| Identification | Back Directory | [Name]
D-LUCIFERIN | [CAS]
2591-17-5 | [Synonyms]
LUCIFERIN
D-LUCIFERIN
D-Leciferin
LUCIFERIN, D-
AURORA KA-6717
D(-)-LUCIFERIN
BEETLE LUCIFERIN
FIREFLY LUCIFERIN
Photinus luciferin
D-LUCIFERIN FIREFLY
D-(-)-Luciferin
D-LUCIFERIN SYNTHETIC
D-LUCIFERIN SIGMAULTRA
D-LUCIFERINFREEACID,99%
D-Luciferin≥ 99% (HPLC)
D-Luciferin free acid, 99%
D-Luciferin, Free acid >99.5%
D-LUCIFERIN,FREEACID,ULTRAPURE
D -LUCIFERIN SYNTHETIC CRYSTALLINE
Beetle luciferin
Firefly luciferin
D-(-)-Luciferin [Chemiluminescence Reagent]
(S)-2-[6-HYDROXY-2-BENZOTHIAZOLYL]-2-THIAZOLENE-4
4,5-DIHYDRO-2-(6-HYDROXY-2-BENZOTHIAZOLYL)-4-THIAZOLECARBOXY
(S)-2-(6-HYDROXY-2-BENZOTHIAZOLYL)-2-THIAZOLINE-4-CARBOXYLIC ACID
4,5-DIHYDRO-(6-HYDROXY-2-BENZOTHIAZOYL)-4-THIAZOLE CARBOXYLIC ACID
(4S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4β-carboxylic acid
(4S)-2-(6-Hydroxybenzothiazole-2-yl)-2-thiazoline-4-carboxylic acid
4,5-DIHYDRO-2-[6-HYDROXY-2-BENZOTHIAZOLYL]-4-THIAZOLE-CARBOXYLIC ACID
D(-)-2-(6'-HYDROXY-BENZOTHIAZOLYL)-DELTA2-THIAZOLINE-4-CARBOXYLIC ACID
(4S)-4,5-Dihydro-(6-hydroxy-2-benzothiazoyl)-4-thiazolecarboxylic acid
2-(6-Hydroxy-benzothiazol-2-yl)-thiazole-4-carboxylic acid D-Luciferin
(S)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4
thiazolecarboxylic acid
(S)-4,5-dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazole-4-carboxylic acid
(S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
(4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
(D)-4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid, Firefly (synthetic), 99%
Firefly Luciferin, (S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid, 4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid | [EINECS(EC#)]
219-981-3 | [Molecular Formula]
C11H8N2O3S2 | [MDL Number]
MFCD00042929 | [MOL File]
2591-17-5.mol | [Molecular Weight]
280.32 |
| Chemical Properties | Back Directory | [Appearance]
off-white to light yellow powder | [Melting point ]
200-204 °C
| [alpha ]
D22 -36° (c = 1.2 in DMF) | [Boiling point ]
587.6±60.0 °C(Predicted) | [density ]
1.4916 (rough estimate) | [refractive index ]
1.5650 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMF:30.0(Max Conc. mg/mL);107.02(Max Conc. mM)
DMSO:35.33(Max Conc. mg/mL);126.05(Max Conc. mM) | [form ]
Powder | [pka]
8.31±0.40(Predicted) | [color ]
Off-white to light yellow | [biological source]
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 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light yellow powder | [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. | [Uses]
In the assay of ATP. | [Description]
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.
| [General Description]
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. | [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.] |
|
|