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D-Luciferin

D-Luciferin ??? ???
?? ??:
2591-17-5
???:
D-Luciferin
???(??):
uciferin;LUCIFERIN;D-LUCIFERIN;D-Leciferin;LUCIFERIN, D-;D(-)-LUCIFERIN;AURORA KA-6717;BEETLE LUCIFERIN;FIREFLY LUCIFERIN;Photinus luciferin
CBNumber:
CB8283216
???:
C11H8N2O3S2
??? ??:
280.32
MOL ??:
2591-17-5.mol
MSDS ??:
SDS

D-Luciferin ??

???
200-204 °C
??
D22 -36° (c = 1.2 in DMF)
?? ?
587.6±60.0 °C(Predicted)
??
1.4916 (rough estimate)
???
1.5650 (estimate)
?? ??
-20°C
???
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)
??? ??
??
??
????? ?? ?????
???? ??
synthetic
?? ??(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
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xi
?? ???? ?? 36/37/38
????? 26-36/37/39-24/25
WGK ?? 3
F ?????? 8-10
HS ?? 29342000
????(GHS): GHS hazard pictograms
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ?? GHS hazard pictograms
??????:
P261 ??·?·??·???·??·...·????? ??? ????.
P271 ?? ?? ??? ? ?? ???? ?????.
P280 ????/???/???/?????? ?????.

D-Luciferin C??? ??, ??, ??

??

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.

??? ??

off-white to light yellow powder

??

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.

??

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.

?? ??

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

Purification Methods

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.]

D-Luciferin ?? ?? ? ???

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?? ??


D-Luciferin ?? ??

???( 364)?? ??
??? ?? ??? ?? ?? ? ??
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D-Luciferin ?? ??:

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