L9504
D-Luciferin
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:
Molecular Weight:
280.32
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352204
EC Number:
219-981-3
MDL number:
Beilstein/REAXYS Number:
30484
Product Name
D-Luciferin, synthetic
biological source
synthetic
Quality Level
assay
≥98% (HPLC)
form
powder
solubility
DMSO: 10 mg/mL, clear, colorless to faintly yellow
fluorescence
λex 328 nm; λem 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
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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