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L6152

Sigma-Aldrich

D-Luciferin

BioXtra, ≥99% (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
Beilstein:
30484
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.32

product name

D-Luciferin, synthetic, BioXtra, ≥99% (HPLC)

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

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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.

Linkage

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Multiplexed reporter gene assays: monitoring the cell viability and the compound kinetics on luciferase activity
Didiot M C, et al.
Journal of Biomolecular Screening, 16(7), 786-793 (2011)
Detection of nitric oxide production in cell cultures by luciferin-luciferase chemiluminescence
Woldman Y Y, et al.
Biochemical and biophysical research communications, 465(2), 232-238 (2015)
Matthias N van Oosterom et al.
EJNMMI research, 4, 56-56 (2014-11-12)
In vivo bioluminescence, fluorescence, and single-photon emission computed tomography (SPECT) imaging provide complementary information about biological processes. However, to date these signatures are evaluated separately on individual preclinical systems. In this paper, we introduce a fully integrated bioluminescence-fluorescence-SPECT platform. Next
Real-time imaging after cerebral ischemia: model systems for visualization of inflammation and neuronal repair
Methods in Enzymology, 506, 117-133 (2012)
Isabelle Navizet et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 12(17), 3064-3076 (2011-10-15)
Firefly luciferase is one of the most studied bioluminescent systems, both theoretically and experimentally. Herein we review the current understanding of the bioluminescent process from a chemical functionality perspective based on those investigations. Three key components are emphasized: the chemiluminophore

Articles

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.

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

Chromatograms

application for HPLCapplication for HPLC

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