L9504

D-Luciferin

Name: <SC>D</SC>-Luciferin
Brand: SIGMA

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

NACRES:

NA.32

PubChem Substance ID:

24896524

UNSPSC Code:

12352204

EC Number:

219-981-3

MDL number:

MFCD00042929

Beilstein/REAXYS Number:

30484

Product Name

D-Luciferin, synthetic

InChI key

BJGNCJDXODQBOB-SSDOTTSWSA-N

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

SMILES string

OC(=O)[C@H]1CSC(=N1)c2nc3ccc(O)cc3s2

biological source

synthetic

assay

≥98% (HPLC)

form

powder

solubility

DMSO: 10 mg/mL, clear, colorless to faintly yellow

fluorescence

λ_ex 328 nm; λ_em 532 nm in H₂O

storage temp.

−20°C

Quality Level

300

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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.

General description

D-Luciferin is a small molecule present abundantly in bioluminescent organisms. This molecule is sensitive to oxygen and light.

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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Imaging and Spectroscopic Analysis of Living Cells

Test (2012)

U-SPECT-BioFluo: an integrated radionuclide, bioluminescence, and fluorescence imaging platform.

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

Near-infrared fluorescence imaging of both colorectal cancer and ureters using a low-dose integrin targeted probe.

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

CXCL10-induced migration of adoptively transferred human natural killer cells toward solid tumors causes regression of tumor growth in vivo.

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

The chemistry of bioluminescence: an analysis of chemical functionalities.

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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