
Molecular Weight and Structure
- Formula: C18H14NNaO9; MW 411.29 g/mol.
- Sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3-oxo-3H-phenoxazin-7-yloxy)tetrahydro-2H-pyran-2-carboxylate.
Sugar Specificity
- Selective β-D-glucuronide for β-glucuronidases (GUS).
- Negligible activity with glucosidases/galactosidases.
Biological Activity
- Fluorogenic reporter; no toxicity.
- GUS substrate sensitivity <1 pM enzyme.
Purity and Microbial Contamination
- ≥90% (HPLC); water-soluble analytical grade.
- Synthetic/biochemical; non-sterile.
Identity and Quality Control
- ¹H-NMR (uronic anomeric H-1 ~5.3 ppm); HRMS m/z 390 [M-Na]+.
- Hydrolysis Ex/Em 571/585 nm (ε=56,000).
Shelf Life and Storage
- 2 years −20°C powder; aqueous 0.5 mg/mL stable 1 month 4°C.
- Light-protected; avoid thiols.
Applications
- GUS reporter assays (plants, bacteria); UGT/glucuronidase HTS.
- Drug metabolism studies, single-cell analytics.
Key Characteristics
- Water-soluble; >500x fluorescence gain.
- Cytoplasmic; pH 6-10 stable; GFP-orthogonal.
Citation Links
- https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2120605.htm
- https://pubchem.ncbi.nlm.nih.gov/compound/16219929
- https://www.sigmaaldrich.com/US/en/product/sigma/r2886
- https://pubchem.ncbi.nlm.nih.gov/compound/102358581
- https://www.chemicalbook.com/ChemicalProductProperty_US_CB2120605.aspx
- https://www.bocsci.com/product/resorufin-b-d-glucuronide-sodium-salt-cas-125440-91-7-195649.html
- https://www.chemsrc.com/en/cas/125440-91-7_361575.html
- https://www.sigmaaldrich.com/JP/en/product/sigma/r2886
- https://pubchem.ncbi.nlm.nih.gov/compound/Resorufin
- https://www.abcam.com/en-us/products/biochemicals/resorufin-d-galactopyranoside-ab273639
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