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L9504

Sigma-Aldrich

D-Luciferin

luminescent, ≥98% (HPLC), powder

Sinonimo/i:

(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

Formula empirica (notazione di Hill):
C11H8N2O3S2
Numero CAS:
2591-17-5
Peso molecolare:
280.32
Beilstein:
30484
Numero CE:
219-981-3
Numero MDL:
MFCD00042929
Codice UNSPSC:
12352204
ID PubChem:
24896524
NACRES:
NA.32

product name

D-Luciferin, synthetic

Origine biologica

synthetic

Saggio

≥98% (HPLC)

Forma fisica

powder

Solubilità

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

Fluorescenza

λex 328 nm; λem 532 nm in H2O

Temperatura di conservazione

−20°C

Stringa SMILE

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
BJGNCJDXODQBOB-SSDOTTSWSA-N

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Categorie correlate

Descrizione generale

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

Applicazioni

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.

Azioni biochim/fisiol

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.

Applicazioni

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Sostituito da

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Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Sigma-Aldrich

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Imaging and Spectroscopic Analysis of Living Cells
Test (2012)
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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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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