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L9504

D-Luciferin

Name: <SC>D</SC>-Luciferin
Brand: SIGMA

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

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About This Item

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

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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 and Arabidopsis thaliana seeds. It has also been used in measuring bioluminescence in neonatal rat ventricular cardiomyocytes.

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Articles

TokeOni: Properties and Applications

Bioluminescence imaging (BLI) systems allows for high-sensitive and noninvasive monitoring of cell proliferation, activity of signaling pathways and protein-protein interactions in living tissues.

Bioluminescent Firefly Luciferase Assays

Firefly luciferase is a sensitive reporter for gene studies due to its absence in mammalian cells or tissues.

TokeOni Analog - seMpai: Properties & Applications

seMpai substrate is suitable for near-infrared BLI in biological experiments, offering high solubility for extended bioluminescent applications.

Global Trade Item Number

SKU	GTIN
L9504-100MG	04061833966648
L9504-10MG	04061833966655
L9504-1MG	04061833966662
L9504-50MG	04061833966679
L9504-5MG	04061833966686