D-Luciferin
SIGMA/L9504 - synthetic
Synonym: (S)
CAS Number: 2591-17-5
Empirical Formula (Hill Notation): C11H8N2O3S2
Molecular Weight: 280.32
EC Number: 219-981-3
MDL Number: MFCD00042929
Linear Formula: C11H8N2O3S2
Product Type: Chemical
ATP is hydrolyzed and light is emitted when firefly luciferase catalyzes the oxidation of D-luciferin. Reaction (1) is reversible and the equilibrium lies far to the right. Reaction (2) is essentially irreversible. When ATP is the limiting reagent, the light emitted is proportional to the ATP present.
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: L9504-100MG
| assay | ≥98% (HPLC) |
| biological source | synthetic |
| fluorescence | λex 328 nm; λem 532 nm in H2O |
| form | powder |
| InChI | 1S/C11H8N2O3S2/c14-5-1-2- |
| InChI key | BJGNCJDXODQBOB-SSDOTTSWSA |
| Quality Level | 300  |
| SMILES string | OC(=O)[C@H]1CSC(=N1)c2nc3 |
| solubility | DMSO: 10 mg/mL, clear, colorless to faintly yellow |
| storage temp. | −20°C |
| Application: | D-Luciferin has been used in determining luciferase activity by luciferase assay in mice and Arabidopsis thaliana seeds. It has also been used in measuring bioluminescence in neonatal rat ventricular cardiomyocytes. |
| Application: | Substrate for firefly luciferase with a Km of approx 2 μM. |
| Biochem/physiol Actions: | D-Luciferin uptake within the cells is regulated by the adenosine triphosphate (ATP)-binding cassette (ABC) transporter inhibitors like ATP-binding cassette transporter G2 (ABCG2)/ breast cancer resistance protein (BCRP) inhibitor fumitremorgin C. This substrate is oxidized by firefly luciferase that results in emitting a photon, which has the capability of passing through living tissues. |
| General description: | D-Luciferin is a small molecule present abundantly in bioluminescent organisms. This molecule is sensitive to oxygen and light. |
| Packaging: | 1, 5 mg in glass bottle |
| Packaging: | 10, 50, 100 mg in poly bottle |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC) |
| Storage Temp. | −20°C |
| UNSPSC | 12352204 |