L9504

D-Luciferin

synthetic

• Synonym(s): (S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid, 4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid, Firefly Luciferin
• Empirical Formula (Hill Notation): C₁₁H₈N₂O₃S₂
• CAS Number: 2591-17-5
• Molecular Weight: 280.32
• Beilstein: 30484
• EC Number: 219-981-3
• MDL number: MFCD00042929
• UNSPSC Code: 12352204
• PubChem Substance ID: 24896524
• NACRES: NA.32

Properties

• biological source: synthetic
• Quality Level: 300
• Assay: ≥98% (HPLC)
• form: powder
• solubility: DMSO: 10 mg/mL, clear, colorless to faintly yellow
• fluorescence: λ_ex 328 nm; λ_em 532 nm in H₂O
• storage temp.: −20°C
• SMILES string: OC(=O)[C@H]1CSC(=N1)c2nc3ccc(O)cc3s2
• InChI: 1S/C11H8N2O3S2/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16/h1-3,7,14H,4H2,(H,15,16)/t7-/m1/s1
• InChI key: BJGNCJDXODQBOB-SSDOTTSWSA-N

Description

General description

D-Luciferin is a small molecule present abundantly in bioluminescent organisms. This molecule is sensitive to oxygen and light.

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.

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.

Safety Information

• 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