D-Luciferin Struktur

(S)-4,5-Dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazol-4-carbonsure

Bezeichnung:(S)-4,5-Dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazol-4-carbonsure

CAS-Nr2591-17-5

Englisch Name:D-Luciferin

CBNumberCB8283216

SummenformelC11H8N2O3S2

Molgewicht280.32

MOL-Datei2591-17-5.mol

Synonyma

(S)-4,5-Dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazol-4-carbonsure

(S)-4,5-Dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazol-4-carbonsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	200-204 °C
alpha	D22 -36° (c = 1.2 in DMF)
Siedepunkt	587.6±60.0 °C(Predicted)
Dichte	1.4916 (rough estimate)
Brechungsindex	1.5650 (estimate)
storage temp.	-20°C
Löslichkeit	DMF:30.0(Max Conc. mg/mL);107.02(Max Conc. mM) DMSO:35.33(Max Conc. mg/mL);126.05(Max Conc. mM)
pka	8.31±0.40(Predicted)
Aggregatzustand	Powder
Farbe	Off-white to light yellow
maximale Wellenlänge (λmax)	360nm(H2O)(lit.)
Merck	14,4086
BRN	30484
InChI	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
InChIKey	BJGNCJDXODQBOB-SSDOTTSWSA-N
SMILES	S1C[C@H](C(O)=O)N=C1C1=NC2=CC=C(O)C=C2S1

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36/37/39-24/25
WGK Germany	3
F	8-10
HS Code	29342000

Gefahreninformationscode (GHS)

D-Luciferin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
D-Luciferin is a popular bioluminescent substrate of luciferase in the presence of ATP, used in luciferase-based bioluminescence imaging and cell-based high-throughput screening applications. In an immunocompetent mouse model of ovarian cancer, the use of D-luciferin substrate and firefly luciferase preserves tumour-host immune interactions since bioluminescent imaging is a more sensitive indication of tumour growth than weight gain.
Chemische Eigenschaften
off-white to light yellow powder
Verwenden
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.
Verwenden
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.
Verwenden
In the assay of ATP.
Definition
ChEBI: A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position.
Allgemeine Beschreibung
D-Luciferin is a small molecule present abundantly in bioluminescent organisms. This molecule is sensitive to oxygen and light.
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.
läuterung methode
D-Luciferin crystallises as pale yellow needles from H2O, or MeOH (83mg/7mL). It has UV max at 263 and 327nm (log 3.88 and 4.27) in 95% EtOH. The Na salt has a solubility of 4mg in 1 mL of 0.05M glycine. [White et al. J Am Chem Soc 83 2402 1961, 85 337 1963, UV and IR: Bitler & McElroy Arch Biochem 72 358 1957, Review: Cormier et al. Fortschr Chem Org Naturst 30 1 1973, Beilstein 27 III/IV 8934.]

(S)-4,5-Dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazol-4-carbonsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

2591-17-5, D-Luciferin Verwandte Suche:

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