L9504

D-Luciferin

luminescent, ≥98% (HPLC), powder

• 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
• NACRES: NA.32
• PubChem Substance ID: 24896524
• UNSPSC Code: 12352204
• EC Number: 219-981-3
• MDL number: MFCD00042929
• Beilstein/REAXYS Number: 30484

Properties

• Product Name: D-Luciferin, synthetic
• 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[1] and Arabidopsis thaliana seeds.[2] It has also been used in measuring bioluminescence in neonatal rat ventricular cardiomyocytes.[3]

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.[4]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)