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

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

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

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

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.

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

In the assay of ATP.

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.]

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