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L6152 Sigma-Aldrich

D-Luciferin

synthetic, BioXtra, ≥99% (HPLC)

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

  • CAS Number 2591-17-5

  • Empirical Formula (Hill Notation) C11H8N2O3S2

  • Molecular Weight 280.32

  •  Beilstein/REAXYS Number 30484

  •  EC Number 219-981-3

  •  MDL number MFCD00042929

  •  PubChem Substance ID 24896428

  •  NACRES NA.32

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Properties

Related Categories Analytical and Industrial Enzymes, Biochemicals and Reagents, Chemiluminescent compounds, Enzyme Substrates, Enzymes, Inhibitors, and Substrates,
Quality Level   200
biological source   synthetic
product line   BioXtra
assay   ≥99% (HPLC)
form   powder
solubility   DMSO: 10 mg/mL, clear, colorless to faintly yellow
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 mainly produced in bioluminescent organisms. It has the ability to simply circulate across the blood testis barrier, blood brain barrier and the blood placenta barrier. This small molecule is sensitive to light and oxygen. It is also sensitive to moisture in its powder form.

Application

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.

Substrate for firefly luciferase with a Km of approx 2 μM.

Packaging

1, 10 mg in glass bottle

Linkage

Highly purified grade with reduced levels of inhibitor relative to L 9504

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

ABC Transporters and Cancer Drug Resistance

Chemotherapy is the treatment of choice against many types of cancer. However, over time chemotherapeutic drugs can become less effective due to the development of resistance that involves a group of...
BioFiles 2007, 2.4, 7.
Keywords: Absorption, Cancer, Clinical, Cloning, Combinatorial synthesis, Diseases, Enzymology, Gene expression, Genetic, Immunology, Pharmaceutical, Reductions, Transfection

HPLC Analysis of Luciferin Enantiomers on Astec® CHIROBIOTIC® V

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Luciferin Enantiomers on Astec® CHIROBIOTIC® V
Keywords: Chromatography, High performance liquid chromatography

HPLC Analysis of Luciferin Enantiomers on CHIRALPAK® AGP

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Luciferin Enantiomers on CHIRALPAK® AGP
Keywords: Chromatography, High performance liquid chromatography, Vitamins

TokeOni: Properties and Applications

Bioluminescence imaging (BLI) systems allow for high-sensitive and noninvasive monitoring of cell proliferation, activity of signaling pathways and protein-protein interactions in living tissues.1-3 ...
Takahiro Kuchimaru and Shinae Kizaka-Kondoh
Graduate School of Bioengineering & Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.
Keywords: Cancer, Cell proliferation, Infrared spectroscopy

Peer-Reviewed Papers
15

References

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