D-Luciferin CAS 2591-17-5

Introduction：Basic information about D-Luciferin CAS 2591-17-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

D-Luciferin Basic information

• Product Name: D-Luciferin
• Synonyms: 4,5-DIHYDRO-2-(6-HYDROXY-2-BENZOTHIAZOLYL)-4-THIAZOLECARBOXY;4,5-DIHYDRO-2-[6-HYDROXY-2-BENZOTHIAZOLYL]-4-THIAZOLE-CARBOXYLIC ACID;4,5-DIHYDRO-(6-HYDROXY-2-BENZOTHIAZOYL)-4-THIAZOLE CARBOXYLIC ACID;LUCIFERIN, D-;LUCIFERIN;D(-)-2-(6'-HYDROXY-BENZOTHIAZOLYL)-DELTA2-THIAZOLINE-4-CARBOXYLIC ACID;D(-)-LUCIFERIN;D-LUCIFERIN
• CAS: 2591-17-5
• MF: C11H8N2O3S2
• MW: 280.32
• EINECS: 219-981-3
• Product Categories: Luciferines;substrate;Heterocycles;2591-17-5
• Mol File: 2591-17-5.mol

D-Luciferin Chemical Properties

• Melting point: 200-204 °C
• alpha: D22 -36° (c = 1.2 in DMF)
• Boiling point: 587.6±60.0 °C(Predicted)
• density: 1.4916 (rough estimate)
• refractive index: 1.5650 (estimate)
• storage temp.: -20°C
• solubility: DMF:30.0(Max Conc. mg/mL);107.02(Max Conc. mM) DMSO:35.33(Max Conc. mg/mL);126.05(Max Conc. mM)
• pka: 8.31±0.40(Predicted)
• form: Powder
• color: Off-white to light yellow
• biological source: synthetic
• λmax: 360nm(H2O)(lit.)
• Merck: 14,4086
• BRN: 30484
• InChI: 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
• InChIKey: BJGNCJDXODQBOB-SSDOTTSWSA-N
• SMILES: S1C[C@H](C(O)=O)N=C1C1=NC2=CC=C(O)C=C2S1

Safety Information

• Hazard Codes: Xi
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• WGK Germany: 3
• F: 8-10
• HS Code: 29342000
• Storage Class: 11 - Combustible Solids

D-Luciferin Usage And Synthesis

Description

D-Luciferin is a popular bioluminescent substrate of luciferase in the presence of ATP, used in luciferase-based bioluminescence imaging and cell-based high-throughput screening applications. In an immunocompetent mouse model of ovarian cancer, the use of D-luciferin substrate and firefly luciferase preserves tumour-host immune interactions since bioluminescent imaging is a more sensitive indication of tumour growth than weight gain.

Chemical Properties

off-white to light yellow powder

Uses

In the assay of ATP.

Uses

D-Luciferin has been used in the preparation of the reaction mixture for nitric oxide determination by minescence measurement. It has also been used in the preparation of D-luciferin stock solution for luciferin assays.

Uses

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.

Definition

ChEBI: A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position.

General Description

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

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.

Purification Methods

D-Luciferin crystallises as pale yellow needles from H2O, or MeOH (83mg/7mL). It has UV max at 263 and 327nm (log 3.88 and 4.27) in 95% EtOH. The Na salt has a solubility of 4mg in 1 mL of 0.05M glycine. [White et al. J Am Chem Soc 83 2402 1961, 85 337 1963, UV and IR: Bitler & McElroy Arch Biochem 72 358 1957, Review: Cormier et al. Fortschr Chem Org Naturst 30 1 1973, Beilstein 27 III/IV 8934.]