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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:
2591-17-5
Molecular Weight:
280.32
Beilstein:
30484
EC Number:
219-981-3
MDL number:
MFCD00042929
UNSPSC Code:
12352204
PubChem Substance ID:
24896428
NACRES:
NA.32

product name

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

biological source

synthetic

Quality Level

200

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

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)
Erik Wennerberg et al.
Cancer immunology, immunotherapy : CII, 64(2), 225-235 (2014-10-27)
Adoptive infusion of natural killer (NK) cells is being increasingly explored as a therapy in patients with cancer, although clinical responses are thus far limited to patients with hematological malignancies. Inadequate homing of infused NK cells to the tumor site
Floris P R Verbeek et al.
Annals of surgical oncology, 21 Suppl 4, S528-S537 (2014-02-12)
Irradical tumor resections and iatrogenic ureteral injury remain a significant problem during lower abdominal surgery. The aim of the current study was to intraoperatively identify both colorectal tumors and ureters in subcutaneous and orthotopic animal models using cRGD-ZW800-1 and near-infrared
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
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