(2Z,4S)-2-(6-oxo-1,3-benzothiazol-2(6H)-ylidene)-1,3-thiazolidine-4-carboxylic acid
D-Luciferin
CAS: 2591-17-5
Molecular Formula: C11H8N2O3S2
(2Z,4S)-2-(6-oxo-1,3-benzothiazol-2(6H)-ylidene)-1,3-thiazolidine-4-carboxylic acid - 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) |
(2Z,4S)-2-(6-oxo-1,3-benzothiazol-2(6H)-ylidene)-1,3-thiazolidine-4-carboxylic acid - Physico-chemical Properties
| Molecular Formula | C11H8N2O3S2 |
| Molar Mass | 280.32 |
| Density | 1.4916 (rough estimate) |
| Melting Point | 200-204°C |
| Boling Point | 587.6±60.0 °C(Predicted) |
| Specific Rotation(α) | D22 -36° (c = 1.2 in DMF) |
| Flash Point | 309.157°C |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | off-white to yellowish powder |
| Color | Off-white to light yellow |
| Maximum wavelength(λmax) | ['360nm(H2O)(lit.)'] |
| Merck | 14,4086 |
| BRN | 30484 |
| pKa | 8.31±0.40(Predicted) |
| Storage Condition | -20°C |
| Refractive Index | 1.5650 (estimate) |
| MDL | MFCD00042929 |
| In vitro study | The 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 study | The 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. |
(2Z,4S)-2-(6-oxo-1,3-benzothiazol-2(6H)-ylidene)-1,3-thiazolidine-4-carboxylic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - 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 Germany | 3 |
| FLUKA BRAND F CODES | 8-10 |
| HS Code | 29342000 |
(2Z,4S)-2-(6-oxo-1,3-benzothiazol-2(6H)-ylidene)-1,3-thiazolidine-4-carboxylic acid - 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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