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D-Luciferin

D-Luciferin

CAS: 2591-17-5

Molecular Formula: C11H8N2O3S2

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D-Luciferin - Names and Identifiers

Name D-Luciferin
Synonyms LUCIFERIN
D-LUCIFERIN
D-Luciferin
LUCIFERIN, D-
D(-)-LUCIFERIN
4,5-DIHYDRO-2-(6-HYDROXY-2-BENZOTHIAZOLYL)-4-THIAZOLECARBOXY
4,5-DIHYDRO-(6-HYDROXY-2-BENZOTHIAZOYL)-4-THIAZOLE CARBOXYLIC ACID
4,5-DIHYDRO-2-[6-HYDROXY-2-BENZOTHIAZOLYL]-4-THIAZOLE-CARBOXYLIC ACID
D(-)-2-(6'-HYDROXY-BENZOTHIAZOLYL)-DELTA2-THIAZOLINE-4-CARBOXYLIC ACID
(S)-4,5-dihydro-2-(6-hydroxybenzothiazol-2-yl)thiazole-4-carboxylic acid
2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
(2E,4S)-2-(6-oxo-1,3-benzothiazol-2(6H)-ylidene)-1,3-thiazolidine-4-carboxylic acid
(2Z,4S)-2-(6-oxo-1,3-benzothiazol-2(6H)-ylidene)-1,3-thiazolidine-4-carboxylic acid
CAS 2591-17-5
EINECS 219-981-3
InChI InChI=1/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)

D-Luciferin - Physico-chemical Properties

Molecular FormulaC11H8N2O3S2
Molar Mass280.32
Density1.4916 (rough estimate)
Melting Point200-204°C
Boling Point587.6±60.0 °C(Predicted)
Specific Rotation(α)D22 -36° (c = 1.2 in DMF)
Flash Point309.157°C
Vapor Presure0mmHg at 25°C
Appearanceoff-white to yellowish powder
ColorOff-white to light yellow
Maximum wavelength(λmax)['360nm(H2O)(lit.)']
Merck14,4086
BRN30484
pKa8.31±0.40(Predicted)
Storage Condition-20°C
Refractive Index1.5650 (estimate)
MDLMFCD00042929
In vitro studyThe D-luciferin reacts with luciferase, ATP and oxygen to emit light, which is detected by sensitive photographic film to visualize the alkaline phosphatase-bound antibody.
In vivo studyThe use of D-luciferin substrates and firefly luciferase preserves tumor-host immune interactions in an immunocompetent mouse model of ovarian cancer, because the bioluminescence program has a more sensitive indication of tumor growth than body weight gain.

D-Luciferin - Risk and Safety

Hazard SymbolsXi - Irritant
Irritant
Risk Codes36/37/38 - Irritating to eyes, respiratory system and skin.
Safety DescriptionS26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
S24/25 - Avoid contact with skin and eyes.
WGK Germany3
FLUKA BRAND F CODES8-10
HS Code29342000

D-Luciferin - Reference Information

Introduction D-fluorescein is a substrate that depends on the adenosine triphosphate (ATP) bioluminescence reaction. The principle of bioluminescence is that fluorescein is in the presence of ATP and oxygen. The chemical reaction formula is as follows: ATP D-Luciferin O2 → Oxyluciferin AMP PPi O2 Light.
Mechanism of action The mechanism of action of D-luciferin is that under the action of ATP and luciferase, luciferin (substrate) can be oxidized to emit light. When luciferin is excessive, the number of light quanta produced is positively correlated with the concentration of luciferase.
Application D-fluorescein is a substrate that depends on the adenosine triphosphate (ATP) bioluminescence reaction. The bioluminescence reaction of luciferin/luciferase is often used for the detection of ATP, metabolites that can be converted into ATP (such as AMP, ADP, cAMP) and enzymes that can produce ATP (such as creatine kinase, etc.), so the bioluminescence reaction can be applied to the detection of biological materials in a wide range.
Biological activity D-Luciferin (Firefly luciferin) is a popular substrate for bioluminescence in the presence of ATP, used as bioluminescent imaging based on luciferase And cell-based high-throughput screening.
Last Update:2024-04-09 19:05:11
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D-Luciferin
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