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L9504

Sigma-Aldrich

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:
2591-17-5
Molecular Weight:
280.32
Beilstein:
30484
EC Number:
219-981-3
MDL number:
MFCD00042929
UNSPSC Code:
12352204
PubChem Substance ID:
24896524
NACRES:
NA.32

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

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

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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.

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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Imaging and Spectroscopic Analysis of Living Cells
Test (2012)
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
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
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
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Chromatograms

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