D-Luciferin

Synonym(s):(S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid;D-Luciferin;4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid;Firefly Luciferin

CAS NO.：2591-17-5
Empirical Formula: C11H8N2O3S2
Molecular Weight: 280.32
MDL number: MFCD00042929
EINECS: 219-981-3
SAFETY DATA SHEET (SDS)
Update Date: 2024-03-08 15:03:12

What is D-Luciferin?

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

The Uses of D-Luciferin

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.

The Uses of D-Luciferin

In the assay of ATP.

The Uses of D-Luciferin

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.

What are the applications of Application

D-Luciferin is a chemiluminescent luciferase substrate

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.]

Properties of D-Luciferin

Melting point:	200-204 °C
Boiling point:	587.6±60.0 °C(Predicted)
alpha	D22 -36° (c = 1.2 in DMF)
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

Safety information for D-Luciferin

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection.