ChemicalBook CAS DataBase List 2591-17-5

2591-17-5

Name	D-LUCIFERIN
CAS	2591-17-5
EINECS(EC#)	219-981-3
Molecular Formula	C11H8N2O3S2
MDL Number	MFCD00042929
Molecular Weight	280.32
MOL File	2591-17-5.mol

Chemical Properties

Appearance	off-white to light yellow powder
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)
form	Powder
pka	8.31±0.40(Predicted)
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 Data

Hazard Codes	Xi
Risk Statements	36/37/38 less more
Safety Statements	26-36/37/39-24/25 less more
WGK Germany	3
F	8-10
HS Code	29342000

Hazard Information

Chemical Properties

off-white to light yellow powder

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.

Uses

In the assay of ATP.

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.

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.]

Spectrum Detail

Supplier

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